Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:56 UTC
HMDB IDHMDB0000543
Secondary Accession Numbers
  • HMDB00543
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
Data?1676999696
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 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 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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point47 - 49 °CNot Available
Boiling Point290.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility18 mg/mLNot Available
LogP2.42HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
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]+136.84431661259
DarkChem[M-H]-133.06231661259
AllCCS[M+H]+135.6532859911
AllCCS[M-H]-137.31532859911
DeepCCS[M+H]+135.30130932474
DeepCCS[M-H]-132.27630932474
DeepCCS[M-2H]-169.16130932474
DeepCCS[M+Na]+144.730932474
AllCCS[M+H]+135.732859911
AllCCS[M+H-H2O]+131.332859911
AllCCS[M+NH4]+139.732859911
AllCCS[M+Na]+140.932859911
AllCCS[M-H]-137.332859911
AllCCS[M+Na-2H]-138.432859911
AllCCS[M+HCOO]-139.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzenebutanoic acidOC(=O)CCCC1=CC=CC=C12689.4Standard polar33892256
Benzenebutanoic acidOC(=O)CCCC1=CC=CC=C11430.2Standard non polar33892256
Benzenebutanoic acidOC(=O)CCCC1=CC=CC=C11467.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzenebutanoic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC1=CC=CC=C11535.3Semi standard non polar33892256
Benzenebutanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC1=CC=CC=C11769.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Benzenebutanoic acid EI-B (Non-derivatized)splash10-0udl-7900000000-3308656352d708576a122017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Benzenebutanoic acid EI-B (Non-derivatized)splash10-0udl-7900000000-3308656352d708576a122018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9600000000-e2844824b9414ffe6a332017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00xu-9600000000-697bd170bbcde4b6eefc2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzenebutanoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzenebutanoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-03di-4900000000-2b18919d21183949b0f02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzenebutanoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0006-9000000000-6e1432dc108281f8c5fb2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzenebutanoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0006-9100000000-9477dfafb0c27b1670ab2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzenebutanoic acid 20V, Negative-QTOFsplash10-0006-9100000000-847b406c3e1866a2b19c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzenebutanoic acid 10V, Negative-QTOFsplash10-03dl-8900000000-008ea7253ace5d9b714b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Benzenebutanoic acid 40V, Negative-QTOFsplash10-0a4l-9000000000-f40db15584357863f25f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Positive-QTOFsplash10-014j-0900000000-bf56905d0da6a4541a842017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Positive-QTOFsplash10-014i-3900000000-8aa8880d8b02b7d0b5ec2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Positive-QTOFsplash10-054o-9400000000-5ad6828916a1d92c36632017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Negative-QTOFsplash10-03di-0900000000-765256d50bc87d3eff052017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Negative-QTOFsplash10-03xr-1900000000-6dfb6698bd016b6dc1df2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Negative-QTOFsplash10-0aou-9400000000-da376d49262f9db124da2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Positive-QTOFsplash10-0aor-2900000000-42af6d3b6a736fac50b42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Positive-QTOFsplash10-05mo-9700000000-3618f3c5894df7c477b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Positive-QTOFsplash10-0006-9000000000-8743c8410c72e7bc32412021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 10V, Negative-QTOFsplash10-03di-0900000000-7b5ca54ec317098c43b22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 20V, Negative-QTOFsplash10-07vl-7900000000-834b13602e441659f91c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzenebutanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-c1806dc2d8c81a391a3f2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, 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 Locations
  • Pancreas
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06819
Phenol Explorer Compound IDNot Available
FooDB IDFDB022106
KNApSAcK IDNot Available
Chemspider ID4611
KEGG Compound IDNot Available
BioCyc IDCPD-14367
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5528
PubChem Compound4775
PDB IDNot Available
ChEBI ID41500
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1206621
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. [PubMed: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. [PubMed: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. [PubMed:12458151 ]
  4. Kerem E: Mutation specific therapy in CF. Paediatr Respir Rev. 2006;7 Suppl 1:S166-9. Epub 2006 Jun 5. [PubMed:16798551 ]