NPASS drugs

Drug Information

Drug ID:	NPD5023
Drug Name:	NO-COX-2 inhibitor, NitroMed/Merck & Co
Molecular Formula:	C22H24N2O4S
Canonical SMILES:	COC1(CCCO1)c1nn(c(c1)c1ccc(cc1)S(=O)(=O)C)c1ccc(cc1)C
Standard InCHI:	InChI=1S/C22H24N2O4S/c1-16-5-9-18(10-6-16)24-20(17-7-11-19(12-8-17)29(3,25)26)15-21(23-24)22(27-2)13-4-14-28-22/h5-12,15H,4,13-14H2,1-3H3
Standard InCHIKey:	XMAKNORZQOWEMY-UHFFFAOYSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD5023

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	386
0.1-0.2	2278
0.2-0.3	10243
0.3-0.4	12404
0.4-0.5	3433
0.5-0.6	1911
0.6-0.7	233
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
Intermediate Similarity	0.7231	NPC56618
Intermediate Similarity	0.7053	NPC316910
Remote Similarity	0.6995	NPC473177
Remote Similarity	0.698	NPC473189
Remote Similarity	0.685	NPC211997
Remote Similarity	0.68	NPC134586
Remote Similarity	0.6763	NPC471593
Remote Similarity	0.6746	NPC473178
Remote Similarity	0.6715	NPC46413
Remote Similarity	0.67	NPC168486
Remote Similarity	0.67	NPC222592
Remote Similarity	0.6667	NPC180504
Remote Similarity	0.6602	NPC284559
Remote Similarity	0.6582	NPC474791
Remote Similarity	0.6555	NPC242928
Remote Similarity	0.6538	NPC204385
Remote Similarity	0.6512	NPC128823
Remote Similarity	0.6505	NPC206201
Remote Similarity	0.6496	NPC24802
Remote Similarity	0.6485	NPC158129
Remote Similarity	0.6471	NPC84347
Remote Similarity	0.6459	NPC160381
Remote Similarity	0.6457	NPC94157
Remote Similarity	0.6447	NPC26850
Remote Similarity	0.6442	NPC320394
Remote Similarity	0.6441	NPC199667
Remote Similarity	0.6435	NPC32200
Remote Similarity	0.6432	NPC192306
Remote Similarity	0.6404	NPC132642
Remote Similarity	0.6396	NPC473181
Remote Similarity	0.6393	NPC475774
Remote Similarity	0.6389	NPC72211
Remote Similarity	0.6384	NPC473180
Remote Similarity	0.6378	NPC26872
Remote Similarity	0.6373	NPC34508
Remote Similarity	0.6364	NPC284678
Remote Similarity	0.6359	NPC283152
Remote Similarity	0.6355	NPC279401
Remote Similarity	0.6355	NPC79293
Remote Similarity	0.6346	NPC474798
Remote Similarity	0.6346	NPC314394
Remote Similarity	0.6343	NPC243834
Remote Similarity	0.6343	NPC70956
Remote Similarity	0.6341	NPC312872
Remote Similarity	0.6335	NPC474145
Remote Similarity	0.6335	NPC476106
Remote Similarity	0.6335	NPC475841
Remote Similarity	0.633	NPC214428
Remote Similarity	0.6329	NPC270009
Remote Similarity	0.6329	NPC472443
Remote Similarity	0.6326	NPC205934
Remote Similarity	0.6326	NPC131017
Remote Similarity	0.6326	NPC43787
Remote Similarity	0.6324	NPC126492
Remote Similarity	0.6318	NPC8104
Remote Similarity	0.6318	NPC162484
Remote Similarity	0.6318	NPC118511
Remote Similarity	0.6316	NPC176127
Remote Similarity	0.6316	NPC472444
Remote Similarity	0.6313	NPC141353
Remote Similarity	0.6298	NPC478032
Remote Similarity	0.6296	NPC472193
Remote Similarity	0.6296	NPC70259
Remote Similarity	0.6279	NPC475190
Remote Similarity	0.6275	NPC477888
Remote Similarity	0.6272	NPC312645
Remote Similarity	0.6269	NPC177404
Remote Similarity	0.6266	NPC153467
Remote Similarity	0.6262	NPC472097
Remote Similarity	0.6261	NPC277350
Remote Similarity	0.6261	NPC477533
Remote Similarity	0.6256	NPC62510
Remote Similarity	0.625	NPC88363
Remote Similarity	0.625	NPC6093
Remote Similarity	0.6238	NPC163055
Remote Similarity	0.6234	NPC477532
Remote Similarity	0.6233	NPC135549
Remote Similarity	0.6233	NPC313189
Remote Similarity	0.6228	NPC36405
Remote Similarity	0.6227	NPC476044
Remote Similarity	0.622	NPC249662
Remote Similarity	0.6217	NPC473179
Remote Similarity	0.6216	NPC470930
Remote Similarity	0.621	NPC18487
Remote Similarity	0.6209	NPC84478
Remote Similarity	0.6209	NPC190007
Remote Similarity	0.6205	NPC470280
Remote Similarity	0.6205	NPC314957
Remote Similarity	0.6204	NPC198673
Remote Similarity	0.6202	NPC248454
Remote Similarity	0.6201	NPC79386
