1. 1 Advanced Structure Search

2. 2 Structure search in BEILSTEIN <253 non-H atoms Search type controls substitution: EXA, FAM CSS SSS

3. 3 G-groups

4. 4 Elements Shortcuts Variable groups (Ak, Cy, X, etc.) Structural fragments (that you draw) Other G-groups

5. 5 G-groups Cl Cl N, O, Me, X Ring Isolated Bond all exact

6. 6 G-groups Cl Cl G1 G1 = O,N,Me,X Ring Isolated Bond all exact

7. 7 Run a sss sample search => l1 SAMPLE SEARCH INITIATED 18:20:45 SAMPLE SCREEN SEARCH COMPLETED - 1648 TO ITERATE 60.7% PROCESSED 1000 ITERATIONS 14 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 30525 TO 35395 PROJECTED ANSWERS: 173 TO 749 CSS Search

8. 8

9. 9 Run a css full search => l1 css full FULL SEARCH INITIATED 18:20:22 FULL SCREEN SEARCH COMPLETED - 33296 TO ITERATE 100.0% PROCESSED 33296 ITERATIONS 4 ANSWERS SEARCH TIME: 00.00.01 L3 4 SEA CSS FUL L1 => d scan CSS Search

10. 10 CSS Search

11. 11 CSS Search Be carefull : You can pay CSS search as a SSS search and get results as a Family search. Look at the following example:

12. 12 CSS Search => Uploading C:\Program Files\stnexp\Queries\css.str chain nodes : 7 8 9 ring nodes : 1 2 3 4 5 6 chain bonds : 4-7 5-9 6-8 ring bonds : 1-2 1-6 2-3 3-4 4-5 5-6 exact bonds : 1-2 1-6 2-3 3-4 4-5 4-7 5-6 5-9 6-8 L1 STRUCTURE UPLOADED

13. 13 CSS Search => s l1 full css L3 4 SEA CSS FUL L1 => d cost COST IN U.S. DOLLARS SINCE FILE TOTAL ENTRY SESSION CONNECT CHARGES 0.37 0.52 NETWORK CHARGES 0.06 0.12 SEARCH CHARGES 160.90 160.90 ------- ------- FULL ESTIMATED COST 161.33 161.54

14. 14 CSS Search => s l1 full fam L5 4 SEA FAM FUL L1 => d cost COST IN U.S. DOLLARS SINCE FILE TOTAL ENTRY SESSION CONNECT CHARGES 0.74 0.89 NETWORK CHARGES 0.12 0.18 SEARCH CHARGES 64.00 64.00 ------- ------- FULL ESTIMATED COST 64.86 65.07 => l3 or l5 L6 4 L3 OR L5

15. 15 Structural fragments (that you draw) Other G-groups G-groups

16. 16 G-groups

17. 17 Search Question: Locate analogs of the following substances to be used as possible synthetic intermediates G-groups

18. 18 Challenges R’ represents several classes of cpds The carboxy derivatives are further defined Solution Create a G-group Embed a G-group within a G-group G-groups

19. 19 Draw the fragment(s) Label them as fragments: assign the @ to the points of attachment for each fragment Save the G-group G-groups

20. 20

21. 21

22. 22

23. 23

24. 24

25. 25

26. 26

27. 27

28. 28

29. 29

30. 30

31. 31 => Uploading "advstr1.str" in the current file L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR G1G2 G-groups

32. 32 => S L1 SS SAM SAMPLE SEARCH INITIATED FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** L2 50 SEA SSS SAM L1 => D SCAN L2 50 ANSWERS REGISTRY COPYRIGHT 1998 ACS IN Ethanone, 1-(5-chloro-1-methyl-1H-indol-3-yl)- MF C11 H10 Cl N O G2 = An acyl analog G-groups

33. 33 L2 50 ANSWERS REGISTRY COPYRIGHT 1998 ACS IN 1H-Indole-2-carboxylic acid, 3-cyano-1-methyl-, ethyl ester (9CI) MF C13 H12 N2 O2 G2 = A cyano analog G-groups

34. 34 => S L1 SSS FULL FULL SEARCH INITIATED 13:43:28 FILE 'REGISTRY' FULL SCREEN SEARCH COMPLETED - 12107 TO ITERATE 100.0% PROCESSED 12107 ITERATIONS 797 ANSWERS SEARCH TIME: 00.00.15 L3 1166 SEA SSS FUL L1 => FILE CAPLUS => S L3/RCT 342 L3 2185962 RCT/RL L4 171 L3/RCT (L3 (L) RCT/RL) => D IBIB ABS HITSTR 38 Role indexing to limit retrieval RCT = reactant Which substance from L3 is indexed to this record? HITSTR provides hit CAS RN, index name and structure G-groups

35. 35 Drawing specific structures –Fragments with 2 points of attachment –Variable points of attachment on multiple rings G-groups

36. 36 G-groups

37. 37 G-groups 1. Draw all the fragments. 2. Label with @ point of attachments. 3. Create separate G-groups. 4. “Orient” fragments with 2 points of attachment during the SAVE operation.

38. 38 G-groups The quinoline ring is drawn twice to account for 2 points of attachment. All fragments in G1 (Y) are given 2 points of attachment. The amide fragment in Y is drawn twice, to account for both orientations. Carbons are left open for substitution.

39. 39 G-groups 1. In the Define New G-Group dialog box, click Fragments. 2. Use Next Fragment to navigate through the fragments in the structure, including the desired fragments.

40. 40 G-groups The Ak variable was chosen from the Variables menu. Fragments with 2 points of attachment show up as [*1-*2].

41. 41 G-groups Orientation of a fragment takes place during the SAVE operation. It cannot be bypassed! 1 2 Two nodes are highlighted. Show Fragment is used to see a fragment and select the node attachment to G2.

42. 42 G-groups 3 Select the appropriate node for each fragment. In the case of the amide (an unsymmetrical fragment), the node selection is carefully chosen to orient the selected node to the highlighted node in the structure window (G2).

43. 43 G-groups Each end of each fragment is highlighted during query verification. This shows the orientation of the fragment to the rest of the structure.

