NPASS drugs

Drug Information

Drug ID:	NPD5841
Drug Name:	Avosentan
Molecular Formula:	C24H22N4O5S
Canonical SMILES:	COc1nc(nc(c1Oc1ccccc1OC)CS(=O)(=O)c1ccc(cn1)C)c1ccncc1
Standard InCHI:	InChI=1S/C24H22N4O5S/c1-16-8-9-21(26-14-16)34(29,30)15-18-22(33-20-7-5-4-6-19(20)31-2)24(32-3)28-23(27-18)17-10-12-25-13-11-17/h4-14H,15H2,1-3H3
Standard InCHIKey:	QSYBKYXDCRITDE-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5841

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	704
0.1-0.2	9973
0.2-0.3	4316
0.3-0.4	11713
0.4-0.5	3085
0.5-0.6	965
0.6-0.7	132
0.7-0.8	2
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	0.7269	NPC316756
Intermediate Similarity	0.7098	NPC56271
Remote Similarity	0.675	NPC290689
Remote Similarity	0.6667	NPC472031
Remote Similarity	0.6667	NPC472066
Remote Similarity	0.6667	NPC472067
Remote Similarity	0.6641	NPC30540
Remote Similarity	0.6617	NPC150447
Remote Similarity	0.6611	NPC476581
Remote Similarity	0.6611	NPC16452
Remote Similarity	0.6611	NPC36229
Remote Similarity	0.6567	NPC133140
Remote Similarity	0.6567	NPC195268
Remote Similarity	0.6564	NPC168486
Remote Similarity	0.6564	NPC222592
Remote Similarity	0.654	NPC4071
Remote Similarity	0.654	NPC476578
Remote Similarity	0.654	NPC476582
Remote Similarity	0.6535	NPC160666
Remote Similarity	0.6527	NPC472068
Remote Similarity	0.6522	NPC20249
Remote Similarity	0.6522	NPC314954
Remote Similarity	0.6485	NPC31930
Remote Similarity	0.6466	NPC308906
Remote Similarity	0.6466	NPC74382
Remote Similarity	0.6466	NPC206251
Remote Similarity	0.6463	NPC162530
Remote Similarity	0.6456	NPC267928
Remote Similarity	0.6438	NPC472289
Remote Similarity	0.6437	NPC39092
Remote Similarity	0.6423	NPC112206
Remote Similarity	0.6423	NPC202605
Remote Similarity	0.6423	NPC202768
Remote Similarity	0.6423	NPC53069
Remote Similarity	0.6423	NPC296482
Remote Similarity	0.6412	NPC477795
Remote Similarity	0.6412	NPC477796
Remote Similarity	0.6412	NPC477805
Remote Similarity	0.6412	NPC477806
Remote Similarity	0.6407	NPC284559
Remote Similarity	0.6395	NPC24802
Remote Similarity	0.6392	NPC315822
Remote Similarity	0.6386	NPC473513
Remote Similarity	0.6378	NPC153467
Remote Similarity	0.6378	NPC103687
Remote Similarity	0.6378	NPC132631
Remote Similarity	0.6368	NPC224327
Remote Similarity	0.6364	NPC130570
Remote Similarity	0.6352	NPC313189
Remote Similarity	0.6342	NPC201508
Remote Similarity	0.6329	NPC226202
Remote Similarity	0.6307	NPC19872
Remote Similarity	0.6295	NPC173080
Remote Similarity	0.629	NPC171409
Remote Similarity	0.629	NPC96405
Remote Similarity	0.6281	NPC469308
Remote Similarity	0.627	NPC329708
Remote Similarity	0.627	NPC47059
Remote Similarity	0.627	NPC264166
Remote Similarity	0.627	NPC274291
Remote Similarity	0.627	NPC118832
Remote Similarity	0.627	NPC165349
Remote Similarity	0.6266	NPC287437
Remote Similarity	0.626	NPC287208
Remote Similarity	0.626	NPC216612
Remote Similarity	0.6255	NPC469554
Remote Similarity	0.6255	NPC101543
Remote Similarity	0.625	NPC242923
Remote Similarity	0.625	NPC144114
Remote Similarity	0.624	NPC477019
Remote Similarity	0.6231	NPC141053
Remote Similarity	0.6231	NPC96584
Remote Similarity	0.6231	NPC180504
Remote Similarity	0.6231	NPC255800
Remote Similarity	0.623	NPC473822
Remote Similarity	0.623	NPC475774
Remote Similarity	0.6229	NPC230805
Remote Similarity	0.6227	NPC41982
Remote Similarity	0.6225	NPC471603
Remote Similarity	0.622	NPC135549
Remote Similarity	0.6206	NPC250178
Remote Similarity	0.6184	NPC164664
Remote Similarity	0.6179	NPC323345
Remote Similarity	0.6179	NPC470164
Remote Similarity	0.6178	NPC177404
Remote Similarity	0.6174	NPC312872
Remote Similarity	0.6163	NPC107160
Remote Similarity	0.6157	NPC105758
Remote Similarity	0.6157	NPC476688
Remote Similarity	0.6157	NPC476686
Remote Similarity	0.6151	NPC288349
