NPASS drugs

Drug Information

Drug ID:	NPD4953
Drug Name:	Darusentan
Molecular Formula:	C22H22N2O6
Canonical SMILES:	COC([C@@H](C(=O)O)Oc1nc(OC)cc(n1)OC)(c1ccccc1)c1ccccc1
Standard InCHI:	InChI=1S/C22H22N2O6/c1-27-17-14-18(28-2)24-21(23-17)30-19(20(25)26)22(29-3,15-10-6-4-7-11-15)16-12-8-5-9-13-16/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1
Standard InCHIKey:	FEJVSJIALLTFRP-LJQANCHMSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4953

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	220
0.1-0.2	1162
0.2-0.3	4059
0.3-0.4	8631
0.4-0.5	9122
0.5-0.6	7561
0.6-0.7	135
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	0.6683	NPC320394
Remote Similarity	0.6667	NPC144114
Remote Similarity	0.6616	NPC208060
Remote Similarity	0.6584	NPC477891
Remote Similarity	0.6582	NPC51854
Remote Similarity	0.6547	NPC128115
Remote Similarity	0.6542	NPC317572
Remote Similarity	0.654	NPC9729
Remote Similarity	0.6513	NPC224632
Remote Similarity	0.6507	NPC160666
Remote Similarity	0.6482	NPC476688
Remote Similarity	0.6482	NPC105758
Remote Similarity	0.6482	NPC476686
Remote Similarity	0.6465	NPC278874
Remote Similarity	0.6429	NPC79293
Remote Similarity	0.6429	NPC279401
Remote Similarity	0.6398	NPC280638
Remote Similarity	0.6376	NPC243850
Remote Similarity	0.6359	NPC26850
Remote Similarity	0.6355	NPC283152
Remote Similarity	0.633	NPC313796
Remote Similarity	0.633	NPC314855
Remote Similarity	0.633	NPC315638
Remote Similarity	0.633	NPC313345
Remote Similarity	0.6311	NPC314270
Remote Similarity	0.6306	NPC292517
Remote Similarity	0.6303	NPC141915
Remote Similarity	0.6303	NPC280964
Remote Similarity	0.6303	NPC114335
Remote Similarity	0.6301	NPC315545
Remote Similarity	0.6301	NPC314297
Remote Similarity	0.6296	NPC54537
Remote Similarity	0.629	NPC314834
Remote Similarity	0.6283	NPC48317
Remote Similarity	0.6278	NPC151781
Remote Similarity	0.6278	NPC74562
Remote Similarity	0.6278	NPC316181
Remote Similarity	0.6269	NPC164664
Remote Similarity	0.6261	NPC242923
Remote Similarity	0.6256	NPC469439
Remote Similarity	0.6225	NPC288943
Remote Similarity	0.6222	NPC30570
Remote Similarity	0.6211	NPC136924
Remote Similarity	0.6205	NPC26872
Remote Similarity	0.6203	NPC470785
Remote Similarity	0.6202	NPC62069
Remote Similarity	0.6195	NPC162812
Remote Similarity	0.619	NPC254762
Remote Similarity	0.619	NPC148860
Remote Similarity	0.6181	NPC177404
Remote Similarity	0.6176	NPC312872
Remote Similarity	0.6161	NPC61435
Remote Similarity	0.616	NPC184680
Remote Similarity	0.6157	NPC477912
Remote Similarity	0.6144	NPC208898
Remote Similarity	0.6143	NPC204385
Remote Similarity	0.6143	NPC194040
Remote Similarity	0.614	NPC308906
Remote Similarity	0.6136	NPC164374
Remote Similarity	0.6136	NPC314648
Remote Similarity	0.6136	NPC137929
Remote Similarity	0.6134	NPC470784
Remote Similarity	0.6134	NPC474183
Remote Similarity	0.613	NPC46970
Remote Similarity	0.6129	NPC150447
Remote Similarity	0.6121	NPC289786
Remote Similarity	0.6116	NPC475533
Remote Similarity	0.6114	NPC66083
Remote Similarity	0.6114	NPC174760
Remote Similarity	0.6114	NPC132771
Remote Similarity	0.6106	NPC470474
Remote Similarity	0.6103	NPC469390
Remote Similarity	0.6103	NPC129909
Remote Similarity	0.61	NPC188400
Remote Similarity	0.6099	NPC472752
Remote Similarity	0.6098	NPC471015
Remote Similarity	0.6094	NPC187145
Remote Similarity	0.6094	NPC475601
Remote Similarity	0.6091	NPC472068
Remote Similarity	0.6091	NPC324619
Remote Similarity	0.6091	NPC469440
Remote Similarity	0.6091	NPC475315
Remote Similarity	0.6085	NPC150698
Remote Similarity	0.6085	NPC96801
Remote Similarity	0.6085	NPC230805
Remote Similarity	0.6083	NPC102008
Remote Similarity	0.6079	NPC477907
Remote Similarity	0.6079	NPC62995
Remote Similarity	0.6079	NPC148183
Remote Similarity	0.6079	NPC42678
Remote Similarity	0.6079	NPC152768
Remote Similarity	0.6079	NPC477909
Remote Similarity	0.6078	NPC473449
Remote Similarity	0.6078	NPC35761
Remote Similarity	0.6078	NPC233727
Remote Similarity	0.6074	NPC180668
Remote Similarity	0.6074	NPC471013
Remote Similarity	0.6074	NPC148896
Remote Similarity	0.6071	NPC269367
Remote Similarity	0.6068	NPC194724
Remote Similarity	0.6068	NPC84347
Remote Similarity	0.6065	NPC473053
Remote Similarity	0.6061	NPC207675
Remote Similarity	0.6061	NPC212699
Remote Similarity	0.6059	NPC474192
Remote Similarity	0.6059	NPC475720
Remote Similarity	0.6056	NPC471978
Remote Similarity	0.6055	NPC192674
Remote Similarity	0.6053	NPC169402
Remote Similarity	0.6049	NPC191310
Remote Similarity	0.6047	NPC471979
Remote Similarity	0.6041	NPC10904
