ChemACE
Users
Manual
Contributors:
Kelly Mayo-Bean3, Kendra Moran-Bruce®, Jay L. Tunkelb
aU.S. EPA, Risk Assessment Division
1200 Pennsylvania Ave., N.W.
Washington, DC 20460
bSRC, Inc.
7502 Round Pond Road
North Syracuse, NY 13212-2558
January 30, 2011
ChemACE Beta Test Version

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Table of Contents
1.	ChemACE Methodology	3
2.	ChemACE Download/Set-up	3
3.	Creating a Chemical Input File	3
4.	ChemACE Model Interface	4
4.A Input Tab	5
4.B Advanced Options Tab	6
4.C Default Setting Tab	8
5.	ChemACE Output Report	9
Appendix A - ChemACE Chemical Fragment Library	12

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1. ChemACE Methodology
The Chemical Assessment Clustering Engine (ChemACE) is designed to cluster a list
of chemicals based on structure using predefined similarity rules. The ChemACE
methodology is based on logic implemented in the Analog Identification Methodology
(AIM) tool (http://aim.epa.gov) that identifies analogs based on the presence of
common fragments using a tiered approach.
In AIM, the first tier search strategy referred to as 'Pass V consists of matching all the
same fragments (and ring systems) between the query chemical and chosen analogs
and is based on an extensive fragment list. If analogs were not found during Pass 1, a
second pass (Pass 2) would commence to identify analogs using a smaller, less
restrictive list of possible fragments. The final Pass 3 allows simple substitutions.
ChemACE is designed cluster chemicals that are analogs of one another using the
same fragment generation system found in AIM, but uses a more complex method for
identifying analogs for the clustering exercises that is based on advanced queries in
multidimensional space and by allowing users to design rules to modify the approach.
Below, operation of ChemACE will be described in detail.
2.	ChemACE Download/Set-Up
ChemACE is a self-extracting file. Once it is downloaded and saved to diskette or hard
drive, execute (double-click) the file to install the program (if you selected "Run" and
not "Save" at the download prompt, it should install automatically). Note: The
ChemACE installation program includes a version of the Java Runtime Environment
(JRE).
3.	Creating a Chemical Input File
Prior to operating ChemACE, the user needs to identify or create a chemical inventory
input file. Input files must be in simple tab delimited text format and must be formatted
so that:
•	The first row must contain column headings
•	Each chemical (and its corresponding information) is entered on its own
line
•	The first column contains a representation of chemical structure using
SMILES format (for more information see
http://www.epa.gov/ncct/dsstox/MoreonSMILES.html)
•	The second column contains a chemical identifier that can be any
combination of numbers and characters, and

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• No more than 5 additional (optional) columns (e.g., columns containing
of information may be carried over to the output file. Any additional
columns beyond that present in the input file will not be displayed in the
output report
Creation of an input file is most easily done in Microsoft EXCEL or ACCESS followed
by export of the table into a text (.txt) delimited file. A depiction of a table (as it would
look in Microsoft EXCEL) is shown below in Figure 1.
Figure 1: Sample Input File
Column 1 Column 2 Column 3 Column 4 Column 5 Column 6 Column 7
Header
SMILES
Unique ID
Attribute 1
Attribute 2
Attribute 3
Attribute 4
Attribute 5
Data 1
ccoc
500-01-2
Optional
Optional
Optional
Optional
Optional
Data 2
CC(=0)0CC
500-02-3
Optional
Optional
Optional
Optional
Optional
Data 3
CC(=0)0CCC
500-03-4
Optional
Optional
Optional
Optional
Optional
Data 4
ccoccccc
500-01-5
Optional
Optional
Optional
Optional
Optional
•	The 'Header' for columns 1 and 2 will not show up in the output.
•	Column two must reflect a unique identifier for the chemical.
•	If attribute data are not to be included (shown above at columns 3-7), then
these columns (including the heading) can be left blank. Conversely, the
header is required for inclusion of attribute data.
•	Proper formatting is required since ChemACE ignores rows that are not
compatible with the formatting requirements or which contain
incorrect/incompatible SMILES notations.
Two example input files (SampleDataFile.txt and Advanced example.txt) are provided
in the ChemACE program folder under the "input" folder as reference. Users are
advised to refer to these files when creating their input files. The former
"SampleDataFile.txt" file represents a basic input file and the later "Advanced
Example.txt" file represents an input file containing attributes. The "Advanced
Example.txt" input file was included to 1) demonstrate the use of Data fields within
ChemACE and 2) to demonstrate the clustering results of all of the current user
options (including those on the advanced tab).
Special Note: Long text fields, especially those with no natural breaking points,
may wrap unpredictably in the output file in this version of ChemACE.

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4. ChemACE Model Interface
If standard set-up procedures were followed, a shortcut for ChemACE [ £L ] should be
present on the user's desktop. Otherwise, the program should be available in the
'Start' menu under 'Programs'. Either double-click on the desktop icon or navigate the
start menu and select the ChemACE program, which has a similar icon (shown above)
adjacent to the name, to open the program.
The first screen to appear contains information that should be acknowledged by all
users and is related to the operation of the program. Once the user has read this
information, the user can click on the 'OK' button at the bottom of the screen to
proceed to the actual program.
4.A Input Tab
The default screen that comes up (see Figure 2) displays the 'Input' tab with tab
headings for 'Advanced Options' and 'Default Settings'. To navigate to another screen,
select the tab heading for the screen to be accessed.
Figure 2: Initial Input Screen
Chemical Assessment Clustering Engine
Input [ Advanced Options Default Settings
~0®
Select Input File:
Browse...
~ Less restrictive clustering (AIM Pass 2 method)
Select Report Format	1 rReport Layout
® HTML O PDF O Excel (?) Linear O Horizontal
Structure Image Size
(§) Normal O Large O Extra Large
Run Clustering Engine
f Help
The 'Help' button at the button of the screen allows access to this 'Tutorial' document.
4.A.1. Select the chemical inventory to be clustered
From the 'Input' interface (see Figure 2), click on the 'Browse' button under the
'Selected Input File' heading. A window will appear that allows the user to navigate
through the computer files of the computer they are using. Navigate and select the file
you wish to use by highlighting it, and then press the 'Select' button.

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Special Note: If the data source you select is incompatible with the ChemACE
program, the output will be blank; no warning message is displayed.
4.A.2. Select Report Format
ChemACE provides a user with the ability to customize the output report under the
'Input' tab shown in Figure 2 above. Alternatively, the user can refer to the 'Default
Settings' tab to establish output report preferences for every run. To see a description
of the various options for the report, refer to Section 4.c below.
4.A.3. Run the clustering tool with no remapping or exclusion rules.
Click the 'Run Clustering Engine' button. The completed report will open automatically
in the selected format. Generation of the report may take a few minutes depending on
the number of chemicals runs and depending on whether the output format includes
structures (i.e., HTML and Adobe PDF formats).
4.A.3. Run clustering tool with reduced fragments (less restrictive).
As in the AIM tool, ChemACE allows user to cluster compounds based on a reduced
fragment list referred to as 'Less Restrictive Clustering (AIM Pass 2 Method). Pass 2
removes approximately one half of the fragments from consideration during fragment
matching. The user should click the check-box for 'less restrictive clustering' under the
input file field to implement this rule.
4.B Advanced Options Tab
ChemACE was designed to mimic the AIM Methodology with pass 1 and 2 logic
embedded in ChemACE's general clustering rules. However, ChemACE also allows
the user to manually enhance and even customize the clustering process by using
"exclusion rules" for specific fragments, or fragment types and enabling remapping,
which allows user to define different fragments as the same during the clustering
process. These additional remapping and exclusion functions are carried out under the
'Advanced Options' tab and are shown below in Figure 3.

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Figure 3: Advanced Options Tab
© Chemical Assessment Clustering Engine
Input f Advanced Options ] Default Settings
Select the following optional features to customize the clustering process
(see Help file for instructions)
Built-in Fragment Remapping Options:
~	Treat adjacent halogens as equivalent
~	Make methyl, methylene, methine equivalent
~	Make primary, secondary, & tertiary amines equivalent
User defined fragment remapping file
	 Browse...
Built-in Fragment Exclusion Options:
~	Exclude aromatic thiols
User defined fragment exclusion file
~HI®
Browse...
4.B.1. Predefined Remapping and/or Exclusion Rules.
Check-boxes representing predefined exclusions and remapping are available under
the 'Advanced Options' tab; a brief identification and description of each is below.
•	Treat adjacent halogens as equivalent - represents a remapping operation,
which allows F to be substituted for CI, CI for Br, Br for I.
•	Make methyl, methylene, methine equivalent- represents a remapping
operation, which makes the identified groups equivalent.
•	Primary, secondary & tertiary amines - represents a remapping operation, which
makes the identified groups equivalent.
•	Exclude aromatic thiols - represent an exclusion operation, which removes
thiols from consideration.
4.B.2. User Defined Re-Mapping and Exclusion Rules
In addition to the predefined exclusion/remap operations above, the advanced tab
allows user to create their own custom clustering rules; these can be used to make
clustering either more or less restrictive. These are described in more detail, below.
When re-mapping and exclusion rules are created, the user should keep in mind the
following.
•	Rules are to be created in text documents (.txt) separate from the ChemACE
program.

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•	Remapping and exclusion rules should be separated into individual text files.
ChemACE has separate input fields for remapping and exclusion rules and
treats the rules differently.
•	Lines that start with '#' or'//' are not read by the program, but benefit users by
allowing comments about the nature of the rule to be included with the rule text
document.
•	A fragment should be defined in a rule in only one way. If a fragment is defined
in both a remapping and an exclusion rule or if a fragment is modified by a
selected pre-programmed rule and is defined in a user-created rule, the
program will get confused and may output a single compound multiple times.
For example, you cannot require ChemACE to exclude CI under a user defined
rule, and then initiate the default rule to make all halogens equivalent at the
same time.
Example remapping and exclusion rules can be found within the 'config' folder of the
ChemACE program folder (created during instillation at C:/ChemACE/config) under the
map or exclude folders, respectively. These example documents include added
instructions and explanation. Also, the advanced example provides an additional
column with information about clustering tendencies that may be useful in
experimenting with the use and/or creation of remapping and exclusion rules. A
complete list of fragment numbers used by ChemACE is required to create remapping
and exclusion files, and can be found under Appendix A on page 12 of this document.
4.C Default Setting Tab
ChemACE provides users with the ability to customize the output report for different
purposes. The user can specify the output format under the 'Input' tab each time they
perform a cluster operation (see Figure 2). However, if the user wants to establish
universal default output setting, changes should be made to the 'Default Settings' tab.
The user also has the option to select a default input and output file directory.

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Figure 4: Default Settings Tab
€$ Chemical Assessment Clustering Engine

Input | Advanced Options | Default Settings
Default Input File Directory
C:\ChemACE\input\
Browse...
Reports
Default Output Directory


| C:\ChemACE\output\
Browse...
Default Format


® HTML O PDF O Excel

Default Layout


Linear O Horizontal

Default Structure Image Size


® Normal G Large O Extra Large



Apply Default Settings Reset



Listed below are the available fields for output format as seen on both the Input tab
(Figure 2) and the Default Settings tab (Figure 4) followed by a brief description.
•	Report format/Default Format - The user has the option to output the cluster
results in HTML, Adobe PDF, or Microsoft EXCEL file formats. HTML or PDF
files include structures; Excel does not include structures.
•	Report Layout/Default Layout - The user has the option to output the clustering
results in a horizontal or vertical layout for Adobe PDF and HTML outputs. The
horizontal layout accommodates up to six structures per row.
•	Structure Image size/Default Structure Image Size - The user can select the
size of the structure from pre-define sizes to be displayed in the HTML or Adobe
PDF documents. The user should consider the molecular size of the
compounds in their data source when selecting the size of the output structure.
The settings tab allows users to save their preferences so that they appear by default
each time ChemACE starts. By hitting the 'Apply' button, the setting choices selected
on the screen will be saved as the default for future clustering runs.
5. ChemACE Output Report
Depicted below are sample outputs (created from data shown in Figure 1 table). HTML
and Adobe PDF outputs are identical except for their file format and, thus, separate
sample outputs are not displayed for these file formats.

