NPASS drugs

Drug Information

Drug ID:	NPD5273
Drug Name:	Sildenafil
Molecular Formula:	C22H30N6O4S
Canonical SMILES:	CCCc1nn(c2c1nc([nH]c2=O)c1cc(ccc1OCC)S(=O)(=O)N1CCN(CC1)C)C
Standard InCHI:	InChI=1S/C22H30N6O4S/c1-5-7-17-19-20(27(4)25-17)22(29)24-21(23-19)16-14-15(8-9-18(16)32-6-2)33(30,31)28-12-10-26(3)11-13-28/h8-9,14H,5-7,10-13H2,1-4H3,(H,23,24,29)
Standard InCHIKey:	BNRNXUUZRGQAQC-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5273

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	401
0.1-0.2	3505
0.2-0.3	9292
0.3-0.4	6933
0.4-0.5	8718
0.5-0.6	1934
0.6-0.7	107
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	0.6967	NPC471762
Remote Similarity	0.6926	NPC157931
Remote Similarity	0.6898	NPC66777
Remote Similarity	0.6857	NPC257851
Remote Similarity	0.6749	NPC323969
Remote Similarity	0.6696	NPC198401
Remote Similarity	0.6477	NPC303374
Remote Similarity	0.6475	NPC50562
Remote Similarity	0.6466	NPC122436
Remote Similarity	0.6449	NPC67658
Remote Similarity	0.6437	NPC168209
Remote Similarity	0.6429	NPC194740
Remote Similarity	0.642	NPC101350
Remote Similarity	0.6389	NPC187145
Remote Similarity	0.6381	NPC235685
Remote Similarity	0.6377	NPC244543
Remote Similarity	0.6371	NPC288987
Remote Similarity	0.636	NPC220851
Remote Similarity	0.636	NPC175150
Remote Similarity	0.636	NPC243633
Remote Similarity	0.6345	NPC128115
Remote Similarity	0.6328	NPC329631
Remote Similarity	0.6324	NPC478078
Remote Similarity	0.6316	NPC152768
Remote Similarity	0.6316	NPC148183
Remote Similarity	0.6314	NPC260434
Remote Similarity	0.6292	NPC295898
Remote Similarity	0.629	NPC305984
Remote Similarity	0.6289	NPC196718
Remote Similarity	0.627	NPC174672
Remote Similarity	0.626	NPC264176
Remote Similarity	0.6255	NPC243850
Remote Similarity	0.625	NPC322064
Remote Similarity	0.6245	NPC194967
Remote Similarity	0.6245	NPC148889
Remote Similarity	0.6226	NPC102593
Remote Similarity	0.6215	NPC472099
Remote Similarity	0.621	NPC477979
Remote Similarity	0.6202	NPC141053
Remote Similarity	0.6192	NPC472061
Remote Similarity	0.6189	NPC161801
Remote Similarity	0.6166	NPC478141
Remote Similarity	0.6165	NPC63971
Remote Similarity	0.6165	NPC91868
Remote Similarity	0.6163	NPC287208
Remote Similarity	0.616	NPC471197
Remote Similarity	0.6148	NPC53534
Remote Similarity	0.6145	NPC477586
Remote Similarity	0.6145	NPC477585
Remote Similarity	0.6145	NPC477588
Remote Similarity	0.6145	NPC477590
Remote Similarity	0.6142	NPC322482
Remote Similarity	0.6138	NPC174758
Remote Similarity	0.6135	NPC303658
Remote Similarity	0.6135	NPC471198
Remote Similarity	0.6129	NPC472098
Remote Similarity	0.6123	NPC471648
Remote Similarity	0.6122	NPC16249
Remote Similarity	0.612	NPC62995
Remote Similarity	0.6119	NPC67401
Remote Similarity	0.6113	NPC123839
Remote Similarity	0.6107	NPC473239
Remote Similarity	0.6098	NPC82548
Remote Similarity	0.6094	NPC46895
Remote Similarity	0.6089	NPC478083
Remote Similarity	0.6085	NPC115595
Remote Similarity	0.6082	NPC26543
Remote Similarity	0.6076	NPC92803
Remote Similarity	0.6073	NPC152620
Remote Similarity	0.6069	NPC477589
Remote Similarity	0.6069	NPC477587
Remote Similarity	0.6067	NPC93390
Remote Similarity	0.6066	NPC258048
Remote Similarity	0.6063	NPC198503
Remote Similarity	0.6059	NPC18890
Remote Similarity	0.6055	NPC471615
Remote Similarity	0.6055	NPC21638
Remote Similarity	0.6052	NPC314659
Remote Similarity	0.6048	NPC471304
Remote Similarity	0.6048	NPC269367
Remote Similarity	0.6047	NPC311906
Remote Similarity	0.6043	NPC150308
Remote Similarity	0.6042	NPC472789
Remote Similarity	0.604	NPC74562
Remote Similarity	0.604	NPC151781
Remote Similarity	0.604	NPC316181
Remote Similarity	0.6034	NPC73994
Remote Similarity	0.6032	NPC27041
Remote Similarity	0.6032	NPC266249
Remote Similarity	0.6031	NPC477549
Remote Similarity	0.6028	NPC315411
