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Record Information
Version1.0
Creation Date2016-07-13 19:43:34 UTC
Update Date2018-04-30 21:14:37 UTC
LmdbLMDB00155
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-Hydroxyphenylacetic acid
Description3-Hydroxyphenylacetic acid, also known as (m-hydroxyphenyl)acetate or 3-hydroxybenzeneacetate, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. 3-Hydroxyphenylacetic acid exists in all living organisms, ranging from bacteria to humans. 3-Hydroxyphenylacetic acid has been detected, but not quantified in, milk (cow). This could make 3-hydroxyphenylacetic acid a potential biomarker for the consumption of these foods. 3-Hydroxyphenylacetic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 3-Hydroxyphenylacetic acid, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis and colorectal cancer; 3-hydroxyphenylacetic acid has also been linked to the inborn metabolic disorder phenylketonuria. Based on a literature review a significant number of articles have been published on 3-Hydroxyphenylacetic acid.
Structure
Thumb
Synonyms
ValueSource
(m-Hydroxyphenyl)acetic acidChEBI
3-Hydroxybenzeneacetic acidChEBI
m-Hydroxyphenylacetic acidChEBI
(m-Hydroxyphenyl)acetateGenerator
3-HydroxybenzeneacetateGenerator
m-HydroxyphenylacetateGenerator
3-HydroxyphenylacetateGenerator
(3-Hydroxy-phenyl)-acetateHMDB
(3-Hydroxy-phenyl)-acetic acidHMDB
3-Hydroxy-benzeneacetateHMDB
3-Hydroxy-benzeneacetic acidHMDB
Meta-hydroxyphenylacetic acidHMDB
3'-Hydroxyphenylacetic acidHMDB
2-(3-Hydroxyphenyl)acetic acidHMDB
3-Hydroxyphenylacetic acidKEGG
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Name2-(3-hydroxyphenyl)acetic acid
Traditional Name3-hydroxyphenylacetic acid
CAS Registry Number621-37-4
SMILES
OC(=O)CC1=CC(O)=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-2-6(4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
InChI KeyFVMDYYGIDFPZAX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-4-unsubstituted benzenoids
Direct Parent1-hydroxy-4-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted 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
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.93ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m³·mol⁻¹ChemAxon
Polarizability14.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-1940000000-6378ab49a38d6170a2c7Spectrum
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4l-2970000000-c0a0a7b13f6da1df88aaSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0950000000-26683d1d8cf72cac5bc1Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-1940000000-6378ab49a38d6170a2c7Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4l-2970000000-c0a0a7b13f6da1df88aaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ot-0920000000-fe0044d1e19c78b17eb6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-6172123969b2e568c06aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5930000000-ac6c8b167a6f6d3d0521Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0900000000-64f3b80f6fa4b2ca0d3aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-066r-9600000000-cd1ada1ac0e33b3478b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-066r-9300000000-6a96a42ca7818fbc430dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-acff5d00da3be2a5c74aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-97c0564c13ebd3284f50Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-3900000000-a80e9eddf44bc0095f79Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014i-9000000000-96b630f0c24804af9aeeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00mo-9000000000-3efd8d8db4dc2eae90ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0fb9-2900000000-f3873a7ac7ad570e403dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-e90d6c5d8bf401d57e4eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-1900000000-ce3129eea4958f02c7b6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000f-9400000000-a325a8a905a878e9c037Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-ca93ecdc5cf66e6d1291Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-b499e6492f74c3b1cd54Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0900000000-95cdec832fdad733908aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-052b-9600000000-17540945d3efb5ed0aeeSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00ou-9300000000-9803bf9d8616a80e7c46Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0900000000-7f6b0589d86943d38ebfSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0gdl-9000000000-7b58085ace82f3720778Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-2c8a7cef25cc353fd182Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-3df834bace0a8802e668Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kto-9600000000-42568fc5a5b34539aa51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-163da322055a76a2c202Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0900000000-06fd2ca96cf98a192ad7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-d43171f0cd0bce73a080Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified104 +/- 4.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified54.5 +/- 2.0 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified62.0 +/- 3.0 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified47 +/- 15 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified53 +/- 10 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified53 +/- 10 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified63 +/- 25 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified65 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified67 +/- 13 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified293 +/- 31 uMNot AvailableCaprine details
Ruminal FluidDetected and Quantified52.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified62.8 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified65.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified67.1 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified36.1 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified42.9 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified45.7 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified56.7 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
DrugBank IDNot Available
HMDB IDHMDB0000440
FooDB IDFDB022047
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc ID3-HYDROXYPHENYLACETATE
METLIN ID5429
PDB IDNot Available
Wikipedia Link4-Hydroxyphenylacetic acid
Chemspider ID11624
ChEBI ID17445
PubChem Compound ID12122
Kegg Compound IDC05593
YMDB IDNot Available
ECMDB IDM2MDB004469
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Carey LC, Fabri PJ: Respiratory distress syndrome. Arch Surg. 1979 Mar;114(3):343. [155437 ]