NPASS drugs

Drug Information

Drug ID:	NPD4376
Drug Name:	Entinostat
Molecular Formula:	C21H20N4O3
Canonical SMILES:	OC(=NCc1ccc(cc1)C(=O)Nc1ccccc1N)OCc1cccnc1
Standard InCHI:	InChI=1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
Standard InCHIKey:	INVTYAOGFAGBOE-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4376

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	257
0.1-0.2	2090
0.2-0.3	9809
0.3-0.4	8836
0.4-0.5	6665
0.5-0.6	1769
0.6-0.7	1390
0.7-0.8	74
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	0.763	NPC471323
Intermediate Similarity	0.7528	NPC107287
Intermediate Similarity	0.7463	NPC118940
Intermediate Similarity	0.7435	NPC207851
Intermediate Similarity	0.7424	NPC474916
Intermediate Similarity	0.7419	NPC249614
Intermediate Similarity	0.7401	NPC112741
Intermediate Similarity	0.7394	NPC476419
Intermediate Similarity	0.7387	NPC103361
Intermediate Similarity	0.7366	NPC123839
Intermediate Similarity	0.736	NPC135950
Intermediate Similarity	0.7358	NPC90415
Intermediate Similarity	0.7353	NPC266249
Intermediate Similarity	0.7296	NPC138370
Intermediate Similarity	0.7293	NPC263455
Intermediate Similarity	0.7292	NPC243058
Intermediate Similarity	0.7263	NPC219848
Intermediate Similarity	0.7255	NPC313345
Intermediate Similarity	0.7255	NPC313796
Intermediate Similarity	0.7255	NPC314855
Intermediate Similarity	0.7255	NPC315638
Intermediate Similarity	0.7255	NPC309498
Intermediate Similarity	0.7254	NPC203635
Intermediate Similarity	0.7225	NPC256268
Intermediate Similarity	0.722	NPC314297
Intermediate Similarity	0.722	NPC315545
Intermediate Similarity	0.7214	NPC123395
Intermediate Similarity	0.7206	NPC327592
Intermediate Similarity	0.7191	NPC167400
Intermediate Similarity	0.7171	NPC472064
Intermediate Similarity	0.7171	NPC317373
Intermediate Similarity	0.7166	NPC41717
Intermediate Similarity	0.7143	NPC477979
Intermediate Similarity	0.7143	NPC471944
Intermediate Similarity	0.7128	NPC282103
Intermediate Similarity	0.7115	NPC314834
Intermediate Similarity	0.7108	NPC472062
Intermediate Similarity	0.7108	NPC57398
Intermediate Similarity	0.7108	NPC472069
Intermediate Similarity	0.7108	NPC472063
Intermediate Similarity	0.7107	NPC44354
Intermediate Similarity	0.7079	NPC239954
Intermediate Similarity	0.7071	NPC83111
Intermediate Similarity	0.7067	NPC472070
Intermediate Similarity	0.7056	NPC278434
Intermediate Similarity	0.705	NPC198673
Intermediate Similarity	0.7049	NPC312860
Intermediate Similarity	0.7048	NPC244856
Intermediate Similarity	0.7048	NPC318299
Intermediate Similarity	0.7044	NPC284338
Intermediate Similarity	0.7039	NPC289086
Intermediate Similarity	0.7039	NPC159630
Intermediate Similarity	0.7039	NPC314648
Intermediate Similarity	0.7039	NPC230085
Intermediate Similarity	0.7037	NPC229893
Intermediate Similarity	0.7033	NPC470020
Intermediate Similarity	0.7031	NPC471743
Intermediate Similarity	0.7031	NPC84347
Intermediate Similarity	0.703	NPC106824
Intermediate Similarity	0.7028	NPC471192
Intermediate Similarity	0.7028	NPC477909
Intermediate Similarity	0.7028	NPC36405
Intermediate Similarity	0.7028	NPC477907
Intermediate Similarity	0.7028	NPC42678
Intermediate Similarity	0.7024	NPC328318
Intermediate Similarity	0.7024	NPC328596
Intermediate Similarity	0.7015	NPC202812
Intermediate Similarity	0.7014	NPC317752
Intermediate Similarity	0.7014	NPC306644
Intermediate Similarity	0.7014	NPC236424
Intermediate Similarity	0.701	NPC73994
Intermediate Similarity	0.701	NPC470279
Intermediate Similarity	0.701	NPC24864
Intermediate Similarity	0.7	NPC72956
Remote Similarity	0.6995	NPC67288
Remote Similarity	0.6995	NPC131887
Remote Similarity	0.6995	NPC168911
Remote Similarity	0.6995	NPC27041
Remote Similarity	0.699	NPC317701
Remote Similarity	0.699	NPC284678
Remote Similarity	0.6989	NPC114310
Remote Similarity	0.6986	NPC472752
Remote Similarity	0.6981	NPC274842
Remote Similarity	0.698	NPC245916
Remote Similarity	0.6971	NPC475835
Remote Similarity	0.6967	NPC6865