44. 44 A Search Question: Locate benzyl substituted N-containing ring systems described by compound A N R N N N N N A R = N N - C NULL CH 2 Ph G-groups

45. 45 Challenges R is describing 3 ring systems How to describe “NULL” Solution Create a G-group, with fragments, embedded in ring Start with a five members ring Use a [0-1] repeating group on G in a six members ring G-groups

46. 46 Draw the 5-member ring desired Draw fragments to account for other ring sizes Label the fragments with two points of @ttachment Define the G-group; put it in the ring Verify the orientation of the fragments G-groups

47. 47 Challenges (cont) The N-C fragments must be orientated to retrieve 1,3 systems Solution Use two Points of Attachments and assign orientation during the SAVE process G-groups

48. 48 G-groups

49. 49 G-groups

50. 50 G-groups

51. 51 => Uploading "advstr2.str" in the current file L6 STRUCTURE UPLOADED => D L6 HAS NO ANSWERS L6 STR G-groups

52. 52 => S L6 SS SAM SAMPLE SEARCH INITIATED FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** L7 50 SEA SSS SAM L1 => D SCAN L7 50 ANSWERS REGISTRY COPYRIGHT 1999 ACS IN 2H-1,3-Diazepin-2-one, o o o MF C36 H36 N4 O4 S A seven membered Diazepine ring G-groups

53. 53 L7 50 ANSWERS REGISTRY COPYRIGHT 1998 ACS IN 2-Pyrrolidinone, 1-(benzoyloxy)-4-methyl-5,5- bis(phenylmethyl)- (9CI) MF C26 H25 N O3 A five membered pyrrolidine ring G-groups

54. 54 Draw the 6-member ring desired Draw fragments to account for other ring sizes Label the fragments with two points of @ttachment Define the G-group; put it in the ring Use a [0-1] repeating group on G Verify the orientation of the fragments G-groups

55. 55 G-groups

56. 56 G-groups => fil reg => Uploading C:\Program Files\stnexp\Queries\w8.str L1 STRUCTURE UPLOADED => l1 SAMPLE SEARCH INITIATED 13:07:26 SAMPLE SCREEN SEARCH COMPLETED - 12012 TO ITERATE L2 20 SEA SSS SAM L1

57. 57 G-groups

58. 58 G-groups

59. 59 G-groups

60. 60 Hydrgen in G-groups Hydrgen in G-groups

61. 61 G-groups Ring Isolated Bond all exact

62. 62 G-groups => l1 sss full L3 12 SEA SSS FUL L1 G1 = H, OH, Me ?????? How can you get the desired compounds?

63. 63 G-groups Ring Isolated Bond all exact => l1 css full L3 7 SEA CSS FUL L1

64. 64 G-groups => l1 css full L3 7 SEA CSS FUL L1

65. 65 G-groups Ring Isolated Bond all exact => l1 sss full L3 739 SEA SSS FUL L1

66. 66 G-groups

67. 67 G-groups

68. 68 G-groups => l1 SAMPLE SEARCH INITIATED 13:05:49 SAMPLE SCREEN SEARCH COMPLETED - 1642 TO ITERATE 60.9% PROCESSED 1000 ITERATIONS 4 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 30410 TO 35270 PROJECTED ANSWERS: 4 TO 284 L2 4 SEA SSS SAM L1

69. 69 G-groups

70. 70 G-groups 1)On the Nitrogen can be attached only H or Ak 2)The ring is isolated 3)Any substitution allowed in the open sites

71. 71 G-groups

72. 72 G-groups => fil reg => c6/ea and nrs=1 and nc=1 L1 1536728 C6/EA AND NRS=1 AND NC=1 => Uploading C:\Program Files\stnexp\Queries\zanzola.str L2 STRUCTURE UPLOADED

73. 73 G-groups => l2 sample subset=l1 PROJECTIONS (WITHIN SPECIFIED SUBSET):ONLINE **COMPLETE** L3 50 SEA SUB=L1 SSS SAM L2 => d scan

74. 74 G-groups How can you run the previous search, obtaining good results?

75. 75 G-groups

76. 76 G-groups => Uploading C:\Program Files\stnexp\Queries\zanzolabis.str L4 STRUCTURE UPLOADED => l4 sample subset=l1 PROJECTIONS (WITHIN SPECIFIED SUBSET):ONLINE **COMPLETE** L5 50 SEA SUB=L1 SSS SAM L4 => d scan

77. 77 G-groups

78. 78 Repeating Groups

79. 79 Highlight all atoms in repeating group [ ] m-nDrawSelect [ ] m-n from the Draw menu Enter the repeat values unspecifiedUse unspecified bond between atoms in repeating group to allow any bonding in the repetition To specify a repeating group: Repeating Groups

80. 80 0-20 A repeating group may range from 0-20 only, however: may repeat a single atom or group of atoms may have multiple repeating groups Repeating Groups

81. 81 Repeating Groups Search Question: Locate studies on carboxylic acids in milk that have the following structures: Where R’ = an unsubstituted carbon chain of 10-40 atoms with any type of bonding between the atoms

82. 82 Challenges R = 10-40 atom carbon chain with any type of bonding Solution repeating group Use [ ] m-n (repeating group) Repeating Groups

83. 83 0-20 A repeating group may range from 0-20 only, however: may repeat a single atom or group of atoms 0-15-20 --(C) 0-1 (C--C) 5-20 --- Repeating Groups

84. 84 Repeating Groups

85. 85 => FILE REGISTRY => Uploading acid.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR Repeating Groups

86. 86 D SCAN L2 46 ANSWERS REGISTRY COPYRIGHT 1998 ACS IN Chitosan, octadecanoate (salt) (9CI) MF C18 H36 O2. x Unspecified CM 1 *** STRUCTURE DIAGRAM IS NOT AVAILABLE CM 2 Repeating Groups

87. 87 L2 34 ANSWERS REGISTRY COPYRIGHT 1999 ACS IN 9-Dodecenoic acid (7CI, 8CI, 9CI) MF C12 H22 O2 Repeating Groups

88. 88 Blocking Substitution

89. 89 Specify substitution with G-groups Use H ConnectivityUse Non-H Attachments (Connectivity) Exclude atoms CSS - closed substructure search Blocking Substitution

90. 90 Blocking Substitution Connectivity

91. 91 Blocking Substitution Connectivity

92. 92 Blocking Substitution Connectivity

93. 93 Search Question: Locate substances with the following general structure characteristics Blocking Substitution

94. 94 Challenges R’ is any atom except Br The N may be in a ring or chain Solution exclude Use exclude Br Assign Ring/chain Node Characteristics Blocking Substitution

95. 95 Challenges (cont) Two Br, with no additional substitution on one ring. Substitution is allowed at other open sites. Solution G1=H/Br SSS search 1: Use G1=H/Br on 4 positions and a SSS search Variable Point of AttachmentCSS searchNon- hydrogen Attachments 2: Use a Variable Point of Attachment and a CSS search with VPA’s and Non- hydrogen Attachments(Connectivity) Blocking Substitution

96. 96 => Uploading dye1.str L1 STRUCTURE UPLOADED => D L1 HAS NO ANSWERS L1 STR Approach 1: G1=H/Br Blocking Substitution

97. 97 Blocking Substitution BUT

98. 98 => L1 SSS SAM SAMPLE SEARCH INITIATED FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** L2 50 SEA SSS SAM L1 => D SCAN L2 50 ANSWERS REGISTRY COPYRIGHT 1998 ACS IN 3-Pyrrolidinol, 1-[4-[(4-nitrophenyl)azo]phenyl]-, (R)- (9CI) MF C16 H16 N4 O3 All G1 values are H Blocking Substitution

