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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:39:48 UTC
HMDB IDHMDB0000440
Secondary Accession Numbers
  • HMDB00440
Metabolite Identification
Common Name3-Hydroxyphenylacetic acid
Description3-Hydroxyphenylacetic acid is a rutin metabolite and an antioxidant. It has a protective biological activity in human. It is a substrate of enzyme 4-hydroxyphenylacetate 3-monooxygenase [EC 1.14.13.3] in the pathway tyrosine metabolism. (KEGG, PMID 155437 ).
Structure
Thumb
Synonyms
ValueSource
(m-Hydroxyphenyl)acetic acidChEBI
3-Hydroxybenzeneacetic acidChEBI
m-Hydroxyphenylacetic acidChEBI
(m-Hydroxyphenyl)acetateGenerator
3-HydroxyphenylacetateGenerator
3-HydroxybenzeneacetateGenerator
m-HydroxyphenylacetateGenerator
(3-Hydroxy-phenyl)-acetateHMDB
(3-Hydroxy-phenyl)-acetic acidHMDB
3-Hydroxy-benzeneacetateHMDB
3-Hydroxy-benzeneacetic acidHMDB
Meta-hydroxyphenylacetic acidMeSH
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=CC(O)=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
DescriptionThis compound belongs to the class of chemical entities known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
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
Physiological effect

Health effect:

  Health condition:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP0.85HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility6.98 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-1940000000-6378ab49a38d6170a2c7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4l-2970000000-c0a0a7b13f6da1df88aaView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0950000000-26683d1d8cf72cac5bc1View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-1940000000-6378ab49a38d6170a2c7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4l-2970000000-c0a0a7b13f6da1df88aaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ot-0920000000-fe0044d1e19c78b17eb6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-6172123969b2e568c06aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5930000000-ac6c8b167a6f6d3d0521View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0900000000-64f3b80f6fa4b2ca0d3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-066r-9600000000-cd1ada1ac0e33b3478b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-066r-9300000000-6a96a42ca7818fbc430dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-acff5d00da3be2a5c74aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-2c8a7cef25cc353fd182View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-3df834bace0a8802e668View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kto-9600000000-42568fc5a5b34539aa51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-163da322055a76a2c202View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0900000000-06fd2ca96cf98a192ad7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-d43171f0cd0bce73a080View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.012 +/- 0.01 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.466 +/- 0.192 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.129 +/- 0.031 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.677 +/- 0.238 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.583 +/- 0.161 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.133 +/- 0.04 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.152 +/- 0.026 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified0.149 +/- 0.055 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified2.318 +/- 2.231 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
Cerebrospinal Fluid (CSF)Detected and Quantified0.007 - 0.03 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected and Quantified122.250 +/- 132.109 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified14.262 +/- 8.0185 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified32.797 +/- 38.121 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected and Quantified59.548 +/- 53.829 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Male
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Not SpecifiedBoth
Normal
details
FecesDetected and Quantified86.0350 +/- 56.130 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not Quantified Adult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified0.6 (0.4 - 0.9) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified5.255 +/- 4.639 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
UrineDetected and Quantified1.0-2.4 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
UrineDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.1 +/- 4.1 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified17.6 +/- 6.0 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952 details
UrineDetected and Quantified0.81-2.0 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected and Quantified3.115 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified3.300 +/- 2.450 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified7.7 (1.4-22.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified7.732 +/- 3.666 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified5.6 (1.4-15.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
UrineDetected and Quantified5.812 +/- 6.755 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected and Quantified5.687 +/- 6.645 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Gastroesophageal reflux disease
    • Mordechai, Hien, ...
details
UrineDetected and Quantified2.854 +/- 2.31 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Mordechai, Hien, ...
details
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not Quantified Adult (>18 years old)Both
Hypertension (mild)
details
UrineDetected and Quantified0.67 +/- 2.94 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Phenylketonuria
  1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite ID952
FoodDB IDFDB022047
KNApSAcK IDNot Available
Chemspider ID11624
KEGG Compound IDC05593
BioCyc ID3-HYDROXYPHENYLACETATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5429
PubChem Compound12122
PDB ID3HP
ChEBI ID17445
References
Synthesis ReferenceStaudenmaier, Horst Ralf; Hauer, Bernhard; Ladner, Wolfgang; Mueller, Ursula; Pressler, Uwe; Meyer, Joachim. Fermentative manufacture of 3-hydroxyphenylacetic acid. Ger. Offen. (1993), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Young SN, Davis BA, Gauthier S: Precursors and metabolites of phenylethylamine, m and p-tyramine and tryptamine in human lumbar and cisternal cerebrospinal fluid. J Neurol Neurosurg Psychiatry. 1982 Jul;45(7):633-9. [PubMed:6181210 ]
  2. Davis BA, Durden DA, Boulton AA: Plasma concentrations of p- and m-hydroxyphenylacetic acid and phenylacetic acid in humans: gas chromatographic--high-resolution mass spectrometric analysis. J Chromatogr. 1982 Jul 9;230(2):219-30. [PubMed:7107773 ]
  3. Davis BA, Boulton AA: Longitudinal urinary excretion of some "trace" acids in a human male. J Chromatogr. 1981 Feb 13;222(2):161-9. [PubMed:7251734 ]
  4. Nahmias C, Wahl LM, Amano S, Asselin MC, Chirakal R: Equilibration of 6-[18F]fluoro-L-m-tyrosine between plasma and erythrocytes. J Nucl Med. 2000 Oct;41(10):1636-41. [PubMed:11037992 ]
  5. Baba S, Furuta T, Horie M, Nakagawa H: Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans. J Pharm Sci. 1981 Jul;70(7):780-2. [PubMed:7264927 ]
  6. Konishi Y: Transepithelial transport of microbial metabolites of quercetin in intestinal Caco-2 cell monolayers. J Agric Food Chem. 2005 Feb 9;53(3):601-7. [PubMed:15686408 ]
  7. Carey LC, Fabri PJ: Respiratory distress syndrome. Arch Surg. 1979 Mar;114(3):343. [PubMed:155437 ]

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-Hydroxyphenylacetic acid → 6-[3-(carboxymethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-Hydroxyphenylacetic acid → 3,4,5-trihydroxy-6-{[2-(3-hydroxyphenyl)acetyl]oxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3-Hydroxyphenylacetic acid → 2-[3-(sulfooxy)phenyl]acetic aciddetails