NPASS drugs

Drug Information

Drug ID:	NPD5567
Drug Name:	Avanafil
Molecular Formula:	C23H26ClN7O3
Canonical SMILES:	OC[C@@H]1CCCN1c1ncc(c(=NCc2ccc(c(c2)Cl)OC)[nH]1)C(=NCc1ncccn1)O
Standard InCHI:	InChI=1S/C23H26ClN7O3/c1-34-19-6-5-15(10-18(19)24)11-27-21-17(22(33)28-13-20-25-7-3-8-26-20)12-29-23(30-21)31-9-2-4-16(31)14-32/h3,5-8,10,12,16,32H,2,4,9,11,13-14H2,1H3,(H,28,33)(H,27,29,30)/t16-/m0/s1
Standard InCHIKey:	WEAJZXNPAWBCOA-INIZCTEOSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5567

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	431
0.1-0.2	4097
0.2-0.3	8808
0.3-0.4	10870
0.4-0.5	4328
0.5-0.6	2089
0.6-0.7	263
0.7-0.8	4
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	0.7457	NPC160666
Intermediate Similarity	0.7321	NPC242923
Intermediate Similarity	0.7254	NPC56271
Intermediate Similarity	0.7249	NPC250178
Remote Similarity	0.6987	NPC471603
Remote Similarity	0.6983	NPC30540
Remote Similarity	0.6953	NPC308906
Remote Similarity	0.6885	NPC471614
Remote Similarity	0.6881	NPC472289
Remote Similarity	0.6867	NPC472031
Remote Similarity	0.6867	NPC472067
Remote Similarity	0.6867	NPC472066
Remote Similarity	0.6765	NPC130570
Remote Similarity	0.6734	NPC477796
Remote Similarity	0.6734	NPC477795
Remote Similarity	0.6734	NPC477806
Remote Similarity	0.6734	NPC477805
Remote Similarity	0.672	NPC472068
Remote Similarity	0.6694	NPC115595
Remote Similarity	0.6681	NPC113369
Remote Similarity	0.668	NPC150447
Remote Similarity	0.6667	NPC469592
Remote Similarity	0.6667	NPC471080
Remote Similarity	0.6638	NPC469589
Remote Similarity	0.6609	NPC285558
Remote Similarity	0.6606	NPC144114
Remote Similarity	0.6578	NPC280638
Remote Similarity	0.6557	NPC471178
Remote Similarity	0.6555	NPC469594
Remote Similarity	0.6543	NPC187145
Remote Similarity	0.6542	NPC17305
Remote Similarity	0.6527	NPC193267
Remote Similarity	0.6527	NPC213530
Remote Similarity	0.6524	NPC475910
Remote Similarity	0.6513	NPC12100
Remote Similarity	0.6485	NPC173080
Remote Similarity	0.6478	NPC232727
Remote Similarity	0.6475	NPC107160
Remote Similarity	0.6466	NPC165349
Remote Similarity	0.6466	NPC264166
Remote Similarity	0.6466	NPC274291
Remote Similarity	0.6466	NPC329708
Remote Similarity	0.6466	NPC118832
Remote Similarity	0.6466	NPC47059
Remote Similarity	0.6465	NPC164664
Remote Similarity	0.6462	NPC124542
Remote Similarity	0.6462	NPC59779
Remote Similarity	0.6462	NPC471177
Remote Similarity	0.6456	NPC162530
Remote Similarity	0.6435	NPC105758
Remote Similarity	0.6435	NPC476688
Remote Similarity	0.6435	NPC476686
Remote Similarity	0.6429	NPC295452
Remote Similarity	0.6429	NPC171393
Remote Similarity	0.6426	NPC174758
Remote Similarity	0.6419	NPC278874
Remote Similarity	0.6408	NPC323244
Remote Similarity	0.6404	NPC251090
Remote Similarity	0.6398	NPC123976
Remote Similarity	0.6398	NPC167860
Remote Similarity	0.6395	NPC470500
Remote Similarity	0.6393	NPC166655
Remote Similarity	0.6388	NPC307963
Remote Similarity	0.6383	NPC476465
Remote Similarity	0.6382	NPC314954
Remote Similarity	0.638	NPC477891
Remote Similarity	0.638	NPC161887
Remote Similarity	0.638	NPC219963
Remote Similarity	0.6371	NPC328924
Remote Similarity	0.6368	NPC472111
Remote Similarity	0.6364	NPC469975
Remote Similarity	0.6364	NPC121772
Remote Similarity	0.6364	NPC19872
Remote Similarity	0.6352	NPC475774
Remote Similarity	0.6337	NPC473317
Remote Similarity	0.6332	NPC314882
Remote Similarity	0.633	NPC208060
Remote Similarity	0.6329	NPC5145
Remote Similarity	0.6327	NPC125597
Remote Similarity	0.6318	NPC266931
Remote Similarity	0.6316	NPC289786
Remote Similarity	0.6314	NPC287208
Remote Similarity	0.6304	NPC267928
Remote Similarity	0.6301	NPC103687
Remote Similarity	0.6301	NPC132631
Remote Similarity	0.63	NPC92111
Remote Similarity	0.6299	NPC39092
Remote Similarity	0.6295	NPC295228
Remote Similarity	0.6293	NPC329747
