NPASS drugs

Drug Information

Drug ID:	NPD1394
Drug Name:	Vorinostat
Molecular Formula:	C14H20N2O3
Canonical SMILES:	ON=C(CCCCCCC(=Nc1ccccc1)O)O
Standard InCHI:	InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)
Standard InCHIKey:	WAEXFXRVDQXREF-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD1394

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	83
0.1-0.2	1557
0.2-0.3	10272
0.3-0.4	12924
0.4-0.5	4747
0.5-0.6	1145
0.6-0.7	129
0.7-0.8	29
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

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
High Similarity	1.0	NPC476483
High Similarity	0.8636	NPC15839
Intermediate Similarity	0.8409	NPC307456
Intermediate Similarity	0.802	NPC178681
Intermediate Similarity	0.7812	NPC78154
Intermediate Similarity	0.7706	NPC205652
Intermediate Similarity	0.7706	NPC470550
Intermediate Similarity	0.7526	NPC470877
Intermediate Similarity	0.75	NPC471638
Intermediate Similarity	0.7449	NPC141139
Intermediate Similarity	0.7449	NPC121872
Intermediate Similarity	0.7449	NPC471307
Intermediate Similarity	0.7449	NPC209764
Intermediate Similarity	0.7449	NPC92689
Intermediate Similarity	0.7449	NPC74936
Intermediate Similarity	0.7449	NPC159178
Intermediate Similarity	0.7449	NPC78041
Intermediate Similarity	0.7411	NPC147957
Intermediate Similarity	0.7383	NPC76327
Intermediate Similarity	0.7248	NPC255721
Intermediate Similarity	0.7228	NPC471309
Intermediate Similarity	0.7222	NPC37584
Intermediate Similarity	0.7222	NPC66775
Intermediate Similarity	0.72	NPC226438
Intermediate Similarity	0.7182	NPC9336
Intermediate Similarity	0.7157	NPC161972
Intermediate Similarity	0.7157	NPC303045
Intermediate Similarity	0.7143	NPC474926
Intermediate Similarity	0.7087	NPC25565
Intermediate Similarity	0.7019	NPC311242
Intermediate Similarity	0.7019	NPC475439
Intermediate Similarity	0.7019	NPC473501
Intermediate Similarity	0.7009	NPC474430
Remote Similarity	0.6957	NPC301874
Remote Similarity	0.6931	NPC316108
Remote Similarity	0.6931	NPC172128
Remote Similarity	0.6917	NPC317758
Remote Similarity	0.6889	NPC271732
Remote Similarity	0.686	NPC325013
Remote Similarity	0.6852	NPC471317
Remote Similarity	0.6842	NPC264782
Remote Similarity	0.6829	NPC101372
Remote Similarity	0.6827	NPC58674
Remote Similarity	0.6774	NPC314431
Remote Similarity	0.6733	NPC297532
Remote Similarity	0.6699	NPC245259
Remote Similarity	0.6697	NPC202613
Remote Similarity	0.6697	NPC471310
Remote Similarity	0.6694	NPC259098
Remote Similarity	0.6694	NPC197680
Remote Similarity	0.6636	NPC224610
Remote Similarity	0.6636	NPC88267
Remote Similarity	0.6636	NPC194390
Remote Similarity	0.6636	NPC113326
Remote Similarity	0.6634	NPC473031
Remote Similarity	0.6607	NPC44836
Remote Similarity	0.6598	NPC192623
Remote Similarity	0.6589	NPC159589
Remote Similarity	0.6587	NPC316746
Remote Similarity	0.6585	NPC205946
Remote Similarity	0.6577	NPC313810
Remote Similarity	0.6569	NPC12429
Remote Similarity	0.6569	NPC325441
Remote Similarity	0.6518	NPC327481
Remote Similarity	0.6514	NPC70201
Remote Similarity	0.6508	NPC226662
Remote Similarity	0.6476	NPC323164
Remote Similarity	0.6462	NPC475707
Remote Similarity	0.6446	NPC317564
Remote Similarity	0.6442	NPC191444
Remote Similarity	0.6442	NPC258627
Remote Similarity	0.6436	NPC229477
Remote Similarity	0.6429	NPC278451
Remote Similarity	0.6422	NPC12730
Remote Similarity	0.6412	NPC287358
Remote Similarity	0.6412	NPC166667
Remote Similarity	0.6408	NPC30445
Remote Similarity	0.6406	NPC476685
Remote Similarity	0.6406	NPC476687
Remote Similarity	0.6406	NPC476689
Remote Similarity	0.64	NPC134825
Remote Similarity	0.6396	NPC311660
Remote Similarity	0.6396	NPC164859
Remote Similarity	0.6391	NPC316202
Remote Similarity	0.6389	NPC33168
Remote Similarity	0.6346	NPC176858
Remote Similarity	0.6346	NPC315403
Remote Similarity	0.6339	NPC256838
Remote Similarity	0.6316	NPC243162
Remote Similarity	0.6311	NPC262295
Remote Similarity	0.6308	NPC184437
Remote Similarity	0.6299	NPC471313
Remote Similarity	0.6299	NPC471311
Remote Similarity	0.6296	NPC314287
Remote Similarity	0.6293	NPC319579
Remote Similarity	0.629	NPC328683
Remote Similarity	0.629	NPC283130
Remote Similarity	0.6283	NPC211551
Remote Similarity	0.6279	NPC313466
Remote Similarity	0.6273	NPC75496
Remote Similarity	0.6273	NPC323726
Remote Similarity	0.6261	NPC164802
Remote Similarity	0.625	NPC280807
Remote Similarity	0.625	NPC111233
Remote Similarity	0.6239	NPC329011
Remote Similarity	0.6218	NPC471318
Remote Similarity	0.6216	NPC326792
