NPASS drugs

Drug Information

Drug ID:	NPD3889
Drug Name:	Flibanserin
Molecular Formula:	C20H21F3N4O
Canonical SMILES:	Oc1nc2c(n1CCN1CCN(CC1)c1cccc(c1)C(F)(F)F)cccc2
Standard InCHI:	InChI=1S/C20H21F3N4O/c21-20(22,23)15-4-3-5-16(14-15)26-11-8-25(9-12-26)10-13-27-18-7-2-1-6-17(18)24-19(27)28/h1-7,14H,8-13H2,(H,24,28)
Standard InCHIKey:	PPRRDFIXUUSXRA-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3889

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	642
0.1-0.2	9485
0.2-0.3	13656
0.3-0.4	3501
0.4-0.5	1854
0.5-0.6	1350
0.6-0.7	378
0.7-0.8	24
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	0.7895	NPC317054
Intermediate Similarity	0.7888	NPC114209
Intermediate Similarity	0.764	NPC476341
Intermediate Similarity	0.7545	NPC476219
Intermediate Similarity	0.7515	NPC300238
Intermediate Similarity	0.744	NPC476297
Intermediate Similarity	0.743	NPC471609
Intermediate Similarity	0.7317	NPC42483
Intermediate Similarity	0.7267	NPC216159
Intermediate Similarity	0.7225	NPC470203
Intermediate Similarity	0.7173	NPC469308
Intermediate Similarity	0.7168	NPC470204
Intermediate Similarity	0.7126	NPC204141
Intermediate Similarity	0.7126	NPC225018
Intermediate Similarity	0.7118	NPC469975
Intermediate Similarity	0.7045	NPC195507
Intermediate Similarity	0.7045	NPC2165
Intermediate Similarity	0.7041	NPC470111
Intermediate Similarity	0.7035	NPC120070
Intermediate Similarity	0.703	NPC104483
Intermediate Similarity	0.702	NPC143156
Intermediate Similarity	0.7006	NPC20144
Intermediate Similarity	0.7	NPC288445
Intermediate Similarity	0.7	NPC282531
Remote Similarity	0.6989	NPC478182
Remote Similarity	0.6985	NPC471603
Remote Similarity	0.6971	NPC122141
Remote Similarity	0.6952	NPC472289
Remote Similarity	0.6944	NPC208060
Remote Similarity	0.6932	NPC478185
Remote Similarity	0.6914	NPC293487
Remote Similarity	0.6902	NPC477891
Remote Similarity	0.6882	NPC478186
Remote Similarity	0.6879	NPC325903
Remote Similarity	0.686	NPC40070
Remote Similarity	0.6845	NPC88121
Remote Similarity	0.6833	NPC164664
Remote Similarity	0.6828	NPC108011
Remote Similarity	0.6826	NPC88097
Remote Similarity	0.6816	NPC478183
Remote Similarity	0.6807	NPC314102
Remote Similarity	0.6807	NPC251722
Remote Similarity	0.6798	NPC478184
Remote Similarity	0.6796	NPC476688
Remote Similarity	0.6796	NPC476686
Remote Similarity	0.6796	NPC105758
Remote Similarity	0.6788	NPC198988
Remote Similarity	0.6786	NPC284635
Remote Similarity	0.6786	NPC115611
Remote Similarity	0.6784	NPC63545
Remote Similarity	0.6778	NPC278874
Remote Similarity	0.6744	NPC179787
Remote Similarity	0.6744	NPC469811
Remote Similarity	0.6744	NPC201380
Remote Similarity	0.6742	NPC224632
Remote Similarity	0.6731	NPC162689
Remote Similarity	0.6731	NPC54102
Remote Similarity	0.6724	NPC470233
Remote Similarity	0.6722	NPC56233
Remote Similarity	0.672	NPC144114
Remote Similarity	0.672	NPC307191
Remote Similarity	0.6707	NPC125746
Remote Similarity	0.6705	NPC321911
Remote Similarity	0.6685	NPC81229
Remote Similarity	0.6685	NPC255229
Remote Similarity	0.6667	NPC33421
Remote Similarity	0.6648	NPC32534
Remote Similarity	0.6648	NPC91895
Remote Similarity	0.6647	NPC325252
Remote Similarity	0.6632	NPC254762
Remote Similarity	0.663	NPC49217
Remote Similarity	0.6629	NPC6436
Remote Similarity	0.6629	NPC475990
Remote Similarity	0.6629	NPC474880
Remote Similarity	0.6629	NPC221786
Remote Similarity	0.6629	NPC477591
Remote Similarity	0.6628	NPC470440
Remote Similarity	0.6617	NPC116555
Remote Similarity	0.6611	NPC247987
Remote Similarity	0.6611	NPC317105
Remote Similarity	0.661	NPC51054
Remote Similarity	0.6607	NPC150259
Remote Similarity	0.6605	NPC75999
Remote Similarity	0.6603	NPC476566
Remote Similarity	0.6595	NPC280852
Remote Similarity	0.6592	NPC229173
Remote Similarity	0.6588	NPC2949
Remote Similarity	0.6588	NPC59084
Remote Similarity	0.6584	NPC122718
Remote Similarity	0.6578	NPC16659
