NPASS drugs

Drug Information

Drug ID:	NPD4949
Drug Name:	GW-660511
Molecular Formula:	C22H22N2O3S2
Canonical SMILES:	SC[C@H](C(=N[C@H](C(=O)O)Cc1ccc(cc1)c1nccs1)O)Cc1ccccc1
Standard InCHI:	InChI=1S/C22H22N2O3S2/c25-20(18(14-28)12-15-4-2-1-3-5-15)24-19(22(26)27)13-16-6-8-17(9-7-16)21-23-10-11-29-21/h1-11,18-19,28H,12-14H2,(H,24,25)(H,26,27)/t18-,19+/m1/s1
Standard InCHIKey:	YPGILAVWVRBSAJ-MOPGFXCFSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4949

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	251
0.1-0.2	1840
0.2-0.3	10445
0.3-0.4	13875
0.4-0.5	2135
0.5-0.6	1835
0.6-0.7	490
0.7-0.8	19
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	NPC161143
Intermediate Similarity	0.75	NPC272483
Intermediate Similarity	0.7473	NPC469938
Intermediate Similarity	0.7231	NPC321708
Intermediate Similarity	0.7196	NPC149155
Intermediate Similarity	0.7196	NPC203468
Intermediate Similarity	0.7196	NPC110500
Intermediate Similarity	0.7192	NPC143325
Intermediate Similarity	0.7173	NPC213468
Intermediate Similarity	0.7158	NPC267885
Intermediate Similarity	0.7136	NPC239660
Intermediate Similarity	0.7136	NPC106235
Intermediate Similarity	0.712	NPC248454
Intermediate Similarity	0.7083	NPC248041
Intermediate Similarity	0.7083	NPC283219
Intermediate Similarity	0.7083	NPC126709
Intermediate Similarity	0.7077	NPC49051
Intermediate Similarity	0.7047	NPC164228
Intermediate Similarity	0.7041	NPC235684
Remote Similarity	0.6984	NPC78020
Remote Similarity	0.6974	NPC163055
Remote Similarity	0.6965	NPC294693
Remote Similarity	0.6963	NPC477976
Remote Similarity	0.6954	NPC94752
Remote Similarity	0.6943	NPC84827
Remote Similarity	0.6943	NPC145885
Remote Similarity	0.6943	NPC14113
Remote Similarity	0.6853	NPC228835
Remote Similarity	0.6842	NPC323927
Remote Similarity	0.684	NPC31385
Remote Similarity	0.684	NPC75726
Remote Similarity	0.684	NPC110602
Remote Similarity	0.6821	NPC248462
Remote Similarity	0.6816	NPC117244
Remote Similarity	0.6816	NPC473763
Remote Similarity	0.6812	NPC476874
Remote Similarity	0.6806	NPC63751
Remote Similarity	0.68	NPC188104
Remote Similarity	0.6786	NPC249662
Remote Similarity	0.6784	NPC62749
Remote Similarity	0.6782	NPC165538
Remote Similarity	0.6779	NPC75498
Remote Similarity	0.6769	NPC64436
Remote Similarity	0.6769	NPC111275
Remote Similarity	0.6766	NPC122427
Remote Similarity	0.6757	NPC216713
Remote Similarity	0.6754	NPC474561
Remote Similarity	0.6754	NPC49954
Remote Similarity	0.6754	NPC475920
Remote Similarity	0.6735	NPC55772
Remote Similarity	0.672	NPC161108
Remote Similarity	0.6705	NPC322488
Remote Similarity	0.6702	NPC477975
Remote Similarity	0.6683	NPC329961
Remote Similarity	0.6667	NPC17059
Remote Similarity	0.6667	NPC160105
Remote Similarity	0.665	NPC262898
Remote Similarity	0.665	NPC11126
Remote Similarity	0.6648	NPC324611
Remote Similarity	0.6648	NPC65408
Remote Similarity	0.6634	NPC255909
Remote Similarity	0.6634	NPC157828
Remote Similarity	0.6634	NPC195239
Remote Similarity	0.6632	NPC279918
Remote Similarity	0.6631	NPC469760
Remote Similarity	0.6631	NPC25008
Remote Similarity	0.6631	NPC469786
Remote Similarity	0.6631	NPC469763
Remote Similarity	0.6631	NPC73952
Remote Similarity	0.6631	NPC469765
Remote Similarity	0.6631	NPC259644
Remote Similarity	0.662	NPC478158
Remote Similarity	0.6619	NPC138562
Remote Similarity	0.6618	NPC474916
Remote Similarity	0.6614	NPC129721
Remote Similarity	0.6614	NPC469762
Remote Similarity	0.6609	NPC471311
Remote Similarity	0.6609	NPC471313
Remote Similarity	0.6602	NPC179701
Remote Similarity	0.6602	NPC11445
Remote Similarity	0.6599	NPC183662
Remote Similarity	0.6599	NPC59269
Remote Similarity	0.6599	NPC15573
Remote Similarity	0.6599	NPC217372
Remote Similarity	0.6597	NPC282231
Remote Similarity	0.6596	NPC212376
Remote Similarity	0.6596	NPC75540
Remote Similarity	0.6596	NPC80597
Remote Similarity	0.6596	NPC211572
