NPASS drugs

Drug Information

Drug ID:	NPD6774
Drug Name:	Bosentan
Molecular Formula:	C27H29N5O6S
Canonical SMILES:	OCCOc1nc(nc(c1Oc1ccccc1OC)NS(=O)(=O)c1ccc(cc1)C(C)(C)C)c1ncccn1
Standard InCHI:	InChI=1S/C27H29N5O6S/c1-27(2,3)18-10-12-19(13-11-18)39(34,35)32-23-22(38-21-9-6-5-8-20(21)36-4)26(37-17-16-33)31-25(30-23)24-28-14-7-15-29-24/h5-15,33H,16-17H2,1-4H3,(H,30,31,32)
Standard InCHIKey:	GJPICJJJRGTNOD-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD6774

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	465
0.1-0.2	3499
0.2-0.3	9708
0.3-0.4	9653
0.4-0.5	6497
0.5-0.6	983
0.6-0.7	84
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	0.7102	NPC160666
Remote Similarity	0.6731	NPC56271
Remote Similarity	0.6642	NPC150447
Remote Similarity	0.6628	NPC472067
Remote Similarity	0.6628	NPC477806
Remote Similarity	0.6628	NPC472031
Remote Similarity	0.6628	NPC477795
Remote Similarity	0.6628	NPC472066
Remote Similarity	0.6628	NPC477796
Remote Similarity	0.6628	NPC477805
Remote Similarity	0.6626	NPC250178
Remote Similarity	0.6615	NPC472068
Remote Similarity	0.6559	NPC308906
Remote Similarity	0.65	NPC316756
Remote Similarity	0.6473	NPC30540
Remote Similarity	0.6426	NPC226202
Remote Similarity	0.6417	NPC314954
Remote Similarity	0.6407	NPC20249
Remote Similarity	0.6382	NPC471603
Remote Similarity	0.6367	NPC290689
Remote Similarity	0.6345	NPC267928
Remote Similarity	0.6342	NPC469554
Remote Similarity	0.6341	NPC242923
Remote Similarity	0.6333	NPC19872
Remote Similarity	0.6328	NPC115595
Remote Similarity	0.6314	NPC107160
Remote Similarity	0.6304	NPC21461
Remote Similarity	0.6288	NPC472434
Remote Similarity	0.6279	NPC101543
Remote Similarity	0.625	NPC112206
Remote Similarity	0.625	NPC202605
Remote Similarity	0.623	NPC16452
Remote Similarity	0.623	NPC36229
Remote Similarity	0.623	NPC476581
Remote Similarity	0.6207	NPC219963
Remote Similarity	0.6207	NPC161887
Remote Similarity	0.6198	NPC471614
Remote Similarity	0.6196	NPC130570
Remote Similarity	0.6185	NPC26679
Remote Similarity	0.6178	NPC201508
Remote Similarity	0.6176	NPC133140
Remote Similarity	0.6176	NPC195268
Remote Similarity	0.6169	NPC123976
Remote Similarity	0.6169	NPC167860
Remote Similarity	0.6166	NPC193267
Remote Similarity	0.6166	NPC213530
Remote Similarity	0.6165	NPC470504
Remote Similarity	0.6162	NPC472435
Remote Similarity	0.6157	NPC476578
Remote Similarity	0.6157	NPC4071
Remote Similarity	0.6157	NPC476582
Remote Similarity	0.6154	NPC287208
Remote Similarity	0.6151	NPC289786
Remote Similarity	0.6145	NPC295228
Remote Similarity	0.613	NPC141053
Remote Similarity	0.613	NPC255800
Remote Similarity	0.613	NPC96584
Remote Similarity	0.6122	NPC245816
Remote Similarity	0.6122	NPC476138
Remote Similarity	0.6107	NPC31930
Remote Similarity	0.6107	NPC469308
Remote Similarity	0.6096	NPC162530
Remote Similarity	0.6096	NPC476287
Remote Similarity	0.6095	NPC472436
Remote Similarity	0.6087	NPC12100
Remote Similarity	0.6085	NPC132631
Remote Similarity	0.6085	NPC103687
Remote Similarity	0.6074	NPC51854
Remote Similarity	0.6068	NPC266551
Remote Similarity	0.6064	NPC185782
Remote Similarity	0.6063	NPC473822
Remote Similarity	0.6056	NPC296482
Remote Similarity	0.6056	NPC202768
Remote Similarity	0.6056	NPC53069
Remote Similarity	0.6047	NPC470799
Remote Similarity	0.6047	NPC8022
Remote Similarity	0.6047	NPC288349
Remote Similarity	0.6037	NPC9729
Remote Similarity	0.603	NPC39092
Remote Similarity	0.6025	NPC134079
Remote Similarity	0.6008	NPC74382
Remote Similarity	0.6008	NPC206251
Remote Similarity	0.6008	NPC180504
Remote Similarity	0.6	NPC110151
Remote Similarity	0.6	NPC173080
Remote Similarity	0.5993	NPC99891
Remote Similarity	0.5992	NPC475774
Remote Similarity	0.5992	NPC17305
Remote Similarity	0.5985	NPC24802
Remote Similarity	0.5984	NPC313189
Remote Similarity	0.5983	NPC472289
Remote Similarity	0.5976	NPC113369
Remote Similarity	0.5974	NPC14651
Remote Similarity	0.5974	NPC121658
Remote Similarity	0.5968	NPC118832
Remote Similarity	0.5968	NPC165349
Remote Similarity	0.5968	NPC329708
Remote Similarity	0.5968	NPC47059
Remote Similarity	0.5968	NPC470500
Remote Similarity	0.5968	NPC264166
Remote Similarity	0.5968	NPC274291
Remote Similarity	0.5967	NPC473053
Remote Similarity	0.5956	NPC26543
Remote Similarity	0.5942	NPC258048
Remote Similarity	0.5939	NPC187145
Remote Similarity	0.5938	NPC197141
Remote Similarity	0.5932	NPC118776
Remote Similarity	0.5931	NPC476518
Remote Similarity	0.5929	NPC96405
Remote Similarity	0.5929	NPC171409
Remote Similarity	0.5926	NPC280638
Remote Similarity	0.5917	NPC110741
Remote Similarity	0.5913	NPC5145
Remote Similarity	0.5911	NPC232727
Remote Similarity	0.5907	NPC216612
Remote Similarity	0.5907	NPC122463
Remote Similarity	0.5906	NPC266931
Remote Similarity	0.5904	NPC285558
Remote Similarity	0.5898	NPC473513
Remote Similarity	0.5889	NPC316224
Remote Similarity	0.5889	NPC75179
Remote Similarity	0.5882	NPC471891
Remote Similarity	0.587	NPC477019
Remote Similarity	0.5866	NPC251160
Remote Similarity	0.5865	NPC144114
Remote Similarity	0.5865	NPC470474
Remote Similarity	0.5865	NPC158055
Remote Similarity	0.5862	NPC35761
Remote Similarity	0.5857	NPC135549
Remote Similarity	0.5853	NPC136924
Remote Similarity	0.5851	NPC224327
Remote Similarity	0.5848	NPC53534
Remote Similarity	0.5847	NPC470586
Remote Similarity	0.5836	NPC152620
Remote Similarity	0.5833	NPC308392
Remote Similarity	0.5833	NPC477111
Remote Similarity	0.583	NPC287437
Remote Similarity	0.5826	NPC97367
Remote Similarity	0.582	NPC84853
Remote Similarity	0.5816	NPC284559
Remote Similarity	0.5814	NPC314270
Remote Similarity	0.5814	NPC467439
Remote Similarity	0.5812	NPC111624
Remote Similarity	0.581	NPC469589
Remote Similarity	0.5808	NPC310118
Remote Similarity	0.5806	NPC176538
Remote Similarity	0.5801	NPC471178
Remote Similarity	0.5798	NPC477110
Remote Similarity	0.5795	NPC237978
Remote Similarity	0.5795	NPC476997
Remote Similarity	0.5793	NPC171393
Remote Similarity	0.5793	NPC295452
Remote Similarity	0.5787	NPC317054
Remote Similarity	0.5785	NPC46970
Remote Similarity	0.5783	NPC471177
Remote Similarity	0.5783	NPC59779
Remote Similarity	0.5783	NPC124542
Remote Similarity	0.5781	NPC472168
Remote Similarity	0.5781	NPC469592
Remote Similarity	0.5781	NPC471080
Remote Similarity	0.5779	NPC2497
Remote Similarity	0.5774	NPC476996
Remote Similarity	0.5774	NPC476998
Remote Similarity	0.5766	NPC18487
Remote Similarity	0.5766	NPC187558
Remote Similarity	0.5762	NPC473183
Remote Similarity	0.5759	NPC50511
Remote Similarity	0.5756	NPC222592
Remote Similarity	0.5756	NPC168486
Remote Similarity	0.5754	NPC323345
Remote Similarity	0.5754	NPC470164
Remote Similarity	0.5754	NPC478013
Remote Similarity	0.5753	NPC469594
Remote Similarity	0.575	NPC284678
Remote Similarity	0.5748	NPC174672
Remote Similarity	0.5748	NPC174758
Remote Similarity	0.5746	NPC473184
Remote Similarity	0.5745	NPC208060
Remote Similarity	0.5743	NPC234197
Remote Similarity	0.5743	NPC121772
Remote Similarity	0.5736	NPC476994
Remote Similarity	0.5732	NPC477891
Remote Similarity	0.5731	NPC292958
Remote Similarity	0.5726	NPC239954
Remote Similarity	0.5725	NPC118121
Remote Similarity	0.572	NPC230805
Remote Similarity	0.572	NPC312872
Remote Similarity	0.572	NPC477861
Remote Similarity	0.572	NPC236668
Remote Similarity	0.5714	NPC324149
Remote Similarity	0.5714	NPC63109
Remote Similarity	0.5714	NPC477633
Remote Similarity	0.5714	NPC177404
Remote Similarity	0.5709	NPC174049
Remote Similarity	0.5703	NPC476167
Remote Similarity	0.5698	NPC146976
Remote Similarity	0.5698	NPC235076
Remote Similarity	0.5697	NPC3715
Remote Similarity	0.5694	NPC478006
Remote Similarity	0.5693	NPC476451

