NPASS drugs

Drug Information

Drug ID:	NPD4950
Drug Name:	Ambrisentan
Molecular Formula:	C22H22N2O4
Canonical SMILES:	COC([C@@H](C(=O)O)Oc1nc(C)cc(n1)C)(c1ccccc1)c1ccccc1
Standard InCHI:	InChI=1S/C22H22N2O4/c1-15-14-16(2)24-21(23-15)28-19(20(25)26)22(27-3,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-14,19H,1-3H3,(H,25,26)/t19-/m1/s1
Standard InCHIKey:	OUJTZYPIHDYQMC-LJQANCHMSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4950

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	211
0.1-0.2	1045
0.2-0.3	3737
0.3-0.4	9246
0.4-0.5	13417
0.5-0.6	2846
0.6-0.7	382
0.7-0.8	6
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	0.7053	NPC243850
Intermediate Similarity	0.7016	NPC208060
Intermediate Similarity	0.7005	NPC313796
Intermediate Similarity	0.7005	NPC315638
Intermediate Similarity	0.7005	NPC313345
Intermediate Similarity	0.7005	NPC314855
Remote Similarity	0.6974	NPC144114
Remote Similarity	0.6974	NPC477891
Remote Similarity	0.6971	NPC314297
Remote Similarity	0.6971	NPC315545
Remote Similarity	0.6952	NPC314834
Remote Similarity	0.6915	NPC224632
Remote Similarity	0.6893	NPC54537
Remote Similarity	0.6875	NPC105758
Remote Similarity	0.6875	NPC476688
Remote Similarity	0.6875	NPC476686
Remote Similarity	0.6859	NPC278874
Remote Similarity	0.6856	NPC84347
Remote Similarity	0.685	NPC61435
Remote Similarity	0.6818	NPC320394
Remote Similarity	0.6794	NPC314648
Remote Similarity	0.6782	NPC129909
Remote Similarity	0.6753	NPC191310
Remote Similarity	0.6748	NPC102008
Remote Similarity	0.6715	NPC192674
Remote Similarity	0.6667	NPC311858
Remote Similarity	0.6667	NPC317572
Remote Similarity	0.6651	NPC244856
Remote Similarity	0.665	NPC285923
Remote Similarity	0.665	NPC470003
Remote Similarity	0.6649	NPC164664
Remote Similarity	0.662	NPC236424
Remote Similarity	0.662	NPC316181
Remote Similarity	0.662	NPC306644
Remote Similarity	0.662	NPC74562
Remote Similarity	0.662	NPC151781
Remote Similarity	0.659	NPC274842
Remote Similarity	0.6584	NPC194040
Remote Similarity	0.6584	NPC90415
Remote Similarity	0.6575	NPC314270
Remote Similarity	0.6567	NPC203635
Remote Similarity	0.6553	NPC51854
Remote Similarity	0.6552	NPC254762
Remote Similarity	0.6545	NPC48317
Remote Similarity	0.6535	NPC35208
Remote Similarity	0.652	NPC320324
Remote Similarity	0.652	NPC319880
Remote Similarity	0.652	NPC244839
Remote Similarity	0.6517	NPC243058
Remote Similarity	0.6516	NPC128115
Remote Similarity	0.6511	NPC9729
Remote Similarity	0.6507	NPC327904
Remote Similarity	0.6507	NPC38959
Remote Similarity	0.6498	NPC292517
Remote Similarity	0.6494	NPC253482
Remote Similarity	0.6491	NPC237702
Remote Similarity	0.6489	NPC146824
Remote Similarity	0.6481	NPC475648
Remote Similarity	0.6476	NPC473689
Remote Similarity	0.6476	NPC292416
Remote Similarity	0.6476	NPC241024
Remote Similarity	0.6468	NPC317752
Remote Similarity	0.6463	NPC475406
Remote Similarity	0.646	NPC475362
Remote Similarity	0.6455	NPC312645
Remote Similarity	0.6444	NPC473506
Remote Similarity	0.6435	NPC472752
Remote Similarity	0.6429	NPC250807
Remote Similarity	0.6429	NPC76565
Remote Similarity	0.6429	NPC57797
Remote Similarity	0.6425	NPC55493
