NPASS drugs

Drug Information

Drug ID:	NPD4909
Drug Name:	Rimonabant
Molecular Formula:	C22H21Cl3N4O
Canonical SMILES:	Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=NN1CCCCC1)O
Standard InCHI:	InChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
Standard InCHIKey:	JZCPYUJPEARBJL-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4909

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	424
0.1-0.2	3007
0.2-0.3	10007
0.3-0.4	12527
0.4-0.5	2700
0.5-0.6	1710
0.6-0.7	511
0.7-0.8	4
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	0.7513	NPC471593
Intermediate Similarity	0.7471	NPC477890
Intermediate Similarity	0.7143	NPC158129
Intermediate Similarity	0.7065	NPC472193
Remote Similarity	0.6995	NPC293472
Remote Similarity	0.6973	NPC141353
Remote Similarity	0.6943	NPC134586
Remote Similarity	0.6907	NPC211997
Remote Similarity	0.6888	NPC192270
Remote Similarity	0.6856	NPC150048
Remote Similarity	0.6856	NPC203754
Remote Similarity	0.6839	NPC471294
Remote Similarity	0.6798	NPC471312
Remote Similarity	0.6793	NPC288445
Remote Similarity	0.6772	NPC131718
Remote Similarity	0.6769	NPC288785
Remote Similarity	0.6768	NPC133306
Remote Similarity	0.6768	NPC48938
Remote Similarity	0.6734	NPC472294
Remote Similarity	0.6722	NPC315348
Remote Similarity	0.6722	NPC32002
Remote Similarity	0.6715	NPC476175
Remote Similarity	0.6702	NPC476118
Remote Similarity	0.6702	NPC476464
Remote Similarity	0.6702	NPC477889
Remote Similarity	0.6684	NPC44161
Remote Similarity	0.6684	NPC317430
Remote Similarity	0.6667	NPC34508
Remote Similarity	0.6648	NPC60553
Remote Similarity	0.6633	NPC314394
Remote Similarity	0.6632	NPC477591
Remote Similarity	0.6617	NPC476319
Remote Similarity	0.6615	NPC97367
Remote Similarity	0.6615	NPC102423
Remote Similarity	0.6614	NPC285469
Remote Similarity	0.6613	NPC37548
Remote Similarity	0.6598	NPC63751
Remote Similarity	0.6582	NPC313791
Remote Similarity	0.6579	NPC477887
Remote Similarity	0.6579	NPC129721
Remote Similarity	0.6566	NPC326575
Remote Similarity	0.6557	NPC475070
Remote Similarity	0.6553	NPC329541
Remote Similarity	0.655	NPC477891
Remote Similarity	0.6548	NPC189812
Remote Similarity	0.6548	NPC329688
Remote Similarity	0.6542	NPC477111
Remote Similarity	0.6535	NPC15102
Remote Similarity	0.6533	NPC472443
Remote Similarity	0.6533	NPC133261
Remote Similarity	0.6533	NPC270009
Remote Similarity	0.6528	NPC159319
Remote Similarity	0.6524	NPC187951
Remote Similarity	0.6517	NPC19679
Remote Similarity	0.651	NPC81229
Remote Similarity	0.651	NPC255229
Remote Similarity	0.6508	NPC469786
Remote Similarity	0.6508	NPC259644
Remote Similarity	0.6508	NPC73952
Remote Similarity	0.6508	NPC469760
Remote Similarity	0.6508	NPC469763
Remote Similarity	0.6508	NPC25008
Remote Similarity	0.6508	NPC469765
Remote Similarity	0.6507	NPC102008
Remote Similarity	0.6507	NPC212213
Remote Similarity	0.6505	NPC99666
Remote Similarity	0.6505	NPC324149
Remote Similarity	0.6497	NPC208060
Remote Similarity	0.6497	NPC259545
Remote Similarity	0.6497	NPC472123
Remote Similarity	0.6492	NPC26850
Remote Similarity	0.6486	NPC242556
Remote Similarity	0.6485	NPC284678
Remote Similarity	0.6482	NPC59269
Remote Similarity	0.648	NPC314940
Remote Similarity	0.648	NPC473764
Remote Similarity	0.648	NPC477888
Remote Similarity	0.6477	NPC278451
Remote Similarity	0.6477	NPC59779
Remote Similarity	0.6477	NPC47298
Remote Similarity	0.6477	NPC315214
Remote Similarity	0.6477	NPC16667
Remote Similarity	0.6477	NPC471177
Remote Similarity	0.6477	NPC124542
Remote Similarity	0.6474	NPC80597
Remote Similarity	0.6474	NPC212376
Remote Similarity	0.6474	NPC38736
Remote Similarity	0.6474	NPC207726
Remote Similarity	0.6474	NPC70922
Remote Similarity	0.6474	NPC75540
Remote Similarity	0.6474	NPC470507
Remote Similarity	0.6474	NPC211572
