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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:10 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 ). 3-Hydroxyphenylacetic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism. It is also a marker of gut Clostridium species. Higher levels are associated with higher levels of Clostridia (PMID: 27123458 ). 3-Hydroxyphenylacetic acid can also be found in Klebsiella (PMID: 1851804 ).
Structure
Data?1563860650
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 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
Disposition

Source:

Biological location:

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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-03di-1940000000-6378ab49a38d6170a2c7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0a4l-2970000000-c0a0a7b13f6da1df88aaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0002-0950000000-26683d1d8cf72cac5bc1JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-03di-1940000000-6378ab49a38d6170a2c7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0a4l-2970000000-c0a0a7b13f6da1df88aaJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01ot-0920000000-fe0044d1e19c78b17eb6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4900000000-6172123969b2e568c06aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-5930000000-ac6c8b167a6f6d3d0521JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-0900000000-64f3b80f6fa4b2ca0d3aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-066r-9600000000-cd1ada1ac0e33b3478b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-066r-9300000000-6a96a42ca7818fbc430dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-0900000000-acff5d00da3be2a5c74aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udr-0900000000-2c8a7cef25cc353fd182JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-3df834bace0a8802e668JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kto-9600000000-42568fc5a5b34539aa51JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-0900000000-163da322055a76a2c202JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-0900000000-06fd2ca96cf98a192ad7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-2900000000-d43171f0cd0bce73a080JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
BloodDetected and Quantified0.094-0.764 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.007 - 0.03 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified122.250 +/- 132.109 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified14.262 +/- 8.0185 nmol/g wet fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified32.797 +/- 38.121 nmol/g wet 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 wet 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 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 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified3.746 (0.0329-20.401) nmol/g wet fecesAdult (>18 years old)Both
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 Quantified0.61(0-38.1) umol/mmol creatinineChildren (1 - 13 years old)BothNormal 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 but not Quantified Adult (>18 years old)BothNormal 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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal 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 but not Quantified Adult (>18 years old)BothBladder cancer details
UrineDetected and Quantified0.67 +/- 2.94 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 ]
Eosinophilic esophagitis
  1. (). Mordechai, Hien, and David S. Wishart. .
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022047
KNApSAcK IDNot Available
Chemspider ID11624
KEGG Compound IDC05593
BioCyc ID3-HYDROXYPHENYLACETATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5429
PubChem Compound12122
PDB IDNot Available
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 ]
  8. Xiong X, Liu D, Wang Y, Zeng T, Peng Y: Urinary 3-(3-Hydroxyphenyl)-3-hydroxypropionic Acid, 3-Hydroxyphenylacetic Acid, and 3-Hydroxyhippuric Acid Are Elevated in Children with Autism Spectrum Disorders. Biomed Res Int. 2016;2016:9485412. doi: 10.1155/2016/9485412. Epub 2016 Mar 30. [PubMed:27123458 ]
  9. Martin M, Gibello A, Fernandez J, Ferrer E, Garrido-Pertierra A: Catabolism of 3- and 4-hydroxyphenylacetic acid by Klebsiella pneumoniae. J Gen Microbiol. 1991 Mar;137(3):621-8. doi: 10.1099/00221287-137-3-621. [PubMed:1851804 ]

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