Remote Similarity	0.6422	NPC318299
Remote Similarity	0.6419	NPC474905
Remote Similarity	0.6416	NPC122968
Remote Similarity	0.6416	NPC476110
Remote Similarity	0.6416	NPC87152
Remote Similarity	0.6416	NPC475600
Remote Similarity	0.6416	NPC328186
Remote Similarity	0.6416	NPC477787
Remote Similarity	0.6416	NPC475631
Remote Similarity	0.6416	NPC475601
Remote Similarity	0.6416	NPC228377
Remote Similarity	0.6413	NPC477912
Remote Similarity	0.6409	NPC30570
Remote Similarity	0.6409	NPC477907
Remote Similarity	0.6409	NPC42678
Remote Similarity	0.6409	NPC62995
Remote Similarity	0.6409	NPC477909
Remote Similarity	0.6404	NPC150698
Remote Similarity	0.6404	NPC475596
Remote Similarity	0.6404	NPC316841
Remote Similarity	0.6404	NPC475303
Remote Similarity	0.6404	NPC96801
Remote Similarity	0.64	NPC473850
Remote Similarity	0.64	NPC475137
Remote Similarity	0.64	NPC475498
Remote Similarity	0.64	NPC233727
Remote Similarity	0.6393	NPC89508
Remote Similarity	0.6391	NPC327769
Remote Similarity	0.6388	NPC471977
Remote Similarity	0.6388	NPC475644
Remote Similarity	0.6388	NPC471190
Remote Similarity	0.6388	NPC470486
Remote Similarity	0.6385	NPC123019
Remote Similarity	0.638	NPC162812
Remote Similarity	0.6376	NPC30456
Remote Similarity	0.6372	NPC317373
Remote Similarity	0.6372	NPC18661
Remote Similarity	0.6372	NPC148860
Remote Similarity	0.6368	NPC256268
Remote Similarity	0.6364	NPC280638
Remote Similarity	0.6364	NPC57994
Remote Similarity	0.6364	NPC289299
Remote Similarity	0.6364	NPC319128
Remote Similarity	0.6364	NPC228331
Remote Similarity	0.636	NPC116622
Remote Similarity	0.6359	NPC183805
Remote Similarity	0.6359	NPC230805
Remote Similarity	0.6359	NPC175474
Remote Similarity	0.6351	NPC62367
Remote Similarity	0.6347	NPC476467
Remote Similarity	0.6345	NPC470894
Remote Similarity	0.634	NPC322644
Remote Similarity	0.6337	NPC475685
Remote Similarity	0.6332	NPC160666
Remote Similarity	0.6327	NPC328154
Remote Similarity	0.6327	NPC477902
Remote Similarity	0.6326	NPC327592
Remote Similarity	0.6324	NPC207851
Remote Similarity	0.6323	NPC216428
Remote Similarity	0.6323	NPC301368
Remote Similarity	0.6323	NPC84815
Remote Similarity	0.6321	NPC26850
Remote Similarity	0.6321	NPC280714
Remote Similarity	0.6321	NPC123395
Remote Similarity	0.632	NPC475426
Remote Similarity	0.6318	NPC14812
Remote Similarity	0.6318	NPC219848
Remote Similarity	0.6316	NPC279401
Remote Similarity	0.6316	NPC79293
Remote Similarity	0.6313	NPC63041
Remote Similarity	0.6313	NPC470280
Remote Similarity	0.6311	NPC127026
Remote Similarity	0.6311	NPC127720
Remote Similarity	0.6306	NPC471016
Remote Similarity	0.6301	NPC242923
Remote Similarity	0.63	NPC312872
Remote Similarity	0.6296	NPC277350
Remote Similarity	0.6291	NPC249150
Remote Similarity	0.6291	NPC214428
Remote Similarity	0.6291	NPC81654
Remote Similarity	0.6291	NPC195461
Remote Similarity	0.6291	NPC49196
Remote Similarity	0.6291	NPC313985
Remote Similarity	0.6291	NPC79129
Remote Similarity	0.6284	NPC472550
Remote Similarity	0.6284	NPC304179
Remote Similarity	0.6284	NPC48042
Remote Similarity	0.6283	NPC471980
Remote Similarity	0.6279	NPC476115