Remote Similarity	0.6024	NPC146418
Remote Similarity	0.6022	NPC165964
Remote Similarity	0.6018	NPC471130
Remote Similarity	0.6017	NPC473814
Remote Similarity	0.6017	NPC78767
Remote Similarity	0.6015	NPC316224
Remote Similarity	0.6009	NPC197335
Remote Similarity	0.6008	NPC248601
Remote Similarity	0.6008	NPC184680
Remote Similarity	0.6008	NPC121772
Remote Similarity	0.6008	NPC473041
Remote Similarity	0.6008	NPC96321
Remote Similarity	0.6	NPC133609
Remote Similarity	0.6	NPC196449
Remote Similarity	0.6	NPC88970
Remote Similarity	0.6	NPC314222
Remote Similarity	0.5992	NPC208898
Remote Similarity	0.5992	NPC274982
Remote Similarity	0.5992	NPC182222
Remote Similarity	0.5992	NPC471155
Remote Similarity	0.5986	NPC315061
Remote Similarity	0.5985	NPC470785
Remote Similarity	0.5985	NPC470784
Remote Similarity	0.5984	NPC471944
Remote Similarity	0.5978	NPC189079
Remote Similarity	0.5977	NPC216612
Remote Similarity	0.5968	NPC270241
Remote Similarity	0.5968	NPC244425
Remote Similarity	0.5968	NPC285192
Remote Similarity	0.5968	NPC15384
Remote Similarity	0.5967	NPC81535
Remote Similarity	0.5966	NPC61011
Remote Similarity	0.5957	NPC21429
Remote Similarity	0.5955	NPC142385
Remote Similarity	0.5953	NPC314633
Remote Similarity	0.5952	NPC66191
Remote Similarity	0.5952	NPC316297
Remote Similarity	0.5952	NPC314817
Remote Similarity	0.5952	NPC16066
Remote Similarity	0.5951	NPC472287
Remote Similarity	0.5951	NPC472286
Remote Similarity	0.5951	NPC225400
Remote Similarity	0.5938	NPC280799
Remote Similarity	0.5929	NPC478013
Remote Similarity	0.5927	NPC470786
Remote Similarity	0.5927	NPC270918
Remote Similarity	0.5927	NPC472538
Remote Similarity	0.5926	NPC100863
Remote Similarity	0.5925	NPC131486
Remote Similarity	0.5922	NPC269270
Remote Similarity	0.5916	NPC477516
Remote Similarity	0.5913	NPC236668
Remote Similarity	0.5909	NPC472193
Remote Similarity	0.5904	NPC51854
Remote Similarity	0.5902	NPC475816
Remote Similarity	0.5901	NPC478012
Remote Similarity	0.5898	NPC14686
Remote Similarity	0.5897	NPC329982
Remote Similarity	0.5896	NPC75179
Remote Similarity	0.5896	NPC242923
Remote Similarity	0.5894	NPC180504
Remote Similarity	0.5894	NPC143977
Remote Similarity	0.5892	NPC198673
Remote Similarity	0.5892	NPC473821
Remote Similarity	0.5889	NPC146976
Remote Similarity	0.5885	NPC74153
Remote Similarity	0.588	NPC99891
Remote Similarity	0.588	NPC83774
Remote Similarity	0.588	NPC472070
Remote Similarity	0.5878	NPC160666
Remote Similarity	0.5878	NPC121327
Remote Similarity	0.5876	NPC472435
Remote Similarity	0.5875	NPC60621
Remote Similarity	0.587	NPC41216
Remote Similarity	0.5868	NPC280638
Remote Similarity	0.5867	NPC9729
Remote Similarity	0.5865	NPC474183
Remote Similarity	0.5861	NPC168911
Remote Similarity	0.5859	NPC315804
Remote Similarity	0.5859	NPC313804
Remote Similarity	0.5859	NPC298436
Remote Similarity	0.5858	NPC124300
Remote Similarity	0.5858	NPC72905
Remote Similarity	0.5856	NPC474192
Remote Similarity	0.5856	NPC49547
Remote Similarity	0.5856	NPC475720
Remote Similarity	0.5855	NPC318068
Remote Similarity	0.5852	NPC471652
Remote Similarity	0.5851	NPC473639
Remote Similarity	0.5849	NPC473187
Remote Similarity	0.5847	NPC472259
Remote Similarity	0.5847	NPC132539
Remote Similarity	0.5844	NPC470787
Remote Similarity	0.5844	NPC472539
Remote Similarity	0.5844	NPC102592
Remote Similarity	0.5844	NPC79356
Remote Similarity	0.5844	NPC472540
Remote Similarity	0.5843	NPC41501
Remote Similarity	0.584	NPC87391
Remote Similarity	0.5837	NPC103361
Remote Similarity	0.5836	NPC291609
Remote Similarity	0.5836	NPC478010
Remote Similarity	0.5833	NPC473105
Remote Similarity	0.5833	NPC45389
Remote Similarity	0.5833	NPC63109
Remote Similarity	0.5833	NPC220337
Remote Similarity	0.583	NPC88110
Remote Similarity	0.583	NPC472069
Remote Similarity	0.583	NPC472062