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Figure 5: PDF and HTML Output Using Horizontal Layout
w	ChemACE Cluster Report
Input File:	TutoriaLtxt
Options:	Pass 2
Date:	Feb 6, 2012 12:37 PM
Cluster: 1
CHj
ID	500-01-2
SMILES	ccoc
Attribute 1	Optional
Attribute 2	Optional
Attribute 3	Optional
Attribute 4	Optional
Attribute 5	Optional
Cluster: 2
ID	500-01-3	500-01-4
SMILES	CC(=0)0CC	CC(=0)OCCC
Attribute 1	Optional	Optional
Attribute 2	Optional	Optional
Attribute 3	Optional	Optional
Attribute 4	Optional	Optional
Attribute 5	Optional	Optional
The above horizontal output (Figure 5) differs from the vertical output (Figure 6, below)
only by how cluster data are shown.
•	The horizontal output facilitates read-across of clustered chemicals/information
•	Vertical output just lists all chemicals/information under cluster headings
Additional information shown in the upper left corner of the output file includes:
•	Name of the input file
•	The remapping and exclusion rules applied
•	The date of the ChemACE run
500-01-5
CCOCCCCC
Optional
Optional
Optional
Optional
Optional

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Figure 6: Adobe PDF and HTML Output Using Vertical Layout
(jft)	ChemACE Cluster Report
Input File: TutoriaI.txt
Options: Pass 2, Remap Fragments
Date:	Feb 6, 2012 12:35 PM
Cluster:	1
500-01-2	CH,
ccoc
Attribute 1	Optional
Attribute 2 Optional
Attribute 3 Optional
Attribute 4 Optional
Attribute 5 Optional
500-01-5
ccoccccc
Attribute 1	Optional
Attribute 2	Optional
Attribute 3	Optional
Attribute 4	Optional
Attribute 5	Optional
Cluster:	2
500-01-3	HjC
CC(=0)0CC	^ \
Attribute 1	Optional
Attribute 2	Optional	c
Attribute 3	Optional
Attribute 4	Optional
Attribute 5	Optional
500-01-4
CC(=0)0CCC
Attribute 1 Optional
Attribute 2 Optional
Attribute 3 Optional
Attribute 4 Optional
CH,

Attribute 5 Optional
CHaj
The below Microsoft EXCEL output (Figure 7) lists data under cluster headings
regardless of whether the horizontal or vertical layout is selected. The additional
information (similar to Adobe PDF and HTML outputs) shown in the output includes the
file name for the input file, an option field that displays some of the remapping and
exclusions applied to the cluster run, and the date of the run.

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Figure 7; Microsoft EXCEL Output
1

ChemACE Cluster Report

2
Input File:
Tutorial.txt

3
Options:
Pass 2

4
Date:
Feb 6.201212:39 PM

5
Cluster:

ri

6
500-01-2
CCOC
7
Attribute 1
Optional

8
Attribute 2
Optional

9
Attribute 3
Optional

10
Attribute 4
Optional

11
Attribute 5
Optional

12
500-01-5
CCOCCCCC
13
Attribute 1
Optional

14
Attribute 2
Optional

15
Attribute 3
Optional

16
Attribute *
Optional

17
Attribute 5
Optional

IS
Cluster:

r2

19
500-01-3
CC(=0)OCC
20
Attribute 1
Optional

21
Attribute 2
Optional

22
Attribute 3
Optional

23
Attribute 4
Optional

24
Attribute 5
Optional

25
500-01-4
CC(=0)OCCC
26
Attribute 1
Optional

27
Attribute 2
Optional

23
Attribute 3
Optional

29
Attribute 4
Optional

30
Attribute 5
Optional

Note on Chemicals that Could Not be Clustered: After all chemicals that could be
grouped together are identified and numbered sequentially, the very last cluster
contains all substances that could not be grouped based on structural similarity to
other members within the input file. These chemicals are preceded by the title "Not
Clustered". The substances listed under this heading contained sufficient structural
diversity from the other chemicals in the list that they could not be grouped using the
current clustering parameters.
To minimize the number of chemicals "Not Clustered" it is suggested that users inspect
their chemical set and employ the exclusion and remapping options to tailor the
clustering logic as appropriate.

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Appendix A - ChemACE Chemical Fragment Library
Fragment
Number
Modified Name
General Comments
Structure
-CH3 [aliphatic carbon]
0
Methyl; Primary carbon


-CH2- [aliphatic carbon]
1
Secondary carbon

R
1
r/CH2
-CH [aliphatic carbon]
2
Tertiary carbon

R
1
.CH
R "R
C [aliphatic carbon - No
H, not tert]
3
Quaternary carbon

R
1
R—C—R
1
R
=CH2 [olefinic carbon]
4
Alkene

r*CH*
=CH- or =C< [olefinc
carbon]
5
Vinyl
R's are undefined
x..rA
#C [acetylenic carbon]
6
Alkyne

R^
-OH [hydroxy, aliphatic
attach]
7
Hydroxy

.OH
R
-0- [oxygen, aliphatic
attach]
8
Ether


-NH2 [aliphatic attach]
9
Primary amine

r-NH*
-NH- [aliphatic attach]
10
Secondary amine

R
1
.NH
R
-N< [aliphatic attach]
11
Tertiary amine

R
1
-CL [chlorine, aliphatic
attach]
12
Alkyl chloride

R-Cl
-CL [chlorine, olefinic
attach]
13
Vinyl chloride

R^^CI
-F [fluorine, aliphatic
attach]
14
Alkyl fluoride

r-f
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

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Fragment
Number
Modified Name
General Comments
Structure
-F [fluorine, olefinic
attach]
15
Vinyl fluoride


-Br [bromine, aliphatic
attach]
16
Alkyl bromide

R-Br
-Br [bromine, olefinic
attach]
17
Vinyl bromide

R^s^Br
-1 [iodine, aliphatic
attach]
18
Alkyl iodide

R-1
Aromatic Carbon
19

Example: Benzene
(CAS No. 71-43-2)
0
Representative structure
Aromatic Nitrogen
20

Example: Pyridine
(CAS No. 110-86-1)
Repres
.entative structure
-CL [chlorine, aromatic
attach]
21
Chloro-aromatic

o
\
oc
<
-Br [bromine, aromatic
attach]
22
Bromo-aromatic

/Br
AR
-OH [hydroxy, aromatic
attach]
23
Hydroxy-aromatic

JDH
AR
-N [aliphatic N, one
aromatic attach]
24
Aryl alkyl amine

R^ AR
-0- [oxygen, one
aromatic attach]
25
Aryl alkyl ether

oc
/
o
\
oc
<
-0- [aliphatic 0, two
aromatic attach]
26
Diaryl ether

AR AR
-CHO [aldehyde, aliphatic
attach]
27
Alkyl aldehyde

A
-CHO [aldehyde,
aromatic attach]
28
Aryl aldehyde

A
-C(=0)- [carbonyl,
aliphatic attach]
29
Alkyl ketone
R' cannot be
aromatic
A,
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2

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Fragment
Number
Modified Name
General Comments
Structure
-C(=0)- [carbonyl, one
aromatic attach]
30
Alkyl aryl ketone

O
.A,
AR R
-C#N [cyano, aliphatic
attach]
31
Alkyl nitrile

R-C=N
-C#N [cyano, aromatic
attach]
32
Aryl nitrile

AR—C=N
-N02 [nitro, aliphatic
attach]
33
Alkyl nitro

r.n°2
-N02 [nitro, aromatic
attach]
34
Aryl nitro

aR-N0>
-COOH [acid, aliphatic
attach]
35
Alkyl carboxylic acid

x„
-COOH [acid, aromatic
attach]
36
Aryl carboxylic acid

O
x
AR^iDH
-N=0 [nitroso]
37

R' is undefined
O
II
R
-S- [aliphatic sulfur,one
aromatic attach]
38
Alkyl aryl sulfide

R^S^AR





Aromatic Sulfur
39

Example: Thiophene
(CAS No. 110-02-1)
O
Representative Structure
-C(=0)0 [ester, aliphatic
attach]
40
Alkyl ester
R' is undefined
h°
o
\
XJ
-C(=0)0 [ester, aromatic
attach]
41
Aryl ester
R' is undefined
h°
o
\
>
73
-F [fluorine, aromatic
attach]
42
Aryl fluoride

AR—F
-C(=0)N [aliphatic attach]
43
Alkyl amide

0
x
r^^nh2
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2

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Fragment
Number
Modified Name
General Comments
Structure
-C(=0)N [aromatic
attach]
44
Aryl amide

0
x
ar^^nh2
-NC(=S)N- [thiourea]
45

R's are undefined
s
r,\ Jk /r"
N N
H H
-SH [aliphatic attach]
46
Alkyl thiol

.SH
R
-S02-0H [sulfonic],
[coef*(l+0.3*(NUM-l))]
47

R' = Alkyl C, Aryl C, N;
Cannot be 0
0
II
0 W R'
0
-S- [aliphatic attach]
48
Dialkyl sulfide

R R
S=P [thio=phosphorus]
49
Thiophosphorus
R' = N, S, 0, or C (any
combination)
S
II
R' — P—R'
1
R'
-O-P [aliphatic attach]
50

R's are undefined
HO 0 HO O
,PN HPV
0' OH HO' OH
-O-P [aromatic attach]
51


AR AR
\ \
HO O HO 0
Hps ,PN
HO' OH 0' OH
-S-P [sulfur, phosphorus
attach]
52


S—PH,
/
0=P
53


O
II
CL
\
-N-P [nitrogen,
phosphorus attach]
54

R's are undefined
r r"-p'r"
N=P ^iV.
/ R'
-1 [aromatic attach]
55
Aryl iodide

>
1
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

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Fragment
Number
Modified Name
General Comments
Structure
-S02-N [aromatic attach]
56
Aryl sulfonamide
R's are undefined
o ,R'
s-N
AR \\ V
0
-S02- [aromatic attach]
57
Aryl sulfonyl
R' undefined
o
Js-R'
AR \\
o
-NC(=0)N- [urea]
58
Urea
R's are undefined;
Unlikely alternative
structure using
higher valence
Nitrogen (+5)
0
R'\ ^R""
N N
1 1
R" R'"
-O-N [oxygen, nitrogen
attach]
59


R'—0
N-R"
1
R,"
Aromatic Oxygen
60


0
Representative Structure
-0C(=0)N [carbamate]
61
Carbamate
R' cannot be H;
R", R'" are undefined
O
R'^ ^R"
O N
1
R",
-S02- [sulfone, aliphatic
attach]
62
Sulfone
R' = 0, H, R;
R" is undefined
^R"
R^\
-S(=0)- [sulfoxide,
aliphatic attach]
63
Sulfoxide
R' = 0, H, R;
R" is undefined
0
II
R R"
-N- [aliphatic N, two
aromatic attach]
64
Diaryl amine

R"
1
A
AR AR
Aromatic n=0 [nitrogen
oxide]
65

R' is undefined
O
11 R'
n—k
O
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2

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Fragment
Number
Modified Name
General Comments
Structure
-SS- [disulfide]
66
Disulfide
R's are undefined
S^R"
/
R'-"S




R
1





Aromatic Nitrogen [5-
member ring]
67


i)
-S- [aliphatic S, two
aromatic attach]
68


>
7J
\
7J




0
-C(=0)- [two aromatic
attach, in ring]
69


Representative Structure
-S-N [sulfur, nitrogen
attach]
70

R, R' and R" are
undefined
R'" = 0 or N
~ ^ D'"
V--N R P
s V Ns-N




R"
1
-S-C(=0)-N-
[Thiocarbamate]
71
Thiocarbamate
R's are undefined
r yzo
R"S
Olefinic Carbon [two
aromatic attach]
72
Diaryl alkene

AR^R
AR
-S(=0)- [sulfoxide,
aromatic attach]
73

R'=not 0
0
II
R AR
-N=C=S [isothiocyanate,
aliphatic attach]
74


R-N=C=S
-N=C=S [isothiocyanate,
aromatic attach]
75


>
73
I
Z
II
o
II
CO
-tert Carbon [3 or more
carbon attach]
76

R' cannot be H

R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

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Fragment
Number
Modified Name
General Comments
Structure
-SH [thiol, aromatic
attach]
77


AR—S—H
Ketone in a ring [olefin,
aromatic attach]
78


oS
Representative structure
-N=N- [Azo]
79

R's are undefined
R'—N=N—R"
-C(=S)N [aromatic attach]
80

R's are undefined
S
!L -R'
/ N
AR \
R"
-OH [alcohol, olefinic
attach]
81
Vinyl alcohol

R^^OH
-S02-N [aliphatic attach]
82

R' = not 0;
R", R'" are undefined
O R"
II /
R'—S—N
A R'"
O R
-OH [hydroxy, nitrogen
attach]
83

R's are undefined
R'
1
R" OH
R'
ho-.i,-R-
/ V
R"" R'"
-N=C [aliphatic attach]
84

R's are undefined
R'—N=C—R"
C#N-S [cyano, sulfur
attach]
85

R' is undefined
R'—S-C=N
C#N-N [cyano, nitrogen
attach]
86

R's are undefined
R'\ C^N
/
R"
C#N-C=N [cyano, -C=N
attach]
87

R' is undefined
C
II
Ns
R'
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
Carbonyl, non-cylic, two
aromatic attach
88
Diaryl carbonyl

0
x
AR AR
Aldehyde, [-N-CHO;
aromatic attach]
89

R' is undefined
R AR
Aldehyde, [-N-CHO;
aliphatic attach]
90

R's are undefined
R R"
-0N02 [aliphatic attach]
91


V
/
O
s
R
-C(=0)- [carbonyl, olefinic
attach]
92

R'= not 0 or H; R",
R'" = undefined
O
R'\
-S02-0 [sulfonate,
aromatic attach]
93
Aryl sulfonate
R' is undefined
0 R'
II /
0—s—0
1
AR
S02 [two aromatic
attach]
94
Diaryl sulfone

0
II
0=S—AR
1
AR
-N-S02-N- [sulfamide]
95

R's are undefined
0 ~
II /
0=S-N
| \
R""
R R"
-CO-CO [aromatic attach]
96


O
V
AR
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
-C(=S)N- [aliphatic attach]
97

R's are undefined
s
Vl ,r'
/ N
R \
R"
-S-C= [S to aliphatic,
double bonded C]
98

R's are undefined
R"v
r\
-Si- [silicon, aliphat
attach (not oxy)]
99

R , R'= not oxygen
R'\
VR
-Si- [silicon, aromatic or
oxygen attach]
100

R' is undefined
R XS-AR R ns-OH
>P- [phosphine type]
101

R's are undefined
R,"
/
R""P\
R"
-OH [phosphorus attach]
102

R's are undefined
OH
/
R-Ps
R"
-S02-0 [sulfonate, aliph
att]
103

R = not O;
R' is undefined
0
II
R-S-O-R'
II
0
>N< [+5 valence; single
bonds;no H attach]
104

R's are undefined
R
R'-rlrR"
/ N
R'" H
Aromatic nitrogen [fused
ring location]
105


H
r^N^l
Representative structure
Aromatic nitrogen [+5
valence type; no H]
106


R'\ ,R"
Representative structure
Halogen {-CL,-Br,-F,-I}
[Nitrogen attach]
107

R's are undefined
R"\ /X
N
1
R'
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
-S- [aliphatic sulfur, 2
nitrogen attach]
108

R's are undefined
R'
/ FT
RH--N /
R Ss-N.
R""
N#N {alias: charged
=N[+]=N[-] }
109

R's are undefined
R'
R"
-Hg- [mercury]
110

R's are undefined
R' R'x R"
Hg^R Hg
Formaldehyde
experimental value -
constant
111


H
Y°
H
#C [acetylenic carbon-
acetylenic attach]
112

R's are undefined
R—
-N(=0)=C [nitrone,
aromatic attach]
113


0
ar"n^>-r
-C#N=0 [cyanooxide,
aromatic attach]
114


AR—=N=0
S=C=S [carbon disulfide,
experimental]
115


S=S
-C(=0)-S [thioester,
aliphatic attach]
116

R,R' = not H; R=not 0
O
s
/
R'
-0-S02-0- [sulfate,
linear]
117

R,R' = not H; R=not 0
0
II
R-O-S-O-R'
II
0
-CO-CO [aliphatic attach]
118

R = not H or 0;
R' is undefined
R'
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
Aldehyde, [-N-CHO;
olefinic attach]
119

R' is undefined
o
¦V
-C(=0)-SH [aliphatic
attach]
120


o
Kh
R
N=0 [nitroso; N+5
valence]
121

R's are undefined
0
II
R"—N-H
1
R'
N-C(=S)-S [cyclic]
122


S
x
HN^^S
u
Representative Structure
-Se- [aromatic attach]
123

R' is undefined
R'
/
AR^Se
-N(=0)- [N-oxide +4 type;
no H attach]
124

R's are undefined
O
II
ri NH
R"
-N(=0)=C
[nitrone,aliphatic
attach;linear]
125

R's are undefined
0
II
r'"N^-R"
Aromatic Selenium
126


^Se
0
Representative Structure
>N< [+5 valence; single
bonds; H attach]
127

R's are undefined
R"
/ \
H R'"
Aromatic nitrogen [+5
valence; H attach]
128


R
HN'h
Representative Structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
-C#N [cyano attach]
129


N=C-C=N
-0C(=0)0-
[carbonate,aliphatic
attach]
130

R's are undefined
0
JL ^R"
0	0
1
R"
-0C(=0)0-
[carbonate,aromatic
attachs]
131


>—O
73 \	
o
\
>
73
0=C=0 [carbon dioxide,
experimental]
132


O
II
o
II
o
Halogen [mono- or dioxy-
type][one/struct]
133

R' is undefined
0
II
X
1
0
1
33
-C(=0)-S [thioester,
olefinic attach]
134

R' = not H;
R", R'", R"" are
undefined
rV
R'M R,,M
-N< [two or three olefinic
attach]
135

Rs =undefined
R""
f	
fN^R	
R"-%,
-0- [oxygen, two olefinic
attach]
136

Rs =undefined
R" O—"
[Pb] (Lead)
137
This entry appears no matter
how many R groups are
added.
Rs =undefined
R"	/
^Pb
[As] (Arsenic)
138
This entry appears no matter
how many R groups are
added.
Rs =undefined
R"'
As-R'
/
R"
[Ge] (Germanium)
139
This entry appears no matter
how many R groups are
added.
R's are undefined
R""
\ D'
		Ge
R \
R"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
Boron
140
This entry appears no matter
how many R groups are
added.
R's are undefined
R'
1
R" R"




\
OH
Representative structure
/




H°-SV/	
-OH { Metal or
miscellaneous attach)
141


)
Representative structure




H
/
R'—^Sn
Tin [Sn]
142
Sn can be II or IV valence
R', R", R'", R"" = not
0, X or AR
R'
\ nim
RM^-Sn*K
Q n \
R	
II
R,^Sn
K R„
Tin [Sn] { oxygen attach }
143
Sn can be II or IV valence
R' = not H;
R", R'", R"" = not OH
or X or AR
R""
Qn V •R"'
^Sn
9 R" 0 x
/ K 1 R"
R' R'
Tin [Sn] { oxygen and
aromatic attach }
144
Sn can be II or IV valence
R' = not H;
R", R"" are
undefined
AR
^-Sn V-R'"
9 nar o-SNn
X, 1 R"
R' R'
Tin [Sn] { halogen or -OH
attach }
145
Sn can be II or IV valence
R' = X, 0
R",R'",R"" are not X
if R' is X
R"
\ .D""
Cn 		Sn
R"^bn R \
R' R'"
Aluminum [Al]
146

R's are undefined
R"'
ai-r'
/
R"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
Gold [Au]=P { Phosphorus
attach }
147

R's are undefined
RS
II
r,,x-Au
Platinum [Pt] { halogen &
nitrogen attach}
148

R'= halogen or N(R)2;
R", R'", R"" are
undefined
R'n R""
/p<
R" R'"
-O-P [phosphine
phosphorus attach]
149

R's are undefined
^R'
R-O-P
1
R"
—C(—0)— [di-carbonyl
attach]
150

R's are undefined
o o
o
S02(-0H)-0 [sulfonic]
151


0
II
R-O-S-OH
II
0
Technetium [Tc](-S)(-S)(-
N)(-N)
152


R	
R. 0 /
N-Tc^
R" / g—R	
R'"—N s
\
R""
Krypton [Measured]
153


Kr
Argon [Measured]
154


Ar
Neon [Measured]
155


Ne
Xenon [Measured]
156


Xe
Radon [Measured]
157


Rn
Helium [Measured]
158


He
0=0 [oxygen;
experimental]
159


0=0
[H][H] { Hydrogen gas;
experimental}
160


H-H
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
0 [oxygen,no attach;
water, experimental]
161


h'°~h
N#N [Nitrogen gas,
experimental]
162


N=N
-S02- [additional
sulfone,aliphat attach]
163


O O
II II
R—S—R-S—R
II II
o o
N=0 [nitroso; N+5
valence; single bonds]
164

R's are undefined
0
II
R'—N—FT
1
R"
Mercury [Measured]
165


Hg
Aromatic n=0 [nitrogen
oxide,nitrogen att]
166


o
II
^l\L
N ^
o
Representative Structure
Tin [Sn] { divalent; carbon
attach }
167

R',R"=C
R"
R'—Sn
Tin [Sn] { divalent;
aromatic attach }
168


AR
AR-Sn

169




170



Ring aliphatic Carbon
171

Representative
structure =
Camphene (CAS No.
79-92-5)
Representative structure
Ring olefinic Carbon
172

Representative
structure = 2-Methyl-
1,4-Naphthoquinone
(CAS No. 58-27-5)
Oir
0
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
Ring aliphatic Oxygen
173

Representative
structure = 2,3-
epoxy-2-ethyl-l-
hexanol (CAS No. 78-
72-8)
HO
Representative structure
Ring aliphatic Nitrogen
174

Representative
structure =
Guanethidine (CAS
No. 55-65-2)
xo
Representative structure
Ring aliphatic Sulfur
175

Representative
structure =
Chlorprothixene (CAS
No. 113-59-7)
CI
-/
Representative structure
Ring Carbonyl
176

Representative
structure =
Anthrimide (CAS No.
82-22-4)
Representative structure
Aliphatic N-N hydrazine
type
178

Representative
structure = Isoniazid
(CAS No. 54-85-3)
9
o^n'NH2
Representative structure
Sodium [Na]
179


Na
Potassium [K]
180


K
Lithium [Li]
181


Li
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
Ring Silicon
182

Representative
structure =
Octamethylcyclotetr
asiloxane (CAS No.
556-67-2)
~y~*c
\ 4r
^|'-o \
Representative structure
Ring Phosphorus
183

Representative
structure = 2-
Phenoxy-1,3,2-
dioxaphospholane
(CAS No. 1077-05-0)
,JK-s o-p'OHQ
V-/ Cl
Representative structure
Class - Acetyl Halide
200

Representative
structure = Methyl
chloroformate (CAS
No. 79-22-1)
.0
ci-^
Representative structures
Class - Sulfur Halide
201

Representative
structure = 4-Chloro-
benzenesulfonyl
chloride (CAS No. 98-
60-2)
o
J,
Representative structure
Class - Linear Anhydride
202

Representative
structure = Acetic
anhydride (CAS No.
108-24-7)
Representative structure
Class - Cyclic Anhydride
203

Representative
structure = Phthalic
anhydride (CAS No.
85-44-9)
0
Representative structure
Class - Nitrogen-Nitrogen
204

Representative
structure =
Phenylbutazone (CAS
No. 50-33-9)
b
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2

-------
Fragment
Number
Modified Name
General Comments
Structure
Class - aromatic
Nitrogen-O-
205


CXj-°h
Representative structure
Class - Acrylamide
206

Representative
structure =
Acrylamide (CAS No.
76-06-1)
H2N^O
Representative structure
Class - Acrylate
207

Representative
structure = 7-
Dimethylamino-4-
methylcoumarin
(CAS No. 87-04-1)
o
Representative structure
Class - Acid-olefin
208

Representative
structure = 3,4,5-
Trimethoxycinnamic
acid (CAS No. 90-50-
6)
0
s°
Representative structure
Class - Aldehyde-olefin
209

Representative
structure =
Tribasenaldehyde
(CAS No. 84-83-3)
1
-
-------
Fragment
Number
Modified Name
General Comments
Structure
Class - Vinyl Ether
211

Representative
structure = Paracotin
(CAS No. 91-89-4)
Representative structure
Class - Vinyl
sulfone/sulfoxide
212

Representative
structure =
Benzo(B)thiophene-
S,S-dioxide (CAS No.
825-44-5)
*° ^
Representative structure
Class - Benzyl amine -
NH2
213

Representative
structure =
Benzylamine (CAS
No. 100-46-9)
NH,
cy
Representative structure
Class - Benzyl alcohol
214

Representative
structure = Pyridoxal
(CAS No. 66-72-8)
h°. JL
0H
^0
Representative structure
Class - Benzyl ether type
215

Representative
structure = Benzyl
methyl ether (CAS
No. 538-86-3)
o"
o"
Representative structure
Class - Benzyl amine -NH-
, >N-
216

Representative
structure =
Phenoxybenzamine
(CAS No. 59-96-1)
Representative structure

217




218



R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Group la
219

Structures containing
the following
elements: Li, Na, K,
Rb, Cs, and Fr.
Representative
structure = Sodium
salicylate (CAS No.
54-21-7)
^0
Na
Representative structure
Group lla
220

Structures containing
the following
elements: Be, Mg,
Ca, Sr, Ba, and Ra.
Representative
structure = Calcium
oxalate (CAS No.
563-72-4)
nf
Cax0^°
Representative structure
Group 1Mb
221

Structures containing
the following
elements: Sc, Y.
Representative
structure = Scandium
trichloride (CAS No.
10361-84-9)
ScCI3
Representative structure
GroupIVb
222

Structures containing
the following
elements: Ti, Zr, Hf,
Rf.
Representative
structure = Titanium
isopropylate (CAS
No. 546-68-9)
VoY
/ \ yO
/Ti /
A \
Representative structure
Group Vb
223

Structures containing
the following
elements: V, Nb, Ta,
Db.
Representative
structure =
Vanadocene
dichloride (CAS No.
12083-48-6)
<>P
<5
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Group Vlb
224
Structures containing
the following
elements: Cr, Mo, W,
and Sg.
Representative
structure = Chromic
acetate (CAS No.
1066-30-4)

Xr
o x0
o
o
Representative structure
Group VIlb
225
Structures containing
the following
elements: Mn, Tc,
Re, and Bh.
Representative
structure =
Manganese
carbonate (CAS No.
598-62-9)
Mn—O
A- s
No
Representative structure
Group VIII
226
Structures containing
the following
elements: Fe, Ru, Os,
Hs.
Representative
structure =
Ferrocene (CAS No.
102-54-5)
/Z
Fe
Representative structure
Group lb
227
Structures containing
the following
elements: Cu, Ag, Au,
and Rg.
Representative
structure = Cupric
acetate (CAS No.
142-71-2)
O
/Cu
cr o o
Representative structure
Group lib
228
Structures containing
the following
elements: Zn, Cd, Hg,
and Cn.
Representative
structure =
(Methoxyethyl)merc
uric acetate (CAS No.
151-38-2)
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Group Ilia
229

Structures containing
the following
elements: B, Al, Ga,
In, Tl.
Representative
structure =
Aluminum ethoxide
(CAS No. 555-75-9).
1
/Al
Representative structure
GroupIVa
230

Structures containing
the following
elements: Ge, Sn, Pb,
Fl.
Representative
structure =
Trimethyltin
hydroxide (CAS No.
56-24-6)
/ ^
HO
Representative structure
Group Va
231

Structures containing
the following
elements: Sb and Bi
(does not include As,
P, N).
Representative
structure = Stibacetin
(CAS No. 138-31-8)
0
0^ //
Sb
UkA
Representative structure
Group Lanthanides
232

Structures containing
the following
elements: La, Ce, Pr,
Nd, Pm, Sm, Eu, Gd,
Tb, Dy, Ho, Er, Tm,
Yb, Lu.
Representative
structure = Acetic
acid, lanthanum(3)
salt (CAS No. 917-70-
4)
cr 0 0
M
Representative structure
Group Actinides
233

Structures containing
the following
elements: Ac, Th, Pa,
U, Np, Pu, Am, Cm,
Bk, Cf, Es, Fm, Md,
No, Lr.
Representative
structure = Uranyl
°V° I
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure



acetate (CAS No.
541-09-3)




Structures containing
the following
elements: He, Ne, Ar,
Ar, Kr,Xe, Rn.
XeF6
Group Noble Gases
234

Representative
structure = Xenon
fluoride (CAS No.
13693-09-9)
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
N02-N [nitro, nitrogen attach]
OE
Nitro amine
R' is undefined
no9
1 2
%¦
-0N02 [aromatic attach]
IE
Aryl nitrate

NO,
1 2
AR
-S(=0)- [two aromatic attach]
2E
Diaryl sulfoxide

0
II
AR^S^AR
-OH [hydroxy, sulfur (no oxide)
attach]
3E


R'v. JDH
S
-0C(=0)0- [carbonate,cyclic]
4E
Cyclic carbonate
Example: 1,3-
Dioxolan-2-one
(CAS No. 96-49-1)
0
A
VJ
Representative structure
-S(=0)-N- [aromatic attach]
5E
Aryl sulfinamide

0
II
AR/S^N
-S(=0)-0H
6E
Sulfinic acid
R' = C, N, S
0
II
R'/S^OH
-C(=0)-S [thioester, aromatic
attach]
7E
Aryl thioester
R' cannot be H
0
/R'
ARY S
-0-C(=S)-N- [thiocarbamate]
8E
Thiocarbamate
R's are undefined
S
r,\ /r"
0 N
-0-C(=S)-0- [thiocarbonate]
9E
Thiocarbonate
R', R" = C, H, X, N, S
S
R'\ A R"
o o
-S-C(=0)-S [dithioester]
10E
Diothioester
R', R" = Aryl C, Alkyl
C, N, S
h:
\
CO
CO
/
a:
-0-S02-0- [sulfate, cyclic]
HE
Cyclic sulfate

0
o	II
^-s—0
o
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-S0-0 [sulfonate, aromat att]
12E
Aryl sulfonate

AR"*0*
-S0-0 [sulfonate, aliph att]
13E
Alkyl sulfonate

^S02
>P< [phosphonium +5 type]
14 E


-V
/ Br
Representative structure
-S-C(=0)-S [dithioester, cyclic]
15E
Cyclic dithioester
Example:
Oxythioquinox (CAS
No. 2439-01-2)
XXJ-Y
Representative structure
-N=C=0 [isocyanate, aliphatic
attach]
16E
Alkyl isocyanate

0
1
1
-O-SO-O- [sulfite, linear]
17E

R', R" = Aliphatic C,
aromatic C, cannot
be H
0
II
R-o-S-o-R"
-N=C=0 [isocyanate, aromatic
attach]
18 E
Aryl isocyanate

o
J2
<
-O-SO-O- [sulfite, cyclic]
19 E
Cyclic sulfite

o
II
c/%
w
Representative structure
-N-SO-N- [sulfamide]
20 E
Sulfamide
R', R" = H, aliphatic
C, aromatic C
0
II
R'\ ^R"
N N
-S(=0)-N- [aliphatic attach]
21E
Alkyl sulfonamide
R' = H, aliphatic C,
aromatic C
0
II
^R'
R N
P-O-P [oxygen, two phosphorus
attach]
22E

R', R" = H, aliphatic
C, aromatic C
R'\p/0\p/R"
-0- [oxygen, two silicon attach,
linear]
23E
Siloxane
R', R" = H, aliphatic
C, aromatic C
R\ — ^R
Si Si
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-0- [oxygen, two silicon attach,
cyclic]
24 E
Cyclosiloxane
Example:
Tetracyclotetramet
hylenecyclotetrasilo
xane (CAS No. 177-
49-1)
o
Ssi-o, r\
o Sk y
/\i i\/
\n °
\	/ o-s\—^
Representative structure
-C(=0)- [aromatic nitrogen,carbon
attach]
25E


Representative structure
-OH [oxygen attach]
26E
Hydroperoxide
R' is undefined
R'\ .OH
0
-0- [oxygen attach]
27E
Peroxide
R's are undefined
73
/"
o
\
o
^R"
-C(=0)-SH [aromatic attach]
28 E


0
x
AR^^SH
-C(=S)- [olefinic attach]
29E
Vinyl thione
R' is undefined
S
-C(=S)- [aromatic attach]
30E
Aryl thione
R' is undefined
S
B
R'^^AR
-C(=S)- [aliphatic attach]
31E
Alkyl thione
R' is undefined
J
K
-C(=S)-C(=0)
32E

R's are undefined
J
0
/R"
-C(=S)-0 [aromatic attach]
33E
Aryl thionoester
R' is undefined
X
q:
<
\
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-C(=S)-0 [aliphatic attach]
34 E
Alkyl thionoester
R' is undefined
R 0
-C(=S)-0 [cyclic]
35E
Cyclic thionoester
Example: G-
Thiobutyrolactone
(CAS No. 39700-44-
2)
S
6
Representative structure
N-C(=S)-S [linear]
36E
Dithiocarbamate

S
JK /R
N S
-C(=S)-S [thioester, aromatic
attach]
37E


S
x
AR^^S
-C(=S)-S [thioester, aliphatic
attach]
38 E


S
A

39 E



Aromatic n=S [nitrogen sulfide]
40 E


s
II
O
Representative structure
{-0- or -S-} to nitrogen (+5
valence)]
41E


\ /O \ /S
—N —N
/\ /\
C#N-Se [cyano, selenium attach]
42 E
Cyano selenide
R' is undefined
R\
Se
-S-C(=0)-0-
43 E

R's are undefined
0
RS^o'R"
-Se- [aliphatic attach]
44 E
Alkyl selenide

Se
-Se- [phosphorus attach]
45 E
Phosphorus selenide
R' is undefined
R'\ ,P
Se
-Se- [nitrogen attach]
46E
Nitrogen selenide
R' is undefined
R'\ .N
Se
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure




o
II
-S-S(=0) [sulfur, S(=0) attach]
47 E
Thiosulfinic acid
R' is undefined
R S
-SeH [aliphatic attach]
48 E
Alkyl hydrogen selenide

.R
SeH
-SeH [aromatic attach]
49 E
Aryl hydrogen selenide

^AR
SeH




0
II
-C(=0)-SeH
50 E


11
R'^^SeH




R"
1
-C(=0)=Se-
51E

R', R" are
undefined
^Se
sC,' R'




0
A
1
CHO-S-
52E

R' is undefined
R'
CHO-Se-
53E

R' is undefined
Se may have 1 or 3
attachments
Ae
i
R'




^ J
-------
Fragment
Number
Modified Name
General Comments
Structure
-O-SO-N- [sulfoxide,N and 0
attach]
58 E

R' cannot be H;
R" can be H
0
II
R,\
O N




0
II





-CO-CO [olefinic attach]
59 E

R' is undefined
T
0




s
II
S=CH [thioaldehyde type]
60 E
Thioaldehyde
R' can be H

-N=S [aliphatic attach]
61E


s*%




R'\ R"
R XR...
-S [sulfur +4 or +6
valence;miscellaneous]
62 E

R's are undefined
R. R"
Nq/-R"'
niiini-o'O
K / \
/ dmm
	 W




s
||
-C(=S)N- [both aromatic attach]
63 E


AR^A.N/AR
Gold [Au]
64 E


Au
Bismuth [Bi]
65 E


Bi
Calcium [Ca]
66E


Ca
Magnesium [Mg]
67E


Mg
Antimony [Sb]
68 E


Sb
Zinc [Zn]
69 E


Zn
Gold [Au] { halogen attach }
70E

R' = Halogen;
R" can be H
R'—Au
\
R"
Platinum [Pt] { halogen attach }
71E

R' = Halogen
/R'
pr
Platinum [Pt]
72 E


pt
Iron [Fe]
74E


Fe
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Cadmium [Cd]
75 E


Cd
Cadmium [Cd] { halogen attach }
76E

R' = Halogen
Cd-R'
Miscellaneous Metal [Ni,Cu,Zr,Be]
77E

Representative
structure = Bis(8-
quinolinolato-
(Nl,08))copper
(CAS No. 10380-28-
6)
Q~°c* Q
\Z/
Representative structure
Oxygen [aromatic; not +2 valence;
misc.]
78 E


6
Representative structure




1
Oxygen [aliphatic; not +2 valence;
misc]
79 E


Representative structure
-S- [di-,poly- sulfur attach]
80E

R', R" can be H
R'^PS>v"S/S^]n-R"
Tin [Sn] { multi-halogen or -0N02 }
83E

R', R" = Halogen
only;
R'", R"" = May be
halogen
0" Sn(N) 0"
Sn^Ao W
R'\ R"
R'\c .R" /Sn
Sn R" V"
[P] Phosphorus {four single bonds}
84E

R's cannot be H
R'
R„„—p—R"
R,"
Miscellaneous sulfide (=S) or oxide
(—0)
85E

Representative
structure =
Oxorhenium-23
0^—
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-N02 [-N02 attach]
86E


0
ii
CU
N ^0
II
0
Tin [Sn] { nitrogen attach }
87E

Sn can be II or IV
valence;
R', R" can be H
/R'
Sn—n'
\
R"
[Zn]-S {zinc-sulfur}
88 E

R' is undefined;
Zn substitution
undefined
Zn—S—R'
Oxygen [ #0 ]
89 E

R' is undefined
R'=0
[Sn]-0-[Sn] { bis-tin ether}
90E

Sn can be II or IV
valence
Sn Sn
-C#N [Phosporus attach]
91E


P—C=N
=N< [nitrogen +5 valence;hydrogen
attach]
92E


R'
II
R"—N—H
1
R,"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ortho reaction -> hydroxy/acid
correc
OC


HO^O
u
Representative structure
Multi-aliphatic carboxylic acids
1C

Example: Folic acid (CAS
No. 59-30-3)
HO
HO Q=\
P
N
^=N
N
Representative structure
-CO-N-CO-N-CO- structure
correction
2C

R', R" can be H
0 0 0
AAA
-N-CO-N-CO- structure
correction
3C

R', R" can be H
R'\ ^
N
0 0
AA,
HO-C-COOH (alcohol-acid
carbon)
4C
Lactic acid-type correction
R' is undefined
HO^J
R'
A
Cyclic ester correction
5C


