NPASS drugs

Drug Information

Drug ID:	NPD3396
Drug Name:	Pioglitazone
Molecular Formula:	C19H20N2O3S
Canonical SMILES:	CCc1ccc(nc1)CCOc1ccc(cc1)CC1SC(=O)N=C1O
Standard InCHI:	InChI=1S/C19H20N2O3S/c1-2-13-3-6-15(20-12-13)9-10-24-16-7-4-14(5-8-16)11-17-18(22)21-19(23)25-17/h3-8,12,17H,2,9-11H2,1H3,(H,21,22,23)
Standard InCHIKey:	HYAFETHFCAUJAY-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3396

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	247
0.1-0.2	2089
0.2-0.3	9973
0.3-0.4	3063
0.4-0.5	11266
0.5-0.6	2936
0.6-0.7	1161
0.7-0.8	153
0.8-0.85	2
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	0.8142	NPC222592
Intermediate Similarity	0.8142	NPC168486
Intermediate Similarity	0.7978	NPC177404
Intermediate Similarity	0.7742	NPC283152
Intermediate Similarity	0.772	NPC195268
Intermediate Similarity	0.772	NPC133140
Intermediate Similarity	0.7696	NPC74382
Intermediate Similarity	0.7696	NPC206251
Intermediate Similarity	0.768	NPC289786
Intermediate Similarity	0.764	NPC26872
Intermediate Similarity	0.7602	NPC473053
Intermediate Similarity	0.7596	NPC471178
Intermediate Similarity	0.7582	NPC471177
Intermediate Similarity	0.7582	NPC59779
Intermediate Similarity	0.7582	NPC124542
Intermediate Similarity	0.7563	NPC224928
Intermediate Similarity	0.7562	NPC118832
Intermediate Similarity	0.7562	NPC329708
Intermediate Similarity	0.7562	NPC165349
Intermediate Similarity	0.7562	NPC274291
Intermediate Similarity	0.7562	NPC264166
Intermediate Similarity	0.7562	NPC47059
Intermediate Similarity	0.7527	NPC121658
Intermediate Similarity	0.7527	NPC14651
Intermediate Similarity	0.7526	NPC219963
Intermediate Similarity	0.7514	NPC26850
Intermediate Similarity	0.75	NPC307963
Intermediate Similarity	0.7475	NPC285558
Intermediate Similarity	0.7475	NPC267928
Intermediate Similarity	0.7474	NPC224327
Intermediate Similarity	0.7473	NPC476518
Intermediate Similarity	0.7463	NPC290689
Intermediate Similarity	0.745	NPC477019
Intermediate Similarity	0.7435	NPC161887
Intermediate Similarity	0.7435	NPC266551
Intermediate Similarity	0.7424	NPC251090
Intermediate Similarity	0.7415	NPC174758
Intermediate Similarity	0.7413	NPC232727
Intermediate Similarity	0.7407	NPC288943
Intermediate Similarity	0.74	NPC476578
Intermediate Similarity	0.74	NPC4071
Intermediate Similarity	0.74	NPC476582
Intermediate Similarity	0.74	NPC287437
Intermediate Similarity	0.7391	NPC202605
Intermediate Similarity	0.7391	NPC112206
Intermediate Similarity	0.7389	NPC16452
Intermediate Similarity	0.7389	NPC36229
Intermediate Similarity	0.7389	NPC476581
Intermediate Similarity	0.7381	NPC473822
Intermediate Similarity	0.7358	NPC62069
Intermediate Similarity	0.7354	NPC312872
Intermediate Similarity	0.7351	NPC473057
Intermediate Similarity	0.7347	NPC76748
Intermediate Similarity	0.7344	NPC470474
Intermediate Similarity	0.734	NPC475774
Intermediate Similarity	0.731	NPC92111
Intermediate Similarity	0.7302	NPC111624
Intermediate Similarity	0.7296	NPC296527
Intermediate Similarity	0.7282	NPC287208
Intermediate Similarity	0.7277	NPC19872
Intermediate Similarity	0.7277	NPC234197
Intermediate Similarity	0.7273	NPC266931
Intermediate Similarity	0.7268	NPC323345
Intermediate Similarity	0.7268	NPC472111
Intermediate Similarity	0.7268	NPC470164
Intermediate Similarity	0.7264	NPC213530
Intermediate Similarity	0.7264	NPC193267
Intermediate Similarity	0.7247	NPC471323
Intermediate Similarity	0.7246	NPC469589
Intermediate Similarity	0.7246	NPC174672
Intermediate Similarity	0.7245	NPC66083
Intermediate Similarity	0.7241	NPC31930
Intermediate Similarity	0.7236	NPC79293
Intermediate Similarity	0.7236	NPC279401
Intermediate Similarity	0.7233	NPC313189
Intermediate Similarity	0.7233	NPC193238
Intermediate Similarity	0.7225	NPC296482
Intermediate Similarity	0.7225	NPC202768
Intermediate Similarity	0.7225	NPC53069
Intermediate Similarity	0.7222	NPC469390
Intermediate Similarity	0.7212	NPC123976
Intermediate Similarity	0.7212	NPC11464
Intermediate Similarity	0.7212	NPC167860
Intermediate Similarity	0.7204	NPC274982
Intermediate Similarity	0.7204	NPC288349
Intermediate Similarity	0.7198	NPC82548
Intermediate Similarity	0.7198	NPC475910
Intermediate Similarity	0.7196	NPC60621
Intermediate Similarity	0.7194	NPC204385
Intermediate Similarity	0.7192	NPC315957
Intermediate Similarity	0.7192	NPC176538
Intermediate Similarity	0.7183	NPC168209
Intermediate Similarity	0.7182	NPC255800
Intermediate Similarity	0.7182	NPC96584
Intermediate Similarity	0.7177	NPC242923
Intermediate Similarity	0.7172	NPC134079
Intermediate Similarity	0.7169	NPC201508
Intermediate Similarity	0.7164	NPC13880
Intermediate Similarity	0.7151	NPC25899
Intermediate Similarity	0.715	NPC226202
Intermediate Similarity	0.7143	NPC295158
Intermediate Similarity	0.7143	NPC20249
Intermediate Similarity	0.7143	NPC99891
Intermediate Similarity	0.7143	NPC316981
Intermediate Similarity	0.7143	NPC251160
Intermediate Similarity	0.7129	NPC470020
Intermediate Similarity	0.7116	NPC310118
Intermediate Similarity	0.7109	NPC476287
Intermediate Similarity	0.7109	NPC236668
Intermediate Similarity	0.7108	NPC121772
Intermediate Similarity	0.7107	NPC61350
Intermediate Similarity	0.7105	NPC473764
Intermediate Similarity	0.7105	NPC314940
Intermediate Similarity	0.71	NPC280964
Intermediate Similarity	0.71	NPC324149
Intermediate Similarity	0.71	NPC114335
Intermediate Similarity	0.71	NPC141915
Intermediate Similarity	0.71	NPC99666
Intermediate Similarity	0.7094	NPC127085
Intermediate Similarity	0.7092	NPC84478
Intermediate Similarity	0.7092	NPC320394
Intermediate Similarity	0.709	NPC108469
Intermediate Similarity	0.7087	NPC476138
Intermediate Similarity	0.7087	NPC245816
Intermediate Similarity	0.7085	NPC3715
Intermediate Similarity	0.7083	NPC243633
Intermediate Similarity	0.7083	NPC175150
Intermediate Similarity	0.7077	NPC206201
Intermediate Similarity	0.7075	NPC146976
Intermediate Similarity	0.7074	NPC118511
Intermediate Similarity	0.7071	NPC46580
Intermediate Similarity	0.707	NPC174049
Intermediate Similarity	0.7067	NPC135549
Intermediate Similarity	0.7064	NPC153467
Intermediate Similarity	0.7062	NPC26679
Intermediate Similarity	0.7062	NPC96405
Intermediate Similarity	0.7062	NPC264176
Intermediate Similarity	0.7062	NPC171409
Intermediate Similarity	0.7059	NPC18487
Intermediate Similarity	0.7056	NPC173080
Intermediate Similarity	0.7053	NPC470500
Intermediate Similarity	0.7053	NPC210256
Intermediate Similarity	0.7042	NPC170114
Intermediate Similarity	0.7039	NPC295898
Intermediate Similarity	0.7032	NPC110151
Intermediate Similarity	0.7028	NPC471080
Intermediate Similarity	0.7028	NPC469592
Intermediate Similarity	0.7024	NPC329747
Intermediate Similarity	0.7021	NPC48192
Intermediate Similarity	0.7014	NPC208284
Intermediate Similarity	0.7011	NPC256893
Intermediate Similarity	0.701	NPC211997
Intermediate Similarity	0.701	NPC239954
Intermediate Similarity	0.7005	NPC53144
Intermediate Similarity	0.7005	NPC122463
Remote Similarity	0.6995	NPC470549
Remote Similarity	0.6984	NPC97367
Remote Similarity	0.6984	NPC263439
Remote Similarity	0.698	NPC329541
Remote Similarity	0.698	NPC84853
Remote Similarity	0.698	NPC198673
Remote Similarity	0.6978	NPC161292
Remote Similarity	0.697	NPC314002
Remote Similarity	0.697	NPC42591
Remote Similarity	0.6963	NPC8022
Remote Similarity	0.6963	NPC470799
Remote Similarity	0.6961	NPC243834
Remote Similarity	0.6961	NPC70956
Remote Similarity	0.6959	NPC134586
Remote Similarity	0.6959	NPC203754
Remote Similarity	0.6959	NPC150048
Remote Similarity	0.6957	NPC475112
Remote Similarity	0.6957	NPC475085
Remote Similarity	0.6957	NPC291535
Remote Similarity	0.6954	NPC163055
Remote Similarity	0.6952	NPC470931
Remote Similarity	0.6948	NPC162530
Remote Similarity	0.6944	NPC17565
Remote Similarity	0.6938	NPC476106
Remote Similarity	0.6935	NPC171171
Remote Similarity	0.6927	NPC72211
Remote Similarity	0.6927	NPC168911
Remote Similarity	0.6923	NPC223427
Remote Similarity	0.6923	NPC246381
Remote Similarity	0.6923	NPC248454
Remote Similarity	0.6923	NPC96890
Remote Similarity	0.6923	NPC469440
Remote Similarity	0.6919	NPC185782
Remote Similarity	0.6919	NPC204717
Remote Similarity	0.6915	NPC84508
Remote Similarity	0.6912	NPC54066
Remote Similarity	0.6912	NPC128115
Remote Similarity	0.6901	NPC472098
Remote Similarity	0.69	NPC472434
Remote Similarity	0.6898	NPC314270
Remote Similarity	0.6898	NPC204446
Remote Similarity	0.6898	NPC469594
Remote Similarity	0.6895	NPC311276
Remote Similarity	0.6895	NPC122436
Remote Similarity	0.6892	NPC469792