Remote Similarity	0.6278	NPC187494
Remote Similarity	0.6274	NPC149708
Remote Similarity	0.6273	NPC235900
Remote Similarity	0.6272	NPC211920
Remote Similarity	0.6272	NPC124029
Remote Similarity	0.6269	NPC134586
Remote Similarity	0.6262	NPC160381
Remote Similarity	0.6261	NPC470306
Remote Similarity	0.6261	NPC85702
Remote Similarity	0.6261	NPC477910
Remote Similarity	0.6256	NPC234999
Remote Similarity	0.625	NPC52254
Remote Similarity	0.625	NPC170751
Remote Similarity	0.6244	NPC32200
Remote Similarity	0.6239	NPC477911
Remote Similarity	0.6239	NPC477788
Remote Similarity	0.6238	NPC230403
Remote Similarity	0.6238	NPC45850
Remote Similarity	0.6238	NPC211997
Remote Similarity	0.6238	NPC14325
Remote Similarity	0.6238	NPC283152
Remote Similarity	0.6238	NPC28848
Remote Similarity	0.6234	NPC469748
Remote Similarity	0.6233	NPC206343
Remote Similarity	0.6233	NPC6981
Remote Similarity	0.6233	NPC477908
Remote Similarity	0.6233	NPC475408
Remote Similarity	0.6233	NPC471014
Remote Similarity	0.6233	NPC328596
Remote Similarity	0.6233	NPC328318
Remote Similarity	0.6232	NPC472323
Remote Similarity	0.6232	NPC473815
Remote Similarity	0.6221	NPC309498
Remote Similarity	0.6219	NPC303225
Remote Similarity	0.6216	NPC471284
Remote Similarity	0.6209	NPC85066
Remote Similarity	0.6209	NPC181502
Remote Similarity	0.6205	NPC82070
Remote Similarity	0.6205	NPC144779
Remote Similarity	0.6205	NPC294579

Drug Structure

NPD4950 OpenBabel08211706322D 29 31 0 0 1 0 0 0 0 0999 V2000 -0.0000 3.0000 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 4.9641 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9641 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4641 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9641 -2.5981 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 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9641 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.7321 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 5.1962 0.0000 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 -0.0000 2.0000 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 2.9641 -0.8660 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 0.5000 0.0000 C 0 0 2 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 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 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9641 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 16 1 0 0 0 0 3 27 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 17 2 0 0 0 0 11 17 1 0 0 0 0 12 18 2 0 0 0 0 13 18 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 23 1 0 0 0 0 16 24 2 0 0 0 0 17 22 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 6 0 0 0 19 22 1 0 0 0 0 19 28 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 28 1 0 0 0 0 22 27 1 0 0 0 0 26 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001441
DrugBank	DB06403
ChEMBL	CHEMBL1111
IUPHAR/BPS	3951
PharmaGKB	PA165860521
KEGG Drug
PubChem CID	6918493
ChEBI	135949
CAS Number	177036-94-1

Drug Properties

Molecular Weight	378.16
ALogP	-0.0087
MLogP	3.22
XLogP	6.656
HDA	5
HBD	1
Rotatable Bonds	11
TPSA	81.54
RO5 Violation	1