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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:52 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
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP0.85HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
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. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022047
KNApSAcK IDNot Available
Chemspider ID11624
KEGG Compound IDC05593
BioCyc ID3-HYDROXYPHENYLACETATE
BiGG IDNot Available
Wikipedia Link4-Hydroxyphenylacetic acid
METLIN ID5429
PubChem Compound12122
PDB IDNot Available
ChEBI ID17445
Food Biomarker OntologyNot Available
VMH ID3HPHAC
MarkerDB IDMDB00000161
Good Scents IDrw1190711
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)Not Available
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