Remote Similarity	0.6293	NPC315957
Remote Similarity	0.6293	NPC176538
Remote Similarity	0.6287	NPC174672
Remote Similarity	0.6283	NPC230805
Remote Similarity	0.6282	NPC245816
Remote Similarity	0.6282	NPC476138
Remote Similarity	0.6281	NPC303658
Remote Similarity	0.6278	NPC315467
Remote Similarity	0.6276	NPC26679
Remote Similarity	0.6275	NPC110151
Remote Similarity	0.6272	NPC133140
Remote Similarity	0.6272	NPC195268
Remote Similarity	0.6271	NPC194699
Remote Similarity	0.6271	NPC219350
Remote Similarity	0.627	NPC60621
Remote Similarity	0.627	NPC310118
Remote Similarity	0.6266	NPC274982
Remote Similarity	0.6266	NPC470799
Remote Similarity	0.6266	NPC8022
Remote Similarity	0.6265	NPC21461
Remote Similarity	0.6265	NPC300114
Remote Similarity	0.6261	NPC473053
Remote Similarity	0.6261	NPC11464
Remote Similarity	0.6261	NPC242209
Remote Similarity	0.6256	NPC76748
Remote Similarity	0.6255	NPC17565
Remote Similarity	0.6255	NPC478009
Remote Similarity	0.6255	NPC475070
Remote Similarity	0.625	NPC287437
Remote Similarity	0.625	NPC471762
Remote Similarity	0.625	NPC66777
Remote Similarity	0.6245	NPC82548
Remote Similarity	0.624	NPC473513
Remote Similarity	0.6234	NPC208751
Remote Similarity	0.6233	NPC266551
Remote Similarity	0.6233	NPC224632
Remote Similarity	0.6223	NPC477019
Remote Similarity	0.622	NPC65277
Remote Similarity	0.6217	NPC93390
Remote Similarity	0.6213	NPC223427
Remote Similarity	0.6211	NPC296527
Remote Similarity	0.6208	NPC316981
Remote Similarity	0.6208	NPC112206
Remote Similarity	0.6208	NPC202605
Remote Similarity	0.6201	NPC324149
Remote Similarity	0.6198	NPC63109
Remote Similarity	0.6194	NPC35761
Remote Similarity	0.619	NPC223223
Remote Similarity	0.6187	NPC228206
Remote Similarity	0.6184	NPC51047
Remote Similarity	0.6178	NPC84478
Remote Similarity	0.6176	NPC18348
Remote Similarity	0.6175	NPC469554
Remote Similarity	0.6174	NPC478006
Remote Similarity	0.6169	NPC319232
Remote Similarity	0.6169	NPC24370
Remote Similarity	0.6169	NPC2497
Remote Similarity	0.6167	NPC277306
Remote Similarity	0.6167	NPC469442
Remote Similarity	0.6164	NPC224928
Remote Similarity	0.6164	NPC78767
Remote Similarity	0.6164	NPC473814
Remote Similarity	0.616	NPC323345
Remote Similarity	0.616	NPC470164
Remote Similarity	0.6157	NPC177404
Remote Similarity	0.6154	NPC249040
Remote Similarity	0.6154	NPC51854
Remote Similarity	0.6151	NPC185782
Remote Similarity	0.6151	NPC180504
Remote Similarity	0.6148	NPC316756
Remote Similarity	0.6144	NPC53144
Remote Similarity	0.6142	NPC28945
Remote Similarity	0.6141	NPC264176
Remote Similarity	0.614	NPC478011
Remote Similarity	0.6134	NPC478010
Remote Similarity	0.6133	NPC99891
Remote Similarity	0.6132	NPC288349
Remote Similarity	0.6132	NPC170114
Remote Similarity	0.613	NPC99666
Remote Similarity	0.6129	NPC97367
Remote Similarity	0.6122	NPC136924
Remote Similarity	0.6121	NPC13880
Remote Similarity	0.612	NPC237978
Remote Similarity	0.6118	NPC36229
Remote Similarity	0.6118	NPC470784
Remote Similarity	0.6118	NPC476581
Remote Similarity	0.6118	NPC16452
Remote Similarity	0.6117	NPC314176
Remote Similarity	0.6116	NPC25539
Remote Similarity	0.6115	NPC9729
Remote Similarity	0.6114	NPC471593
Remote Similarity	0.6113	NPC280272
Remote Similarity	0.6111	NPC476582
Remote Similarity	0.6111	NPC18487
Remote Similarity	0.6111	NPC4071
Remote Similarity	0.6111	NPC476578
Remote Similarity	0.6104	NPC226202
Remote Similarity	0.6102	NPC295898
Remote Similarity	0.6102	NPC470678
Remote Similarity	0.61	NPC208284
Remote Similarity	0.6099	NPC96890
Remote Similarity	0.6098	NPC128115
Remote Similarity	0.6096	NPC46580
Remote Similarity	0.6091	NPC470549
Remote Similarity	0.6091	NPC50511
Remote Similarity	0.6089	NPC470474
Remote Similarity	0.6087	NPC323198
Remote Similarity	0.6087	NPC220852
Remote Similarity	0.6085	NPC329793
Remote Similarity	0.6082	NPC197141
Remote Similarity	0.608	NPC157931

