NPASS drugs

Drug Information

Drug ID:	NPD1966
Drug Name:	Metolazone
Molecular Formula:	C16H16ClN3O3S
Canonical SMILES:	CC1Nc2cc(Cl)c(cc2C(=O)N1c1ccccc1C)S(=O)(=O)N
Standard InCHI:	InChI=1S/C16H16ClN3O3S/c1-9-5-3-4-6-14(9)20-10(2)19-13-8-12(17)15(24(18,22)23)7-11(13)16(20)21/h3-8,10,19H,1-2H3,(H2,18,22,23)
Standard InCHIKey:	AQCHWTWZEMGIFD-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1966

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	413
0.1-0.2	4556
0.2-0.3	12092
0.3-0.4	10614
0.4-0.5	2659
0.5-0.6	503
0.6-0.7	52
0.7-0.8	1
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	0.7257	NPC117032
Remote Similarity	0.6824	NPC316104
Remote Similarity	0.6824	NPC162417
Remote Similarity	0.6591	NPC2823
Remote Similarity	0.6575	NPC473329
Remote Similarity	0.6571	NPC469560
Remote Similarity	0.6566	NPC268534
Remote Similarity	0.6529	NPC321053
Remote Similarity	0.6506	NPC257490
Remote Similarity	0.6494	NPC300299
Remote Similarity	0.6465	NPC17273
Remote Similarity	0.6465	NPC141612
Remote Similarity	0.6465	NPC135601
Remote Similarity	0.6446	NPC179605
Remote Similarity	0.6446	NPC279385
Remote Similarity	0.6417	NPC276085
Remote Similarity	0.6407	NPC103292
Remote Similarity	0.6404	NPC471164
Remote Similarity	0.6386	NPC291962
Remote Similarity	0.6386	NPC177684
Remote Similarity	0.6384	NPC83214
Remote Similarity	0.6373	NPC177261
Remote Similarity	0.6364	NPC222029
Remote Similarity	0.6347	NPC112373
Remote Similarity	0.6347	NPC161956
Remote Similarity	0.6347	NPC258531
Remote Similarity	0.634	NPC470548
Remote Similarity	0.6337	NPC209389
Remote Similarity	0.6321	NPC355
Remote Similarity	0.6271	NPC471123
Remote Similarity	0.6235	NPC254698
Remote Similarity	0.623	NPC138293
Remote Similarity	0.623	NPC113056
Remote Similarity	0.6203	NPC295021
Remote Similarity	0.6169	NPC133003
Remote Similarity	0.6167	NPC207554
Remote Similarity	0.6162	NPC109787
Remote Similarity	0.6136	NPC207428
Remote Similarity	0.6122	NPC242269
Remote Similarity	0.612	NPC136002
Remote Similarity	0.6105	NPC477887
Remote Similarity	0.6105	NPC192533
Remote Similarity	0.6096	NPC66936
Remote Similarity	0.6095	NPC226143
Remote Similarity	0.6087	NPC313850
Remote Similarity	0.6082	NPC39818
Remote Similarity	0.6053	NPC84317
Remote Similarity	0.6048	NPC106118
Remote Similarity	0.6034	NPC322433
Remote Similarity	0.6	NPC214960
Remote Similarity	0.6	NPC279527
Remote Similarity	0.6	NPC475094
Remote Similarity	0.6	NPC325599
Remote Similarity	0.599	NPC154478
Remote Similarity	0.5989	NPC130251
Remote Similarity	0.5981	NPC472539
Remote Similarity	0.5981	NPC470787
Remote Similarity	0.5981	NPC472540
Remote Similarity	0.5978	NPC313352
Remote Similarity	0.5978	NPC253476
Remote Similarity	0.5971	NPC128582
Remote Similarity	0.5961	NPC21429
Remote Similarity	0.5956	NPC471574
Remote Similarity	0.5953	NPC225400
Remote Similarity	0.5952	NPC472542
Remote Similarity	0.5952	NPC472541
Remote Similarity	0.595	NPC14849
Remote Similarity	0.5944	NPC173295
Remote Similarity	0.5943	NPC252794
Remote Similarity	0.5939	NPC472118
Remote Similarity	0.5926	NPC472538
Remote Similarity	0.5926	NPC470786
Remote Similarity	0.5926	NPC471155
Remote Similarity	0.5904	NPC181390
Remote Similarity	0.5899	NPC285192
Remote Similarity	0.5899	NPC270241
Remote Similarity	0.5897	NPC189116
Remote Similarity	0.5894	NPC324091
Remote Similarity	0.5892	NPC478040
Remote Similarity	0.5879	NPC122553
Remote Similarity	0.5879	NPC285622
Remote Similarity	0.5876	NPC472102
Remote Similarity	0.5876	NPC309531
Remote Similarity	0.587	NPC43477
Remote Similarity	0.5867	NPC471130
Remote Similarity	0.5854	NPC172170
Remote Similarity	0.585	NPC248862
Remote Similarity	0.585	NPC328611
Remote Similarity	0.5846	NPC88970
Remote Similarity	0.5843	NPC194562
Remote Similarity	0.5843	NPC187231
Remote Similarity	0.5842	NPC182057
Remote Similarity	0.5842	NPC147298
Remote Similarity	0.5842	NPC131450
Remote Similarity	0.5838	NPC182131
Remote Similarity	0.5837	NPC471663
Remote Similarity	0.5833	NPC470205
Remote Similarity	0.5802	NPC134657
Remote Similarity	0.5798	NPC324445
Remote Similarity	0.5789	NPC476440
Remote Similarity	0.5787	NPC328590
Remote Similarity	0.5784	NPC301760
Remote Similarity	0.5784	NPC470301
Remote Similarity	0.5778	NPC40364
Remote Similarity	0.5756	NPC470317
Remote Similarity	0.5754	NPC472245
Remote Similarity	0.575	NPC318183
Remote Similarity	0.575	NPC292265
Remote Similarity	0.5744	NPC471122
Remote Similarity	0.5743	NPC471743
Remote Similarity	0.5741	NPC291610
Remote Similarity	0.574	NPC57051
Remote Similarity	0.5737	NPC237649
Remote Similarity	0.5737	NPC300596
Remote Similarity	0.5731	NPC125416
Remote Similarity	0.5729	NPC63047
Remote Similarity	0.5729	NPC475248
Remote Similarity	0.5728	NPC471199
Remote Similarity	0.5722	NPC469537
Remote Similarity	0.5722	NPC476464
Remote Similarity	0.5714	NPC68650
Remote Similarity	0.5707	NPC144691
Remote Similarity	0.5707	NPC471124
Remote Similarity	0.5706	NPC113099
Remote Similarity	0.57	NPC471943
Remote Similarity	0.5692	NPC61013
Remote Similarity	0.5691	NPC470822
Remote Similarity	0.5689	NPC471197
Remote Similarity	0.5673	NPC473615
Remote Similarity	0.5664	NPC471198
Remote Similarity	0.5664	NPC248601
Remote Similarity	0.5663	NPC36495
Remote Similarity	0.5663	NPC193410
Remote Similarity	0.5652	NPC477003
Remote Similarity	0.5646	NPC229484
Remote Similarity	0.5645	NPC315051
Remote Similarity	0.5642	NPC145754
Remote Similarity	0.5642	NPC295548
Remote Similarity	0.5642	NPC477179
Remote Similarity	0.5636	NPC243850
Remote Similarity	0.5635	NPC126458
Remote Similarity	0.5635	NPC248117
Remote Similarity	0.5625	NPC259626
Remote Similarity	0.5625	NPC316141
Remote Similarity	0.5619	NPC292675
Remote Similarity	0.5618	NPC472244
Remote Similarity	0.5618	NPC470343
Remote Similarity	0.5616	NPC254850
Remote Similarity	0.5616	NPC477178
Remote Similarity	0.5616	NPC477181
Remote Similarity	0.5616	NPC477180
Remote Similarity	0.5612	NPC113946
Remote Similarity	0.5611	NPC150863
Remote Similarity	0.5606	NPC176983
Remote Similarity	0.5604	NPC32858
Remote Similarity	0.5604	NPC194857
Remote Similarity	0.5604	NPC314659

Drug Structure

NPD1966 OpenBabel08211701392D 27 29 0 0 1 0 0 0 0 0999 V2000 3.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 0.8660 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 1.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 2.5981 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 -1.0000 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 0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.8660 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 9 2 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 15 1 0 0 0 0 8 12 1 0 0 0 0 8 13 2 0 0 0 0 9 14 1 0 0 0 0 10 19 1 0 0 0 0 10 20 1 0 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 15 2 0 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 0 0 0 0 15 24 1 0 0 0 0 16 20 1 0 0 0 0 16 21 2 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 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	DAP000749
DrugBank	DB00524
ChEMBL	CHEMBL878
IUPHAR/BPS	4838
PharmaGKB	PA164781022
KEGG Drug	D00431
PubChem CID	4170
ChEBI	64354
CAS Number	17560-51-9

Drug Properties

Molecular Weight	365.06
ALogP	-0.1321
MLogP	2.34
XLogP	2.547
HDA	6
HBD	2
Rotatable Bonds	6
TPSA	100.88
RO5 Violation	0