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CHEBI:41500 - 4-phenylbutyric acid

Default Structure
ChEBI IDCHEBI:41500
ChEBI Name4-phenylbutyric acid
Stars
DefinitionA monocarboxylic acid the structure of which is that of butyric acid substituted with a phenyl group at C-4. It is a histone deacetylase inhibitor that displays anticancer activity. It inhibits cell proliferation, invasion and migration and induces apoptosis in glioma cells. It also inhibits protein isoprenylation, depletes plasma glutamine, increases production of foetal haemoglobin through transcriptional activation of the γ-globin gene and affects hPPARγ activation.
Secondary ChEBI IDCHEBI:64058
Last Modified22 February 2017
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC10H12O2
Net Charge0
Average Mass164.204
Monoisotopic Mass164.08373
SMILESO=C(O)CCCc1ccccc1
InChIInChI=1S/C10H12O2/c11-10(12)8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8H2,(H,11,12)
InChIKeyOBKXEAXTFZPCHS-UHFFFAOYSA-N
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
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).
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
Applications:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
antitubercular agent  A substance that kills or slows the growth of Mycobacterium tuberculosis and is used in the treatment of tuberculosis.
ChEBI Ontology
Outgoing Relation(s)
4-phenylbutyric acid (CHEBI:41500) has functional parent butyric acid (CHEBI:30772)
4-phenylbutyric acid (CHEBI:41500) has role anti-HIV agent (CHEBI:64946)
4-phenylbutyric acid (CHEBI:41500) has role antineoplastic agent (CHEBI:35610)
4-phenylbutyric acid (CHEBI:41500) has role antitubercular agent (CHEBI:33231)
4-phenylbutyric acid (CHEBI:41500) has role apoptosis inducer (CHEBI:68495)
4-phenylbutyric acid (CHEBI:41500) has role EC 3.5.1.98 (histone deacetylase) inhibitor (CHEBI:61115)
4-phenylbutyric acid (CHEBI:41500) has role prodrug (CHEBI:50266)
4-phenylbutyric acid (CHEBI:41500) is a monocarboxylic acid (CHEBI:25384)
4-phenylbutyric acid (CHEBI:41500) is conjugate acid of 4-phenylbutyrate (CHEBI:75317)
Incoming Relation(s)
4-phenylbutyrate (CHEBI:75317) is conjugate base of 4-phenylbutyric acid (CHEBI:41500)
IUPAC Name 
4-phenylbutanoic acid
Synonyms  Source
4-PHENYL-BUTANOIC ACIDPDBeChem
4-Phenyl-n-butyric acidNIST Chemistry WebBook
Benzenebutyric acidChemIDplus
PBAChEBI
phenylbutanoic acidChEMBL
Phenylbutanoic acidChEMBL
Manual XrefsDatabases
24DrugCentral
CLTPDBeChem
CPD-14367MetaCyc
HMDB0000543HMDB
LSM-5751LINCS
Registry NumbersSources
Reaxys:638180Reaxys
CAS:1821-12-1ChemIDplus
CAS:1821-12-1NIST Chemistry WebBook
Citations