Remote Similarity	0.6214	NPC203076
Remote Similarity	0.6207	NPC470127
Remote Similarity	0.6204	NPC472242
Remote Similarity	0.6194	NPC472243
Remote Similarity	0.619	NPC107135
Remote Similarity	0.619	NPC173991
Remote Similarity	0.6186	NPC474584
Remote Similarity	0.6172	NPC150863
Remote Similarity	0.6168	NPC108800
Remote Similarity	0.6167	NPC222982
Remote Similarity	0.6154	NPC43655
Remote Similarity	0.6154	NPC329358
Remote Similarity	0.6154	NPC198747
Remote Similarity	0.6148	NPC314113
Remote Similarity	0.614	NPC313362
Remote Similarity	0.6134	NPC35850
Remote Similarity	0.6134	NPC322735
Remote Similarity	0.6134	NPC276949
Remote Similarity	0.6134	NPC314141
Remote Similarity	0.6131	NPC472103
Remote Similarity	0.6126	NPC213774
Remote Similarity	0.6121	NPC302790
Remote Similarity	0.6115	NPC254798
Remote Similarity	0.6111	NPC315632
Remote Similarity	0.6107	NPC324611
Remote Similarity	0.6103	NPC472241
Remote Similarity	0.6098	NPC321869
Remote Similarity	0.6095	NPC262393
Remote Similarity	0.6094	NPC72473
Remote Similarity	0.6094	NPC307437
Remote Similarity	0.6094	NPC58827
Remote Similarity	0.6094	NPC476950
Remote Similarity	0.6087	NPC231705
Remote Similarity	0.6083	NPC118202
Remote Similarity	0.6083	NPC329190
Remote Similarity	0.6083	NPC33742
Remote Similarity	0.6071	NPC469457
Remote Similarity	0.6068	NPC258056
Remote Similarity	0.6066	NPC192209
Remote Similarity	0.6045	NPC126637
Remote Similarity	0.6045	NPC122553
Remote Similarity	0.6043	NPC472100
Remote Similarity	0.6034	NPC20322
Remote Similarity	0.6033	NPC197470
Remote Similarity	0.6033	NPC317254
Remote Similarity	0.6019	NPC265521
Remote Similarity	0.6018	NPC291610
Remote Similarity	0.6017	NPC474149
Remote Similarity	0.6016	NPC229353
Remote Similarity	0.6014	NPC477890
Remote Similarity	0.6	NPC1986
Remote Similarity	0.6	NPC187036
Remote Similarity	0.6	NPC296163
Remote Similarity	0.6	NPC472245
Remote Similarity	0.6	NPC474544
Remote Similarity	0.5984	NPC82963
Remote Similarity	0.5984	NPC2265
Remote Similarity	0.5984	NPC470544
Remote Similarity	0.598	NPC14326
Remote Similarity	0.5971	NPC470824
Remote Similarity	0.5965	NPC178902
Remote Similarity	0.5962	NPC3210
Remote Similarity	0.5952	NPC39818
Remote Similarity	0.5941	NPC309279
Remote Similarity	0.594	NPC297584
Remote Similarity	0.594	NPC91615
Remote Similarity	0.5938	NPC208302
Remote Similarity	0.5935	NPC311737
Remote Similarity	0.5935	NPC38458
Remote Similarity	0.5935	NPC313449
Remote Similarity	0.5935	NPC470545
Remote Similarity	0.5935	NPC169328
Remote Similarity	0.5935	NPC254088
Remote Similarity	0.5929	NPC259678
Remote Similarity	0.592	NPC53596
Remote Similarity	0.592	NPC130931
Remote Similarity	0.592	NPC289330
Remote Similarity	0.592	NPC471308
Remote Similarity	0.592	NPC160120
Remote Similarity	0.592	NPC17388
Remote Similarity	0.592	NPC150323
Remote Similarity	0.5913	NPC275467
Remote Similarity	0.5902	NPC288232
Remote Similarity	0.5899	NPC470403
Remote Similarity	0.5899	NPC470404
Remote Similarity	0.5899	NPC470394
Remote Similarity	0.5897	NPC172170
Remote Similarity	0.5897	NPC142297
Remote Similarity	0.5891	NPC314278
Remote Similarity	0.5887	NPC470546
Remote Similarity	0.5887	NPC314992
Remote Similarity	0.5887	NPC264580
Remote Similarity	0.5887	NPC81561

Drug Structure

NPD1394 OpenBabel08211700192D 22 22 0 0 0 0 0 0 0 0999 V2000 1.7321 -2.0000 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 1.7321 1.0000 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 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 2.5981 -3.5000 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 -0.0000 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 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -6.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 0.0000 O 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 0.8660 -6.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -6.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 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 8 1 0 0 0 0 5 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 1 0 0 0 0 12 15 1 0 0 0 0 13 15 2 3 0 0 0 13 17 1 0 0 0 0 14 16 2 3 0 0 0 14 18 1 0 0 0 0 16 19 1 0 0 0 0 17 20 1 0 0 0 0 18 21 1 0 0 0 0 19 22 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001082
DrugBank	DB02546
ChEMBL	CHEMBL98
IUPHAR/BPS	6852
PharmaGKB	PA164748224
KEGG Drug
PubChem CID	5311
ChEBI	45716
CAS Number	149647-78-9

Drug Properties

Molecular Weight	264.15
ALogP	-1.3619
MLogP	2.45
XLogP	4.307
HDA	3
HBD	3
Rotatable Bonds	11
TPSA	85.41
RO5 Violation	0