Remote Similarity	0.6967	NPC153980
Remote Similarity	0.6965	NPC103230
Remote Similarity	0.6964	NPC101350
Remote Similarity	0.6963	NPC62367
Remote Similarity	0.6963	NPC273532
Remote Similarity	0.6959	NPC122436
Remote Similarity	0.6951	NPC477549
Remote Similarity	0.6948	NPC177996
Remote Similarity	0.6948	NPC147983
Remote Similarity	0.6939	NPC102755
Remote Similarity	0.6938	NPC63041
Remote Similarity	0.6935	NPC213914
Remote Similarity	0.6934	NPC234078
Remote Similarity	0.6934	NPC221100
Remote Similarity	0.6932	NPC29702
Remote Similarity	0.693	NPC216428
Remote Similarity	0.693	NPC301368
Remote Similarity	0.693	NPC84815
Remote Similarity	0.6923	NPC61011
Remote Similarity	0.6923	NPC471997
Remote Similarity	0.6923	NPC472065
Remote Similarity	0.692	NPC235685
Remote Similarity	0.6919	NPC160381
Remote Similarity	0.6919	NPC209362
Remote Similarity	0.6919	NPC62749
Remote Similarity	0.6916	NPC312645
Remote Similarity	0.6916	NPC471016
Remote Similarity	0.6912	NPC127026
Remote Similarity	0.6912	NPC127720
Remote Similarity	0.6905	NPC304179
Remote Similarity	0.6905	NPC48042
Remote Similarity	0.6905	NPC472550
Remote Similarity	0.6901	NPC4421
Remote Similarity	0.6901	NPC478157
Remote Similarity	0.69	NPC469489
Remote Similarity	0.69	NPC154339
Remote Similarity	0.6898	NPC323969
Remote Similarity	0.6897	NPC109922
Remote Similarity	0.6895	NPC24370
Remote Similarity	0.6895	NPC319232
Remote Similarity	0.6895	NPC473506
Remote Similarity	0.689	NPC243850
Remote Similarity	0.6887	NPC471194
Remote Similarity	0.6887	NPC476467
Remote Similarity	0.6887	NPC471193
Remote Similarity	0.6884	NPC6576
Remote Similarity	0.6884	NPC212768
Remote Similarity	0.6884	NPC473089
Remote Similarity	0.6884	NPC17059
Remote Similarity	0.6884	NPC473115
Remote Similarity	0.6884	NPC158020
Remote Similarity	0.6884	NPC75600
Remote Similarity	0.6881	NPC57797
Remote Similarity	0.6881	NPC250807
Remote Similarity	0.6881	NPC471980
Remote Similarity	0.6881	NPC76565
Remote Similarity	0.6875	NPC472259
Remote Similarity	0.6872	NPC164340
Remote Similarity	0.6869	NPC280290
Remote Similarity	0.6869	NPC470306
Remote Similarity	0.6866	NPC60621
Remote Similarity	0.6866	NPC477912
Remote Similarity	0.6864	NPC122968
Remote Similarity	0.6864	NPC475600
Remote Similarity	0.6864	NPC228377
Remote Similarity	0.6864	NPC475631
Remote Similarity	0.6864	NPC328186
Remote Similarity	0.6864	NPC87152
Remote Similarity	0.6864	NPC476110
Remote Similarity	0.6864	NPC477787
Remote Similarity	0.686	NPC306397
Remote Similarity	0.6854	NPC236668
Remote Similarity	0.6854	NPC89508
Remote Similarity	0.6853	NPC470205
Remote Similarity	0.6853	NPC48938
Remote Similarity	0.6852	NPC168209
Remote Similarity	0.685	NPC196251
Remote Similarity	0.685	NPC111602
Remote Similarity	0.685	NPC63199
Remote Similarity	0.685	NPC102338
Remote Similarity	0.6849	NPC475137
Remote Similarity	0.6849	NPC475498
Remote Similarity	0.6849	NPC473850
Remote Similarity	0.6847	NPC260434
Remote Similarity	0.6847	NPC475303
Remote Similarity	0.6847	NPC19692
Remote Similarity	0.6847	NPC220151
Remote Similarity	0.6847	NPC475596
Remote Similarity	0.6847	NPC316841
Remote Similarity	0.6842	NPC82053
Remote Similarity	0.6842	NPC238457
Remote Similarity	0.684	NPC82370
Remote Similarity	0.6839	NPC191310
Remote Similarity	0.6837	NPC206343
Remote Similarity	0.6837	NPC477908
Remote Similarity	0.6837	NPC471014
Remote Similarity	0.6837	NPC472285
Remote Similarity	0.6837	NPC475408
Remote Similarity	0.6837	NPC6981
Remote Similarity	0.6835	NPC477788
Remote Similarity	0.6834	NPC94752
Remote Similarity	0.6834	NPC118084
Remote Similarity	0.6833	NPC471977
Remote Similarity	0.6833	NPC470486
Remote Similarity	0.6833	NPC471190
Remote Similarity	0.6833	NPC475644
Remote Similarity	0.6832	NPC216550
Remote Similarity	0.683	NPC170751
Remote Similarity	0.683	NPC327769
Remote Similarity	0.6829	NPC212213
Remote Similarity	0.6829	NPC324245
Remote Similarity	0.6829	NPC320748
Remote Similarity	0.6827	NPC165599
Remote Similarity	0.6825	NPC174758

