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Record Information
Version3.6
Creation Date2009-04-06 16:21:19 UTC
Update Date2013-05-31 17:39:35 UTC
HMDB IDHMDB12225
Secondary Accession NumbersNone
Metabolite Identification
Common NameEnol-phenylpyruvate
DescriptionEnol-phenylpyruvate is reversibly produced from keto-phenylpyruvate, a reaction catalyzed by phenylpyruvate tautomerase [EC:5.3.2.1]. Phenylpyruvate tautomerase, also known as macrophage migration inhibitory factor (glycosylation-inhibiting factor), is involved in the tyrosine and phenylalanine metabolism pathways.
Structure
Thumb
Synonyms
  1. 2-Hydroxy-3-phenylpropenoate
  2. 2-Hydroxy-3-phenylpropenoic acid
  3. Enol-alpha-ketohydrocinnamic acid
  4. Enol-phenylpyruvic acid
  5. Phenylpyruvate
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2Z)-2-hydroxy-3-phenylprop-2-enoic acid
Traditional Name(2Z)-2-hydroxy-3-phenylprop-2-enoic acid
CAS Registry Number5801-57-0
SMILES
OC(=O)C(\O)=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-6,10H,(H,11,12)/b8-6-
InChI KeyDEDGUGJNLNLJSR-VURMDHGXSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassCinnamic Acid Derivatives
Sub ClassN/A
Other Descriptors
  • 2-hydroxy monocarboxylic acid(ChEBI)
  • Organic Compounds
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Enol
  • Enone
  • Phenylpropene
Direct ParentCinnamic Acid Derivatives
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Microbial
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 Solubility1.05 g/LALOGPS
logP1.55ALOGPS
logP1.62ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.59ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.03ChemAxon
Polarizability16.22ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 IDFDB028869
KNApSAcK IDNot Available
Chemspider ID556910
KEGG Compound IDC02763
BioCyc IDENOL-PHENYLPYRUVATE
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12225
Metagene LinkHMDB12225
METLIN IDNot Available
PubChem Compound641637
PDB IDNot Available
ChEBI ID16815
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
Phenylpyruvic acid → Enol-phenylpyruvatedetails
Phenylpyruvic acid → Enol-phenylpyruvatedetails
References
  1. KNOX WE, PITT BM: Enzymic catalysis of the keto-enol tautomerization of phenylpyruvic acids. J Biol Chem. 1957 Apr;225(2):675-88. Pubmed: 13416270