NPASS drugs

Drug Information

Drug ID:	NPD5749
Drug Name:	Gisadenafil
Molecular Formula:	C23H33N7O5S
Canonical SMILES:	COCCn1nc2c(c1CC)[nH]c(nc2=O)c1cc(cnc1OCC)S(=O)(=O)N1CCN(CC1)CC
Standard InCHI:	InChI=1S/C23H33N7O5S/c1-5-18-19-20(27-30(18)12-13-34-4)22(31)26-21(25-19)17-14-16(15-24-23(17)35-7-3)36(32,33)29-10-8-28(6-2)9-11-29/h14-15H,5-13H2,1-4H3,(H,25,26,31)
Standard InCHIKey:	YPFZMBHKIVDSNR-UHFFFAOYSA-N
Max Developmental Stage:	Phase 2
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5749

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	549
0.1-0.2	7128
0.2-0.3	6706
0.3-0.4	12252
0.4-0.5	2414
0.5-0.6	1717
0.6-0.7	124
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	0.6574	NPC257851
Remote Similarity	0.6561	NPC260434
Remote Similarity	0.6548	NPC66777
Remote Similarity	0.6548	NPC471762
Remote Similarity	0.652	NPC122436
Remote Similarity	0.6508	NPC157931
Remote Similarity	0.6504	NPC53534
Remote Similarity	0.6502	NPC123839
Remote Similarity	0.6486	NPC148889
Remote Similarity	0.6473	NPC101350
Remote Similarity	0.6471	NPC196718
Remote Similarity	0.6437	NPC75179
Remote Similarity	0.6434	NPC235685
Remote Similarity	0.6426	NPC168209
Remote Similarity	0.6421	NPC152620
Remote Similarity	0.642	NPC287208
Remote Similarity	0.642	NPC266249
Remote Similarity	0.6406	NPC102593
Remote Similarity	0.6381	NPC141053
Remote Similarity	0.6364	NPC161801
Remote Similarity	0.6349	NPC243633
Remote Similarity	0.6349	NPC175150
Remote Similarity	0.6346	NPC178664
Remote Similarity	0.6335	NPC323969
Remote Similarity	0.6329	NPC135950
Remote Similarity	0.6327	NPC472070
Remote Similarity	0.6318	NPC329631
Remote Similarity	0.6316	NPC26543
Remote Similarity	0.6308	NPC472061
Remote Similarity	0.6296	NPC258048
Remote Similarity	0.6296	NPC472259
Remote Similarity	0.6292	NPC103361
Remote Similarity	0.6287	NPC198673
Remote Similarity	0.6285	NPC216612
Remote Similarity	0.6281	NPC472069
Remote Similarity	0.6281	NPC472063
Remote Similarity	0.6281	NPC143977
Remote Similarity	0.6281	NPC472062
Remote Similarity	0.6277	NPC196449
Remote Similarity	0.6277	NPC314222
Remote Similarity	0.6269	NPC477549
Remote Similarity	0.6266	NPC121327
Remote Similarity	0.6265	NPC50511
Remote Similarity	0.626	NPC174672
Remote Similarity	0.626	NPC174758
Remote Similarity	0.6255	NPC180504
Remote Similarity	0.625	NPC168911
Remote Similarity	0.625	NPC118940
Remote Similarity	0.6234	NPC61011
Remote Similarity	0.6234	NPC73994
Remote Similarity	0.6229	NPC134079
Remote Similarity	0.6224	NPC284338
Remote Similarity	0.6223	NPC46895
Remote Similarity	0.622	NPC82548
Remote Similarity	0.6217	NPC91868
Remote Similarity	0.6217	NPC63971
Remote Similarity	0.6208	NPC106824
Remote Similarity	0.6206	NPC472789
Remote Similarity	0.6204	NPC472064
Remote Similarity	0.62	NPC477979
Remote Similarity	0.6196	NPC322482
Remote Similarity	0.6189	NPC315411
Remote Similarity	0.6183	NPC239954
Remote Similarity	0.6169	NPC182222
Remote Similarity	0.6162	NPC472435
Remote Similarity	0.6154	NPC472436
Remote Similarity	0.6147	NPC83774
Remote Similarity	0.6146	NPC315061
Remote Similarity	0.6125	NPC93390
Remote Similarity	0.612	NPC26679
Remote Similarity	0.612	NPC6865
Remote Similarity	0.612	NPC153980
Remote Similarity	0.612	NPC318299
Remote Similarity	0.6114	NPC249614
Remote Similarity	0.6111	NPC471192
Remote Similarity	0.6111	NPC274982
Remote Similarity	0.6105	NPC472434
Remote Similarity	0.6103	NPC303374
Remote Similarity	0.6102	NPC288987
Remote Similarity	0.61	NPC194740
Remote Similarity	0.61	NPC314954
Remote Similarity	0.6098	NPC327592
Remote Similarity	0.6096	NPC317752
Remote Similarity	0.6096	NPC476287
Remote Similarity	0.6093	NPC478013
Remote Similarity	0.6092	NPC49547
Remote Similarity	0.6091	NPC123395
Remote Similarity	0.6091	NPC81535
Remote Similarity	0.608	NPC72956
Remote Similarity	0.6077	NPC115595