Drug Structure

NPD5567 OpenBabel08211708292D 37 40 0 0 1 0 0 0 0 0999 V2000 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8147 -1.2024 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 -3.3147 -0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 5.1962 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 -1.8366 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 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 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8535 1.3849 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 -2.6456 0.4067 0.0000 C 0 0 1 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 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 5.1962 -1.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 N 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 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.8046 1.6939 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 5.1962 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5477 1.0248 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 4 1 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 8 1 0 0 0 0 4 16 1 0 0 0 0 5 6 2 0 0 0 0 5 15 1 0 0 0 0 6 19 1 0 0 0 0 7 25 1 0 0 0 0 8 26 2 0 0 0 0 9 31 1 0 0 0 0 10 15 2 0 0 0 0 10 18 1 0 0 0 0 11 15 1 0 0 0 0 11 27 1 0 0 0 0 12 17 2 0 0 0 0 12 29 1 0 0 0 0 13 20 1 0 0 0 0 13 28 1 0 0 0 0 14 32 1 0 0 0 0 16 14 1 1 0 0 0 16 31 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 24 1 0 0 0 0 19 34 1 0 0 0 0 20 25 2 0 0 0 0 20 26 1 0 0 0 0 21 27 2 3 0 0 0 21 30 1 0 0 0 0 22 28 2 3 0 0 0 22 33 1 0 0 0 0 23 29 2 0 0 0 0 23 30 1 0 0 0 0 23 31 1 0 0 0 0 30 35 1 0 0 0 0 32 36 1 0 0 0 0 33 37 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DNAP001693
DrugBank	DB06237
ChEMBL	CHEMBL1963681
IUPHAR/BPS	7448
PharmaGKB
KEGG Drug	D03217
PubChem CID	9869929
ChEBI	66876
CAS Number	330784-47-9

Drug Properties

Molecular Weight	483.18
ALogP	-2.1165
MLogP	2.78
XLogP	2.999
HDA	9
HBD	3
Rotatable Bonds	12
TPSA	127.82
RO5 Violation	0