O
6
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Amino acid (alpha-position)
correction
6C
Alpha-amino acid

R'
°h
h2n Y
o
Alcohol - amino acid correction
7C


nh2
°^^R'
OH OH
Nitroso (urea/carbamate type)
correction
8C

R's can be H
0
R'\ /R"'
N N
1 1
R" N.
0
rOL^r-
0 N
1
^0
C-O-C-O-C structure correction
9C

R's are undefined

C-CO-C-CO-C structure
correction
IOC

R's are undefined
-JUL-
N-aromatic -CO-N-CO-
structure correction
11C

R', R" cannot be H
0 0
,anx,
1
AR
Di-N urea/acetamide aromatic
correction
12C

R's are undefined
O N
R'\ /R"
N N N
1
AR
Ring reaction -> -N02 with -
OH/amino/azo
13C

R' = -OH, -NH2, -N=N- at
ortho, meta, or para
positions
NO,
6"
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure




OH
1




R^R



Must be an aliphatic



carbon. Cannot be
OH
Multi-alcohol correction
14C

aromatic.
Representative structure




R'
1
1,2,3-Triazole correction
15C

R' can be H
O
^—N




R'
1
N-substitution on 123-triazole



u N
(at 1-pos)
16C

R' cannot be H
\\ fl
^—N
-NH-NH- structure correction
17C

R', R" can be H
R'\ /R"
N—N
H H
Amino urea correction
18C

R' can be H
0
R'\ JK /NH2
N N




R'





-CO-N-CO- 5-member ring [not
pyrroledione]



A J
19C

R's are undefined
/
R"




R'\ /R"
N N
-N=N-N- structure correction
20C
Amino diazene correction
R', R", R'" can be H
R,"




R,"


Hydrazine - type
R' cannot be H;
1
R'\
N R""
>N-N<- structure correction
21C
correction
R", R'", R"" can be H
1
R"




R' O
1 II
Ring reaction -> ortho to




aromatic acid
22C
O-substituted benzoic acid
R' is undefined
u
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring reaction->ortho to O-
phenyl carbamate
23C
R' can be H;
R"= Undefined
R"
NR'
di-N-aliphatic substitution
[carbamate]
A.
24C
N-dialkyl carbamate
R' cannot be H
O N
I
R
sym-Triazine ring correction
25C
R'
A.
R's are undefined
N
A A
R" N R"
Amino
triazine/pyrazine/pyrimidine
26C
NH,
1
N^-N
X,
R N R"
Amino triazine
RV
R N R'"
Amino pyrazine
NH,
1
N^N
R y R'"
R"
R,"
R,"
.X.
R	R"
N"	NH,
R y NH^
R"
R's are undefined
Amino pyrimidine
Ortho-substituted N-phenyl
CO-N-CO correc.
27C
O O
XJL
R N R'
R', R" can be H;
R'" can be X
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ortho-substituted aromatic at
ncn location
28C

R' = C, X;
R" = C or N
R'
rN-
rJ
\l
F
>'

Cyclic ester [olefinic type]
correction
29C

Representative
structure = Coumarin
(CAS No. 91-64-5)
Rf
spresentative structure
Di-ketone [CO-C-CO..olefinic C]
correction
30C

R's are undefined
O 0
"V
R
^R"
N=N-N-CO-aromatic structure
correction
31C

Example: 3-
Methylbenzotriazin-4-
one (CAS No. 22305-44-
8)
c&
Representative structure
Ortho-Amino pyridine
correction
32C


5
5
/NH2
Ortho-Alkyloxy(thio) to 1
aromat nitrogen
33C

R' cannot be H
/R' q/r'
6 6
Representative structures
o-Alkyloxy to 2 aromat
nitrogens/pyrazine
34C

R' cannot be H
/R' /R'
?
u U
Representative structures
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Di Aromatic-S02-N correction
42C
Representative
structure = 3-
Methylhydrochlorothiaz
ide (CAS No. 890-67-5)
Representative structure
SO-C(polyhalo) structure
correction
43C
R', R" = Must be X;
R'" can be X
x
ii
o
Mono-halo acetamide [-N-CO-
C-halo]
44C
O
R', R" can be H;
R'" = X
R'v
N
I
R"
Poly-halo acetamide [-N-CO-C-
polyhalo]
45C
R', R" can be H;
R'" = X (at least 2)
R'>
u
y
VN^^CR'",
I
R"
-N-C-(C-OH)-C-OH structure
correction
46C
R', R", R'" can be H
-CH=N-OH [oxime,aliphatic
attach] corr.
47C
Alkyl oxime correction
R N
C=C-(C#N)-C#N [dicyano]
48 C
R' is undefined
Aromatic-C[-C or -H]-COOH
correction
49 C
ARY
OH
OH
Ring reaction -> 1,2,3-
trihydroxy
50C
OH
OH
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Aromatic n-oxide rx with
N02/C#N/amino
51C

R' = Nitro, cyano, amino;
in ortho, meta, or para
position
0
rS
V
R'
Representative structure
Ortho-subst on di-aromatic
ether (non-cyl)
52C


6""
Di-N-sub(alph carbon)
aromatic carboxamide
53C


qV
Halo-sulfo [SO-halo] correction
54C


0
II
R CI
Pyridine ester [2-position]
correction
55C

R' is undefined
o
\
33
Arom nitrogens-> Amino
(fused ring) correc
56C

Representative
structure = 2,4,7-
Triamino-6-Phenyl-p-
teridine (CAS No. 396-
01-0)
»yyy
Qm
Representative structure
C-S-C-S-C structure correction
57C

R', R" are undefined

Amidino urea (-N-C(=N)-N-CO-
N-) correction
58C
Amidino urea correction
R', R", R'", R"" can be H
N 0
^ A X
N N N
1 1
R" R""
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
N=C< di-aromatic (or cyclic)
correction
59C

Representative
structure = Oxazepam
(CAS No. 604-75-1)
cr
Representative structure
Ortho-substitutes on N=C<
attached aromats
60C

R' = Aliphatic, Halogen;
Structure must contain
7-membered ring with
C=N and fused aromatic
ring, in addition to
ortho-substituted
aromatic.
Representative structure
-N-C-O- structure correction
61C

R' cannot be H;
R" is undefined
N 0^
R R"
H0-CH-C(-0-)-CH-0H structure
correction
62C

More than likely cyclic
OH
/J
'^^OH
Representative structure
HO-CH-C(-OH)-CH-OH
structure correction
63C

R', R" can be H;
Structure may be cyclic
HO
HO )—R'
H
R' OH
-0-C(-0H)-C-N- structure
correction
64C

R' cannot be H;
R" can be H
O
R'\0^/NR"2
-0-C(-N-)-C-0H structure
correction
65C

R' cannot be H;
R" can be H
NR"2
R'\0^^0H
-0-C(-0H)-C-0H structure
correction
66C

R' cannot be H
OH
R'\0^/0H
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Pyrrole-2,5-dione ring
correction
67C

R' is undefined
R"
R" R'"
-N-C(-amino)=N- aliphatic ring
correction
68C

R' can be H
NR'
1
N^N
u
Representative structure
Carboxamide ortho to
aromatic nitrogen
69C

R' can be H
o^nr-2
0
Representative structure
Pyrazine/Pyrimidine (2-posit)/
carboxamide
70C

R' can be H
qKt,
N
Carboxamide pyrazine
O
^N^^nr'2
2-carboxamide pyrimidine
-CO-N-C(-amino)=N aliphatic
ring correc.
71C

R', R" can be H
X,
Representative structure
Ring reaction (pyridine) -> -NH-
C(=0)-
72C

Can be ortho, meta,
para substitution;
R' cannot be H
CxV
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
C-(C#N)-C(=0)N structure
correction
73C

R', R" can be H
N
II
NR"2
-Biguanide (aliphatic attach)
correction
74C
Alkyl biguanide
R', R" can be H
N N
X 1
NR'^~ N' NR"„
1
R
-Biguanide (aromatic attach)
correction
75C
Aryl biguanide
R', R" can be H
N N
X X
NR'f^N NR",
1
AR
Furan -> carbonyl (at 2-
position) correct.
76C

R' can be H
(jr1*
C-(C(=0)-)-C(=0)N structure
correction
11C

R', R" can be H

Ring reaction -> 1,2,3-
trialkyloxy
ISC


OR
be
Thiazole -> 2-sulfonamide
correction
79C



Imidazole type -> 2-amino type
correction
80C

R' can be H
/n\^nri
\\ //
x	N
Oxazole type -> 2-amino type
correction
81C

R' can be H
\\ Tr
N	N
Fused aliphatic ring unit
correction
82C


Oo
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
H0-C-C(=0)-C-0H structure



O
II
correction
83C


H°^^OH
H0-C-C(=0)-C-0- structure



0
II
correction
84C

R' cannot be H





°T^Cl



Representative




structure =




Clobetasone-17-

Internal aliphatic fused-ring


propionate-des-cl (CAS
ketone cor.
85C

No. 4351-59-1)
Representative structure
-C-C(=0)-C-0H structure



0
correction
86C

R' can be H
R'^^0H
substituted carbon on [-SO-N-
C-N-] corr.
87C

R', R"" can be H;
R", R'" is undefined
1 ' f
R' R"' 1
R R""




0
II
-C(=0)-C=C-C(=0)- [aliphatic



°Y^R"
R'
attachs] cor.
88C

R's are undefined
Pyridine ring (non-fused)




correction
89C








Benzene to -C-C-N- correction
90C

R' can be H
U



Representative
structure = 2-
N\



Pyridinemethaneamine
Mx J
N	'



(CAS No. 3731-51-9);



Methyl or ethylamine
Representative structure
Methyl/ethylamine to


attached to an aromatic

aromatic (Nar ring)
91C

ring containing nitrogen.

R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-CO-C(-OH)-N=C structure
correction
92C

R', R", R'" can be H
OH R'"
R'
Non-fused n=0 aromatic ring
correction
93C


0
II
o
Representative structure
-CH2- (aliphatic), 2 phenyl
attach correc
94C

Substitution on the
phenyls

>C< (aliphatic), 2 phenyl attach
correc
95C
Diphenyl alkane correction
R', R" can be H; no
aromatic attach
R'
Oxazole ring (non-fused)
correction
96C

R', R", R'" is undefined
jr
R"
1,3,4-Oxadiazole ring
correction
97C

R's are undefined
R,xVR"
N—N
Ring reaction -> -OH ortho to
ester
98C

R' cannot be H
OH O
Ring reaction -> -N< / -OH
(non-ortho)
99C

R' can be H
NR' NR'
OH
Ring reaction -> -N< / ester
(non-ortho)
100C

R' can be H;
R" cannot be H
NR' NR'
6cV
O R"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring react -> -OH(mono)/ester
(non-ortho)
101C

R' cannot be H
OH 9H
civ 9
o R'\ As-
R ° °
Ring reaction-> -NH2 ortho to
acid (COOH)
102C


NH, 0
(V-
-SO-N=C-N- [thiadiazine type]
correction
103C
Thiadiazine-type
correction
R', R" can be H
/N^./NR"2
R
substituted carbon on [-SO-
N=C-N-] corr.
104C

R', R" can be H;
R'" cannot be H
0^s-nYNR"2
R' FT
Guanidine [N-C(=N-)-N](2-
arom,cyclic type)
105C

Does not have to 6-
membered ring.
.NL .N.
S AR
Representative structure
Ring reaction -> N02/-NC(=0)
[cyclic]
106C


no2
Representative structure
Ring reaction -> N02/-NC(=0)
[non-cyclic]
107C

R' cannot be H
no2 no2
&r (ii,
A
R1 R
^NHy^N°2
Ring reaction -> ortho to -
NHC(=0) type
108C

R', R" cannot be H
6rV
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring reaction -> NS02- with an
ester
109C


o
Representative structure
Ring reaction -> -NH2 ortho to
-N02(mono)
HOC


no2
cr
Ring reaction -> 1,2-dialkyloxy
111C


o-R
dr-
Ring reaction -> di-ortho to -
NHC(=0)
112C

R', R", R'" cannot be H

Ring reaction -> ortho to -
C(=0)NH-
113C


cV-
Representative structure
Ring reaction -> di-ortho to -
C(=0)NH-
114C


R' 0
cbc^NHz
Representative structure
Ring reaction -> alkyloxy ortho
to -OH
115C

Substitution can be
ortho, meta, or para
0'R
6-"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring Rx (1+ aromatic n) ->
>N(C(=0)-)-
116C

R', R", R'" cannot be H
R" R'"
i i+
°YnyS
R'
Extended aromatic nitrogen at
ncn position
117C

Can be 5- or 6- member
aromatics
[0JN^
Representative structure
Ring Rx (2+ aromatic n) -> -
NHC(=0)-
118C

