CHEBI:132082 - entinostat

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ChEBI Name entinostat
ChEBI ID CHEBI:132082
Definition A member of the class of benzamides resulting from the formal condensation of the carboxy group of the pyridin-3-ylmethyl carbamate derivative of p-(aminomethyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an inhibitor of histone deacetylase isoform 1 (HDAC1) and isoform 3 (HDAC3).
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Sabrina Toro
Secondary ChEBI IDs CHEBI:94191
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Formula C21H20N4O3
Net Charge 0
Average Mass 376.409
Monoisotopic Mass 376.154
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)
InChIKey INVTYAOGFAGBOE-UHFFFAOYSA-N
SMILES C(=O)(OCC1=CN=CC=C1)NCC2=CC=C(C=C2)C(=O)NC3=CC=CC=C3N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 3.5.1.98 (histone deacetylase) inhibitor
An EC 3.5.1.* (non-peptide linear amide C-N hydrolase) inhibitor that interferes with the function of histone deacetylase (EC 3.5.1.98).
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing entinostat (CHEBI:132082) has functional parent 1,2-phenylenediamine (CHEBI:34043)
entinostat (CHEBI:132082) has role antineoplastic agent (CHEBI:35610)
entinostat (CHEBI:132082) has role apoptosis inducer (CHEBI:68495)
entinostat (CHEBI:132082) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115)
entinostat (CHEBI:132082) is a benzamides (CHEBI:22702)
entinostat (CHEBI:132082) is a carbamate ester (CHEBI:23003)
entinostat (CHEBI:132082) is a primary amino compound (CHEBI:50994)
entinostat (CHEBI:132082) is a pyridines (CHEBI:26421)
entinostat (CHEBI:132082) is a substituted aniline (CHEBI:48975)
Incoming pyridin-3-ylmethyl {4-[(2-amino-4-fluorophenyl)carbamoyl]benzyl}carbamate (CHEBI:125311) has functional parent entinostat (CHEBI:132082)
IUPAC Name
pyridin-3-ylmethyl {4-[(2-aminophenyl)carbamoyl]benzyl}carbamate
INNs Sources
entinostat WHO MedNet
entinostat WHO MedNet
entinostat WHO MedNet
entinostatum WHO MedNet
Synonyms Sources
BAY 86-5274 ChemIDplus
BAY86-5274 ChemIDplus
MS 27-275 ChemIDplus
MS 275 ChemIDplus
MS-27-275 ChemIDplus
MS-275 ChemIDplus
N-(2-aminophenyl)-4-(N-(pyridin-3-ylmethoxycarbonyl)aminomethyl)benzamide ChemIDplus
N-[[4-[(2-aminoanilino)-oxomethyl]phenyl]methyl]carbamic acid 3-pyridinylmethyl ester LINCS
SNDX 275 ChemIDplus
SNDX-275 ChemIDplus
Manual Xrefs Databases
D09338 KEGG DRUG
Entinostat Wikipedia
LSM-4811 LINCS
View more database links
Registry Numbers Types Sources
209783-80-2 CAS Registry Number KEGG DRUG
209783-80-2 CAS Registry Number ChemIDplus
8442710 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10200307 PubMed citation Europe PMC
12414635 PubMed citation Europe PMC
21767511 PubMed citation Europe PMC
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25610877 PubMed citation Europe PMC
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26464689 PubMed citation Europe PMC
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Last Modified
29 January 2018