Remote Similarity	0.6465	NPC61637
Remote Similarity	0.6462	NPC160105
Remote Similarity	0.6462	NPC474561
Remote Similarity	0.6462	NPC49954
Remote Similarity	0.645	NPC72980
Remote Similarity	0.645	NPC88363
Remote Similarity	0.645	NPC232340
Remote Similarity	0.645	NPC149402
Remote Similarity	0.6449	NPC477113
Remote Similarity	0.6448	NPC104483
Remote Similarity	0.6445	NPC249040
Remote Similarity	0.6443	NPC32028
Remote Similarity	0.6436	NPC472444
Remote Similarity	0.6435	NPC476116
Remote Similarity	0.6432	NPC56618
Remote Similarity	0.6432	NPC472122
Remote Similarity	0.6432	NPC24594
Remote Similarity	0.6425	NPC322644
Remote Similarity	0.6422	NPC171171
Remote Similarity	0.6419	NPC180504
Remote Similarity	0.6418	NPC478032
Remote Similarity	0.6414	NPC474409
Remote Similarity	0.641	NPC471178
Remote Similarity	0.6406	NPC316910
Remote Similarity	0.6406	NPC5145
Remote Similarity	0.6404	NPC204717
Remote Similarity	0.6404	NPC190007
Remote Similarity	0.6402	NPC105818
Remote Similarity	0.6402	NPC24678
Remote Similarity	0.6402	NPC470505
Remote Similarity	0.6402	NPC470500
Remote Similarity	0.6398	NPC32200
Remote Similarity	0.6398	NPC476167
Remote Similarity	0.6392	NPC282231
Remote Similarity	0.6392	NPC177404
Remote Similarity	0.6387	NPC471458
Remote Similarity	0.6382	NPC469938
Remote Similarity	0.6382	NPC471579
Remote Similarity	0.6381	NPC77555
Remote Similarity	0.6373	NPC135141
Remote Similarity	0.6373	NPC92796
Remote Similarity	0.6373	NPC314002
Remote Similarity	0.6373	NPC67056
Remote Similarity	0.6373	NPC84508
Remote Similarity	0.6373	NPC94943
Remote Similarity	0.6364	NPC476686
Remote Similarity	0.6364	NPC105758
Remote Similarity	0.6364	NPC476688
Remote Similarity	0.6364	NPC195314
Remote Similarity	0.6359	NPC311276
Remote Similarity	0.6359	NPC246700
Remote Similarity	0.6359	NPC128751
Remote Similarity	0.6359	NPC194640
Remote Similarity	0.6355	NPC243058
Remote Similarity	0.6355	NPC220765
Remote Similarity	0.6354	NPC469785
Remote Similarity	0.6351	NPC239954
Remote Similarity	0.6351	NPC265576
Remote Similarity	0.6351	NPC192315
Remote Similarity	0.6351	NPC474916
Remote Similarity	0.6349	NPC124005
Remote Similarity	0.6345	NPC201700
Remote Similarity	0.6345	NPC154293
Remote Similarity	0.6345	NPC278874
Remote Similarity	0.634	NPC279918
Remote Similarity	0.6339	NPC314102
Remote Similarity	0.6339	NPC251722
Remote Similarity	0.6337	NPC187827
Remote Similarity	0.6337	NPC54102
Remote Similarity	0.6337	NPC15840
Remote Similarity	0.6337	NPC472105
Remote Similarity	0.6337	NPC162689
Remote Similarity	0.6337	NPC314919
Remote Similarity	0.6335	NPC26872
Remote Similarity	0.6333	NPC256893
Remote Similarity	0.6333	NPC205403
Remote Similarity	0.6333	NPC324611
Remote Similarity	0.6332	NPC314603
Remote Similarity	0.6329	NPC106833
Remote Similarity	0.6329	NPC95783
Remote Similarity	0.6329	NPC469497
Remote Similarity	0.6324	NPC284559
Remote Similarity	0.6324	NPC470003
Remote Similarity	0.6324	NPC59084
Remote Similarity	0.6321	NPC469762
Remote Similarity	0.6318	NPC151939
Remote Similarity	0.6316	NPC198673
Remote Similarity	0.6313	NPC116961
Remote Similarity	0.6313	NPC280548
Remote Similarity	0.6313	NPC126481
Remote Similarity	0.6308	NPC328318
Remote Similarity	0.6308	NPC57398
Remote Similarity	0.6308	NPC470678
Remote Similarity	0.6308	NPC328596
Remote Similarity	0.6307	NPC122718
Remote Similarity	0.6305	NPC144114
Remote Similarity	0.6305	NPC233936
Remote Similarity	0.6303	NPC232130
Remote Similarity	0.63	NPC472586
Remote Similarity	0.63	NPC103687
Remote Similarity	0.63	NPC132631
Remote Similarity	0.63	NPC312872
Remote Similarity	0.6296	NPC474145
Remote Similarity	0.6296	NPC475841
Remote Similarity	0.6294	NPC98187
Remote Similarity	0.6293	NPC62510
Remote Similarity	0.6292	NPC471313
Remote Similarity	0.6292	NPC471311