Remote Similarity	0.6596	NPC70922
Remote Similarity	0.6595	NPC477974
Remote Similarity	0.6588	NPC473376
Remote Similarity	0.6583	NPC71037
Remote Similarity	0.658	NPC41717
Remote Similarity	0.6578	NPC470823
Remote Similarity	0.6576	NPC285731
Remote Similarity	0.6566	NPC219336
Remote Similarity	0.6562	NPC194640
Remote Similarity	0.6561	NPC469785
Remote Similarity	0.6552	NPC213629
Remote Similarity	0.655	NPC143533
Remote Similarity	0.6535	NPC315555
Remote Similarity	0.6531	NPC314603
Remote Similarity	0.6528	NPC251036
Remote Similarity	0.6528	NPC75634
Remote Similarity	0.6528	NPC207020
Remote Similarity	0.6526	NPC54420
Remote Similarity	0.6517	NPC207851
Remote Similarity	0.6509	NPC257511
Remote Similarity	0.6507	NPC293917
Remote Similarity	0.6505	NPC471957
Remote Similarity	0.6502	NPC472323
Remote Similarity	0.6502	NPC238242
Remote Similarity	0.6495	NPC54988
Remote Similarity	0.6493	NPC57398
Remote Similarity	0.649	NPC227582
Remote Similarity	0.6485	NPC96016
Remote Similarity	0.6477	NPC311276
Remote Similarity	0.6477	NPC287895
Remote Similarity	0.6476	NPC315491
Remote Similarity	0.6476	NPC45459
Remote Similarity	0.6468	NPC478157
Remote Similarity	0.6465	NPC162860
Remote Similarity	0.6462	NPC201700
Remote Similarity	0.6456	NPC47190
Remote Similarity	0.6455	NPC149014
Remote Similarity	0.6455	NPC281049
Remote Similarity	0.645	NPC271792
Remote Similarity	0.645	NPC15840
Remote Similarity	0.6445	NPC300183
Remote Similarity	0.6436	NPC165495
Remote Similarity	0.6429	NPC91895
Remote Similarity	0.6422	NPC278434
Remote Similarity	0.6418	NPC113626
Remote Similarity	0.6415	NPC193761
Remote Similarity	0.6409	NPC173344
Remote Similarity	0.6409	NPC29702
Remote Similarity	0.6406	NPC82370
Remote Similarity	0.6404	NPC280290
Remote Similarity	0.6398	NPC252338
Remote Similarity	0.6398	NPC314372
Remote Similarity	0.6393	NPC313640
Remote Similarity	0.639	NPC175474
Remote Similarity	0.6389	NPC145178
Remote Similarity	0.6389	NPC475350
Remote Similarity	0.6389	NPC14877
Remote Similarity	0.6385	NPC98715
Remote Similarity	0.6381	NPC131887
Remote Similarity	0.6381	NPC67288
Remote Similarity	0.6381	NPC171317
Remote Similarity	0.6378	NPC24990
Remote Similarity	0.6376	NPC63279
Remote Similarity	0.6368	NPC469896
Remote Similarity	0.6368	NPC216221
Remote Similarity	0.6368	NPC200214
Remote Similarity	0.6368	NPC471997
Remote Similarity	0.6359	NPC83111
Remote Similarity	0.6355	NPC472119
Remote Similarity	0.6351	NPC50997
Remote Similarity	0.6351	NPC160127
Remote Similarity	0.635	NPC284775
Remote Similarity	0.635	NPC151939
Remote Similarity	0.6348	NPC297642
Remote Similarity	0.6347	NPC54744
Remote Similarity	0.6347	NPC229348
Remote Similarity	0.6345	NPC476103
Remote Similarity	0.6339	NPC253987
Remote Similarity	0.6338	NPC476073
Remote Similarity	0.6338	NPC182507
Remote Similarity	0.6337	NPC233936
Remote Similarity	0.6327	NPC56233
Remote Similarity	0.6324	NPC282103
Remote Similarity	0.6324	NPC15102
Remote Similarity	0.6323	NPC77022
Remote Similarity	0.6321	NPC92796
Remote Similarity	0.6321	NPC135141
Remote Similarity	0.632	NPC478028
Remote Similarity	0.6316	NPC57994
Remote Similarity	0.6316	NPC202812
Remote Similarity	0.6316	NPC289299
Remote Similarity	0.6311	NPC103119
Remote Similarity	0.6308	NPC40779
Remote Similarity	0.6305	NPC159125
Remote Similarity	0.6303	NPC149708
Remote Similarity	0.6303	NPC102008
Remote Similarity	0.6302	NPC51054
Remote Similarity	0.6296	NPC46225
Remote Similarity	0.6296	NPC225821
Remote Similarity	0.6293	NPC478077
Remote Similarity	0.629	NPC190296
Remote Similarity	0.6289	NPC131718
Remote Similarity	0.6287	NPC91179
Remote Similarity	0.6287	NPC300688
Remote Similarity	0.6284	NPC471312
Remote Similarity	0.6283	NPC19170
Remote Similarity	0.6279	NPC314930
Remote Similarity	0.6279	NPC91958
Remote Similarity	0.6279	NPC214827
Remote Similarity	0.6278	NPC256893
Remote Similarity	0.6275	NPC46895