Remote Similarity	0.6145	NPC167860
Remote Similarity	0.6145	NPC123976
Remote Similarity	0.614	NPC278874
Remote Similarity	0.6138	NPC285558
Remote Similarity	0.6134	NPC134079
Remote Similarity	0.613	NPC208060
Remote Similarity	0.6115	NPC115595
Remote Similarity	0.6114	NPC476518
Remote Similarity	0.6113	NPC471614
Remote Similarity	0.6111	NPC118776
Remote Similarity	0.6111	NPC51854
Remote Similarity	0.6111	NPC266551
Remote Similarity	0.6111	NPC161887
Remote Similarity	0.6111	NPC219963
Remote Similarity	0.6111	NPC477891
Remote Similarity	0.6107	NPC234197
Remote Similarity	0.6098	NPC476138
Remote Similarity	0.6098	NPC245816
Remote Similarity	0.6096	NPC26679
Remote Similarity	0.6096	NPC251160
Remote Similarity	0.6094	NPC472168
Remote Similarity	0.6087	NPC121658
Remote Similarity	0.6087	NPC14651
Remote Similarity	0.6082	NPC472434
Remote Similarity	0.6076	NPC204385
Remote Similarity	0.6074	NPC9729
Remote Similarity	0.6071	NPC236668
Remote Similarity	0.6071	NPC476287
Remote Similarity	0.6061	NPC295228
Remote Similarity	0.6047	NPC146976
Remote Similarity	0.6047	NPC235076
Remote Similarity	0.6044	NPC26850
Remote Similarity	0.604	NPC185782
Remote Similarity	0.6039	NPC100079
Remote Similarity	0.6039	NPC23614
Remote Similarity	0.6031	NPC21461
Remote Similarity	0.6016	NPC188420
Remote Similarity	0.6016	NPC213530
Remote Similarity	0.6016	NPC193267
Remote Similarity	0.6009	NPC118511
Remote Similarity	0.6008	NPC271215
Remote Similarity	0.6008	NPC149471
Remote Similarity	0.6	NPC12100
Remote Similarity	0.5991	NPC111624
Remote Similarity	0.5985	NPC322482
Remote Similarity	0.5982	NPC26872
Remote Similarity	0.5977	NPC187145
Remote Similarity	0.5977	NPC314270
Remote Similarity	0.5975	NPC470474
Remote Similarity	0.5965	NPC224632
Remote Similarity	0.5964	NPC472435
Remote Similarity	0.5958	NPC110741
Remote Similarity	0.5953	NPC17565
Remote Similarity	0.5953	NPC46451
Remote Similarity	0.5951	NPC470586
Remote Similarity	0.5946	NPC122463
Remote Similarity	0.5945	NPC266931
Remote Similarity	0.5936	NPC477111
Remote Similarity	0.5934	NPC26543
Remote Similarity	0.5932	NPC249662
Remote Similarity	0.593	NPC174049
Remote Similarity	0.5926	NPC289786
Remote Similarity	0.5925	NPC470889
Remote Similarity	0.5923	NPC65277
Remote Similarity	0.5919	NPC161801
Remote Similarity	0.5913	NPC471178
Remote Similarity	0.5911	NPC121772
Remote Similarity	0.5907	NPC206201
Remote Similarity	0.5907	NPC17305
Remote Similarity	0.5899	NPC472436
Remote Similarity	0.5898	NPC8022
Remote Similarity	0.5898	NPC470799
Remote Similarity	0.5895	NPC59779
Remote Similarity	0.5895	NPC471177
Remote Similarity	0.5895	NPC124542
Remote Similarity	0.5894	NPC476997
Remote Similarity	0.5887	NPC232727
Remote Similarity	0.5885	NPC118121
Remote Similarity	0.5878	NPC473053
Remote Similarity	0.5878	NPC2497
Remote Similarity	0.5873	NPC476465
Remote Similarity	0.5872	NPC224764
Remote Similarity	0.5871	NPC476998
Remote Similarity	0.5871	NPC469792
Remote Similarity	0.5871	NPC476996
Remote Similarity	0.587	NPC187558
Remote Similarity	0.587	NPC97367
Remote Similarity	0.5863	NPC66815
Remote Similarity	0.5861	NPC84853
Remote Similarity	0.5853	NPC197141
Remote Similarity	0.5853	NPC204446
Remote Similarity	0.5851	NPC254762
Remote Similarity	0.585	NPC174672
Remote Similarity	0.585	NPC174758
Remote Similarity	0.5849	NPC476999
Remote Similarity	0.5847	NPC315957
Remote Similarity	0.5847	NPC283152
Remote Similarity	0.584	NPC469440
Remote Similarity	0.584	NPC471615
Remote Similarity	0.5839	NPC270515
Remote Similarity	0.5833	NPC42591
Remote Similarity	0.5833	NPC476994
Remote Similarity	0.5827	NPC219664
Remote Similarity	0.5827	NPC53534
Remote Similarity	0.5824	NPC210434
Remote Similarity	0.5823	NPC42979
Remote Similarity	0.5817	NPC214980
Remote Similarity	0.5812	NPC258773
Remote Similarity	0.5811	NPC24019

Drug Structure

NPD5841 OpenBabel08211708292D 34 37 0 0 0 0 0 0 0 0999 V2000 -0.0000 4.0000 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 -1.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -4.3301 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -3.4641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.4641 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 -4.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 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 -5.5000 -0.8660 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 -1.0000 -0.0000 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 -4.0000 -1.7321 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 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5981 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 -1.0000 -1.7321 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 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -1.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 0.0000 N 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 2.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -3.4641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.7321 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 16 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 19 2 0 0 0 0 7 20 2 0 0 0 0 8 9 2 0 0 0 0 8 16 1 0 0 0 0 9 21 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 13 2 0 0 0 0 11 17 1 0 0 0 0 12 25 2 0 0 0 0 13 25 1 0 0 0 0 14 16 2 0 0 0 0 14 26 1 0 0 0 0 15 18 1 0 0 0 0 15 34 1 0 0 0 0 17 23 1 0 0 0 0 18 22 2 0 0 0 0 18 27 1 0 0 0 0 19 20 1 0 0 0 0 19 31 1 0 0 0 0 20 33 1 0 0 0 0 21 26 2 0 0 0 0 21 34 1 0 0 0 0 22 24 1 0 0 0 0 22 33 1 0 0 0 0 23 27 2 0 0 0 0 23 28 1 0 0 0 0 24 28 2 0 0 0 0 24 32 1 0 0 0 0 29 34 2 0 0 0 0 30 34 2 0 0 0 0 M END $$$$

External Identifiers

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

Drug Properties

Molecular Weight	478.13
ALogP	-0.0293
MLogP	3
XLogP	3.799
HDA	6
HBD	0
Rotatable Bonds	11
TPSA	121.77
RO5 Violation	0