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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:02:40 UTC
HMDB IDHMDB00440
Secondary Accession NumbersNone
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
2-(3-Hydroxyphenyl)acetateGenerator
3-HydroxybenzeneacetateGenerator
m-HydroxyphenylacetateGenerator
(3-Hydroxy-phenyl)-acetateHMDB
(3-Hydroxy-phenyl)-acetic acidHMDB
3-Hydroxy-benzeneacetateHMDB
3-Hydroxy-benzeneacetic acidHMDB
3-HydroxyphenylacetateHMDB
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 KeyInChIKey=FVMDYYGIDFPZAX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Phenol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP0.85HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility6.98 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.35 m3·mol-1ChemAxon
Polarizability14.78 Å3ChemAxon
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
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
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
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 QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
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 QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified86.0350 +/- 56.130 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>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 but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 952
  • Not Applicable
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
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 QuantifiedNot ApplicableAdult (>18 years old)Both
Hypertension (mild)
details
UrineDetected but not QuantifiedNot ApplicableAdult (>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. [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
NuGOwiki LinkHMDB00440
Metagene LinkHMDB00440
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. [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. [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. [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. [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. [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. [15686408 ]
  7. Carey LC, Fabri PJ: Respiratory distress syndrome. Arch Surg. 1979 Mar;114(3):343. [155437 ]