4-Phenylbutanoic acid (CHEM034900)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:18:58 UTC
Update Date2016-11-09 01:21:12 UTC
Accession NumberCHEM034900
Identification
Common Name4-Phenylbutanoic acid
ClassSmall Molecule
DescriptionA 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 gamma-globin gene and affects hPPARgamma activation.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
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
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
BenzenebutanoateGenerator
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 saltHMDB
BuphenylHMDB
Sodium 4-phenylbutyrateHMDB
AmmonapsHMDB
Sodium 4-phenylbutanoateHMDB
4-Phenylbutyric acid, sodium saltHMDB
Sodium phenylbutyrateHMDB
PhenylbutyrateHMDB
Chemical FormulaC10H12O2
Average Molecular Mass164.201 g/mol
Monoisotopic Mass164.084 g/mol
CAS Registry Number1821-12-1
IUPAC Name4-phenylbutanoic acid
Traditional Name4-phenylbutyric acid
SMILESOC(=O)CCCC1=CC=CC=C1
InChI IdentifierInChI=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 KeyOBKXEAXTFZPCHS-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.
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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity46.57 m³·mol⁻¹ChemAxon
Polarizability17.99 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-7900000000-3308656352d708576a12Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udl-7900000000-3308656352d708576a12Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-e2844824b9414ffe6a33Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xu-9600000000-697bd170bbcde4b6eefcSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-03di-4900000000-2b18919d21183949b0f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-6e1432dc108281f8c5fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9100000000-9477dfafb0c27b1670abSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-847b406c3e1866a2b19cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-03dl-8900000000-008ea7253ace5d9b714bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-f40db15584357863f25fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0900000000-bf56905d0da6a4541a84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-3900000000-8aa8880d8b02b7d0b5ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-9400000000-5ad6828916a1d92c3663Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-765256d50bc87d3eff05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-1900000000-6dfb6698bd016b6dc1dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aou-9400000000-da376d49262f9db124daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-2900000000-42af6d3b6a736fac50b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mo-9700000000-3618f3c5894df7c477b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-8743c8410c72e7bc3241Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-7b5ca54ec317098c43b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-07vl-7900000000-834b13602e441659f91cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-c1806dc2d8c81a391a3fSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06819
HMDB IDHMDB0000543
FooDB IDFDB022106
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-14367
METLIN ID5528
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4611
ChEBI ID41500
PubChem Compound ID4775
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19918981
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20399799
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=21237159
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21726539
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21887297
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21894430
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=22101259
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22359472
9. Galat, Alexander. The reaction of phenylpyruvic acid and related compounds with ammonia. Journal of the American Chemical Society (1950), 72 4436-9.
10. Koyama M, Watanabe N, Asakawa N: Radioimmunoassay for ubenimex in human serum. J Pharm Biomed Anal. 1992 Feb-Mar;10(2-3):137-40.
11. 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.
12. 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.
13. Kerem E: Mutation specific therapy in CF. Paediatr Respir Rev. 2006;7 Suppl 1:S166-9. Epub 2006 Jun 5.