Drug Structure

NPD5273 OpenBabel08211706322D 34 37 0 0 0 0 0 0 0 0999 V2000 3.4240 -7.3803 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 -4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1854 -4.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4459 -7.1723 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 2.1369 -6.2213 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 -0.8660 -2.5000 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 0.8660 -1.5000 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 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8060 -5.4781 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 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 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 3.8005 -5.5827 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2072 -4.6691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 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 2.5981 -1.5000 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 26 1 0 0 0 0 4 27 1 0 0 0 0 5 7 1 0 0 0 0 6 32 1 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 15 1 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 26 1 0 0 0 0 12 28 1 0 0 0 0 13 28 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 33 1 0 0 0 0 16 18 2 0 0 0 0 16 21 1 0 0 0 0 17 19 1 0 0 0 0 17 25 2 0 0 0 0 18 32 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 20 27 1 0 0 0 0 21 23 2 0 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 22 29 2 0 0 0 0 24 34 1 0 0 0 0 25 27 1 0 0 0 0 28 33 1 0 0 0 0 30 33 2 0 0 0 0 31 33 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000614; DCL000953
DrugBank	DB00203
ChEMBL	CHEMBL192
IUPHAR/BPS	4743
PharmaGKB	PA451346
KEGG Drug	D02229
PubChem CID	5212
ChEBI	9139
CAS Number	139755-83-2

Drug Properties

Molecular Weight	474.20
ALogP	-1.0417
MLogP	2.67
XLogP	1.267
HDA	9
HBD	1
Rotatable Bonds	11
TPSA	117.51
RO5 Violation	0