Drug Structure

NPD3396 OpenBabel08211703112D 26 28 0 0 1 0 0 0 0 0999 V2000 8.7173 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8512 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1192 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9230 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3871 -3.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5211 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1192 -1.5878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9852 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 -2.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7891 -3.0878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -0.5878 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6180 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2532 -2.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3090 0.9511 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5691 -0.3090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2788 1.7601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6551 -3.5878 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 -2.7770 -1.2872 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 13 1 0 0 0 0 3 6 2 0 0 0 0 3 13 1 0 0 0 0 4 7 1 0 0 0 0 4 14 2 0 0 0 0 5 8 2 0 0 0 0 5 14 1 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 1 0 0 0 0 9 15 1 0 0 0 0 10 24 1 0 0 0 0 11 14 1 0 0 0 0 11 17 1 0 0 0 0 12 13 2 0 0 0 0 12 20 1 0 0 0 0 15 20 2 0 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 25 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 19 21 1 0 0 0 0 19 23 2 0 0 0 0 19 25 1 0 0 0 0 22 26 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000272; DAP001440; DNCL002880
DrugBank	DB01132
ChEMBL	CHEMBL595
IUPHAR/BPS	2694
PharmaGKB	PA450970
KEGG Drug
PubChem CID	4829
ChEBI	8228
CAS Number	111025-46-8

Drug Properties

Molecular Weight	356.12
ALogP	0.0394
MLogP	2.89
XLogP	4.313
HDA	4
HBD	1
Rotatable Bonds	9
TPSA	97.08
RO5 Violation	0