Remote Similarity	0.6578	NPC24864
Remote Similarity	0.6573	NPC129721
Remote Similarity	0.6573	NPC236711
Remote Similarity	0.6568	NPC169433
Remote Similarity	0.6561	NPC81561
Remote Similarity	0.6556	NPC194881
Remote Similarity	0.655	NPC63157
Remote Similarity	0.655	NPC473868
Remote Similarity	0.6541	NPC297034
Remote Similarity	0.6541	NPC469938
Remote Similarity	0.6536	NPC56765
Remote Similarity	0.6535	NPC71238
Remote Similarity	0.6528	NPC158055
Remote Similarity	0.6524	NPC265710
Remote Similarity	0.6522	NPC46358
Remote Similarity	0.6506	NPC256893
Remote Similarity	0.6506	NPC471322
Remote Similarity	0.6505	NPC24594
Remote Similarity	0.6505	NPC472122
Remote Similarity	0.6503	NPC317430
Remote Similarity	0.6497	NPC148140
Remote Similarity	0.6494	NPC143872
Remote Similarity	0.6492	NPC135601
Remote Similarity	0.6492	NPC17273
Remote Similarity	0.6492	NPC141612
Remote Similarity	0.6491	NPC238499
Remote Similarity	0.6486	NPC314557
Remote Similarity	0.6474	NPC21429
Remote Similarity	0.6471	NPC326575
Remote Similarity	0.6467	NPC194411
Remote Similarity	0.6457	NPC21605
Remote Similarity	0.645	NPC218268
Remote Similarity	0.6444	NPC92796
Remote Similarity	0.6444	NPC135141
Remote Similarity	0.6439	NPC242923
Remote Similarity	0.6439	NPC54981
Remote Similarity	0.6437	NPC314372
Remote Similarity	0.6437	NPC469525
Remote Similarity	0.6436	NPC12649
Remote Similarity	0.6436	NPC133261
Remote Similarity	0.6429	NPC271797
Remote Similarity	0.6429	NPC21174
Remote Similarity	0.6417	NPC121903
Remote Similarity	0.6417	NPC315715
Remote Similarity	0.6416	NPC190296
Remote Similarity	0.6409	NPC215584
Remote Similarity	0.6409	NPC44773
Remote Similarity	0.6407	NPC475450
Remote Similarity	0.6404	NPC281094
Remote Similarity	0.6402	NPC472105
Remote Similarity	0.6402	NPC187827
Remote Similarity	0.6402	NPC250361
Remote Similarity	0.6402	NPC15840
Remote Similarity	0.6398	NPC182570
Remote Similarity	0.6398	NPC48564
Remote Similarity	0.6398	NPC265605
Remote Similarity	0.6398	NPC472123
Remote Similarity	0.6387	NPC472294
Remote Similarity	0.6386	NPC476131
Remote Similarity	0.6384	NPC105818
Remote Similarity	0.6384	NPC24678
Remote Similarity	0.6383	NPC473380
Remote Similarity	0.6383	NPC240088
Remote Similarity	0.638	NPC476322
Remote Similarity	0.6378	NPC474897
Remote Similarity	0.6377	NPC282247
Remote Similarity	0.6369	NPC473930
Remote Similarity	0.6364	NPC37423
Remote Similarity	0.6364	NPC275305
Remote Similarity	0.6364	NPC471579
Remote Similarity	0.6364	NPC267811
Remote Similarity	0.6354	NPC318065
Remote Similarity	0.6354	NPC206819
Remote Similarity	0.6352	NPC471402
Remote Similarity	0.6352	NPC297486
Remote Similarity	0.6352	NPC240136
Remote Similarity	0.6347	NPC69914
Remote Similarity	0.6347	NPC22079
Remote Similarity	0.6347	NPC282398
Remote Similarity	0.6344	NPC82331
Remote Similarity	0.6343	NPC159856
Remote Similarity	0.6339	NPC476118
Remote Similarity	0.6337	NPC312092
Remote Similarity	0.6337	NPC73767
Remote Similarity	0.6335	NPC243058
Remote Similarity	0.6335	NPC472109
Remote Similarity	0.6335	NPC472110
Remote Similarity	0.6335	NPC215519
Remote Similarity	0.6328	NPC37548
Remote Similarity	0.6326	NPC187145
Remote Similarity	0.6325	NPC473762
Remote Similarity	0.6324	NPC63751
Remote Similarity	0.6313	NPC25008
Remote Similarity	0.6313	NPC469786
Remote Similarity	0.6313	NPC259644
Remote Similarity	0.6313	NPC469760
Remote Similarity	0.6313	NPC469763
Remote Similarity	0.6313	NPC73952
Remote Similarity	0.6313	NPC469765
Remote Similarity	0.6307	NPC288838
Remote Similarity	0.6304	NPC274229
Remote Similarity	0.6303	NPC250178
Remote Similarity	0.6303	NPC476950
Remote Similarity	0.6302	NPC203635
Remote Similarity	0.6301	NPC469784
Remote Similarity	0.6301	NPC469780
Remote Similarity	0.6301	NPC469767
Remote Similarity	0.6301	NPC469783
Remote Similarity	0.6301	NPC469779
Remote Similarity	0.6301	NPC469768