Remote Similarity	0.6199	NPC475112
Remote Similarity	0.6199	NPC291535
Remote Similarity	0.6199	NPC475085
Remote Similarity	0.619	NPC192270
Remote Similarity	0.6188	NPC16667
Remote Similarity	0.6184	NPC472586
Remote Similarity	0.6182	NPC477019
Remote Similarity	0.6182	NPC329747
Remote Similarity	0.6182	NPC234197
Remote Similarity	0.6182	NPC329793
Remote Similarity	0.6182	NPC11017
Remote Similarity	0.6179	NPC42591
Remote Similarity	0.6179	NPC94943
Remote Similarity	0.6178	NPC469589
Remote Similarity	0.6171	NPC223427
Remote Similarity	0.6168	NPC246700
Remote Similarity	0.6167	NPC96405
Remote Similarity	0.6167	NPC202768
Remote Similarity	0.6167	NPC296482
Remote Similarity	0.6167	NPC171409
Remote Similarity	0.6167	NPC472098
Remote Similarity	0.6167	NPC53069
Remote Similarity	0.6164	NPC102008
Remote Similarity	0.6164	NPC168911
Remote Similarity	0.6161	NPC193777
Remote Similarity	0.6154	NPC98371
Remote Similarity	0.6154	NPC313884
Remote Similarity	0.6154	NPC267423
Remote Similarity	0.615	NPC285469
Remote Similarity	0.615	NPC194040
Remote Similarity	0.6147	NPC194967
Remote Similarity	0.6143	NPC132539
Remote Similarity	0.6143	NPC473239
Remote Similarity	0.614	NPC89508
Remote Similarity	0.614	NPC39500
Remote Similarity	0.6139	NPC255229
Remote Similarity	0.6139	NPC473320
Remote Similarity	0.6139	NPC81229
Remote Similarity	0.6135	NPC191310
Remote Similarity	0.6132	NPC472119
Remote Similarity	0.6131	NPC161108
Remote Similarity	0.6127	NPC470508
Remote Similarity	0.6126	NPC193761
Remote Similarity	0.6124	NPC293472
Remote Similarity	0.6123	NPC187501
Remote Similarity	0.6121	NPC66083
Remote Similarity	0.6119	NPC267928
Remote Similarity	0.6116	NPC472111
Remote Similarity	0.6116	NPC300156
Remote Similarity	0.6116	NPC45190
Remote Similarity	0.6114	NPC477979
Remote Similarity	0.6106	NPC201697
Remote Similarity	0.6102	NPC473185
Remote Similarity	0.61	NPC471458
Remote Similarity	0.6099	NPC477135
Remote Similarity	0.6096	NPC318299
Remote Similarity	0.6093	NPC34271
Remote Similarity	0.6092	NPC475253
Remote Similarity	0.6091	NPC239954
Remote Similarity	0.6089	NPC67056
Remote Similarity	0.6085	NPC212535
Remote Similarity	0.6083	NPC55493
Remote Similarity	0.6083	NPC133140
Remote Similarity	0.6083	NPC195268
Remote Similarity	0.6079	NPC471304
Remote Similarity	0.6077	NPC472122
Remote Similarity	0.6077	NPC24594
Remote Similarity	0.6077	NPC288943
Remote Similarity	0.6076	NPC315822
Remote Similarity	0.6076	NPC252251
Remote Similarity	0.6073	NPC205403
Remote Similarity	0.6071	NPC327592
Remote Similarity	0.607	NPC469592
Remote Similarity	0.607	NPC317752
Remote Similarity	0.607	NPC471080
Remote Similarity	0.6068	NPC144452
Remote Similarity	0.6068	NPC154293
Remote Similarity	0.6068	NPC44161
Remote Similarity	0.6067	NPC473186
Remote Similarity	0.6065	NPC76748
Remote Similarity	0.6063	NPC287437
Remote Similarity	0.6062	NPC475910
Remote Similarity	0.6062	NPC470931
Remote Similarity	0.6061	NPC124005
Remote Similarity	0.6059	NPC472762
Remote Similarity	0.6058	NPC474409
Remote Similarity	0.6056	NPC62069
Remote Similarity	0.6055	NPC307963
Remote Similarity	0.6053	NPC208284
Remote Similarity	0.6052	NPC225279
Remote Similarity	0.6048	NPC28848
Remote Similarity	0.6048	NPC14325
Remote Similarity	0.6045	NPC153042
Remote Similarity	0.6044	NPC317373
Remote Similarity	0.6043	NPC118228
Remote Similarity	0.6039	NPC280548
Remote Similarity	0.6038	NPC118776
Remote Similarity	0.6037	NPC92111
Remote Similarity	0.6036	NPC121772
Remote Similarity	0.6035	NPC469743
Remote Similarity	0.6034	NPC184408
Remote Similarity	0.6034	NPC469594
Remote Similarity	0.603	NPC148592
Remote Similarity	0.6029	NPC189812
Remote Similarity	0.6029	NPC329688
Remote Similarity	0.6028	NPC476319
Remote Similarity	0.6027	NPC245816
Remote Similarity	0.6027	NPC476138
Remote Similarity	0.6027	NPC195314