Drug Structure

NPD4909 OpenBabel08211706322D 31 34 0 0 0 0 0 0 0 0999 V2000 -0.0388 2.5873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 3.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0823 0.1615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9013 1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0768 0.2661 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8958 1.9886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8080 -1.9316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4013 -1.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5468 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 2.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2257 -2.6361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1691 1.6092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4945 0.9706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4836 1.1796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2202 -2.7406 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1810 -1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0827 1.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4781 1.2841 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.6269 -3.6542 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.1756 -1.6180 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 0.2079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 1.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.7024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9487 2.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8147 3.2024 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 3 1 0 0 0 0 2 4 1 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 7 1 0 0 0 0 5 15 2 0 0 0 0 6 8 2 0 0 0 0 6 15 1 0 0 0 0 7 16 2 0 0 0 0 8 16 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 28 1 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 14 21 2 0 0 0 0 15 21 1 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 25 1 0 0 0 0 19 29 1 0 0 0 0 20 22 1 0 0 0 0 20 26 2 0 0 0 0 21 29 1 0 0 0 0 22 27 2 3 0 0 0 22 30 1 0 0 0 0 26 29 1 0 0 0 0 27 28 1 0 0 0 0 30 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000962; DAP000307; DNC001371
DrugBank	DB06155
ChEMBL	CHEMBL111
IUPHAR/BPS	743
PharmaGKB	PA152407999
KEGG Drug	D05731
PubChem CID	104850
ChEBI	34967
CAS Number	168273-06-1

Drug Properties

Molecular Weight	462.08
ALogP	1.9789
MLogP	3
XLogP	6.458
HDA	5
HBD	1
Rotatable Bonds	9
TPSA	53.13
RO5 Violation	1