Drug Structure

NPD3889 OpenBabel08211704332D 29 32 0 0 0 0 0 0 0 0999 V2000 -2.8698 -0.8226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2007 -1.5657 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 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 -2.5608 0.1285 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2226 -1.3578 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 2.5981 -1.5000 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 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -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 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -3.5000 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 -1.5827 0.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9135 -0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1045 0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5622 -5.3660 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 7.0622 -4.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -5.0000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -1.0827 1.2024 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -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 0.6386 1.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4307 2.6418 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 6 1 0 0 0 0 2 7 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 15 1 0 0 0 0 5 16 2 0 0 0 0 6 17 2 0 0 0 0 7 18 2 0 0 0 0 8 11 1 0 0 0 0 8 25 1 0 0 0 0 9 12 1 0 0 0 0 9 25 1 0 0 0 0 10 13 1 0 0 0 0 10 25 1 0 0 0 0 11 26 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 18 27 1 0 0 0 0 19 24 2 0 0 0 0 19 27 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 22 1 0 0 0 0 20 23 1 0 0 0 0 28 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000805
DrugBank	DB04908
ChEMBL	CHEMBL231068
IUPHAR/BPS	8182
PharmaGKB
KEGG Drug	D02577
PubChem CID	6918248
ChEBI	90865
CAS Number	167933-07-5

Drug Properties

Molecular Weight	390.17
ALogP	0.747
MLogP	2.78
XLogP	4.406
HDA	4
HBD	1
Rotatable Bonds	9
TPSA	44.53
RO5 Violation	0