Drug Structure

NPD6774 OpenBabel08211710072D 41 44 0 0 0 0 0 0 0 0999 V2000 4.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 -0.5000 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 -0.0000 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 4.5000 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 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 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 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 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 4.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 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 4.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 -0.0000 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 6.0000 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 -1.0000 0.0000 O 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 -1.7321 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 -3.4641 7.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 27 1 0 0 0 0 4 36 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 9 1 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 20 2 0 0 0 0 9 21 2 0 0 0 0 10 12 1 0 0 0 0 10 18 2 0 0 0 0 11 13 2 0 0 0 0 11 18 1 0 0 0 0 12 19 2 0 0 0 0 13 19 1 0 0 0 0 14 28 1 0 0 0 0 15 29 2 0 0 0 0 16 17 1 0 0 0 0 16 33 1 0 0 0 0 17 37 1 0 0 0 0 18 27 1 0 0 0 0 19 39 1 0 0 0 0 20 21 1 0 0 0 0 20 36 1 0 0 0 0 21 38 1 0 0 0 0 22 23 2 0 0 0 0 22 26 1 0 0 0 0 22 38 1 0 0 0 0 23 30 1 0 0 0 0 23 32 1 0 0 0 0 24 25 1 0 0 0 0 24 28 2 0 0 0 0 24 29 1 0 0 0 0 25 30 2 0 0 0 0 25 31 1 0 0 0 0 26 31 2 0 0 0 0 26 37 1 0 0 0 0 32 39 1 0 0 0 0 32 40 1 0 0 0 0 33 41 1 0 0 0 0 34 39 2 0 0 0 0 35 39 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DNC000341; DAP000030
DrugBank	DB00559
ChEMBL	CHEMBL957
IUPHAR/BPS	3494
PharmaGKB	PA10034
KEGG Drug	D01227
PubChem CID	104865
ChEBI	51450
CAS Number	147536-97-8

Drug Properties

Molecular Weight	551.18
ALogP	-0.1774
MLogP	3.11
XLogP	5.26
HDA	8
HBD	2
Rotatable Bonds	16
TPSA	154.03
RO5 Violation	2