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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:52 UTC
HMDB IDHMDB00543
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzenebutanoic acid
DescriptionBenzenebutanoic 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
Thumb
Synonyms
ValueSource
PhenylbutyrateChEMBL
Phenylbutyric acidGenerator
BenzenebutanoateGenerator
4-Phenyl-butyrateHMDB
4-Phenyl-butyric acidHMDB
4-Phenyl-N-butyrateHMDB
4-Phenyl-N-butyric acidHMDB
4-PhenylbutanoateHMDB
4-Phenylbutanoic acidHMDB
4-PhenylbutyrateHMDB
4-Phenylbutyric acidHMDB
BenzenebutyrateHMDB
Benzenebutyric acidHMDB
g-Phenyl-butyrateHMDB
g-Phenyl-butyric acidHMDB
g-PhenylbutanoateHMDB
g-Phenylbutanoic acidHMDB
g-PhenylbutyrateHMDB
g-Phenylbutyric acidHMDB
gamma-Phenyl-butyrateHMDB
gamma-Phenyl-butyric acidHMDB
gamma-PhenylbutanoateHMDB
gamma-Phenylbutanoic acidHMDB
gamma-PhenylbutyrateHMDB
gamma-Phenylbutyric acidHMDB
Omega-phenylbutanoateHMDB
Omega-phenylbutanoic acidHMDB
W-PhenylbutanoateHMDB
W-Phenylbutanoic acidHMDB
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name4-phenylbutanoic acid
Traditional Name4-phenylbutyric acid
CAS Registry Number1821-12-1
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 KeyInChIKey=OBKXEAXTFZPCHS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point47 - 49 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18 mg/mLNot Available
LogP2.42HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.51 mg/mLALOGPS
logP2.29ALOGPS
logP2.5ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.81ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.57 m3·mol-1ChemAxon
Polarizability17.99 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-4900000000-2b18919d21183949b0f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-6e1432dc108281f8c5fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9100000000-9477dfafb0c27b1670abView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Pancreas
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022106
KNApSAcK IDNot Available
Chemspider ID4611
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00543
Metagene LinkHMDB00543
METLIN ID5528
PubChem Compound4775
PDB IDCLT
ChEBI ID41500
References
Synthesis ReferenceGalat, Alexander. The reaction of phenylpyruvic acid and related compounds with ammonia. Journal of the American Chemical Society (1950), 72 4436-9.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Koyama M, Watanabe N, Asakawa N: Radioimmunoassay for ubenimex in human serum. J Pharm Biomed Anal. 1992 Feb-Mar;10(2-3):137-40. [1391092 ]
  2. Singh L, Field MJ, Hill DR, Horwell DC, McKnight AT, Roberts E, Tang KW, Woodruff GN: Peptoid CCK receptor antagonists: pharmacological evaluation of CCKA, CCKB and mixed CCKA/B receptor antagonists. Eur J Pharmacol. 1995 Nov 14;286(2):185-91. [8605955 ]
  3. Powell K, Zeitlin PL: Therapeutic approaches to repair defects in deltaF508 CFTR folding and cellular targeting. Adv Drug Deliv Rev. 2002 Dec 5;54(11):1395-408. [12458151 ]
  4. Kerem E: Mutation specific therapy in CF. Paediatr Respir Rev. 2006;7 Suppl 1:S166-9. Epub 2006 Jun 5. [16798551 ]