| Common Name |
Benzenebutanoic acid
| Description |
Benzenebutanoic acid (also known as 4-phenylbutyrate, or 4-PBA) is the oral form of butyrate, which is known to be a transcriptional regliator. 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 reticlium) 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 regliator (CFTR) trafficking (PMID 16798551 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
4-PHENYL-butanoIC ACIDChEBI
4-Phenyl-N-butyric acidChEBI
Benzenebutyric acidChEBI
gamma-Phenyl-N-butyric acidChEBI
gamma-Phenylbutyric acidChEBI
Omega-phenylbutanoic acidChEBI
Omega-phenylbutyric acidChEBI
PBAChEBI
4-PHENYL-butanoateGenerator
BenzenebutanoateGenerator
4-Phenyl-N-butyrateGenerator
BenzenebutyrateGenerator
g-Phenyl-N-butyrateGenerator
g-Phenyl-N-butyric acidGenerator
gamma-Phenyl-N-butyrateGenerator
γ-phenyl-N-butyrateGenerator
γ-phenyl-N-butyric acidGenerator
g-PhenylbutyrateGenerator
g-Phenylbutyric acidGenerator
gamma-PhenylbutyrateGenerator
γ-phenylbutyrateGenerator
γ-phenylbutyric acidGenerator
Omega-phenylbutanoateGenerator
Omega-phenylbutyrateGenerator
4-Phenyl-butyrateHMDB
4-Phenyl-butyric acidHMDB
4-PhenylbutanoateHMDB
4-Phenylbutanoic acidHMDB
4-PhenylbutyrateHMDB
4-Phenylbutyric acidHMDB
g-Phenyl-butyrateHMDB
g-Phenyl-butyric acidHMDB
g-PhenylbutanoateHMDB
g-Phenylbutanoic acidHMDB
gamma-Phenyl-butyrateHMDB
gamma-Phenyl-butyric acidHMDB
gamma-PhenylbutanoateHMDB
gamma-Phenylbutanoic acidHMDB
W-PhenylbutanoateHMDB
W-Phenylbutanoic acidHMDB
4-Phenylbutyric acid, calcium saltMeSH
BuphenylMeSH
Sodium 4-phenylbutyrateMeSH
AmmonapsMeSH
Sodium 4-phenylbutanoateMeSH
4-Phenylbutyric acid, sodium saltMeSH
| Chemical Formlia |
C10H12O2
| Average Molecliar Weight |
164.2011
| Monoisotopic Molecliar 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 |
This compound belongs to the class of chemical entities known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Benzenoids
| Sub Class |
Benzene and substituted derivatives
| Direct Parent |
Benzene and substituted derivatives
| Alternative Parents |
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| 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
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
monocarboxylic acid (CHEBI:41500 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Membrane (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point47 – 49 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18 mg/mLNot Available
LogP2.42HANSCH,C ET AL. (1995)
| Predicted Properties |
| Property |
Value |
Source |
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
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Negative (Annotated)splash10-03di-4900000000-2b18919d21183949b0f0View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-6e1432dc108281f8c5fbView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9100000000-9477dfafb0c27b1670abView in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar Locations |
Membrane (predicted from logP)
| Biofluid Locations |
Not Available
| Tissue Location |
Pancreas
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022106
| KNApSAcK ID |
Not Available
| Chemspider ID |
4611
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00543
| Metagene Link |
HMDB00543
| METLIN ID |
5528
| PubChem Compound |
4775
| PDB ID |
CLT
| ChEBI ID |
41500
Product: Sugammadex (sodium)
References |
| Synthesis Reference |
Galat, 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 |
- Koyama M, Watanabe N, Asakawa N: Radioimmunoassay for ubenimex in human serum. J Pharm Biomed Anal. 1992 Feb-Mar;10(2-3):137-40. [PubMed:1391092 ]
- 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. [PubMed:8605955 ]
- 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. [PubMed:12458151 ]
- Kerem E: Mutation specific therapy in CF. Paediatr Respir Rev. 2006;7 Suppl 1:S166-9. Epub 2006 Jun 5. [PubMed:16798551 ]
|
PMID: 24609622