Remote Similarity	0.604	NPC473833
Remote Similarity	0.6035	NPC319128
Remote Similarity	0.6035	NPC228331
Remote Similarity	0.6034	NPC473105
Remote Similarity	0.6033	NPC316224
Remote Similarity	0.6026	NPC62367
Remote Similarity	0.6026	NPC473041
Remote Similarity	0.6018	NPC244856
Remote Similarity	0.6018	NPC476467
Remote Similarity	0.6018	NPC472098
Remote Similarity	0.601	NPC472168
Remote Similarity	0.6009	NPC477902
Remote Similarity	0.6009	NPC477910
Remote Similarity	0.6009	NPC328154
Remote Similarity	0.6008	NPC326930
Remote Similarity	0.6008	NPC53255
Remote Similarity	0.6008	NPC85879
Remote Similarity	0.6008	NPC475301
Remote Similarity	0.6	NPC216428
Remote Similarity	0.6	NPC84815
Remote Similarity	0.6	NPC237978
Remote Similarity	0.6	NPC301368
Remote Similarity	0.6	NPC250178
Remote Similarity	0.5992	NPC328928
Remote Similarity	0.5992	NPC124300
Remote Similarity	0.5991	NPC127720
Remote Similarity	0.5991	NPC236424
Remote Similarity	0.5991	NPC210256
Remote Similarity	0.5991	NPC477911
Remote Similarity	0.5991	NPC306644
Remote Similarity	0.5991	NPC127026
Remote Similarity	0.5991	NPC311858
Remote Similarity	0.5984	NPC13603
Remote Similarity	0.5983	NPC471016
Remote Similarity	0.5982	NPC63041
Remote Similarity	0.5976	NPC472031
Remote Similarity	0.5976	NPC472067
Remote Similarity	0.5976	NPC472066
Remote Similarity	0.5973	NPC87413
Remote Similarity	0.5973	NPC220337
Remote Similarity	0.5972	NPC103230
Remote Similarity	0.5972	NPC470003
Remote Similarity	0.5967	NPC291609
Remote Similarity	0.5966	NPC471980
Remote Similarity	0.5965	NPC274842
Remote Similarity	0.5965	NPC116238
Remote Similarity	0.5965	NPC16066
Remote Similarity	0.5964	NPC304183
Remote Similarity	0.5963	NPC314948
Remote Similarity	0.5958	NPC477589
Remote Similarity	0.5958	NPC477587
Remote Similarity	0.5957	NPC211920
Remote Similarity	0.5957	NPC124029
Remote Similarity	0.5957	NPC96321
Remote Similarity	0.5957	NPC187494
Remote Similarity	0.5956	NPC472550
Remote Similarity	0.5956	NPC304179
Remote Similarity	0.5956	NPC48042
Remote Similarity	0.5953	NPC28510
Remote Similarity	0.5952	NPC215837
Remote Similarity	0.5952	NPC206201
Remote Similarity	0.595	NPC475844
Remote Similarity	0.5944	NPC472435
Remote Similarity	0.5943	NPC42591
Remote Similarity	0.5941	NPC35208
Remote Similarity	0.594	NPC21638
Remote Similarity	0.594	NPC97746
Remote Similarity	0.5939	NPC470306
Remote Similarity	0.5938	NPC193238
Remote Similarity	0.5938	NPC475835
Remote Similarity	0.5936	NPC127085
Remote Similarity	0.5935	NPC183805
Remote Similarity	0.5932	NPC471762
Remote Similarity	0.5926	NPC56170
Remote Similarity	0.5926	NPC195268
Remote Similarity	0.5926	NPC133140
Remote Similarity	0.5924	NPC244839
Remote Similarity	0.5924	NPC319880
Remote Similarity	0.5924	NPC469748
Remote Similarity	0.5924	NPC320324
Remote Similarity	0.5923	NPC237901
Remote Similarity	0.5923	NPC195788
Remote Similarity	0.5921	NPC236668
Remote Similarity	0.5919	NPC289086
Remote Similarity	0.5918	NPC310618
Remote Similarity	0.5917	NPC327904
Remote Similarity	0.5917	NPC38959
Remote Similarity	0.5915	NPC61350

Drug Structure

NPD4953 OpenBabel08211706322D 31 33 0 0 1 0 0 0 0 0999 V2000 -2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0981 -0.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0981 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -4.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5981 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -3.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 -2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 2.5981 -1.5000 0.0000 C 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 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0981 -0.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 28 1 0 0 0 0 3 29 1 0 0 0 0 4 6 2 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 11 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 15 2 0 0 0 0 11 15 1 0 0 0 0 12 16 2 0 0 0 0 13 16 1 0 0 0 0 14 17 2 0 0 0 0 14 18 1 0 0 0 0 15 22 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 17 27 1 0 0 0 0 18 24 2 0 0 0 0 18 28 1 0 0 0 0 19 20 1 6 0 0 0 19 22 1 0 0 0 0 19 30 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 21 30 1 0 0 0 0 22 29 1 0 0 0 0 26 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB015427
DrugBank	DB04883
ChEMBL	CHEMBL23261
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	177236
ChEBI
CAS Number	171714-84-4

Drug Properties

Molecular Weight	410.15
ALogP	-0.9913
MLogP	3
XLogP	5.774
HDA	5
HBD	1
Rotatable Bonds	13
TPSA	100
RO5 Violation	1