Drug Structure

NPD4949 OpenBabel08211706322D 32 34 0 0 1 0 0 0 0 0999 V2000 -6.1667 -3.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -3.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -3.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0327 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4781 0.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9781 -0.2079 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -0.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 -1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9706 1.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 -0.0055 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4347 2.4945 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3007 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 2.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 1.4945 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 1.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 2.4945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3007 3.9945 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4347 -1.5055 0.0000 S 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 -7.0327 0.9945 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1667 4.4945 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5686 -2.0055 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 15 2 0 0 0 0 5 15 1 0 0 0 0 6 8 1 0 0 0 0 6 16 2 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 17 1 0 0 0 0 10 11 2 0 0 0 0 10 23 1 0 0 0 0 11 29 1 0 0 0 0 12 15 1 0 0 0 0 13 16 1 0 0 0 0 14 18 1 0 0 0 0 14 28 1 0 0 0 0 17 21 1 0 0 0 0 18 12 1 1 0 0 0 18 20 1 0 0 0 0 19 13 1 6 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 24 2 3 0 0 0 20 25 1 0 0 0 0 21 23 2 0 0 0 0 21 29 1 0 0 0 0 22 26 2 0 0 0 0 22 27 1 0 0 0 0 25 30 1 0 0 0 0 27 31 1 0 0 0 0 28 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB003264
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	426.11
ALogP	0.8736
MLogP	3.11
XLogP	6.977
HDA	5
HBD	2
Rotatable Bonds	12
TPSA	149.82
RO5 Violation	1