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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:33 UTC
Update Date2023-02-21 17:16:06 UTC
HMDB IDHMDB0002043
Secondary Accession Numbers
  • HMDB02043
Metabolite Identification
Common Name5-Phenylvaleric acid
Description5-Phenylvaleric acid, also known as delta-phenylvalerate or benzenepentanoic-acid, is a monocarboxylic acid that is valeric acid substituted by a phenyl group at the delta-position. It is a monocarboxylic acid and a member of benzenes. It derives from a valeric acid. 5-Phenylvaleric acid belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
Structure
Data?1676999766
Synonyms
ValueSource
Benzenepentanoic-acidChEBI
delta-Phenylvaleric acidChEBI
Phenylpentanoic acidChEBI
Phenylvaleric acidChEBI
delta-PhenylvalerateGenerator
Δ-phenylvalerateGenerator
Δ-phenylvaleric acidGenerator
PhenylpentanoateGenerator
PhenylvalerateGenerator
5-PhenylvalerateGenerator
5-Phenyl valeric acidHMDB
5-Phenyl-pentanoateHMDB
5-Phenyl-pentanoic acidHMDB
5-PhenylpentanoateHMDB, Generator
5-Phenylpentanoic acidHMDB
5-Phenzylvaleric acidHMDB
BenzenepentanoateHMDB
Benzenepentanoic acidHMDB
5-PHENYLVALERIC ACIDChEBI
Chemical FormulaC11H14O2
Average Molecular Weight178.2277
Monoisotopic Molecular Weight178.099379692
IUPAC Name5-phenylpentanoic acid
Traditional Name5-phenylvaleric acid
CAS Registry Number2270-20-4
SMILES
OC(=O)CCCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C11H14O2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-3,6-7H,4-5,8-9H2,(H,12,13)
InChI KeyBYHDDXPKOZIZRV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty 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 Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point57.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.61 mg/mL at 25 °CNot Available
LogP2.94AUSTIN,RP ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP2.81ALOGPS
logP2.94ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)4.94ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity51.17 m³·mol⁻¹ChemAxon
Polarizability20.11 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]+141.55431661259
DarkChem[M-H]-136.67731661259
DeepCCS[M+H]+140.49130932474
DeepCCS[M-H]-137.19930932474
DeepCCS[M-2H]-174.34430932474
DeepCCS[M+Na]+149.88330932474
AllCCS[M+H]+139.732859911
AllCCS[M+H-H2O]+135.532859911
AllCCS[M+NH4]+143.632859911
AllCCS[M+Na]+144.832859911
AllCCS[M-H]-143.032859911
AllCCS[M+Na-2H]-143.932859911
AllCCS[M+HCOO]-145.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Phenylvaleric acidOC(=O)CCCCC1=CC=CC=C12762.3Standard polar33892256
5-Phenylvaleric acidOC(=O)CCCCC1=CC=CC=C11554.4Standard non polar33892256
5-Phenylvaleric acidOC(=O)CCCCC1=CC=CC=C11572.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Phenylvaleric acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCCC1=CC=CC=C11637.6Semi standard non polar33892256
5-Phenylvaleric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCC1=CC=CC=C11871.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 5-Phenylvaleric acid EI-B (Non-derivatized)splash10-0006-9500000000-40d787bf66ca5dda522b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 5-Phenylvaleric acid EI-B (Non-derivatized)splash10-0006-9500000000-40d787bf66ca5dda522b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenylvaleric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6x-8900000000-5296b96690317532ca1e2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenylvaleric acid GC-MS (1 TMS) - 70eV, Positivesplash10-00s6-9700000000-227b64a8a260a32c27ee2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenylvaleric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Phenylvaleric 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 - 5-Phenylvaleric acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-004i-0900000000-2532a979e5230329e9ba2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0059-9300000000-e7e07895512abecadb472012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0059-9300000000-21f8c2e8f7b5da8e34b82012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid 40V, Negative-QTOFsplash10-0006-9000000000-ab446b7012855b1a8a552021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid 20V, Negative-QTOFsplash10-0a6r-0900000000-972070ac34ddee7445b92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid 40V, Positive-QTOFsplash10-004i-9200000000-eea7002b95a52f9508902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid 20V, Positive-QTOFsplash10-0a4i-9400000000-39f4eff93a3c16d00cd22021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid 10V, Negative-QTOFsplash10-004i-0900000000-3802cad446880b5af8302021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 5-Phenylvaleric acid 10V, Positive-QTOFsplash10-0a6r-7900000000-2528c131a2de9ac708de2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 10V, Positive-QTOFsplash10-01t9-0900000000-4f4a037239e73a53cdf82017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 20V, Positive-QTOFsplash10-02cu-3900000000-936e06346a570c6042542017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 40V, Positive-QTOFsplash10-0006-9300000000-92d6e2de2b078e3954dd2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 10V, Negative-QTOFsplash10-004i-0900000000-de1484cb2a2e1d3a5b252017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 20V, Negative-QTOFsplash10-0059-1900000000-9d6f7e74ce616c37025d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 40V, Negative-QTOFsplash10-0a4l-9400000000-ef694ab6a04429c4c1212017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 10V, Positive-QTOFsplash10-00mo-4900000000-b5c629ea77ec81ae3ef12021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 20V, Positive-QTOFsplash10-0006-9700000000-53cb591a2562f9e4a0a22021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 40V, Positive-QTOFsplash10-0006-9200000000-cc3debc3900bcf64ee112021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 10V, Negative-QTOFsplash10-004i-0900000000-583273c8100f9e55b4bd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 20V, Negative-QTOFsplash10-056r-3900000000-133ba70d31d2dfc831cb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Phenylvaleric acid 40V, Negative-QTOFsplash10-0006-9000000000-6f75ad94e1497eec81392021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart 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
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04051
Phenol Explorer Compound IDNot Available
FooDB IDFDB022814
KNApSAcK IDNot Available
Chemspider ID15886
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6456
PubChem Compound16757
PDB IDNot Available
ChEBI ID40131
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. Kim KR, Kim JH, Jeong DH, Paek DJ, Liebich HM: Gas chromatographic profiling analysis of urinary organic acids from nonsmokers and smokers. J Chromatogr B Biomed Sci Appl. 1997 Nov 7;701(1):1-8. [PubMed:9389332 ]