Drug Structure

NPD5023 OpenBabel08211706322D 29 32 0 0 1 0 0 0 0 0999 V2000 3.3517 4.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8680 0.5643 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0947 -2.6859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6389 3.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9916 2.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9479 2.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3006 1.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6408 -1.7949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0824 -2.5295 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6607 3.6622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2788 1.7601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3479 -1.0878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 5.5388 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0848 -0.4119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2389 -1.5418 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 27 1 0 0 0 0 3 29 1 0 0 0 0 4 13 1 0 0 0 0 4 14 1 0 0 0 0 5 9 1 0 0 0 0 5 16 2 0 0 0 0 6 10 2 0 0 0 0 6 16 1 0 0 0 0 7 11 1 0 0 0 0 7 17 2 0 0 0 0 8 12 2 0 0 0 0 8 17 1 0 0 0 0 9 18 2 0 0 0 0 10 18 1 0 0 0 0 11 19 2 0 0 0 0 12 19 1 0 0 0 0 13 22 1 0 0 0 0 14 28 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 17 20 1 0 0 0 0 18 24 1 0 0 0 0 19 29 1 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 23 2 0 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 24 1 0 0 0 0 25 29 2 0 0 0 0 26 29 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB005831
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	412.15
ALogP	-0.418
MLogP	3.11
XLogP	4.926
HDA	6
HBD	0
Rotatable Bonds	8
TPSA	78.28
RO5 Violation	0