NPASS drugs

Drug Information

Drug ID:	NPD3804
Drug Name:	BMS-180448
Molecular Formula:	C20H18ClN5O2
Canonical SMILES:	N#CN=C(N[C@@H]1c2cc(C#N)ccc2OC([C@H]1O)(C)C)Nc1ccc(cc1)Cl
Standard InCHI:	InChI=1S/C20H18ClN5O2/c1-20(2)18(27)17(15-9-12(10-22)3-8-16(15)28-20)26-19(24-11-23)25-14-6-4-13(21)5-7-14/h3-9,17-18,27H,1-2H3,(H2,24,25,26)/t17-,18+/m1/s1
Standard InCHIKey:	VLICJSLDCJXZBG-MSOLQXFVSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD3804

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	282
0.1-0.2	1500
0.2-0.3	8255
0.3-0.4	4829
0.4-0.5	10854
0.5-0.6	4971
0.6-0.7	199
0.7-0.8	0
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
Remote Similarity	0.6701	NPC315257
Remote Similarity	0.6682	NPC25897
Remote Similarity	0.6588	NPC79213
Remote Similarity	0.6566	NPC22014
Remote Similarity	0.6546	NPC13397
Remote Similarity	0.654	NPC475411
Remote Similarity	0.6524	NPC231163
Remote Similarity	0.6524	NPC318591
Remote Similarity	0.6522	NPC247018
Remote Similarity	0.6522	NPC307123
Remote Similarity	0.6522	NPC97870
Remote Similarity	0.6464	NPC141739
Remote Similarity	0.6464	NPC320242
Remote Similarity	0.6464	NPC136112
Remote Similarity	0.6453	NPC85482
Remote Similarity	0.6447	NPC477564
Remote Similarity	0.6447	NPC2295
Remote Similarity	0.6441	NPC477160
Remote Similarity	0.6439	NPC168153
Remote Similarity	0.6417	NPC237227
Remote Similarity	0.6398	NPC232872
Remote Similarity	0.6393	NPC56271
Remote Similarity	0.6389	NPC314948
Remote Similarity	0.638	NPC476106
Remote Similarity	0.638	NPC261388
Remote Similarity	0.6368	NPC212850
Remote Similarity	0.6368	NPC189724
Remote Similarity	0.6368	NPC168861
Remote Similarity	0.6368	NPC83289
Remote Similarity	0.6364	NPC10730
Remote Similarity	0.6364	NPC10875
Remote Similarity	0.6351	NPC33902
Remote Similarity	0.6351	NPC276674
Remote Similarity	0.634	NPC245974
Remote Similarity	0.6338	NPC474059
Remote Similarity	0.6335	NPC204546
Remote Similarity	0.6324	NPC195392
Remote Similarity	0.6321	NPC247298
Remote Similarity	0.6318	NPC311357
Remote Similarity	0.6313	NPC478049
Remote Similarity	0.6292	NPC471614
Remote Similarity	0.6279	NPC475754
Remote Similarity	0.6277	NPC329830
Remote Similarity	0.627	NPC471306
Remote Similarity	0.627	NPC471321
Remote Similarity	0.6269	NPC79328
Remote Similarity	0.6263	NPC277669
Remote Similarity	0.6263	NPC76213
Remote Similarity	0.6256	NPC471080
Remote Similarity	0.6256	NPC469592
Remote Similarity	0.6255	NPC228206
Remote Similarity	0.625	NPC285941
Remote Similarity	0.6244	NPC81247
Remote Similarity	0.6244	NPC476573
Remote Similarity	0.6244	NPC207824
Remote Similarity	0.6244	NPC60538
Remote Similarity	0.6244	NPC35627
Remote Similarity	0.6225	NPC238430
Remote Similarity	0.6219	NPC160931
Remote Similarity	0.6219	NPC29647
Remote Similarity	0.6219	NPC37205
Remote Similarity	0.6217	NPC469594
Remote Similarity	0.6215	NPC320088
Remote Similarity	0.6212	NPC219383
Remote Similarity	0.6207	NPC139506
Remote Similarity	0.6207	NPC292143
Remote Similarity	0.6205	NPC194699
Remote Similarity	0.6205	NPC219350
Remote Similarity	0.6203	NPC160666
Remote Similarity	0.6199	NPC472330
Remote Similarity	0.6199	NPC472329
Remote Similarity	0.6199	NPC111492
Remote Similarity	0.6199	NPC214368
Remote Similarity	0.6184	NPC217903
Remote Similarity	0.6173	NPC469722
Remote Similarity	0.6172	NPC477020
Remote Similarity	0.6172	NPC192135
Remote Similarity	0.6172	NPC66341
Remote Similarity	0.6171	NPC475085
Remote Similarity	0.6171	NPC291535
Remote Similarity	0.6171	NPC475112
Remote Similarity	0.6162	NPC103379
Remote Similarity	0.6162	NPC477565
Remote Similarity	0.6158	NPC230942
Remote Similarity	0.6158	NPC315498
Remote Similarity	0.6157	NPC189661
Remote Similarity	0.6143	NPC473460
Remote Similarity	0.6142	NPC476151
Remote Similarity	0.614	NPC116178
Remote Similarity	0.6139	NPC203784
Remote Similarity	0.6139	NPC126519
Remote Similarity	0.6139	NPC170503
Remote Similarity	0.6136	NPC72211
Remote Similarity	0.6124	NPC475215
Remote Similarity	0.6124	NPC108434
Remote Similarity	0.6123	NPC11464
Remote Similarity	0.6121	NPC219397
Remote Similarity	0.6119	NPC162653
Remote Similarity	0.6119	NPC233926
Remote Similarity	0.6117	NPC209377
Remote Similarity	0.6116	NPC473422
Remote Similarity	0.6111	NPC283207
Remote Similarity	0.6106	NPC475910