99. 99 Variables (Ak, Cb, G-groups) VPA’s Repeating groups Variable bonds Excluded atoms Substitutions set at Non Hydrogen Atoms (Connectivity) Variables (Ak, Cb, G-groups) VPA’s Repeating groups Variable bonds Excluded atoms Substitutions set at Non Hydrogen Atoms (Connectivity) Open Sites A CSS blocks substitution at Open Sites, but allows for: Blocking Substitution

100. 100 SSS CSS G-groups variable groups VPA REP groups Exclusions variable bonds Allows ANY substitution at any open positions yes NO substitution at open positions (unless set by connectivity) Blocking Substitution

101. 101 Exclude an atom From the Draw menu, choose Atom or Variable Select the desired Atom or Variable Click EXCLUDE Blocking Substitution

102. 102 Allow substitution in CSS search Highlight the atom of interest (or click wright) Click QueryDef then Non-H Attachments Set to minimum of 1 Blocking Substitution

103. 103 Build ring system and variably attached fragment Highlight the attachment atom With shift key, highlight attachment points Select VPA from Draw menu Specify variable points of attachment to a ring system by adding a VPA: Blocking Substitution

104. 104 => FILE REGISTRY => Uploading dye2.str L3 STRUCTURE UPLOADED => D L3 L3 HAS NO ANSWERS L3 STR Approach 2: CSS, Non-hydrogen attachments and VPA Blocking Substitution Conn. Min. 2Conn. Min. 1 R/C Conn. Min. 2

105. 105 => S L3 CSS FULL FULL SEARCH INITIATED 16:21:29 FULL SCREEN SEARCH COMPLETED - 1303 TO ITERATE 100.0% PROCESSED 1303 ITERATIONS 338 ANSWERS L4 62 SEA CSS FUL L3 Blocking Substitution

106. 106 Blocking Substitution BUT

107. 107 Blocking Substitution Consider this structure. Same conditons as previous one

108. 108 Blocking Substitution => Uploading C:\Program Files\stnexp\Queries\gbrexluded.str L5 STRUCTURE UPLOADED => l5 full css L6 84 SEA CSS FUL L5 => l6 not l4 L7 22 L6 NOT L4

109. 109 Exclude an atom From the Draw menu, choose Atom or Variable Select the desired Atom or Variable Click EXCLUDE Blocking Substitution BUT if you exclude an atom or variable you exclude also Hydrogen

110. 110 O O C C C Conn. = E1 Max2 CNCN CCl C H 3 C O Ph CF3CF3 No Yes Yes No Skills Practice Query In Registry

111. 111 If you wish Ak unsubstituted could you use the connectivity? If yes, which should be the value? If you put the connectivity E=1 do you get also branched chains? If yes how can you isolate them?

112. 112 If you wish Ak substituted only with a =O what should you do?

113. 113 Connectivity E=2

114. 114 not substituded Alkyl, Cycloalkyl not substituded Other Substitutions allowed R1=H, Alkyl R2= H, Alkyl, Cycloalkyl A = N, Alkyl Skills Practice

115. 115 System Limits

116. 116 System Limits

117. 117 => HELP SLIMIT => HELP CROSSOVER System Limits

118. 118 Strategies when search limits are reached: Query modification Structure drawing techniques Screens STN system-related options Batch searching Range searching Subset searching System Limits

119. 119 => S L1 SSS FULL FULL SEARCH INITIATED 15:30:15 FILE 'REGISTRY' FULL SCREEN SEARCH COMPLETED - >1,000,000 TO ITERATE 15.3% PROCESSED 153323 ITERATIONS 1 ANSWERS 40.0% PROCESSED 400000 ITERATIONS 31 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.01.07 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: EXCEEDS 1000000 PROJECTED ANSWERS: EXCEEDS 419 L2 31 SEA L1 SSS FULL System Limits

120. 120 Strategies when search limits are reached: –Query modification Structure drawing techniques System Limits

121. 121 Ring isolation Changing bond values Additional substitution System Limits Strategies when search limits are reached:

122. 122 Locate references discussing the use of steroidal substances with the following structure as therapeutic agents. Structures must have O- substitution at the specified position. No C-O bond order is specified. O System Limits

123. 123 => FILE REGISTRY => Uploading steroid1.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR Unspecified C-O bond Unspecified bonds for keto/enol Default isolated/embedded ring C-O bond is set to ring/chain System Limits

124. 124 => S L1 SSS SAM SAMPLE SEARCH INITIATED 07:35:47 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 40288 TO ITERATE 2.5% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: 793876 TO 817644 PROJECTED ANSWERS: 101993 TO 110727 L2 50 SEA SSS SAM L1 System Limits

125. 125 Ring Isolation No additional fused, bridged or spiro-fused attachments Improves efficiency of first stage of the search - screening Reduces numbers of substances to iterate, and usually reduces number of answers System Limits

126. 126 => Uploading stlisol.str L9 STRUCTURE UPLOADED => D L9 L9 HAS NO ANSWERS L9 STR Unspecified C-O bond Unspecified bonds for keto/enol C-O bond is set to ring/chain Ring is isolated System Limits

127. 127 => S L9 SSS SAM SAMPLE SEARCH INITIATED 07:51:14 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 17972 TO ITERATE 5.6% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 351444 TO 367436 PROJECTED ANSWERS: 54995 TO 61463 L10 50 SEA SSS SAM L9 System Limits

128. 128 => S L9 SSS FULL FULL SEARCH INITIATED 14:12:28 FILE 'REGISTRY' FULL SCREEN SEARCH COMPLETED - 363218 TO ITERATE 100.0% PROCESSED 363218 ITERATIONS 58645 ANSWERS SEARCH TIME: 00.00.11 L11 58645 SEA SSS FUL L9 => FILE CAPLUS => S L11/THU 59530 L2 368975 THU/RL L12 3082 L11/THU (L11 (L) THU/RL) System Limits

129. 129 => D SCAN L12 3082 ANSWERS CAPLUS COPYRIGHT 2001 ACS IC ICM A61K-031/575 CC 63-6 (Pharmaceuticals) TI Eye drop for the treatment of gray cataract ST eye drop gray cataract bile ext IT Bile Cataract o o o IT 57-88-5, Cholesterol, biological studies 81-25-4, Cholic acid 149-91-7, Gallic acid, biological studies 635-65-4, Bilirubin, biological studies 25312-65-6, Cholanic acid RL: BAC (Biological activity or effector, except adverse); THU(Therapeutic use); BIOL (Biological study); USES (Uses) System Limits