Drug Structure

NPD4376 OpenBabel08211705262D 32 34 0 0 0 0 0 0 0 0999 V2000 1.7321 -1.0000 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 -6.9282 -6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -5.5000 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 -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 -2.5981 -2.5000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -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 -6.0622 -4.5000 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 0.8660 0.5000 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 -1.7321 0.0000 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 0.8660 1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -4.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 N 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 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 5 1 0 0 0 0 2 6 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 16 1 0 0 0 0 5 18 2 0 0 0 0 6 19 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 10 2 0 0 0 0 8 15 1 0 0 0 0 9 17 2 0 0 0 0 10 17 1 0 0 0 0 11 23 2 0 0 0 0 12 16 2 0 0 0 0 12 23 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 16 1 0 0 0 0 14 28 1 0 0 0 0 17 20 1 0 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 25 1 0 0 0 0 20 25 1 0 0 0 0 20 26 2 0 0 0 0 21 24 2 3 0 0 0 21 27 1 0 0 0 0 21 28 1 0 0 0 0 22 29 1 0 0 0 0 22 30 1 0 0 0 0 25 31 1 0 0 0 0 27 32 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000172; DCL000994
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	4261
ChEBI
CAS Number

Drug Properties

Molecular Weight	376.15
ALogP	-1.1165
MLogP	3
XLogP	3.782
HDA	7
HBD	3
Rotatable Bonds	10
TPSA	109.83
RO5 Violation	0