4-phenylbutyric acid (CHEBI:41500)

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CHEBI:41500 - 4-phenylbutyric acid

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ChEBI Name	4-phenylbutyric acid

ChEBI ID	CHEBI:41500

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:64058

Supplier Information	ChemicalBook:CB9733804, eMolecules:535136, Selleckchem:bay-11-7082-bay-11-7821, ZINC000002568458

Download	Molfile XML SDF

more structures >>

Molfile

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24 24 0 0 0 0 999 V2000

-0.0150 -0.7980 2.3140 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0020 -0.1270 0.9390 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0230 -1.2000 -0.1510 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0100 -0.5390 -1.5050 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1920 -0.2590 -2.1260 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.2010 -0.2170 -2.1290 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2040 0.3470 -3.3690 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.1890 0.3920 -3.3690 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0130 0.6730 -3.9900 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0040 0.2570 3.3890 C 0 0 0 0 0 0 0 0 0 0 0 0

0.0270 1.4260 3.0860 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.0020 -0.1010 4.6820 O 0 0 0 0 0 0 0 0 0 0 0 0

0.8620 -1.4370 2.4150 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9170 -1.4020 2.4150 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8800 0.5100 0.8380 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8990 0.4760 0.8380 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8540 -1.8380 -0.0500 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9250 -1.8030 -0.0500 H 0 0 0 0 0 0 0 0 0 0 0 0

2.1220 -0.5140 -1.6410 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1410 -0.4370 -1.6440 H 0 0 0 0 0 0 0 0 0 0 0 0

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0.0220 1.1470 -4.9600 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0110 0.5760 5.3720 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 1 0 0 0 0

1 10 1 0 0 0 0

1 13 1 0 0 0 0

1 14 1 0 0 0 0

2 3 1 0 0 0 0

2 15 1 0 0 0 0

2 16 1 0 0 0 0

3 4 1 0 0 0 0

3 17 1 0 0 0 0

3 18 1 0 0 0 0

4 5 4 0 0 0 0

4 6 4 0 0 0 0

5 7 4 0 0 0 0

5 19 1 0 0 0 0

6 8 4 0 0 0 0

6 20 1 0 0 0 0

7 9 4 0 0 0 0

7 21 1 0 0 0 0

8 9 4 0 0 0 0

8 22 1 0 0 0 0

9 23 1 0 0 0 0

10 11 2 0 0 0 0

10 12 1 0 0 0 0

12 24 1 0 0 0 0

M END): 20 ms

reading 24 atoms

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1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

24 atoms created

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Molfile expand

Formula

C10H12O2

Net Charge

Average Mass

164.20110

Monoisotopic Mass

164.08373

InChI

InChI=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)

InChIKey

OBKXEAXTFZPCHS-UHFFFAOYSA-N

SMILES

OC(=O)CCCc1ccccc1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	apoptosis inducer Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms. 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).

Application(s):	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.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	4-phenylbutyric acid (CHEBI:41500) has functional parent butyric acid (CHEBI:30772) 4-phenylbutyric acid (CHEBI:41500) has role antineoplastic agent (CHEBI:35610) 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	4-phenylbutyrate (CHEBI:75317) is conjugate base of 4-phenylbutyric acid (CHEBI:41500)

IUPAC Name

4-phenylbutanoic acid

Synonyms	Sources
4-PHENYL-BUTANOIC ACID	PDBeChem
4-Phenyl-n-butyric acid	NIST Chemistry WebBook
Benzenebutyric acid	ChemIDplus
γ-Phenyl-n-butyric acid	NIST Chemistry WebBook
γ-phenylbutyric acid	ChemIDplus
ω-Phenylbutanoic acid	NIST Chemistry WebBook
ω-phenylbutyric acid	ChemIDplus
PBA	ChEBI

Manual Xrefs	Databases
24	DrugCentral
CLT	PDBeChem
CPD-14367	MetaCyc
HMDB0000543	HMDB
LSM-5751	LINCS
View more database links

Registry Numbers	Types	Sources
1821-12-1	CAS Registry Number	ChemIDplus
1821-12-1	CAS Registry Number	NIST Chemistry WebBook
638180	Reaxys Registry Number	Reaxys

Citations	Types	Sources
19918981	PubMed citation	Europe PMC
20399799	PubMed citation	Europe PMC
21237159	PubMed citation	Europe PMC
21726539	PubMed citation	Europe PMC
21887297	PubMed citation	Europe PMC
21894430	PubMed citation	Europe PMC
22101259	PubMed citation	Europe PMC
22359472	PubMed citation	Europe PMC

Last Modified

22 February 2017

CHEBI:41500 - 4-phenylbutyric acid

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