ChemFOnt: Showing chemical card for Benzenebutanoic acid (CFc000000419)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:44:48 UTC

Chemfont ID

CFc000000419

Molecule Identification

Common Name

Benzenebutanoic acid

Definition

Benzenebutanoic acid (also known as 4-phenylbutyrate, or 4-PBA) is the oral form of butyrate, which is known to be a transcriptional regulator. Sodium-4-PBA has been shown to induce fetal hemoglobin, and it has been used in clinical trials for sickle cell anemia and β-thalassemia. Because gene expression profiles became more differentiated, it is in phase I trials in several different malignant disorders. The potential for therapeutic benefit in cystic fibrosis (CF) resides in an additional mechanism, involving protein folding and the ER (endoplasmic reticulum) environment (PMID 12458151 ). 4-PBA is a drug that was developed to treat elevated blood ammonia in urea cycle disorders, a histone deacetylase inhibitor that promotes mutation ΔF508 cystic fibrosis transmembrane conductance regulator (CFTR) trafficking (PMID 16798551 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
4-PHENYL-butanoIC ACID	ChEBI
4-Phenyl-N-butyric acid	ChEBI
Benzenebutyric acid	ChEBI
gamma-Phenyl-N-butyric acid	ChEBI
gamma-Phenylbutyric acid	ChEBI
Omega-phenylbutanoic acid	ChEBI
Omega-phenylbutyric acid	ChEBI
PBA	ChEBI
4-PHENYL-butanoate	Generator
4-Phenyl-N-butyrate	Generator
Benzenebutyrate	Generator
g-Phenyl-N-butyrate	Generator
g-Phenyl-N-butyric acid	Generator
gamma-Phenyl-N-butyrate	Generator
Γ-phenyl-N-butyrate	Generator
Γ-phenyl-N-butyric acid	Generator
g-Phenylbutyrate	Generator
g-Phenylbutyric acid	Generator
gamma-Phenylbutyrate	Generator
Γ-phenylbutyrate	Generator
Γ-phenylbutyric acid	Generator
Omega-phenylbutanoate	Generator
Omega-phenylbutyrate	Generator
Benzenebutanoate	Generator
4-Phenyl-butyrate	HMDB
4-Phenyl-butyric acid	HMDB
4-Phenylbutanoate	HMDB
4-Phenylbutanoic acid	HMDB
4-Phenylbutyrate	HMDB
4-Phenylbutyric acid	HMDB
g-Phenyl-butyrate	HMDB
g-Phenyl-butyric acid	HMDB
g-Phenylbutanoate	HMDB
g-Phenylbutanoic acid	HMDB
gamma-Phenyl-butyrate	HMDB
gamma-Phenyl-butyric acid	HMDB
gamma-Phenylbutanoate	HMDB
gamma-Phenylbutanoic acid	HMDB
W-Phenylbutanoate	HMDB
W-Phenylbutanoic acid	HMDB
4-Phenylbutyric acid, calcium salt	HMDB
Buphenyl	HMDB
Sodium 4-phenylbutyrate	HMDB
Ammonaps	HMDB
Sodium 4-phenylbutanoate	HMDB
4-Phenylbutyric acid, sodium salt	HMDB
Sodium phenylbutyrate	HMDB
Phenylbutyrate	HMDB

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

IUPAC Name

4-phenylbutanoic acid

Traditional Name

4-phenylbutyric acid

CAS Registry Number

1821-12-1

SMILES

OC(=O)CCCC1=CC=CC=C1

InChI Identifier

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)

InChI Key

OBKXEAXTFZPCHS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:41500 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0000543)
Cell membrane (HMDB: HMDB0000543)

Organ

Pancreas (HMDB: HMDB0000543)

Source

Exogenous

Exogenous (HMDB: HMDB0000543)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000543)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000543)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	2.29	ALOGPS
logP	2.5	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	4.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	46.57 m³·mol⁻¹	ChemAxon
Polarizability	17.99 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon