NPASS drugs

Drug Information

Drug ID:	NPD5731
Drug Name:	Vardenafil Hydrochloride
Molecular Formula:	C23H32N6O4S.ClH
Canonical SMILES:	CCOc1ccc(cc1c1nc(=O)c2n([nH]1)c(CCC)nc2C)S(=O)(=O)N1CCN(CC1)CC.Cl
Standard InCHI:	InChI=1S/C23H32N6O4S.ClH/c1-5-8-20-24-16(4)21-23(30)25-22(26-29(20)21)18-15-17(9-10-19(18)33-7-3)34(31,32)28-13-11-27(6-2)12-14-28;/h9-10,15H,5-8,11-14H2,1-4H3,(H,25,26,30);1H
Standard InCHIKey:	XCMULUAPJXCOHI-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5731

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	433
0.1-0.2	3759
0.2-0.3	9197
0.3-0.4	9505
0.4-0.5	6791
0.5-0.6	1168
0.6-0.7	37
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	0.6939	NPC187145
Remote Similarity	0.6638	NPC280638
Remote Similarity	0.657	NPC242923
Remote Similarity	0.6482	NPC115595
Remote Similarity	0.6454	NPC471615
Remote Similarity	0.6443	NPC471762
Remote Similarity	0.6403	NPC157931
Remote Similarity	0.6392	NPC160666
Remote Similarity	0.6386	NPC308906
Remote Similarity	0.6378	NPC66777
Remote Similarity	0.6339	NPC257851
Remote Similarity	0.6295	NPC323969
Remote Similarity	0.628	NPC467439
Remote Similarity	0.62	NPC62995
Remote Similarity	0.6187	NPC237978
Remote Similarity	0.6166	NPC128115
Remote Similarity	0.616	NPC50511
Remote Similarity	0.616	NPC50562
Remote Similarity	0.6142	NPC17305
Remote Similarity	0.6135	NPC67658
Remote Similarity	0.6133	NPC35761
Remote Similarity	0.6124	NPC315822
Remote Similarity	0.6118	NPC46970
Remote Similarity	0.6107	NPC295898
Remote Similarity	0.6089	NPC174672
Remote Similarity	0.6073	NPC243850
Remote Similarity	0.6063	NPC136924
Remote Similarity	0.6063	NPC168209
Remote Similarity	0.6063	NPC250178
Remote Similarity	0.6047	NPC12100
Remote Similarity	0.6038	NPC471614
Remote Similarity	0.6037	NPC51854
Remote Similarity	0.6031	NPC122436
Remote Similarity	0.6031	NPC141053
Remote Similarity	0.6017	NPC198401
Remote Similarity	0.6007	NPC303374
Remote Similarity	0.6	NPC9729
Remote Similarity	0.5992	NPC175150
Remote Similarity	0.5992	NPC243633
Remote Similarity	0.5984	NPC287208
Remote Similarity	0.596	NPC174758
Remote Similarity	0.5947	NPC208898
Remote Similarity	0.5945	NPC148183
Remote Similarity	0.5945	NPC152768
Remote Similarity	0.5942	NPC150447
Remote Similarity	0.594	NPC101350
Remote Similarity	0.5939	NPC194740
Remote Similarity	0.5938	NPC48317
Remote Similarity	0.592	NPC82548
Remote Similarity	0.5919	NPC472067
Remote Similarity	0.5919	NPC472066
Remote Similarity	0.5919	NPC472031
Remote Similarity	0.5911	NPC477806
Remote Similarity	0.5911	NPC477795
Remote Similarity	0.5911	NPC477796
Remote Similarity	0.5911	NPC477805
Remote Similarity	0.5902	NPC235685
Remote Similarity	0.5894	NPC260434
Remote Similarity	0.5889	NPC264176
Remote Similarity	0.588	NPC30540
Remote Similarity	0.5869	NPC220851
Remote Similarity	0.5866	NPC151781
Remote Similarity	0.5866	NPC316181
Remote Similarity	0.5866	NPC74562
Remote Similarity	0.5861	NPC26543
Remote Similarity	0.5859	NPC305984
Remote Similarity	0.5858	NPC477590
Remote Similarity	0.5858	NPC477586
Remote Similarity	0.5858	NPC477585
Remote Similarity	0.5858	NPC477588
Remote Similarity	0.5855	NPC244543
Remote Similarity	0.5849	NPC329631
Remote Similarity	0.5848	NPC63109
Remote Similarity	0.5846	NPC472068
Remote Similarity	0.5843	NPC477979
Remote Similarity	0.584	NPC478078
Remote Similarity	0.5836	NPC148889
Remote Similarity	0.5827	NPC74619
Remote Similarity	0.582	NPC274982
Remote Similarity	0.582	NPC322064
Remote Similarity	0.5814	NPC288987
Remote Similarity	0.5811	NPC328924
Remote Similarity	0.581	NPC113369
Remote Similarity	0.5806	NPC41982
Remote Similarity	0.5794	NPC476465
Remote Similarity	0.5792	NPC472099
Remote Similarity	0.5784	NPC477587
Remote Similarity	0.5784	NPC477589
Remote Similarity	0.5779	NPC323244
Remote Similarity	0.575	NPC476341
Remote Similarity	0.5737	NPC473239
Remote Similarity	0.5736	NPC471197
Remote Similarity	0.572	NPC99891
Remote Similarity	0.5714	NPC303658
Remote Similarity	0.5714	NPC198673
Remote Similarity	0.5714	NPC471198
Remote Similarity	0.5709	NPC91868
Remote Similarity	0.5709	NPC63971
Remote Similarity	0.5703	NPC21638
Remote Similarity	0.5703	NPC471603
Remote Similarity	0.5703	NPC472098
Remote Similarity	0.5702	NPC238242
Remote Similarity	0.5699	NPC478083
Remote Similarity	0.5699	NPC53534
Remote Similarity	0.5693	NPC196718
Remote Similarity	0.5691	NPC93390
Remote Similarity	0.569	NPC144114
Remote Similarity	0.5689	NPC152620
Remote Similarity	0.5688	NPC165964
Remote Similarity	0.5687	NPC478141
Remote Similarity	0.5686	NPC471304
Remote Similarity	0.5686	NPC123839
Remote Similarity	0.5685	NPC168911
Remote Similarity	0.5679	NPC258048
Remote Similarity	0.5678	NPC316756
Remote Similarity	0.5668	NPC56271
Remote Similarity	0.5668	NPC67401
Remote Similarity	0.5664	NPC478013
Remote Similarity	0.5663	NPC472435
Remote Similarity	0.566	NPC476688
Remote Similarity	0.566	NPC105758
Remote Similarity	0.566	NPC476686
Remote Similarity	0.5659	NPC316297
Remote Similarity	0.5659	NPC314817
Remote Similarity	0.5659	NPC66191
Remote Similarity	0.5658	NPC472436
Remote Similarity	0.5657	NPC472434
Remote Similarity	0.5656	NPC134079
Remote Similarity	0.5649	NPC168486
Remote Similarity	0.5649	NPC222592
Remote Similarity	0.5649	NPC198503
Remote Similarity	0.5645	NPC78767
Remote Similarity	0.5645	NPC473814
Remote Similarity	0.5641	NPC278874
Remote Similarity	0.5641	NPC295452
Remote Similarity	0.5641	NPC171393
Remote Similarity	0.5641	NPC39092
Remote Similarity	0.564	NPC121772
Remote Similarity	0.564	NPC478012
Remote Similarity	0.5639	NPC179896
Remote Similarity	0.5634	NPC102593
Remote Similarity	0.563	NPC28848
Remote Similarity	0.563	NPC14325
Remote Similarity	0.5625	NPC477891
Remote Similarity	0.5622	NPC239954
Remote Similarity	0.5616	NPC161801
Remote Similarity	0.5615	NPC15384
Remote Similarity	0.5615	NPC27041
Remote Similarity	0.5615	NPC244425
Remote Similarity	0.5613	NPC257511
Remote Similarity	0.5613	NPC180504
Remote Similarity	0.5612	NPC133609
Remote Similarity	0.5609	NPC184680
Remote Similarity	0.5609	NPC472061
Remote Similarity	0.5608	NPC315411
Remote Similarity	0.5608	NPC266249
Remote Similarity	0.5603	NPC177404
Remote Similarity	0.5603	NPC146418
Remote Similarity	0.56	NPC81535