R' cannot be H;
2-N's can be positioned
anywhere on the ring.
/=H
N. />	N
R'
Representative structure
Ring Reaction -> di-S02-N / -
N02
119C

R', R" can be H
no2
%Xas*°
NR'/ 0 ^NR"
2 o 0 2
-0-C(-C-H0)-C-0- structure
correction
120C


.OH
? 1
R O-R
-N-CO-N-S at aromatic ncn
carbon
121C

R' is undefined
r^N 0
N N N
1
Representative structure
-0-C(F)F or -S-C(F)F correction
122C

R' is undefined
R R
F F
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
>N-C(-S-)-C-{0,N,CO}
correction
123C

R', R", R'" can be H
R"-s
R11
X.. NRIII2
NR'f —
C-C(=0)N-C-C00H structure
correction
124C

R' can be H
O
r,\An^Yoh
o
C-C(=0)N-C(-C00H)-C-S-
correction
125C

R' can be H;
R" cannot be H
R"
O
Aryloxy (or -C-0)-C-C(=0)NH-
correction
126C

R' can be H
o
/R'
R — N
H
O
^°vA /r'
ARY — N
H
1,3,4-Thiadiazole ring (non-
fused)
127C
1,3,4-Thiadiazole

N —N
Ring Reaction: amino-type
thiadiazole
128C

R' can be H
cVNR,j
N —N
tertiary-N-hydroxy urea
correction
129C

R' can be OH
0
JK /oh
N N
1
R'
Ring Reaction: amino-type
thiazole
130C

R' can be H
/S\	NR'2
'	N
N-CO-C-N< [Cor H attach]
correction
131C

R', R" can be C or H
0 R'
M
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-C(-N-N=0 [cyclic]) -C-N-
correction
132C


HN ' "1
k/N-N*°
Representative structure
N-Nitroso [linear] -C-C- { 0,S,
or CO} cor
133C

R' can be H
0
II
R N
0
II
R N
0 0
N-Nitroso [cyclic] -C-C- { 0,S, or
CO}cor
134C


M^°
N N N
Q 6 6
o
Representative structures
-C(-N-N=0 [cyclic]) -C-N-N=0
correction
135C


Representative structure
-C(-C-OH)(-C-OH)-C-OH
structure correct.
136C

R' can be H
OH
R'	
OH
/
OH
-CO-NH-C-CO-O-aromatic
structure correc.
137C

R' can be H
O
R'^N^^ARY
O
1,2,3-Triazole /-COOH
(aliphatic) react.
138C

Aliphatic chain can be
greater than 1 carbon.
Ah
1
N >
\J/
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Aromatic nitrogen-C-CO-N<
structure corr.
139C


Cry
NR'/
Representative structure
Ring reaction -> -COOH & -OH
ortho to -OH
140C


OH O
-CH=N-OH [oxime,aromatic
attach] corre.
141C
Aryl oxime correction

H
/C. /OH
ARY N
>C=N-OH [ketoxime]
correction
142C
Ketoxime correction
R', R" cannot be H
.OH
N
,Ar.
Ring rx -> -OH ortho to
aromatic nitrogen
143C


OH
6
>C=NH [ketimine, aromatic
attach] correc
144C
Aryl ketimine
R' = Aromatic or alkyl C;
cannot be H
N
X
ARY R'
>C=N-0-C0- structure
correction
145C

R', R" can be H;
R'" cannot be H
O
O
25
-CH=N-0-C0- structure
correction
146C

R' cannot be H;
R" can be H
R'
R"
Ring reaction -> ortho amino /
ketone
147C

R' can be H;
R" = Aromatic or
aliphatic attachment
NR' R"
Ring reaction -> ortho -NC(=0)
/ ketone
148C

R' cannot be H;
R" = Aromatic or
aliphatic attachment
0
x
R'^^N O
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure




NR' NR"9
11
Ring reaction -> ortho amino-
type/-C(=0)N
149C

R', R" can be H
cr-
-N-CH-C#N
[aminomethylcyano]
correction
150C
Aminomethylcyano
correction
R', R" can be H
R"
\
HC—==N
NR'/
-N-C-C(=0)-carbon structure
correction
151C

R' can be H;
R", R'" cannot be H
R'-n^°
R" R'"
Ring reaction -> 2-thiazole-
type / -N=C-N
152C

R' can be H
\ rT ^NR'2
*	N




0 R'
II 1
r^V'^R"
Ring reaction -> amino-type
ortho to n=0
154C

R', R" can be H
Representative structure
Sulfur halide structure
correction
155C

R' = Halogen;
R" is undefined
R R"
=NNC(=S)N-
[thiosemicarbazone] correct.
156C
Thiosemicarbazone
correction
R', R" can be H
R NR' R"2




)=0
—o
-o




(Xk or
Ring reaction -> -O-CO / -O-CO
157C


,0 R'
R"^( _/=\_
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Fused ring reaction: c-c(-N<)-
c[fused]-n
158C

Representative
structure = 8-
Aminoquinoline (CAS
No. 578-66-5)
nh2
Representative structure
aromatic-CH(-CO-N)-{-N
159C

R' = -N, -0H,-C=0;
R" can be H
R'
ARY^^j^0
NR"2
-N-C(=S)-N-C(=0)- structure
correction
160C

R', R" can be H

aromatic-CO-N-CO-aromatic
[linear] correc
161C

R' can be H
0 0
X X
ARY^^N^^ARY
1
R'
-N-CO-CO-N- structure
correction
162C

R', R" can be H
0
N=N-N-CO-aliphatic structure
correction
163C

R', R" can be H
X
i
r,\ ^
N
HOOC-C-(C-COOH)(C-OH)
structure correction
164C


.OH
OH
Ring reaction -> amino-type
ortho to Azo
165C

R', R" can be H
NR'2
CT-*
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
>C=N-C [cyclic-type imine, ali
carbon att]
174C


G-\
Representative structure
Ortho rx: (-N02/-N-) on
diarylamine(o-Nar)
175C


no2
6*0
=N-NH-P structure correction
176C

R's are undefined
R'
1
HN'P"R"
R,mx^n
R""
=N-N(-aliphatic)-P structure
correction
177C

R's are undefined
R'
1
N R"
R"'^N
R""
=N-N(-aromatic)-P structure
correction
178C

P may have 3 or 5
substituents
R'
1
AR^ ^
N R"
1
oN
R
Ring reaction -> di-ortho to
aromatic acid
179C


R' 0
kAR-
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-O-C-CO-C-O- structure
correction
180C

R', R" and other
substitution undefined
o
R-° 6
\
R"
-C-CO-C-O- structure
correction
181C

R', R" and other
substitution undefined
o
R\Ji
o
\
R"
SO-C(halo) structure correction
182C

R' undefined;
R" and R'" not X or
other halogen
0
II R"
X
Ring rx -> -NH & -NH
(phenyl, non-ortho)
183C


^R'
HN
dx
1
R"
Representative structure
-C(=0)-S-aromatic correction
184C

R' is undefined
0
,AS
I
AR
aromatic-C-N-aromatic
correction
185C

R' and R" are undefined
R'
VR"
ar^nh
/
AR
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring rx -> 2-thiazole-type / -
CH=N-OH
186C


s hO
r\ /)~o
(/ //	N
N
Representative structure
Reaction: nitrogen[+5] / polar
group
187C

Representative
structures =
Isopropoxyethyl
trimethyl ammonium
iodide (CAS No. 21949-
06-4) and 2-
[(Hydroxyimino)methyl]
-1-methyl-pyridinium
(CAS No. 154-97-2)
r '-^°Y
1 N \
/ \
>° o
ri*\ /
\ / /=N
0^ / /
o
Representative structures
aliph-C=N-0-carbon(aliphat)
[iminoxy] cor.
188C

Rs are undefined
R'"
R"---~/
p-R""
N-°
Ring reaction -> n=0 /
aromatic nitrogen
189C


0 0 0
II II II
.l\L .ISL
f ^1 f f ^1
k- J
H0-C-C(-0H)-C(=0)- structure
correction
190C

Rs are undefined
0
HO II
hovV"r'
R-^\ R""
R'"
-0-C-C(-0-)-C(=0)- structure
correction
191C

Rs are undefined
D"i
R"
0 \ J^R""
R. 0^R R
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure





-0-C-C(-N-)-0- structure
correction
192C

R', R", R'" and other
substitution undefined
^R'
R" R"
R'°
-C(=S)-N-C(-amino)=N aliphatic
ring correc
193C


(*!"
N NH2
Representative structure
C=NN-CO-N- [semicarbazone]
correction
194C

R's are undefined
0
R'\^Nk ^R""
y? n n
R" R'" R	
-C-S-C-CO-N- structure
correction
195C

R', R", R'" and other
substitution undefined
R" 1 \
R'" R	
-C0-0-C-{-0-,-N-} [on cyclic
ester] correc
196C


0
6
Representative structure
C(=0)-0-{Na,K,Li}
[coef*(l+0.5*(NUM-l))]
197C

R' = Na, K, Li
O
X -R'
R O
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
S-0-{Na,K,Li}
[coef*(l+0.3*(NUM-l))]
198C

R' = Na, K, Li
R" is undefined
a:
1
0
1
CO
J
a:
Aromatic n-oxide rx with misc -
N
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring rx: -SO-C with 2+ aromatic
nitrogens
204C


a,
1
Representative structure
HOOC-C-N-C-COOH structure
correction
205C


0^
DH
s
0
^OH
>C=NH [cyclic ketimine, aliphat
attachs]
206C


NH
6
Representative structure
Ortho rx: (to -N-) on
diarylamine(o-Nar)
207C

R' cannot be H.
(
R'

Ring -N- to quat carbon-type
correction
208C

R', R", R'" cannot be H
O*
Representative structure
Quaternary carbon(cyclic,2
halogen attach)
209C

R', R" = Halogen
R'
6
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Urea (N & N'-disubstituted;
diaryl) correc
210C

R's are undefined
0
\\ ^AR
ar.n^n
\ p»
R, K
1,2,5-Oxadiazole ring
correction
211C


N
1,2,5-Oxadiazole n-oxide ring
correction
212C


'N==l
N
II
0
Aliph carbon subst. on 1,2,5-
oxadiazole
213C

R' is undefined
<^R
M-^r.
Amino-type subst on 1,2,5-
oxadiazole ring
214C

R' is undefined
R
/wS*
° X
M-^r.
Carbonyl subst. on 1,2,5-
oxadiazole ring
215C

R' is undefined
0
0
-S(=0) subst. on 1,2,5-
oxadiazole ring
216C

R' = -S(=0)-Armoatic or
-S02-C-
<°>
H
R'
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-C(=0)-0-C-C(=0)-N- correction
217C

Rs are undefined
0
X
R"^ sO R"
V-
0
-CO-N-C-CO-N-(linear
C;aliphatic) corr.
218C

Rs are undefined
0
x
R"' ^NH R"
V-
0
C=C(-N-)-N- correction
219C

Rs are undefined
K -R"
~	_ / N
K N \
\ R,M
R""
C=C(-N-)-C(=0)- correction
220C

R', R" can be H;
Must be 5- or 6-
membered cyclic
0 R'
tV*
Representative structure
cyclic C(CO-Car)(CO-Car)-Car
correction
221C


rvL
)	ARY
0
-N-C-C(=0)-C-N-[olefinic
carbons] corr.
222C

Rs are undefined
R'"
0 \
R'\
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Pyrimidin-4-one type ring
[arom att;N-sub]
223C

R' cannot be H;
Fused aromatic can be
5- or 6-membered.
0
Represents
0
ative structure
Pyrimidin-4-one type ring
[aromatic att]
224C

Fused aromatic can be
5- or 6-membered.
0
A
0
Represents
0
tive structure
carbon-C(=0)-aromatic N -
aromatic N cor.
225C


f N
Representative structure
-O-CO-C-N-CO- [no aromatic
attach] cor.
226C

R', R", R'" cannot be
aromatic
0
r,x-^n^R"
yv
0
Ring reaction: -NH-CO with -
S02-N
227C


vCrV
h2n"\
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring reaction: -N-CO with -
S02-N
228C


h2n^ *0
Representative structure
Ring reaction: -S02-C with -
S02-N/-N-C0
229C


°VNH2
° U °
Representative structure
°r
Representative structure
Additional amino-type triazole
correction
230C

R' Can be H; Has to be
1,2,4-triazole, no
amine on N
N	N
Ring rx: -S02-N with SO-Car/-
CO-C [6 mem]
231C


yCrfC
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring rx: -S02-N with SO-Car/-
CO-C [5 mem]
232C