130. 130 Changing Bond Values Change from unspecified to a specific value Improves efficiency of first stage of the search - screening, reducing number of substances to be iterated Change ring/chain to chain OR ring also reduces number of substances to be iterated System Limits

131. 131 => Uploading stlnode.str L11 STRUCTURE UPLOADED => D L11 L11 HAS NO ANSWERS L11 STR Single C-O bond Single ring bonds C-O bond is set to chain Ring is isolated System Limits

132. 132 => S L11 SSS SAM SAMPLE SEARCH INITIATED 07:52:33 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 15539 TO ITERATE 6.4% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 303339 TO 318221 PROJECTED ANSWERS: 44325 TO 50151 L12 50 SEA SSS SAM L11 System Limits

133. 133 Additional Substitution Addition of NON-HYDROGEN substituents decreases number of substances to be iterated Provides a wider selection of screens System Limits

134. 134 => Uploading str1subs.str L13 STRUCTURE UPLOADED => D L13 L13 HAS NO ANSWERS L13 STR Single C-O bond Single ring bonds C-O bond is set to chain Ring is isolated Another C-O bond System Limits

135. 135 => S L13 SSS SAM SAMPLE SEARCH INITIATED 13:03:35 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 10290 TO ITERATE 9.7% PROCESSED 1000 ITERATIONS 11 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 199734 TO 211866 PROJECTED ANSWERS: 1625 TO 2901 L14 11 SEA SSS SAM L13 System Limits

136. 136 Techniques that DO NOT decrease number of substances iterated: –Blocking substitution with hydrogen –Adding stereochemistry –Adding atom attributes These techniques have no effect on number of substances to be iterated, but do typically reduce the number of answers System Limits

137. 137 Strategies when search limits are reached: –Query modification Screens (structure filters) System Limits

138. 138 Add additional “structure filters” or screens to the query Adds screens beyond those automatically generated by STN Narrows potential answer set Added during the structure SAVE process in STN Express System Limits

139. 139 Locate all structures containing this phenolic structure fragment. The benzylic C-O bond can be single or double. If single, the O can be part of a ring. The phenyl ring can be part of a larger ring system. O H O System Limits

140. 140 Enter structure-searchable file, upload query Run SAMPLE search, evaluate answers Add relevant structure filters Upload revised query Run SAMPLE search, evaluate answers Run a FULL file structure search System Limits

141. 141 => FILE REGISTRY => Uploading phenol1.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR Benzylic bond is unspecified O node is set to ring/chain Ring is isolated/embedded System Limits

142. 142 => S L1 SSS SAM SAMPLE SEARCH INITIATED 16:11:32 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 32922 TO ITERATE 3.0% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: 647671 TO 669209 PROJECTED ANSWERS: 140410 TO 150620 L2 50 SEA SSS SAM L1 System Limits

143. 143 System Limits

144. 144 System Limits

145. 145 System Limits

146. 146 STN Express may suggest structure filters May select others from this list Or from this list System Limits

147. 147 =>....Testing the current file.... screen ENTER SCREEN EXPRESSION OR (END):end => SCREEN 1700 AND 1943 AND 2005 AND 1838 L3 SCREEN CREATED => SCREEN 2043 L4 SCREEN CREATED => Uploading C:Filesfilter.str L5 STRUCTURE UPLOADED => QUE L5 AND L3 NOT L4 L6 QUE L5 AND L3 NOT L4 Filters are converted to their “Screen” number The Query command combines the structure and screen terms System Limits

148. 148 => D L6 L6 HAS NO ANSWERS L3 SCR 1700 AND 1943 AND 2005 AND 1838 L4 SCR 2043 L5 STR L6 QUE ABB=ON PLU=ON L5 AND L3 NOT L4 System Limits

149. 149 => S L6 SSS SAM SAMPLE SEARCH INITIATED 16:12:05 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 18039 TO ITERATE 5.5% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **COMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 352769 TO 368791 PROJECTED ANSWERS: 131431 TO 141317 L7 50 SEA SSS SAM L5 AND L3 NOT L4 System Limits

150. 150 => S L6 SSS FULL FULL SEARCH INITIATED 16:12:18 FILE 'REGISTRY' FULL SCREEN SEARCH COMPLETED - 362253 TO ITERATE 100.0% PROCESSED 362253 ITERATIONS 134146 ANSWERS SEARCH TIME: 00.00.06 L8 134146 SEA SSS FUL L5 AND L3 NOT L4 => D SCAN L8 134146 ANSWERS REGISTRY COPYRIGHT 2001 ACS IN Benzoic acid, 5-chloro-2-hydroxy-, [3-[[4- (dimethylamino)phenyl]amino]-1- methyl-3- oxopropylidene]hydrazide (9CI) MF C19 H21 Cl N4 O3 System Limits

151. 151 Strategies when search limits are reached: –STN system-related options Batch searching System Limits

152. 152 Run overnight System limits are higher than for online searches System Limits

153. 153 Locate patents discussing the use of organometallic substances containing the following structural fragment as polymerization catalysts. R = Fe, Ti, Zr, Cr, Mg, Ni, Pd, As, Cu, Mo R System Limits

154. 154 Enter structure-searchable file, upload query Run SAMPLE search, evaluate answers Run a FULL file structure search in BATCH mode Refine results System Limits

155. 155 => FILE REGISTRY => Uploading metallo.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR A G-group is used to define the metals Up to 20 options may be defined for a G-group System Limits

156. 156 => S L1 SSS SAM SAMPLE SEARCH INITIATED 16:23:37 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 21936 TO ITERATE 4.6% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.02 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 429897 TO 447543 PROJECTED ANSWERS: 127189 TO 136919 L2 50 SEA SSS SAM L1 System Limits

157. 157 => D SCAN L2 50 ANSWERS REGISTRY COPYRIGHT 2001 ACS IN 1-Butanaminium, N-[(1'-bromoferrocenyl)methyl]- N,N-dimethyl-, bromide (9CI) MF C17 H25 Br Fe N. Br CI CCS System Limits

158. 158 Batch search is run overnight Results are saved in an answer set ACTIVATE the saved answer set for display or additional searching No additional cost for a batch search System Limits

159. 159 => BATCH ENTER QUERY L# FOR BATCH REQUEST OR (END): L1 ENTER BATCH REQUEST NAME OR (END): ? Enter the name you wish to use for the BATCH request. The name must: o o o METALLO/B ENTER BATCH REQUEST NAME OR (END): METALLO/B ENTER TYPE OF SEARCH (SSS), CSS, FAMILY, OR EXACT: SSS ENTER SCOPE OF SEARCH (FULL) OR RANGE: FULL QUERY L2 HAS BEEN SAVED AS BATCH REQUEST 'METALLO/B' System Limits