Drug Structure

NPD5731 OpenBabel08211708292D 36 38 0 0 0 0 0 0 0 0999 V2000 11.0113 -5.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7242 -0.7399 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7023 -4.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7242 -4.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1340 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1340 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -5.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -5.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -6.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4152 -1.6910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4152 -3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0029 -2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.7321 -2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5981 -3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -6.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -6.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 8.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -7.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0000 -6.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.2095 2.2989 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 7.5981 -4.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 7 1 0 0 0 0 4 16 1 0 0 0 0 5 8 1 0 0 0 0 6 27 1 0 0 0 0 7 33 1 0 0 0 0 8 20 1 0 0 0 0 9 10 2 0 0 0 0 9 17 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 27 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 0 0 0 0 13 28 1 0 0 0 0 14 28 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 21 2 0 0 0 0 16 24 1 0 0 0 0 17 34 1 0 0 0 0 18 19 2 0 0 0 0 18 22 1 0 0 0 0 19 33 1 0 0 0 0 20 24 2 0 0 0 0 20 29 1 0 0 0 0 21 23 1 0 0 0 0 21 29 1 0 0 0 0 22 25 2 0 0 0 0 22 26 1 0 0 0 0 23 25 1 0 0 0 0 23 30 2 0 0 0 0 26 29 1 0 0 0 0 26 36 1 0 0 0 0 28 34 1 0 0 0 0 31 34 2 0 0 0 0 32 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	488.22
ALogP	-1.6439
MLogP	2.78
XLogP	2.605
HDA	9
HBD	1
Rotatable Bonds	12
TPSA	117.51
RO5 Violation	0