Remote Similarity	0.6074	NPC78767
Remote Similarity	0.6074	NPC473814
Remote Similarity	0.6073	NPC317373
Remote Similarity	0.6073	NPC472065
Remote Similarity	0.6071	NPC50562
Remote Similarity	0.6067	NPC316224
Remote Similarity	0.6067	NPC142385
Remote Similarity	0.6066	NPC19872
Remote Similarity	0.6062	NPC478078
Remote Similarity	0.6062	NPC186351
Remote Similarity	0.6056	NPC471193
Remote Similarity	0.6056	NPC264176
Remote Similarity	0.6056	NPC471194
Remote Similarity	0.6054	NPC160666
Remote Similarity	0.6053	NPC99891
Remote Similarity	0.6047	NPC67658
Remote Similarity	0.6034	NPC118084
Remote Similarity	0.6032	NPC473239
Remote Similarity	0.6031	NPC220851
Remote Similarity	0.6026	NPC314281
Remote Similarity	0.6026	NPC40530
Remote Similarity	0.6025	NPC469489
Remote Similarity	0.6024	NPC27041
Remote Similarity	0.6016	NPC472099
Remote Similarity	0.6008	NPC74382
Remote Similarity	0.6008	NPC267928
Remote Similarity	0.6008	NPC206251
Remote Similarity	0.6007	NPC314882
Remote Similarity	0.6007	NPC244543
Remote Similarity	0.6	NPC74575
Remote Similarity	0.6	NPC210123
Remote Similarity	0.6	NPC185782
Remote Similarity	0.6	NPC161887
Remote Similarity	0.6	NPC121772
Remote Similarity	0.5992	NPC311282
Remote Similarity	0.5992	NPC476138
Remote Similarity	0.5992	NPC60621
Remote Similarity	0.5992	NPC245816
Remote Similarity	0.5986	NPC314056
Remote Similarity	0.5984	NPC243850
Remote Similarity	0.5984	NPC177996
Remote Similarity	0.5984	NPC148183
Remote Similarity	0.5984	NPC152768
Remote Similarity	0.5984	NPC147983
Remote Similarity	0.5984	NPC212213
Remote Similarity	0.5977	NPC313804
Remote Similarity	0.5977	NPC315804
Remote Similarity	0.5976	NPC123976
Remote Similarity	0.5976	NPC167860
Remote Similarity	0.597	NPC469554
Remote Similarity	0.597	NPC72905
Remote Similarity	0.5968	NPC289086
Remote Similarity	0.5967	NPC194967
Remote Similarity	0.5962	NPC319232
Remote Similarity	0.5962	NPC24370
Remote Similarity	0.5961	NPC305984
Remote Similarity	0.5959	NPC474767
Remote Similarity	0.5952	NPC242923
Remote Similarity	0.5951	NPC295898
Remote Similarity	0.5951	NPC478012
Remote Similarity	0.5951	NPC478011
Remote Similarity	0.595	NPC473821
Remote Similarity	0.5943	NPC74153
Remote Similarity	0.594	NPC240384
Remote Similarity	0.5939	NPC187145
Remote Similarity	0.5938	NPC314270
Remote Similarity	0.5938	NPC107287
Remote Similarity	0.5934	NPC138370
Remote Similarity	0.5932	NPC219963
Remote Similarity	0.5931	NPC476518
Remote Similarity	0.593	NPC314176
Remote Similarity	0.5929	NPC472098
Remote Similarity	0.5926	NPC208522
Remote Similarity	0.5926	NPC198401
Remote Similarity	0.5921	NPC478006
Remote Similarity	0.5918	NPC474916
Remote Similarity	0.5918	NPC30540
Remote Similarity	0.5917	NPC224327
Remote Similarity	0.5914	NPC17565
Remote Similarity	0.5911	NPC232727
Remote Similarity	0.5909	NPC101543
Remote Similarity	0.5907	NPC315467
Remote Similarity	0.5906	NPC236668
Remote Similarity	0.5905	NPC14651
Remote Similarity	0.5905	NPC121658
Remote Similarity	0.5904	NPC285558
Remote Similarity	0.5898	NPC469727
Remote Similarity	0.5897	NPC165964
Remote Similarity	0.5891	NPC128115
Remote Similarity	0.5887	NPC478009
Remote Similarity	0.5887	NPC478010
Remote Similarity	0.5887	NPC328596
Remote Similarity	0.5887	NPC323752
Remote Similarity	0.5887	NPC328318
Remote Similarity	0.5885	NPC65277
Remote Similarity	0.5885	NPC84853
Remote Similarity	0.5884	NPC63109
Remote Similarity	0.5882	NPC146976
Remote Similarity	0.5882	NPC284678
Remote Similarity	0.588	NPC184680
Remote Similarity	0.5876	NPC137353
Remote Similarity	0.5875	NPC303658
Remote Similarity	0.587	NPC176538
Remote Similarity	0.5865	NPC266551
Remote Similarity	0.5863	NPC143325
Remote Similarity	0.5863	NPC150447
Remote Similarity	0.5863	NPC74619
Remote Similarity	0.5862	NPC21638
Remote Similarity	0.5859	NPC322064
Remote Similarity	0.5859	NPC470799