160. 160 => D SAVED/A NAME CREATED NOTES/TITLE ---------- ---------- -------------------------- METALLO/A METALLO/A 17 APR 2001 118512 ANSWERS IN FILE REG => FILE REGISTRY => ACTIVATE METALLO/A L1 STR L2 118512 SEA FILE=REGISTRY SSS FUL L1 => D SCAN System Limits

161. 161 Up to 300K REG answers may be crossed over to a CAS database The results of a structure search may be refined with additional substance criteria, e.g. –ELS - Element Symbol System Limits

162. 162 => S L2 AND (ZR OR TI)/ELS 109090 ZR/ELS 199331 TI/ELS L3 28115 L2 AND (ZR OR TI)/ELS => FILE CAPLUS => S L3(L)(CAT/RL OR CATAL?) AND POLY? AND PATENT/DT L4 3510 L3(L)(CAT/RL OR CATAL?) AND POLY? AND PATENT/DT This answer set may now be crossed into the CAplus file System Limits

163. 163 => D 1 L5 BIB ABS HITSTR L5 ANSWER 1 OF 3510 CAPLUS AN 2001:235582 CAPLUS TI Metallocene polymerization catalysts for polyolefin preparation IN Yamamoto, Kazuhiro; Maruyama, Yasuo; Kanno, Toshihiko PA Nippon Polychemicals Co., Ltd., Japan SO Jpn. Kokai Tokkyo Koho, 13 pp. CODEN: JKXXAF DT Patent LA Japanese FAN.CNT 1 PATENT NO. KIND DATE APPLICATION NO. DATE ------------ ---- -------- --------------- ----- PI JP2001089512 A2 20010403 1999JP-0266058 19990920 HITSTR shows the “hit” CAS RN’s for each answer. System Limits

164. 164 IT INDEXING IN PROGRESS IT 37206-41-0, Bis(cyclopentadienyl)zirconium dibenzyl RL: CAT (Catalyst use); USES (Uses) (catalyst support; metallocene polymn. catalysts for polyolefin prepn.) RN 37206-41-0 CAPLUS CN Zirconium, bis(.eta.5-2,4-cyclopentadien-1-..... System Limits

165. 165 Strategies when search limits are reached –STN system-related options Range searching System Limits

166. 166 May be used to get the search to run to completion within ONLINE limits Use if the full-file projections is not too large AND projected answers are within limits Conduct an immediate search using two structure searches covering different segments of the file System Limits

167. 167 What has been reported on the use of substances containing the following structural fragment as part of a catalyst or initiator in polymerization processes? R1 = O, S, C Additional substitution may be present. No fusion is allowed on the N-containing ring. N N R1 System Limits

168. 168 Enter structure-searchable file, upload query Run SAMPLE search, evaluate answers Run a FULL file structure search until it reaches system limits and stops Identify the oldest CAS RN in the partial answer set Run a range search over the remaining part of the database Combine answer sets Refine results System Limits

169. 169 => FILE REGISTRY => Uploading C:\Program Files\Stnexp\Queries\n2ring.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR Use a G-group to define the options for R1 Isolate the ring to prevent fusion System Limits

170. 170 => S L1 SSS SAM SAMPLE SEARCH INITIATED 21:38:35 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 22582 TO ITERATE 4.4% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 442690 TO 460590 PROJECTED ANSWERS: 43190 TO 48944 L2 50 SEA SSS SAM L1 => D SCAN System Limits

171. 171 => S L1 SSS FULL FULL SEARCH INITIATED 21:12:15 FILE 'REGISTRY' FULL SCREEN SEARCH COMPLETED - 454927 TO ITERATE 87.9% PROCESSED 400000 ITERATIONS 36444 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.06 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **COMPLETE** PROJECTED ITERATIONS: 454927 TO 454927 PROJECTED ANSWERS: 40838 TO 42058 L3 36444 SEA SSS FUL L1 Newest compounds are in L3 System Limits

172. 172 => D 36444 RN L3 ANSWER 36444 OF 36444 REGISTRY COPYRIGHT 2001 ACS 54833-00-0 RN 54833-00-0 REGISTRY System Limits

173. 173 System Limits

174. 174 54833-00-0 => S L1 SSS RAN=,54833-00-0 RANGE MORE THAN 100,000. WILL BE BILLED AS A FULL FILE SEARCH. INITIATE SEARCH? Y/(N):Y RANGE SEARCH INITIATED 21:14:02 FILE 'REGISTRY' RANGE SCREEN SEARCH COMPLETED - 54955 TO ITERATE 100.0% PROCESSED 54955 ITERATIONS 10234 ANSWERS SEARCH TIME: 00.00.03 L4 10234 SEA RAN=(,54833-00-0) SSS L1 System Limits

175. 175 => S L3 OR L4 L5 46677 L3 OR L4 => FILE CAPLUS => S L5/CAT OR (L5 (L) ?POLYM? and (?CATAL? OR ?INITIAT?)) L6 310 L5/CAT OR (L5 (L) ?POLYM? AND (?CATAL? OR ?INITIAT?)) => D SCAN System Limits

176. 176 Use RANGE= in SEARCH to specify portion of the database Use CAS RNs in REGISTRY to define the range If the range > 100,000 substances, a full-file search fee is charged. If =< 100,000 a lower fee is charged help rnyearhelp rnweek To check RN versus time, use: => help rnyear, => help rnweek System Limits

177. 177 Strategies when search limits are reached: –STN system-related options Subset searching System Limits

178. 178 Structure searches may be run against the entire REGISTRY file, or: Against a subset of the database The subset may be defined using; –Substance terms –Subject terms System Limits

179. 179 System Limits Iterations Compounds in Registry 80 Milions 1000000 40 Milions20 Milions   Structure 1 Structure 2 Structure 1, angular coefficient  is more general Structure 2, angular coefficient  is more specific Subset

180. 180 System Limits

181. 181 System Limits

182. 182 System Limits

183. 183 Skills Practice Search saturated, unsubstituted alkyl alcohols, containing 10-20 carbon atoms, with a chiral center, with reported a BP at 760 Torr.

