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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:29 UTC
Update Date2023-02-21 17:15:59 UTC
HMDB IDHMDB0001955
Secondary Accession Numbers
  • HMDB01955
Metabolite Identification
Common Name3-Phenylbutyric acid
Description3-Phenylbutyric acid, also known as 3-phenylbutyrate or (RS)-3-phenylbutanoate, belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Adverse effects Nearly 1/4 women may experience an adverse effect of amenorrhea or menstrual dysfunction. Sodium phenylbutyrate can act as a chemical chaperone, stabilising the mutant CFTR in the endoplasmic reticulum and allowing it to reach the cell surface. A 5g tablet or powder of sodium phenylbutyrate taken by mouth can be detected in the blood within 15 minutes, and reaches peak concentration in the bloodstream within an hour.
Structure
Data?1676999759
Synonyms
ValueSource
3-PhenylbutyrateGenerator
3-Phenylbutiric acidHMDB
3-PhenylbutirateHMDB
(RS)-3-PhenylbutanoateHMDB
(RS)-3-Phenylbutanoic acidHMDB
3-PhenylbutanoateHMDB
3-Phenylbutanoic acidHMDB
b-MethylbenzenepropanoateHMDB
b-Methylbenzenepropanoic acidHMDB
b-MethylhydrocinnamateHMDB
b-Methylhydrocinnamic acidHMDB
b-Phenyl-N-butyrateHMDB
b-Phenyl-N-butyric acidHMDB
b-PhenylbutyrateHMDB
b-Phenylbutyric acidHMDB
beta-MethylbenzenepropanoateHMDB
beta-Methylbenzenepropanoic acidHMDB
beta-MethylhydrocinnamateHMDB
beta-Methylhydrocinnamic acidHMDB
beta-Phenyl-N-butyrateHMDB
beta-Phenyl-N-butyric acidHMDB
beta-PhenylbutyrateHMDB
beta-Phenylbutyric acidHMDB
3-PBHMDB
3-Phenylbutyric acidMeSH
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name3-phenylbutanoic acid
Traditional Nameβ-phenylbutyric acid
CAS Registry Number4593-90-2
SMILES
CC(CC(O)=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H12O2/c1-8(7-10(11)12)9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,11,12)
InChI KeyZZEWMYILWXCRHZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Benzenoid
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point39 - 37 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.18HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP2.47ALOGPS
logP2.34ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)4.79ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.52 m³·mol⁻¹ChemAxon
Polarizability17.48 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.41731661259
DarkChem[M-H]-134.17431661259
AllCCS[M+H]+134.8532859911
AllCCS[M-H]-136.07432859911
DeepCCS[M+H]+133.53230932474
DeepCCS[M-H]-130.58530932474
DeepCCS[M-2H]-167.23430932474
DeepCCS[M+Na]+142.7430932474
AllCCS[M+H]+134.932859911
AllCCS[M+H-H2O]+130.432859911
AllCCS[M+NH4]+139.032859911
AllCCS[M+Na]+140.232859911
AllCCS[M-H]-136.132859911
AllCCS[M+Na-2H]-137.232859911
AllCCS[M+HCOO]-138.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Phenylbutyric acidCC(CC(O)=O)C1=CC=CC=C12518.3Standard polar33892256
3-Phenylbutyric acidCC(CC(O)=O)C1=CC=CC=C11374.8Standard non polar33892256
3-Phenylbutyric acidCC(CC(O)=O)C1=CC=CC=C11443.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Phenylbutyric acid,1TMS,isomer #1CC(CC(=O)O[Si](C)(C)C)C1=CC=CC=C11418.0Semi standard non polar33892256
3-Phenylbutyric acid,1TBDMS,isomer #1CC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C11661.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Phenylbutyric acid EI-B (Non-derivatized)splash10-0a4i-3900000000-423d6d32dc253ecb2d282017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Phenylbutyric acid EI-B (Non-derivatized)splash10-0a4i-3900000000-423d6d32dc253ecb2d282018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-ee10bd457245240974c62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-6910000000-8c0a5b2f7b10413ec29e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Phenylbutyric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Phenylbutyric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0udi-0900000000-803416460510d3efd6762012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Phenylbutyric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0udi-4900000000-a703bcd75148add4b7262012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3-Phenylbutyric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-004i-9300000000-4d507dc7d650908807eb2012-07-25HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Positive-QTOFsplash10-00kb-0900000000-464ae51a2426beafa36e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Positive-QTOFsplash10-014i-0900000000-4e0d66a3ecda37eaae7a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Positive-QTOFsplash10-1000-6900000000-b5a52c63793f6efc562a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Negative-QTOFsplash10-03xr-0900000000-ca4a300620b1977297122017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Negative-QTOFsplash10-02ta-0900000000-1fdc2e71f61a532b146b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Negative-QTOFsplash10-0pvm-9800000000-763de4b71f394fc907892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Negative-QTOFsplash10-03di-0900000000-b25e5438d8bf2d82f9012021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Negative-QTOFsplash10-014i-3900000000-932a4cd434d1682534bc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Negative-QTOFsplash10-004l-9100000000-befd9306f52f97ef560b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 10V, Positive-QTOFsplash10-0a4i-0900000000-da2ac7c18ef5f321d7242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 20V, Positive-QTOFsplash10-0a4i-3900000000-63cd15f2058ca270ffd72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Phenylbutyric acid 40V, Positive-QTOFsplash10-004i-9400000000-35ede8ec3305c43d9b7b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022762
KNApSAcK IDNot Available
Chemspider ID19513
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSodium phenylbutyrate
METLIN ID6399
PubChem Compound20724
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ki KR, Lee J, Ha D, Kim JH: Configurational analysis of chiral acids as O-trifluoroacetylated (-)-menthyl esters by achiral dual-capillary column gas chromatography. J Chromatogr A. 2000 Sep 8;891(2):257-66. [PubMed:11043786 ]
  2. van Landeghem AA, Somers-Pijnenburg YT, Somers WJ, Stokwielder C, de Bruyn W, van den Berg GB: Adsorption of small hydroxy acids on glass: a pitfall in quantitative urinary organic acid analysis by GC-MS. J Inherit Metab Dis. 1999 May;22(3):293-6. [PubMed:10384390 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3-Phenylbutyric acid → 3,4,5-trihydroxy-6-[(3-phenylbutanoyl)oxy]oxane-2-carboxylic aciddetails