NPASS drugs

Drug Information

Drug ID:	NPD1965
Drug Name:	Indapamide
Molecular Formula:	C16H16ClN3O3S
Canonical SMILES:	CC1Cc2c(N1N=C(c1ccc(c(c1)S(=O)(=O)N)Cl)O)cccc2
Standard InCHI:	InChI=1S/C16H16ClN3O3S/c1-10-8-11-4-2-3-5-14(11)20(10)19-16(21)12-6-7-13(17)15(9-12)24(18,22)23/h2-7,9-10H,8H2,1H3,(H,19,21)(H2,18,22,23)
Standard InCHIKey:	NDDAHWYSQHTHNT-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1965

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	260
0.1-0.2	2416
0.2-0.3	10288
0.3-0.4	11880
0.4-0.5	4562
0.5-0.6	1448
0.6-0.7	36
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	0.6727	NPC184437
Remote Similarity	0.6707	NPC476689
Remote Similarity	0.6707	NPC476687
Remote Similarity	0.6707	NPC476685
Remote Similarity	0.6667	NPC477890
Remote Similarity	0.6564	NPC476950
Remote Similarity	0.6429	NPC476231
Remote Similarity	0.6392	NPC147957
Remote Similarity	0.6287	NPC226662
Remote Similarity	0.6271	NPC254798
Remote Similarity	0.6263	NPC293472
Remote Similarity	0.6257	NPC325599
Remote Similarity	0.625	NPC470824
Remote Similarity	0.625	NPC192270
Remote Similarity	0.6235	NPC313352
Remote Similarity	0.6234	NPC37584
Remote Similarity	0.6216	NPC476118
Remote Similarity	0.6211	NPC288785
Remote Similarity	0.6203	NPC208280
Remote Similarity	0.6175	NPC316910
Remote Similarity	0.6145	NPC300596
Remote Similarity	0.6145	NPC237649
Remote Similarity	0.6138	NPC158129
Remote Similarity	0.6135	NPC317564
Remote Similarity	0.6134	NPC471785
Remote Similarity	0.612	NPC141353
Remote Similarity	0.6111	NPC471593
Remote Similarity	0.6087	NPC477887
Remote Similarity	0.604	NPC472193
Remote Similarity	0.6038	NPC471663
Remote Similarity	0.6022	NPC131718
Remote Similarity	0.6022	NPC37548
Remote Similarity	0.6021	NPC34508
Remote Similarity	0.6011	NPC471132
Remote Similarity	0.6	NPC471312
Remote Similarity	0.6	NPC288430
Remote Similarity	0.5974	NPC471310
Remote Similarity	0.5959	NPC134586
Remote Similarity	0.5951	NPC313449
Remote Similarity	0.5946	NPC285469
Remote Similarity	0.5941	NPC328590
Remote Similarity	0.5934	NPC187951
Remote Similarity	0.5928	NPC211997
Remote Similarity	0.5926	NPC471130
Remote Similarity	0.5922	NPC472103
Remote Similarity	0.5904	NPC191863
Remote Similarity	0.5904	NPC133470
Remote Similarity	0.5904	NPC289776
Remote Similarity	0.5904	NPC85651
Remote Similarity	0.5901	NPC187036
Remote Similarity	0.5897	NPC211551
Remote Similarity	0.5897	NPC270009
Remote Similarity	0.5892	NPC470507
Remote Similarity	0.5892	NPC38736
Remote Similarity	0.5882	NPC471122
Remote Similarity	0.5876	NPC471743
Remote Similarity	0.5876	NPC204156
Remote Similarity	0.5876	NPC472243
Remote Similarity	0.5873	NPC102423
Remote Similarity	0.586	NPC477889
Remote Similarity	0.5858	NPC325013
Remote Similarity	0.5855	NPC313791
Remote Similarity	0.5854	NPC192209
Remote Similarity	0.5847	NPC288445
Remote Similarity	0.5838	NPC469765
Remote Similarity	0.5838	NPC469763
Remote Similarity	0.5838	NPC469760
Remote Similarity	0.5838	NPC25008
Remote Similarity	0.5838	NPC469786
Remote Similarity	0.5838	NPC259644
Remote Similarity	0.5838	NPC73952
Remote Similarity	0.5829	NPC469428
Remote Similarity	0.582	NPC16667
Remote Similarity	0.582	NPC88970
Remote Similarity	0.5816	NPC472443
Remote Similarity	0.5812	NPC472115
Remote Similarity	0.5812	NPC474561
Remote Similarity	0.5812	NPC472114
Remote Similarity	0.5812	NPC49954
Remote Similarity	0.581	NPC472241
Remote Similarity	0.5806	NPC207726
Remote Similarity	0.5806	NPC211572
Remote Similarity	0.5806	NPC75540
Remote Similarity	0.5806	NPC212376
Remote Similarity	0.5806	NPC80597
Remote Similarity	0.5806	NPC70922
Remote Similarity	0.5802	NPC296163
Remote Similarity	0.5801	NPC242556
Remote Similarity	0.5797	NPC476175
Remote Similarity	0.5795	NPC473432
Remote Similarity	0.5789	NPC478079
Remote Similarity	0.5789	NPC311276