184. 184 Uploading C:\Program Files\stnexp\Queries\Alcohol.str chain nodes : 1 2 chain bonds : 1-2 exact/norm bonds : 1-2 Connectivity : 1:1 E exact RC ring/chain 2:1 E exact RC ring/chain Match level : 1:CLASS 2:CLASS Generic attributes : 1: Saturation : Saturated Number of Carbon Atoms : 7 or more L1 STRUCTURE UPLOADED

185. 185 => l1 SAMPLE SEARCH INITIATED 05:28:26 SAMPLE SCREEN SEARCH COMPLETED - 931004 TO ITERATE FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: EXCEEDS 1000000 PROJECTED ANSWERS: EXCEEDS 0 L2 0 SEA SSS SAM L1 => c h o/elf(p)10-20/c(p)1/o and nc=1 and no rsd/fa L3 22012 C H O/ELF(P)10-20/C(P)1/O AND.... => l1 full subset=l3 L4 2003 SEA SUB=L3 SSS FUL L1

186. 186 => l4 and 760 torr/bp.p 12243468 760 TORR/BP.P L5 1694 L4 AND 760 TORR/BP.P => l5 and stereosearch/fs 5211009 STEREOSEARCH/FS L6 529 L5 AND STEREOSEARCH/FS => d qrd L6 ANSWER 1 OF 529 REGISTRY COPYRIGHT 2003 ACS on STN..... Calculated Properties Boiling Point (BP) CODE| VALUE | CONDITION | NOTE ====+==============+=================+======= BP |518.65+/-8.0 K|Press: 760.0 Torr|(1) ACD

187. 187 Locate references discussing the photographic applications of compounds containing the following structural fragment. The heterocyclic ring contains at least 2 N atoms, and at least 6 atoms in total. Bonds in the fragment are all chain bonds. N Hy O System Limits

188. 188 Enter structure-searchable file, upload query Run SAMPLE search, evaluate answers Define a subset Create the subset Run a SAMPLE structure search and evaluate results Run a FULL file structure search Refine results System Limits

189. 189 => FILE REGISTRY => Uploading subset.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR Hy with element count of Nitrogen, minimum 2 is used System Limits

190. 190 => S L1 SSS SAM SAMPLE SEARCH INITIATED 21:49:03 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 123620 TO ITERATE 0.8% PROCESSED 1000 ITERATIONS 9 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: EXCEEDS 1000000 PROJECTED ANSWERS: EXCEEDS 20251 L2 9 SEA SSS SAM L1 System Limits

191. 191 =>....Testing the current file.... screen ENTER SCREEN EXPRESSION OR (END):end => SCREEN 1994 AND 2004 AND 1838 L3 SCREEN CREATED => SCREEN 2043 L4 SCREEN CREATED 3 or more N 1 or more O 1 or more rings Polymers (2043) are excluded System Limits

192. 192 => Uploading C:Files.str L5 STRUCTURE UPLOADED => QUE L5 AND L3 NOT L4 L6 QUE L5 AND L3 NOT L4 => S L6 SSS SAM SAMPLE SEARCH INITIATED 21:50:01 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 73719 TO ITERATE 1.4% PROCESSED 1000 ITERATIONS 23 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: EXCEEDS 1000000 L7 23 SEA SSS SAM L5 AND L3 NOT L4 System Limits

193. 193 => S >=2 N/REL (S) RATC>=6 15045119 REL.CNT >= 2 7536633 N/REL 3983611 >=2 N/REL (REL.CNT >= 2 (T) N/REL) 14208100 RATC>=6 3014063 L8 3014063 >=2 N/REL (S) RATC>=6 2 or more Nitrogen ring elements 6 or more ring atoms System Limits

194. 194 => S L6 SUB=L8 SSS SAM PROJECTIONS (WITHIN SPECIFIED SUBSET): ONLINE **COMPLETE** PROJECTED ITERATIONS (WITHIN SPECIFIED SUBSET): 333170 TO 348750 PROJECTED ANSWERS (WITHIN SPECIFIED SUBSET): 8872 TO 11584 L9 30 SEA SUB=L8 SSS SAM L5 AND L3 NOT L4 System Limits

195. 195 => S L6 SUB=L8 SSS FULL L10 18836 SEA SUB=L8 SSS FUL L5 AND L3 NOT L4 System Limits

196. 196 => FILE CAPLUS => S L10 AND PHOTOG? L11 118 L10 AND PHOTOG? => D SCAN L11 118 ANSWERS CAPLUS COPYRIGHT 2001 ACS IC ICM C09B-023/00 ICS C07D-261/12; C07D-277/30; C07D-403/14; C07D- 413/14; C07D-417/14; G03C-001/14 CC 41-6 (Dyes, Organic Pigments, Fluorescent Brighteners, and Photographic Sensitizers) Section cross-reference(s): 74 TI Methine compounds for spectral sensitizers and silver halide photographic materials using the same o o o System Limits

197. 197 Locate substances containing indole that have been patented for use as fabric dyes. System Limits

198. 198 => FILE REGISTRY => Uploading C:\Program Files\Stnexp\Queries\indole.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR Unlikely this will run within system limits System Limits

199. 199 => S L1 SSS SAM SAMPLE SEARCH INITIATED 13:50:22 FILE 'REGISTRY' SAMPLE SCREEN SEARCH COMPLETED - 74242 TO ITERATE 1.3% PROCESSED 1000 ITERATIONS 50 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.02 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: EXCEEDS 1000000 PROJECTED ANSWERS: EXCEEDS 407163 L2 50 SEA SSS SAM L1 System Limits

200. 200 => FILE CAPLUS => S DYE# (L) FABRIC# 239878 DYE# 96285 FABRIC# L3 17681 DYE# (L) FABRIC# => S L3 AND PATENT/DT 3189643 PATENT/DT L4 11925 L3 AND PATENT/DT System Limits

201. 201 => FILE REGISTRY => TRANSFER ENTER L# (L4) OR ?: L4 ENTER ANSWER NUMBERS, RANGES (1-), OR ?: 1- ENTER DISPLAY FIELDS (TI) OR ?: RN L5 TRANSFER L4 1- RN : 30879 TERMS L6 30670 L5 System Limits

202. 202 => S L1 SUB=L6 SSS SAM SAMPLE SUBSET SEARCH INITIATED 14:00:21 FILE 'REGISTRY' SAMPLE SUBSET SCREEN SEARCH COMPLETED - 54 TO ITERATE 100.0% PROCESSED 54 ITERATIONS 8 ANSWERS SEARCH TIME: 00.00.01 PROJECTIONS (WITHIN SPECIFIED SUBSET):ONLINE **COMPLETE** PROJECTED ITERATIONS (WITHIN SPECIFIED SUBSET): 640 TO 1520 PROJECTED ANSWERS (WITHIN SPECIFIED SUBSET): 8 TO 329 L7 8 SEA SUB=L6 SSS SAM L1 => D SCAN O O O System Limits

203. 203 => S L1 SUB=L6 SSS FULL FULL SUBSET SEARCH INITIATED 14:00:40 FILE 'REGISTRY' FULL SUBSET SCREEN SEARCH COMPLETED - 998 TO ITERATE 100.0% PROCESSED 998 ITERATIONS 110 ANSWERS SEARCH TIME: 00.00.01 L8 110 SEA SUB=L6 SSS FUL L1 System Limits

204. 204 => FILE CAPLUS => S L8 (L) DYE# AND L4 32219 L8 239878 DYE# 301 L8 (L) DYE# L9 34 L8 (L) DYE# AND L4 => D BIB HITSTR 34 patents contain an indole structure as a fabric dye System Limits

205. 205 o o o IT 117584-16-4 RL: PRP (Properties); TEM (Technical or engineered material use); USES (Uses) (dye; ink-jet printing inks containing disperse dyes for printing fabrics with high colorfastness and high black color yield) RN 117584-16-4 CAPLUS CN 1H-Indole, 3-[(2,6-dichloro-4-nitrophenyl)azo]-1-methyl- 2-phenyl- (9CI) (CA INDEX NAME) System Limits

206. 206 This group repeated from 1 to 2. Not other substitutions allowed Skills Practice

207. 207 => fil reg L1 STRUCTURE UPLOADED => d L1 HAS NO ANSWERS L1 STR Structure attributes must be viewed using STN Express query preparation.