R', R" can be H
O
^ \R..
o
^ V
C=C-C(=N-C)-N-C(=0)- [fused
ring type]
233C


06
Representative structure
-C-C(=N-C)-N-C(=0)- [fused ring
type]
234C


o5
Representative structure
-CO-N-C(=NH)-C correction
235C

R' is undefined
0
x
R"'^NH
A
^ NH
C-0-C(-C-0H)-0-C correction
236C

R' undefined
Ether methyl group may
be substituted and
alcohol can be
secondary or tertiary
R' /
0
HO
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
N-C-C(-0H)-C(-0-)(-0-)
correction
237C

R', R" can be H
%
?Vyri
R OH R"
C[-C-0] [C-CO-O] [C-Caromatic-
Naromatic]
238C


0
HO—v y— OH
\=N
Representative structure
Caromatic-N-C(=0)-Caromatic
correction
239C

R' is undefined
O
jf
AR--n/^ AR
1
R'
-P(=0)-S-C-S(=0) correction
240C


0
II
,S R-
0 R"
Reaction: nitrogen[+5] / ester
241C


* o-(
Representative structure
>N-C(-S(=0)-)-C-{0,N,CO}
correction
242C

R' cannot be H
H,N O
\ ''
nh2
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Ring rx: -S02-C with 3+ arom
nitrogens(5R)
243C


0
Representative structure
Car-C(=0)-N(>C
244C

R' can be H

r r'
-S-C[cyclic](=N-C(=0))-N-C(=0)
correction
245C


„A
S^N
H
0
Representative structure
Ring rx: -OH / di-ortho;sec- or
t- carbon
246C


Representative structure
Amino acid (olefin; non-alpha
carbon type)
247C

Rs are undefined
R'" N
1
R,"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-C-(C#N)-CO- structure
correction
248C

Rs are undefined
F
R"—
0^
z
III
o it
L 1 /
>C(=NH)
[ketimine,cyclic,aromatic
attach]
249C


jX-
HO^
Representative structure
-C(=NH)-N [aromatic attach]
correction
250C

Rs are undefined
NH
X
AR N—R'
1
R"
multi: -CO-N-C-CO-N- (cyclic
C;aliphatic)
251C


o O
Q^-nh./
h2n h )=o
N—
"V3
o
Representative structure
-O-CO-N-CO-N-CO- structure
correction
252C

Rs are undefined
,aaI0-
H H
C-S-C-S(=0)- structure
correction
253C

Rs are undefined
r,\-Vr"
// D"
0 R
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-S-C-C(-N-)-C-OH structure
correction
254C

R' and other
substitution undefined
R' NH2
S^^OH
-N-CO-C-OH [linear CO;>C
255C

R' and R" are undefined;
R'" and R"" cannot be H
?!
\ o
>S=C(-N-) structure correction
256C

R's are undefined
R""\ 	
N
R'\
S R'"
1
R"
-C-N=C-N-C- [cyclic] structure
correction
257C


H
a
N
Representative structure
H0-CH2-CH(-0H)-C-0- [linear-
type] correc.
258C

R's are undefined
Vr-'
hoA^h
Hc/C
Azide correction N=N#N
259C

R' is undefined
R'—N=N=N
Special cyclic ester (large
ring;olefin)
260C

Minimum amount of
double bonds and
carbons shown in Rep.
Structure
0
6
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure




0
ii




?\




/
HO
Representative structure
O
II




Q
0-C-C(-0H)-C-0-C(=0)-C (cyclic
ester part)
261C


HO
Representative structure




0
Aa
Epoxide - Cyclic Ketone
enhancement
262C


Representative structure




—O
S:
o
\
-C(-0-C)(-C-0-C)(-C-0-C) {cyclic
type}
263C


Representative structure




Os ,°
Ss
NH




[
nh2
C=C(-N-S02-)( {-N-;-C(=0)-N})
[cyclic]
264C


Representative structure




0
Fused ketone ring (di-aromatic
+ nitrogen)
265C

R' can be H
II
R'
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
N-C-C—O-C-O-C [di-cyclic
ether type]
266C


Cf
Representative structure
N-C=N-0-carbon(aliphatic)
[iminoxy] corr.
267C

R's are undefined
R
/
N-°
R,S Jl
N \
/ R'"
R"
N-C=N-0-carbon(aromatic)
[iminoxy] corr.
268C

R's are undefined
AR
/
N-°
r'n Jl
N \
/ R'"
R"
C=N-N-CO-carbon [acyl
hydrazone]
269C

R's are undefined
O
R'\ Jl
R' / R
\^N
R"
Ring rx: -OH ortho to -C=N-N-
CO-
270C


oc
Nv.
NH
^0
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
N=C-(C#N)-C#N [dicyano]
correction
271C

R' is undefined
N
III
C
R
CH2-(C#N)-C#N [dicyano]
measured corr.
272C


£
Vc
if
H
-C-(C#N)-C#N [dicyano]
correction
273C

R' and R" is undefined
/N
Q//
"X,
MultiQuat carbon(cyclic,2
fluorine attach)
274C

Representative
structure =
Perfluorocyclohexane
(CAS No. 355-68-0)
TXv
F F
Representative structure
C-S-C(=N-)-S(=0)- structure
correction
275C

R's are undefined
0
RM^-N II
Y%
R-S
aromat-N(-CO-aromat)(-S-
aromat)[cyclic]
276C


°?o
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Excessive n=0 ring correction
(type 1)
277C


0
II
N ^
O
N
II
0
Excessive n=0 ring correction
(type 2)
278C


0
II
0 N
aaP
II
0
aliph-C=N-0-carbon(aliphat)
[iminoxy] cor.
279C

R' is undefined
R'
R^N
%
aliph-CH=N-0-carbon(aliphat)
[iminoxy] cor
280C


CX^N-o-'
Representative structure
0=P(carbon)(carbon)(carbon)
correction
281C


R
o-p\
R
0=P(carbon)(carbon)(oxygen)
correction
282C


R
-P-R
o-P\
0
Ry
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
0=P(oxygen)(oxygen)(-CH2-
phenyl) correct
283C

R's are undefined
o-R'
1
0=P-0
6V
0=P(-OH)(-OH)(aliphatic
carbon) correction
284C


HO
-P-OH
o^p\
R
Phosphorus-Fluorine
correction
285C

R's are undefined
R"\
p-l-
/
R"
S=P-S-C-C(=0)-N- correction
286C

R's are undefined
R,"
\
^ XNH
>
A R'
0=P-S-C-C(=0)-N- correction
287C

R's are undefined
R,"
\
NH
>
-p R'
{0,S}=P-S-C-C(=0)-N-C(=0)
correction
288C

R' = 0 or S; R",R'",R"" =
undefined
0
f
>
A R"
R'^p
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
S=P-S-C-S- correction
289C

R's are undefined
,R"
S
rVR"
J R'
0=P-S-C-S- correction
290C

R's are undefined
O
w
2?
S=P-S-C-S- unhindered S(=0)
correction
291C

R's are undefined
0,S'R"
f \R'
A H
Ring rx: S=P(0)(0)0- / 5-mem
(2+ nitrogen)
292C


R"n
1
R'—0—P=S
HN\J
Representative structure
Ring rx: S=P(0)(0)0 / aromat N
+ halogen
293C


Lji«° °"
CI
Representative structure
Ring rx: S=P(0)(0)0 / aromat N
+ amino
294C


i^0V'
LJ"° °H
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure





Ring rx: S=P(0)(0)0 / cyano
(nitrile)
295C


iUU' oh
II
N
Representative structure
S=P(-0)(-0)-N- correction
296C

Rs cannot be H
R"
o /R
oS;P-'Nn
s \ R'"
0
R""/
{0,S}=P-0-C=C-C(=0)-{0,N}
correction
297C

R= 0 or S; R"= 0 or N;
R'" and R"" are
undefined
R"
oX
1 R'"
R'^P
S=P-S-CH2-CH-S- correction
298C

Rs are not defined
pi R"
\ 1
A H
0=P-S-CH2-CH-S- correction
299C

Rs are not defined
pi R"
\ 1
A H
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
CL-CH-CH2-N-CH2-CH-CL
correction
300C


o
o
Tetrahydropyridine (NH-type)
aromat-attach
301C


xr
Representative structure
Tetrahydropyridine (-N-type)
aromat-attach
302C


.cr
Representative structure
di-ortho-halo -c-N=C(-NH)-NH-
correction
303C


X
Representative structure
di-ortho-halo -c-NH-C(=N)-NH-
correction
304C


clY)
X
Representative structure
-CF2(-CF2)(-CF2) (linear -CF2-
core)
305C


F F ^
-Hg- [mercury]
310C


Hg
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
[Pb] (Lead)
311C


Pb
[As] (Arsenic)
312C


As
[Ge] (Germanium)
313C


Ge
Tin [Sn]
314C


Sn
Tin [Sn] { oxygen attach }
315C

R', R", R'" Can be H;
R"" Cannot be H
R""
R' 1
\ .0
/Sn
Tin [Sn] { oxygen and aromatic
attach }
316C

Must have at least one
aromatic attachment.
AR
\ .0^
^Sn R
AR \
AR
Tin [Sn] { halogen or -OH
attach }
317C

R' = Hydroxy, Halogen;
R", R'", R"" can be H
R"
\ .R'
^Sn
R" \
R""
Aluminum [Al]
318C


Al
Gold [Au]=P { Phosphorus
attach }
319C

R's can be H
R'
Au /R""
rAt
Platinum [Pt] { halogen &
nitrogen attach}
320C

R' = Halogen;
R", R'" can be H
R'\ ,R"'
/pt
R \
Technetium [Tc](-S)(-S)(-N)(-N)
321C


S-Vc"°
n/Sn
Krypton [Measured]
322C


Kr
Argon [Measured]
323C


Ar
Neon [Measured]
324C


Ne
Xenon [Measured]
325C


Xe
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Radon [Measured]
326C


Rn
Helium [Measured]
327C


He
Mercury [Measured]
328C


Hg
Tin [Sn] { divalent; carbon
attach }
329C


^Sn
R ""R
Tin [Sn] { divalent; aromatic
attach }
330C


^Sn
ARY "ARY
Sodium [Na]
331C


Na
Potassium [K]
332C


K
Lithium [Li]
333C


Li
Gold [Au]
334C


Au
Bismuth [Bi]
335C


Bi
Calcium [Ca]
336C


Ca
Magnesium [Mg]
337C


Mg
Antimony [Sb]
338C


Sb
Zinc [Zn]
339C


Zn
Gold [Au] { halogen attach }
340C

R' = Halogen;
R" can be H
R'—Au
\
R"
Platinum [Pt] { halogen attach }
341C

R' = Halogen
/R'
p r
Platinum [Pt]
342C


pt
Iron [Fe]
343C


Fe
Cadmium [Cd]
344C


Cd
Cadmium [Cd] { halogen attach
}
345C

R' = Halogen
/R'
Cd
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Miscellaneous Metal
[Ni,Cu,Zr,Be]
346C

Representative
structure = Bis(8-
quinolinolato-
(Nl,08))copper (CAS
No. 10380-28-6)
/ ^—o 2+ / %
Representative structure
Miscellaneous Elements (Value
Unknown)
347C

Representative
structure=
Methylcyclopentadienyl
manganese (CAS No.
12108-13-3)
0 -cv-
c yr
W- -
c—c
Representative structure
Tin [Sn] { multi-halogen or -
0N02 }
348C

R', R" = Halogen (must
have at least two)
/°S
Sn N02
.,Sn
R VR'
Tin [Sn] { nitrogen attach }
349C

R', R" can be H
R'
1
Sn R"
[Zn]-S {zinc-sulfur}
350C

R' can be H
R Zn
[Sn]-0-[Sn] { bis-tin ether}
351C


Sn Sn

352C



[He]
353C


He
[Ne]
354C


Ne
[Ar]
355C


Ar
[Kr]
356C


Kr
[Xe]
357C


Xe
[Rn]
358C


Rn
[At]
359C


At
[Po]
360C


Po
[Bi]
361C


Bi
[Ga]
362C


Ga
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
[In]
363C


In
[Tl]
364C


Tl
[Cu]
365C


Cu
[Ag]
366C


Ag
[Ni]
367C


Ni
[Pd]
368C


Pd
[Co]
369C


Co
[Rh]
370C


Rh
[lr]
371C


lr
[Ru]
372C


Ru
[Os]
373C


Os
[Mn]
374C


Mn
[Tc]
375C


Tc
[Re]
376C


Re
[Cr]
377C


Cr
[Mo]
378C


Mo
[W]
379C


W
[V]
380C


V
[Nb]
381C


Nb
[Ta]
382C


Ta
[Ti]
383C


Ti
[Zr]
384C


Zr
[Hf]
385C


Hf
[Sc]
386C


Sc
[Y]
387C


Y
[La]
388C


La
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
[Ce]
389C


Ce
[Pr]
390C


Pr
[Nd]
391C


Nd
[Pm]
392C


Pm
[Sm]
393C


Sm
[Eu]
394C


Eu
[Gd]
395C


Gd
[Tb]
396C


Tb
[Dy]
397C


Dy
[Ho]
398C


Ho
[Er]
399C


Er
[Tm]
400C


Tm
[Yb]
401C


Yb
[Lu]
402C


Lu
[Ac]
403C


Ac
[Th]
404C


Th
[Pa]
405C


Pa
[U]
406C


U
[Np]
407C


Np
[Pu]
408C


Pu
[Am]
409C


Am
[Cm]
410C


Cm
[Bk]
411C


Bk
[Cf]
412C


Cf
[Es]
413C


Es
[Fm]
414C


Fm
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
[Md]
415C


Md
[No]
416C


No
[Lr]
417C


Lr
[Sr]
418C


Sr
[Ba]
419C


Ba
[Ra]
420C


Ra
[Be]
421C


Be
[Rb]
422C


Rb
[Cs]
423C


Cs
[Fr]
424C


Fr
[Te]
425C


Te
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-C(=0)-C=N-0- structure correction
OX

R' is undefined
o
%
1
R
-C(-0H)(-0H)-C(=0)- structure
correction
IX

R' is undefined
rAt
HcT°H
Carbonyl sub on 1,2,5-oxadiazole n-
oxide
2X


kj
o
N=/
Representative structure
Two or more aromatic n=0 in same
ring
3X


N
w
Representative structure
Linear >N-C=N-aromatic correction
4X


tt:
<
\
y hi
-SO-arom sub on 1,2,5-oxadiazole n-
oxide
5X


0 J 0
II // ^AR
0 0
Linear Si-O-Si correction [coef * NUM -
2]
6X

R' is undefined
R' R'
1 1
R'—Si-O—Si-R'
1 1
R' R'
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Cyclic Si-O-Si correction [coef * NUM -
4]
7X


H,Si SiH,
2 1 1 2
°-Si'°
h2
Representative structure
0=P-C-P=0 structure correction
8X


p"°
R'
Phosphorus-halogen correction
9X

R's are undefined
R"v
P'-'X
1
R'
HO-C-OH (poly-alcohol carbon)
correction
10X

R's are undefined
R"
Jl-OH
R \
OH
Ring Rx: thiadiazole / alkyloxy-
11X


/S^N
y
R"0
-C(=0)-0-C-C(=0)-N-C(=0)- correction
12X


A
V
HN.
1
0
-C(=0)-0-C-S(=0)- correction
13X


0
,A0
^s"°
1
R"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
Guanidine [NC(=N-)N](2-arom,non-
cyclic ty)
14X


nh2
H2N^n
/
AR
N-Nitroso - C - C#N or N02 correction
15X

R' = C#N or N02
n-n
N-Nitroso -C-C- C#N or N02 correction
16X

R' = C#N or N02
R'
N-Nitroso - C - { 0,S, or CO} correction
17X

R' = 0, S, C=0
0
n-n
R'—^
N-Nitroso - C - Nitrogen correction
18X

R's are undefined
0 R'
n\i-N /
N V-N
\
R"
-C(-N-N=0 [linear])-C-N- correction
19X

R's are undefined
R'
1
N N
1
R,"
-C(-N-N=0 [linear])-C-N-N=0 correction
2 OX

R's are undefined
R'
1
0^ _,I\U
— N ^0
R"
-N-C-C(=0)-C-N- correction
2IX

R's can be H
R' 0
R" R""
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure





Aromatic Nitrogen-C-COOH structure
correc
22X


O^/OH
Representative structure
Cyclic ketoxime (>C=N-OH) [aliph
attach]
23X


^N-0„
X
R R
Ring rx -> -CH=N-OH ortho to arom
oxygen
24X


r0iTN'0H
Representative structure
C=C(-N-N)-C(=0)- correction
25X

Representative
structure = CAS No.
73829-38-6
b
Representative structure
-C(=0)-0-0-C(=0)- correction
26X

R's are undefined
0
°Y°
R"
>C=NH [ketimine, aliphat attachs]
correc
27X


NH
A
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-P(=0)-C-C(=0)- correction
28X

R's are undefined
0 0
C=N-0-carbon(aromatic) [iminoxy]
correc.
29X

R's are undefined
R'
/ R"
AR"°
-0-C(=0)-N-C-0H [linear N] correction
3 OX

R' undefined
	OH
0, /
V-N
T H
R'-"0
-CH=N-C [linear imine] correction
3IX

R' is undefined
1
H^N
R'
-0-C(-C-H0)-C-0N02 structure
correction
32X


O
O
o
-0-C-C(-N-)-C-0- structure correction
33X

R' can be H;
R", R'" = Undefined
R"\ /R"'
0 0
NR'
H0-C-C(-N-)-C(=0)N- structure
correction
34X

R's can be H
OH 0
vV
HO-C-C(-S-)-C-OH structure correction
35X

R' is undefined
RS
H0^k/0H
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure





CO-N-CO-C(-N-)-C-S structure
correction
36X

R's can be H
O O
r,AnA^s^r"
-S(=0)-C {-S(=0);-P(=0)} correction
37X

R's are undefined
R' R"" s-0
0" R'
-N=N-C(=0)- structure correction
38X

R's are undefined
oyR'
R'V-N
-S-C(-N-)-C-OH structure correction
39X

R's are undefined
R"S
HOsAN'R"
1
R'
N02-N-C-N-N02 structure correction
40X

R's are undefined
0 0
II II
0" N N ^0
1 1
R' R"
-S(=0)-N-S(=0)- structure correction
41X

R's are undefined
R"
Rv<
R'
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
C=NN-CO-N-N- [aminosemicarbazone]
correc.
42X

R's are undefined
r's J r
/n^n-n.
r/ R~
Ring rx -> -CO-NH ortho to alkyloxy
43X

R' and R" undefined
OV
1
R
Representative Structure
aromatic-O-C-O-CO- structure
correction
44X


Y^O
Representative structure
-N-CO-CH2-OH structure correction
45X

-OH can be attached
aromatic, ortho to
amide
OH
V
R H
Ring reaction -> n=0 / -S(=0)-C
46X

Position not defined
ry1-
0^
Representative structure
S(-C-0-)(-C=N) structure correction
47X


^R'
N
^ I
HO SR"
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
{Na,K,Li} [not oxy attach]
**questionable!
48X


"V
1
Na
Representative structure
Ring rx -> 2-imidazole-type / -C=N-OH
49X


o
N \
\=N
SOH
Representative structure
-C(-S-)(-N-)-C(=0)- correction
50X


0
3
HS—^
N-R"
R''
misc-0-{Na,K,Li} [coef*(l+0.5*(NUM-
i»]
5IX


~°^Na
AR
^=/°^Na
Representative structures
H00C-C-(C-C00H)(C-0-) correction
52X


A
OH
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
MOOC-C-C-COOM {M=metal}
correction
53X

R '= metal
/'
o
zj o
Ring reaction -> -OH ortho to Azo
54X


or
^^N=NH
Representative structure
Ring rx -> -NC(=0)/cyclic C(=0)-
>aromatic
55X

R' cannot be H
Tfr"
Representative structure
Ring rx -> nc-C(-CO-aromatic)-CO-C
56X


Representative structure
Ring rx -> c(OH)c(n)/-C(CO)-CO(or OH)
type
57X


0
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
C(-S-)(-N-)=C-C(=0)- correction
59X

R's are undefined
A
N S
1 1
FT R'
>C=N-C [di-aromatic attached imine]
cor.
60X


n"
A
AR"t\R
N-O-CO-N-CO-N- structure correction
61X

R', R" can be H
0 0
JK /nr,2
NR"f N 0
-C0-C-S02-aliphatic structure
correction
62X


RX>°
R R
-CO-C-S(=0)-aliphat structure
correction
63X


0 0
-C-CO-N-CO-CO- structure correction
64X

R's are undefined
R"
Ring rx -> amino-type ortho to -S02-C
65X


1
o=s=o
J^nh2
u
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure





-S(=0)-to-aromatic nitrogen correction
66X


1
o=s=o
J^nh2
u
Representative structure
Nar Ring rx:-SO-C with di-
N02/C#N/OH/amino
67X

R' and R" = N02, C#N,
OH or Amino
r'Y^n
R,,A^y°
Representative structure
CH2=N-N- hydrazone correction
68X


H
R' N-R'"
r>N
C(-OH)(-C-)(C(=0)-{N,C})-aromatic
carbon
69X

R' = N or C
St*
Ring rx: -SO-C with -S02-C
70X


o=s—
II
0
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-C(=0)-N-C(=S)-olefinic C correction
71X


aX
C(-0-)(C-0H)C-N-C0 ~~combination
effect**
72X

Representative
structure = L-Threo-
alpha-D-galacto-
octopyryanoside (CAS
No. 19096-41-4)
o
CL Jv. .O
Cl nr ir
\ N
Representative structure
C-CO-C(-CO-C)-CO-C structure
correction
74X


0 0
^0
N-P(=S)-N structure correction
75X

R's are undefined
R'\ M /R'
N-P—N
R""' k	V
C[-C-0][C-CO-0][C-Caromatic]
correction
76X

Other substitution
undefined
OH
Representative structure
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure




O^^OH




J?
O
\
73
C=C(-C00H)-0-C structure correction
77X

R's are undefined





1TR
Ring rx: -S02-C with 2+ arom
nitrogens(6R)
78X


flJ
Representative structure




R'\ 0
0^
R'V n-ar
R"'
-N< [aromatic; nitrogen; CO-O attach]
cor.
79X

R's are undefined





0	R
1	1




-O
o
X
H0-C-C(-0-)-C(-0-)(-0-) correction
8 OX


70
\
o—




OTrY
y.0 0
C(=0)N-C-C(-0-C)-0-C(=0)- correction
8IX







^OH
N
A




o
Representative structure
Cyclic ketoxime(>C=N-OH) [2 olefin
attach]
82X



R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
C=C(-S)-S(=0)- correction
83X

R's are undefined
R'"v
R"\ jT
S^\ R.
II S^K
0
C=C(-S)-C#N correction
84X

R's are undefined
s"R'
RV /
/ cN
R'" *N
-N-C-N-CHO [nitrogen/N-
aldehydejcorrection
85X

R's are undefined
R"V 	
N R.
R"	N
r." \=o
C(-C#N)=N-0-carbon [iminoxy]
correction
86X


R ll
-N-C-NC(=S) or -N-C-SC(=S) correction
87X

R's are undefined
?P"YS
R" R""
R'
RJ^S R™
s
C-CO-C(-CO-C)-CO-C [aromatic attach
type]
88X


>
73
o
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure
-CO-C-S02-aromatic structure
correction
89X

R's are undefined
AR^o
A0
R O
-C(=0)-N=C(-amino)-N- [cyclic-type]
9 OX


0
6
H
Representative structure
aromatic N-C(=N-aromatic)-C imine-
type
9IX


&
Representative structure
-N-C(=S)-C(-polyhalo) correction
92X

X = Halogen
v S
>V
H0-C=C(-0H)-C(=0)-0- [cyclic]
correction
93X


HO OH
N-CH=N-OH [oxime-type] correction
94X

R's are undefined
R"v
\ D»i
N-k
r'n J
N
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure





Ring rx: -OH ortho to -C=N-N-carbon
95X

R's are undefined
R'\ ^R"
N
Representative structure
=C-(C#N)-C#N [dicyano] correction
96X

R's are undefined
N
III
C
1
R"
Aromatic nitrogen-C-C(=S)-N< struct
corr.
97X

R's are undefined
R'
Jl-R"
AR-N ^ RM„
S \
R,"
Cyclic ketoxime(>C=N-OH) [1 olefin
attach]
98X

R's are undefined
HO.
N
R'^^^-R""
Rll pill
C=N-0-sulfur(aliphatic) [iminoxy]
correc
99X

R', R", R'" undefined
Y
o'N
1
R
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments	Fragments containing "C" or "X" are not used in Pass 2
-------
Fragment
Number
Modified Name
General Comments
Structure





-S-N(-C(=0)-C)-C(=0)-C struct
correction
100X

R', R", R'" undefined
0 \
K		 ^ R„
S-R,
-Sulfur(+4) charged halide-type
101X

R', R", R'" undefined
R'
1 R"
R,"
Ring rx: S=P(0)(0)0- / 5-mem (2
nitrogen)
102X

R's are undefined
R"
1
0
1
R'—0—P=S
0=P(-0)(-0)-C-0H correction
103X

R', R" undefined
R'\ n
o-p-o
J VR"
HO
R = Must be an aliphatic carbon attachment
AR = Must be an aromatic carbon attachment
R', R", R'", etc. = Defined in General Comments
Fragments containing "C" or "X" are not used in Pass 2
-------