Remote Similarity	0.5789	NPC189116
Remote Similarity	0.5787	NPC243162
Remote Similarity	0.5781	NPC317430
Remote Similarity	0.5781	NPC63751
Remote Similarity	0.5778	NPC478040
Remote Similarity	0.5778	NPC60553
Remote Similarity	0.5775	NPC476464
Remote Similarity	0.5773	NPC471294
Remote Similarity	0.5771	NPC253476
Remote Similarity	0.5769	NPC259678
Remote Similarity	0.5769	NPC472100
Remote Similarity	0.5769	NPC178681
Remote Similarity	0.5769	NPC264589
Remote Similarity	0.5767	NPC470550
Remote Similarity	0.5767	NPC27904
Remote Similarity	0.5767	NPC205652
Remote Similarity	0.5765	NPC248454
Remote Similarity	0.5759	NPC471124
Remote Similarity	0.5756	NPC197680
Remote Similarity	0.5756	NPC259098
Remote Similarity	0.5754	NPC32002
Remote Similarity	0.5754	NPC315348
Remote Similarity	0.5752	NPC33168
Remote Similarity	0.5746	NPC311330
Remote Similarity	0.5745	NPC469762
Remote Similarity	0.5745	NPC129721
Remote Similarity	0.5745	NPC469897
Remote Similarity	0.5742	NPC328793
Remote Similarity	0.5737	NPC282231
Remote Similarity	0.5736	NPC72980
Remote Similarity	0.5735	NPC99666
Remote Similarity	0.5732	NPC288232
Remote Similarity	0.5731	NPC250476
Remote Similarity	0.573	NPC322283
Remote Similarity	0.573	NPC105818
Remote Similarity	0.573	NPC24678
Remote Similarity	0.5729	NPC133306
Remote Similarity	0.5729	NPC472444
Remote Similarity	0.5729	NPC160105
Remote Similarity	0.5714	NPC203754
Remote Similarity	0.5714	NPC475607
Remote Similarity	0.5714	NPC67056
Remote Similarity	0.5714	NPC36495
Remote Similarity	0.5714	NPC472242
Remote Similarity	0.5714	NPC150048
Remote Similarity	0.5707	NPC194640
Remote Similarity	0.5705	NPC291610
Remote Similarity	0.5699	NPC33507
Remote Similarity	0.5698	NPC315051
Remote Similarity	0.5691	NPC469785
Remote Similarity	0.5687	NPC302790
Remote Similarity	0.5685	NPC474081
Remote Similarity	0.5685	NPC326575
Remote Similarity	0.5684	NPC279918
Remote Similarity	0.5684	NPC68650
Remote Similarity	0.5676	NPC124005
Remote Similarity	0.5676	NPC318086
Remote Similarity	0.5676	NPC144691
Remote Similarity	0.5674	NPC316906
Remote Similarity	0.5672	NPC314002
Remote Similarity	0.5672	NPC476319
Remote Similarity	0.5671	NPC471318
Remote Similarity	0.567	NPC477888
Remote Similarity	0.567	NPC280548
Remote Similarity	0.5667	NPC22082
Remote Similarity	0.5667	NPC43477
Remote Similarity	0.5667	NPC186284
Remote Similarity	0.5665	NPC46413
Remote Similarity	0.5663	NPC189812
Remote Similarity	0.5663	NPC475594
Remote Similarity	0.5663	NPC329688
Remote Similarity	0.5663	NPC469938
Remote Similarity	0.5661	NPC211525
Remote Similarity	0.5661	NPC153694
Remote Similarity	0.5654	NPC471177
Remote Similarity	0.5654	NPC59779
Remote Similarity	0.5654	NPC124542
Remote Similarity	0.5654	NPC61637
Remote Similarity	0.5652	NPC129042
Remote Similarity	0.5652	NPC212799
Remote Similarity	0.565	NPC19679
Remote Similarity	0.565	NPC48938
Remote Similarity	0.565	NPC163055
Remote Similarity	0.5648	NPC278887
Remote Similarity	0.5644	NPC171171
Remote Similarity	0.5642	NPC181527
Remote Similarity	0.5638	NPC471458
Remote Similarity	0.5632	NPC92796
Remote Similarity	0.5632	NPC135141
Remote Similarity	0.5629	NPC264580
Remote Similarity	0.5625	NPC472587
Remote Similarity	0.5625	NPC313757
Remote Similarity	0.5622	NPC190007
Remote Similarity	0.5622	NPC472294
Remote Similarity	0.5622	NPC204717
Remote Similarity	0.5621	NPC475915
Remote Similarity	0.5619	NPC44161
Remote Similarity	0.5619	NPC249040
Remote Similarity	0.5619	NPC201700
Remote Similarity	0.5618	NPC159589
Remote Similarity	0.5612	NPC477185
Remote Similarity	0.5612	NPC314603
Remote Similarity	0.5612	NPC474409
Remote Similarity	0.5612	NPC472123
Remote Similarity	0.5606	NPC59269
Remote Similarity	0.5606	NPC477187
Remote Similarity	0.56	NPC314098
Remote Similarity	0.56	NPC231382

Drug Structure

NPD1965 OpenBabel08211701392D 27 29 0 0 1 0 0 0 0 0999 V2000 -2.8255 4.6637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3339 2.1774 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6648 1.4343 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0249 3.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6867 1.6422 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5468 4.2024 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 -3.5686 3.9945 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.0468 3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -4.3776 2.5933 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 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 1.0000 0.0000 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 -1.5000 0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 10 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 11 2 0 0 0 0 5 14 2 0 0 0 0 6 7 2 0 0 0 0 6 12 1 0 0 0 0 7 13 1 0 0 0 0 8 10 1 0 0 0 0 8 11 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 12 16 1 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 19 2 3 0 0 0 16 21 1 0 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 20 1 0 0 0 0 21 27 1 0 0 0 0 22 24 2 0 0 0 0 23 24 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000498
DrugBank	DB00808
ChEMBL	CHEMBL406
IUPHAR/BPS	7203
PharmaGKB	PA449975
KEGG Drug	D00345
PubChem CID	3702
ChEBI	5893
CAS Number	26807-65-8

Drug Properties

Molecular Weight	365.06
ALogP	-0.1973
MLogP	2.34
XLogP	3.744
HDA	6
HBD	2
Rotatable Bonds	7
TPSA	104.37
RO5 Violation	0