Remote Similarity	0.6101	NPC78284
Remote Similarity	0.61	NPC17160
Remote Similarity	0.61	NPC313720
Remote Similarity	0.6098	NPC247251
Remote Similarity	0.6096	NPC469442
Remote Similarity	0.6096	NPC277306
Remote Similarity	0.6094	NPC214988
Remote Similarity	0.6089	NPC469428
Remote Similarity	0.6087	NPC193853
Remote Similarity	0.6087	NPC56887
Remote Similarity	0.6087	NPC328267
Remote Similarity	0.6087	NPC223077
Remote Similarity	0.6085	NPC190461
Remote Similarity	0.6079	NPC469589
Remote Similarity	0.6077	NPC26240
Remote Similarity	0.6077	NPC477562
Remote Similarity	0.6077	NPC69712
Remote Similarity	0.6075	NPC476575
Remote Similarity	0.6073	NPC256124
Remote Similarity	0.6073	NPC230313
Remote Similarity	0.607	NPC127996
Remote Similarity	0.6068	NPC233650
Remote Similarity	0.6068	NPC293871
Remote Similarity	0.6068	NPC124433
Remote Similarity	0.6068	NPC19555
Remote Similarity	0.6066	NPC316161
Remote Similarity	0.6065	NPC477186
Remote Similarity	0.6063	NPC17677
Remote Similarity	0.6062	NPC477999
Remote Similarity	0.6061	NPC115144
Remote Similarity	0.6061	NPC277857
Remote Similarity	0.6061	NPC170114
Remote Similarity	0.6058	NPC210140
Remote Similarity	0.6053	NPC25961
Remote Similarity	0.605	NPC47672
Remote Similarity	0.6045	NPC70259
Remote Similarity	0.6044	NPC14339
Remote Similarity	0.6043	NPC321166
Remote Similarity	0.6043	NPC25539
Remote Similarity	0.6039	NPC134858
Remote Similarity	0.6039	NPC169743
Remote Similarity	0.6038	NPC134413
Remote Similarity	0.6038	NPC45112
Remote Similarity	0.6038	NPC263507
Remote Similarity	0.6038	NPC271958
Remote Similarity	0.6037	NPC474904
Remote Similarity	0.6036	NPC212163
Remote Similarity	0.6029	NPC306366
Remote Similarity	0.6028	NPC179704
Remote Similarity	0.6027	NPC302001
Remote Similarity	0.6027	NPC279401
Remote Similarity	0.6027	NPC79293
Remote Similarity	0.6024	NPC314743
Remote Similarity	0.6019	NPC204179
Remote Similarity	0.6019	NPC2314
Remote Similarity	0.6019	NPC24954
Remote Similarity	0.6019	NPC469479
Remote Similarity	0.6018	NPC243834
Remote Similarity	0.6018	NPC472191
Remote Similarity	0.6018	NPC70956
Remote Similarity	0.6017	NPC470549
Remote Similarity	0.601	NPC204828
Remote Similarity	0.601	NPC276588
Remote Similarity	0.601	NPC469817
Remote Similarity	0.601	NPC110416
Remote Similarity	0.601	NPC184026
Remote Similarity	0.601	NPC39701
Remote Similarity	0.601	NPC193949
Remote Similarity	0.601	NPC189266
Remote Similarity	0.601	NPC295691
Remote Similarity	0.601	NPC2413
Remote Similarity	0.601	NPC151030
Remote Similarity	0.601	NPC278799
Remote Similarity	0.601	NPC5238
Remote Similarity	0.601	NPC127674
Remote Similarity	0.601	NPC249797
Remote Similarity	0.601	NPC172765
Remote Similarity	0.601	NPC269383
Remote Similarity	0.601	NPC207757
Remote Similarity	0.601	NPC54379
Remote Similarity	0.6009	NPC82457
Remote Similarity	0.6009	NPC11296
Remote Similarity	0.6009	NPC274661
Remote Similarity	0.6009	NPC48490
Remote Similarity	0.6009	NPC175890
Remote Similarity	0.6	NPC243626
Remote Similarity	0.6	NPC249405
Remote Similarity	0.6	NPC255253
Remote Similarity	0.6	NPC43787
Remote Similarity	0.6	NPC274732
Remote Similarity	0.6	NPC7393
Remote Similarity	0.6	NPC162484
Remote Similarity	0.6	NPC205934
Remote Similarity	0.6	NPC85651
Remote Similarity	0.6	NPC323204
Remote Similarity	0.6	NPC275132
Remote Similarity	0.5991	NPC288349

Drug Structure

NPD3804 OpenBabel08211704332D 31 33 0 0 1 0 0 0 0 0999 V2000 -0.9659 0.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1305 1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 7.7942 -0.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 8 2 0 0 0 0 3 12 1 0 0 0 0 4 6 1 0 0 0 0 4 13 2 0 0 0 0 5 7 2 0 0 0 0 5 13 1 0 0 0 0 6 14 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 22 3 0 0 0 0 11 23 3 0 0 0 0 11 24 1 0 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 15 16 2 0 0 0 0 15 17 1 0 0 0 0 16 28 1 0 0 0 0 17 18 1 0 0 0 0 17 26 1 6 0 0 0 18 20 1 0 0 0 0 18 27 1 1 0 0 0 19 24 2 3 0 0 0 19 25 1 0 0 0 0 19 26 1 0 0 0 0 20 28 1 0 0 0 0 25 29 1 0 0 0 0 26 30 1 0 0 0 0 27 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB005253
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	395.11
ALogP	0.3233
MLogP	2.78
XLogP	3.83
HDA	6
HBD	3
Rotatable Bonds	8
TPSA	113.46
RO5 Violation	0