Drug Structure

NPD5749 OpenBabel08211708292D 37 40 0 0 0 0 0 0 0 0999 V2000 5.7023 1.5320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -0.8660 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 8.0029 5.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7242 1.7399 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 -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 6.0029 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5029 4.3660 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 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 4.4152 2.6910 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 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 2.5981 4.5000 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 -0.8660 2.5000 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 1.7321 4.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 4.3090 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 -1.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.0029 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 5.5000 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 7.5029 4.3660 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 7 1 0 0 0 0 4 34 1 0 0 0 0 5 18 1 0 0 0 0 6 28 1 0 0 0 0 7 35 1 0 0 0 0 8 10 1 0 0 0 0 8 28 1 0 0 0 0 9 11 1 0 0 0 0 9 28 1 0 0 0 0 10 29 1 0 0 0 0 11 29 1 0 0 0 0 12 13 1 0 0 0 0 12 30 1 0 0 0 0 13 34 1 0 0 0 0 14 16 2 0 0 0 0 14 17 1 0 0 0 0 15 16 1 0 0 0 0 15 24 2 0 0 0 0 16 36 1 0 0 0 0 17 21 1 0 0 0 0 17 23 2 0 0 0 0 18 19 2 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 19 25 1 0 0 0 0 20 22 1 0 0 0 0 20 27 2 0 0 0 0 21 25 1 0 0 0 0 21 26 2 0 0 0 0 22 26 1 0 0 0 0 22 31 2 0 0 0 0 23 24 1 0 0 0 0 23 35 1 0 0 0 0 25 37 1 0 0 0 0 27 30 1 0 0 0 0 29 36 1 0 0 0 0 32 36 2 0 0 0 0 33 36 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000661
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	9892860
ChEBI
CAS Number

Drug Properties

Molecular Weight	519.23
ALogP	-1.824
MLogP	2.56
XLogP	0.368
HDA	11
HBD	1
Rotatable Bonds	14
TPSA	139.63
RO5 Violation	1