Showing Compound 4-Phenylbutanoic acid (FDB022106)

Record Information

Version

1.0

Creation date

2011-09-21 00:08:35 UTC

Update date

2015-10-09 22:29:50 UTC

Primary ID

FDB022106

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

4-Phenylbutanoic acid

Description

4-phenylbutyrate (4-PBA) is known to be a transcriptional regulator, and 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 environment. 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 12458151) [HMDB]

CAS Number

1821-12-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	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
4-Phenyl-n-butyrate	hmdb
4-Phenyl-n-butyric acid	hmdb
Benzenebutanoic acid	hmdb
omega-Phenylbutanoate	hmdb
omega-Phenylbutanoic acid	hmdb
w-Phenylbutanoate	hmdb
w-Phenylbutanoic acid	hmdb
γ-phenyl-N-butyrate	Generator
γ-phenyl-N-butyric acid	Generator
γ-phenylbutyrate	Generator
γ-phenylbutyric acid	Generator

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

Chemical Formula

C10H12O2

IUPAC name

4-phenylbutanoic acid

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

Isomeric SMILES

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

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

Classification

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 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Subcellular:

Organ and components:

Pancreas

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	4-Phenylbutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0udl-7900000000-3308656352d708576a12	Spectrum
GC-MS	4-Phenylbutanoic acid, non-derivatized, GC-MS Spectrum	splash10-0udl-7900000000-3308656352d708576a12	Spectrum
Predicted GC-MS	4-Phenylbutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9600000000-e2844824b9414ffe6a33	Spectrum
Predicted GC-MS	4-Phenylbutanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00xu-9600000000-697bd170bbcde4b6eefc	Spectrum
Predicted GC-MS	4-Phenylbutanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	4-Phenylbutanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-03di-4900000000-2b18919d21183949b0f0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9000000000-6e1432dc108281f8c5fb	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9100000000-9477dfafb0c27b1670ab	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9100000000-847b406c3e1866a2b19c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03dl-8900000000-008ea7253ace5d9b714b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-f40db15584357863f25f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-bf56905d0da6a4541a84	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-3900000000-8aa8880d8b02b7d0b5ec	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-054o-9400000000-5ad6828916a1d92c3663	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-765256d50bc87d3eff05	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03xr-1900000000-6dfb6698bd016b6dc1df	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aou-9400000000-da376d49262f9db124da	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aor-2900000000-42af6d3b6a736fac50b4	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mo-9700000000-3618f3c5894df7c477b6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-8743c8410c72e7bc3241	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-7b5ca54ec317098c43b2	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07vl-7900000000-834b13602e441659f91c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-c1806dc2d8c81a391a3f	2021-09-22	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		Spectrum