208. 208 => l1 SAMPLE SEARCH INITIATED 06:58:14 SAMPLE SCREEN SEARCH COMPLETED - 34814 TO ITERATE 2.9% PROCESSED 1000 ITERATIONS 0 ANSWERS INCOMPLETE SEARCH (SYSTEM LIMIT EXCEEDED) SEARCH TIME: 00.00.01 FULL FILE PROJECTIONS: ONLINE **INCOMPLETE** BATCH **INCOMPLETE** PROJECTED ITERATIONS: 685172 TO 707388 PROJECTED ANSWERS: 0 TO 0 L2 0 SEA SSS SAM L1

209. 209 “Filters” to Reduce Iterations Filters may be added during the save process To add filters: Check “Refine Using Structure Filters” Click SAVE

210. 210 STN Express often suggests filters May add others using AND or NOT logic “Filters” to Reduce Iterations

211. 211

212. 212

213. 213 => nc=1 and no rsd/fa and 5-8/c and c h o/elf 40901379 NC=1 27196220 NO RSD/FA 1761030 5-8/C 2839176 C H O/ELF L3 42352 NC=1 AND NO RSD/FA AND 5-8/C AND C H O/ELF => l1 full subset=l3 FULL SUBSET SEARCH INITIATED 07:01:14 FULL SUBSET SCREEN SEARCH COMPLETED - 4319 TO ITERATE 100.0% PROCESSED 4319 ITERATIONS 70 ANSWERS SEARCH TIME: 00.00.01 L4 70 SEA SUB=L3 SSS FUL L1 Subset Searching using Dictionary

214. 214

215. 215 Troubleshooting Tips

216. 216 Structure Search Matches An answer to a structure search must contain all the following from the query: Atoms Bonds Connections Relevant answers that may not be retrieved include: Incompletely defined compounds Compounds with unanticipated bonding patterns

217. 217 Structure searches return precise results Try MF searches when structure searches turn up no hits to look for: –Incompletely defined compounds –Different bonding patterns Troubleshooting Tips

218. 218 Incompletely Defined Compounds RN 26249-12-7 REGISTRY CN Benzene, dibromo- (8CI, 9CI) (CA INDEX NAME) OTHER NAMES: CN Dibromobenzene MF C6 H4 Br2 CI IDS, COM

219. 219 Unknown point of attachment for one or more known substituent Unknown site of saturation/unsaturation for one or more bonds Unknown branching in specific carbon chains substituents Unknown site for esterification/etherification in polyacids or polyols Incompletely Defined Compounds

220. 220 Queries: IDS not retrieved: Incompletely Defined Compounds

221. 221 Find the CAS RN for this compound. Incompletely Defined Compounds

222. 222 => FILE REGISTRY => Uploading ids.str L1 STRUCTURE UPLOADED => D L1 L1 HAS NO ANSWERS L1 STR Incompletely Defined Compounds

223. 223 => S L1 FAM SAM L20... => S L1 FAM FULL L30... Incompletely Defined Compounds

224. 224 To locate a CAS RN for an IDS Conduct a MF search and refine by name fragments if needed Incompletely Defined Compounds

225. 225 => FILE REGISTRY => E C32H25Cl3N8O14S4 E1 1 C32H25CL3N8O/BI E2 1 C32H25CL3N8O13S4/BI E3 3 --> C32H25CL3N8O14S4/BI ooo => S E3 L13... Incompletely Defined Compounds

226. 226 => D SCAN => S L1 AND 2(W)2 L21 => D L2 1 RN STR REF RN 163499-22-7 REGISTRY

227. 227 Alternating double and single bonds –Tautomers –Aromatic rings Many changed to “normalized” in REGISTRY STN Express changes query structures to allow for exact value or normalized Bonding Patterns

228. 228 Exceptions to “Normalized”assignment in REGISTRY Enol-keto tautomers Pyrazole and pyrazolium rings 1,2,4-Dithiazolium rings 1,2- and 1,3-dithiolium rings Tropolone derivatives Porphines Phorbines Phthalocyanines Cyanine dyes Bonding Patterns

229. 229 CA Index Name: 1H-Pyrazole, 3-chloro-5-methyl- Author structure: REGISTRY structure: Bonding Patterns

230. 230 Locate references discussing the preparation of this pyrazole derivative Bonding Patterns

231. 231 => Uploading pyrazole.str L1 STRUCTURE UPLOADED => D L1 => S L1 FAM SAM L20… => S L1 FAM FULL L30... Bonding Patterns

232. 232 Technique 1: Conduct a MF search and refine with name fragments Technique 2: Build a structure replacing single/double bonds with unspecified bonds and run EXA or FAM search Bonding Patterns

233. 233 => FILE REGISTRY => E C4H5IN2 E1 2 C4H5IMG/BI E2 1 C4H5IMGNO4/BI E3 15 --> C4H5IN2/BI E4 8 C4H5IN2O/BI E5 4 C4H5IN2O2/BI ooo => S E3 L115… Bonding Patterns

234. 234 => S L1 AND PYRAZ? L27… => D SCAN IN 1H-Pyrazole, 3-iodo-5-methyl- (9CI) MF C4 H5 I N2 Compare bonding to query structure Bonding Patterns

235. 235 => S 1H-PYRAZOLE, 3-IODO-5-METHYL-/CN L3 1... => FILE CAPLUS => S L3/PREP L41… Bonding Patterns

236. 236 => Uploading pyrazole.str L1 STRUCTURE UPLOADED => D L1 => S L1 FAM FULL L31... Bonding Patterns

237. 237 Many Structures Searching

238. 238  AND  OR  NOT Many Structures Searching

239. 239 Structure queries with unattached fragments:  Same Structure Query (L1)  Different Structure Queries (L1 AND L2) Many Structures Searching

240. 240 Same Structure Query (L1)  Fragments in the same structure component  No overlap of fragment atoms Many Structures Searching

241. 241 Different Structure Queries (L1 AND L2)  Fragments in the same structure component with no overlap with no overlap  Fragments in the same structure component with overlap with overlap  Fragments in different components Many Structures Searching

242. 242 Searching these two fragments in the same L 1 Skills Practice

243. 243 Is this structure retrieved? Yes

244. 244 Is this structure retrieved? No

245. 245 COMP. 1 COMP. 2 Is this structure retrieved? No In the search L 1 and L 2 ?No

246. 246 In the synth. lab. a substance has been isolated produced by bacteria. From the anal. dept. you got the following information: FW = 1180-2000 The following fragments are inside the compound, in ring or chain: Skills Practice

247. 247 chain nodes : 1 4 5 6 7 ring/chain nodes : 2 3 chain bonds : 1-2 2-5 3-4 3-6 4-7 ring/chain bonds : 2-3 exact/norm bonds : 2-3 3-4 exact bonds : 1-2 2-5 3-6 4-7

248. 248 chain nodes : 3 4 ring/chain nodes : 1 2 chain bonds : 1-3 2-4 ring/chain bonds : 1-2 exact/norm bonds : 1-2 exact bonds : 1-3 2-4

249. 249 chain nodes : 1 6 7 ring/chain nodes : 2 3 4 5 chain bonds : 1-2 3-6 5-7 ring/chain bonds : 2-3 3-4 4-5 exact/norm bonds : 2-3 3-4 3-6 4-5 exact bonds : 1-2 5-7

250. 250 chain nodes : 3 4 5 6 7 8 9 ring/chain nodes : 1 2 chain bonds : 1-4 1-5 2-3 2-6 2-7 3-8 3-9 ring/chain bonds : 1-2 exact/norm bonds : 1-2 2-3 exact bonds : 1-4 1-5 2-6 2-7 3-8 3-9

251. 251 => fil reg => Uploading C:\Program Files\stnexp\Queries\fragments.str L1 STRUCTURE UPLOADED => d L1 HAS NO ANSWERS L1 STR * STRUCTURE DIAGRAM TOO LARGE FOR DISPLAY - AVAILABLE VIA OFFLINE PRINT * Structure attributes must be viewed using STN Express query preparation.

252. 252 => 1180-2000/fw L2 457267 1180-2000/FW => l1 full subset=l2 FULL SUBSET SEARCH INITIATED 06:14:40 FULL SUBSET SCREEN SEARCH COMPLETED - 100272 TO ITERATE 100.0% PROCESSED 100272 ITERATIONS 7 ANSWERS SEARCH TIME: 00.00.02 L3 7 SEA SUB=L2 SSS FUL L1

253. 253 => d 1-7 L3 ANSWER 2 OF 7 REGISTRY COPYRIGHT 2002 ACS RN 184490-65-1 REGISTRY CN..... OTHER NAMES: CN Desertomycin I FS STEREOSEARCH MF C61 H109 N O21 SR CA LC STN Files: CA, CAPLUS

254. 254 Me Me O O OH OH OH OH OH OH S S R S S PAGE 2-A

255. 255 Substitution allowed Substitution not allowed Skills Practice

256. 256 => fil reg => Uploading C:\Program Files\stnexp\Queries\substitution.str chain nodes : 1 2 3 4 5 6 7 chain bonds : 1-2 2-3 2-4 3-6 3-7 4-5 exact/norm bonds : 2-3 2-4 3-7 exact bonds : 1-2 3-6 4-5 L1 STRUCTURE UPLOADED

257. 257 => c h n/elf and no rsd/fa and nc=1 and c<=10 L2 15770 C H N/ELF AND NO RSD/FA AND NC=1 AND C<=10 => l1 full subset=l2 61 L3 61 SEA SUB=L2 SSS FUL L1 => d scan L3 61 ANSWERS REGISTRY COPYRIGHT 2003 ACS IN Ethanimidic acid, N-butyl-, 2,2-dimethylhydrazide (9CI) MF C8 H19 N3

258. 258 => fil reg => Uploading C:\Program Files\stnexp\Queries\substitution.str chain nodes : 1 2 3 4 5 6 7 chain bonds : 1-2 2-3 2-4 3-6 3-7 4-5 exact/norm bonds : 2-3 2-4 3-7 exact bonds : 1-2 3-6 4-5 Connectivity : 4:1 E exact RC ring/chain L1 STRUCTURE UPLOADED

259. 259 => c h n/elf and no rsd/fa and nc=1 and c<=10 L2 15770 C H N/ELF AND NO RSD/FA AND NC=1 AND C<=10 => l1 full subset=l2 25 L3 25 SEA SUB=L2 SSS FUL L1 => d scan L3 25 ANSWERS REGISTRY COPYRIGHT 2003 ACS IN Ethanimidamide, N-cyano- (9CI) MF C3 H5 N3 CI COM

260. 260 SMARTracker

261. 261 SMARTracker => FILE REGISTRY => STR 33069-62-4 :END L1 STRUCTURE CREATED => S L1 FUL FULL SEARCH INITIATED 15:42:29 FULL SCREEN SEARCH COMPLETED - 2420 TO ITERATE 100.0% PROCESSED 2420 ITERATIONS 877 ANSWERS SEARCH TIME: 00.00.06 L2 877 SEA SSS FUL L1

262. 262 SMARTracker => S L2/THU AND P/DT 2047 L2 146546 THU/RL 670 L2/THU (L2 (L) THU/RL) 2188789 P/DT L3 115 L2/THU AND P/DT

263. 263 SMARTracker => SMART SMARTracker INITIATED ENTER QUERY L# FOR SDI REQUEST OR (END):L3 ENTER UPDATE FIELD CODE (UP) OR ?:. ENTER SDI REQUEST NAME, (AA013/S), OR END:TAXOLS/S ENTER COST CENTER (NONE) OR NONE:. ENTER TYPE OF SEARCH (SSS), CSS, FAMILY, OR EXACT:. ENTER TITLE (NONE):. ENTER METHOD OF DELIVERY (OFFLINE), ONLINE, EMAIL, OR FAX:EMAIL ENTER EMAIL ID (1190C):KSA@CAS.ORG.INTERNET KSA@CAS.ORG.INTERNET RECEIVE DELIVERY NOTIFICATION? (Y)/N:N ELIMINATE PREVIOUSLY SEEN ANSWERS WITH EACH SDI RUN? Y/(N):Y ENTER PRINT FORMAT (BIB) OR ?:CBIB ABS HITSTR HIGHLIGHT HIT TERMS? (Y)/N:. ENTER MAXIMUM NUMBER OF HITS TO BE PRINTED PER RUN (100):. SORT SDI ANSWER SET (N)/Y?:N SEND SDI WITH NO ANSWERS? (Y)/N:N ENTER SDI RUN FREQUENCY: (WEEKLY), BIWEEKLY, OR ?:. ENTER SDI EXPIRATION DATE 'YYYYMMDD' OR (NONE):. QUERY 'L3' HAS BEEN SAVED AS SDI REQUEST 'TAXOLS/S' Or => SDI XFILE