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Record Information
Version3.6
Creation Date2008-08-28 21:53:21 UTC
Update Date2013-02-09 00:15:31 UTC
HMDB IDHMDB06915
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
Description2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is an intermediate in tyrosine metabolism. It is reversibly converted from 4-hydroxyphenylpyruvate via phenylpyruvate tautomerase. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid is typically a terminal product of tyrosine metabolism.
Structure
Thumb
Synonyms
  1. 2-Hydroxy-3-(4-hydroxyphenyl)propenoate
  2. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
  3. 4-Hydroxy-enol-phenylpyruvate
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional IUPAC Name(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(\O)=C\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-5,10-11H,(H,12,13)/b8-5-
InChI KeyGQYBCIHRWMPOOF-YVMONPNESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassCinnamic Acid Derivatives
Sub ClassHydroxycinnamic Acid Derivatives
Other Descriptors
  • Cinnamic Acid Derivatives
  • Coumaric Acid Derivatives
  • Organic Compounds
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Enol
  • Enone
  • Phenol
  • Phenol Derivative
  • Phenylpropene
Direct ParentHydroxycinnamic Acid Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.81 g/LALOGPS
logP1.28ALOGPS
logP1.31ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.16ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.01ChemAxon
Polarizability17.25ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tyrosine MetabolismSMP00006map00350
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024152
KNApSAcK IDNot Available
Chemspider ID552441
KEGG Compound IDC05350
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06915
Metagene LinkHMDB06915
METLIN IDNot Available
PubChem Compound636708
PDB IDNot Available
ChEBI ID27683
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in cell surface binding
Specific function:
Pro-inflammatory cytokine. Involved in the innate immune response to bacterial pathogens. The expression of MIF at sites of inflammation suggests a role as mediator in regulating the function of macrophages in host defense. Counteracts the anti-inflammatory activity of glucocorticoids. Has phenylpyruvate tautomerase and dopachrome tautomerase activity (in vitro), but the physiological substrate is not known. It is not clear whether the tautomerase activity has any physiological relevance, and whether it is important for cytokine activity.
Gene Name:
MIF
Uniprot ID:
P14174
Molecular weight:
12476.19
Reactions
4-Hydroxyphenylpyruvic acid → 2-Hydroxy-3-(4-hydroxyphenyl)propenoic aciddetails