Human Metabolome Database Version 3.5

Showing metabocard for Enol-phenylpyruvate (HMDB12225)

Record Information
Version 3.5
Creation Date 2009-04-06 10:21:19 -0600
Update Date 2013-05-31 11:39:35 -0600
Secondary Accession Numbers None
Metabolite Identification
Common Name Enol-phenylpyruvate
Description Enol-phenylpyruvate is reversibly produced from keto-phenylpyruvate, a reaction catalyzed by phenylpyruvate tautomerase [EC:]. Phenylpyruvate tautomerase, also known as macrophage migration inhibitory factor (glycosylation-inhibiting factor), is involved in the tyrosine and phenylalanine metabolism pathways.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
  1. 2-Hydroxy-3-phenylpropenoate
  2. 2-Hydroxy-3-phenylpropenoic acid
  3. Enol-alpha-ketohydrocinnamic acid
  4. Enol-phenylpyruvic acid
  5. Phenylpyruvate
Chemical Formula C9H8O3
Average Molecular Weight 164.158
Monoisotopic Molecular Weight 164.047344122
IUPAC Name (2Z)-2-hydroxy-3-phenylprop-2-enoic acid
Traditional IUPAC Name (2Z)-2-hydroxy-3-phenylprop-2-enoic acid
CAS Registry Number 5801-57-0
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-
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Cinnamic Acid Derivatives
Sub Class N/A
Other Descriptors
  • 2-hydroxy monocarboxylic acid(ChEBI)
  • Organic Compounds
  • Allyl Alcohol
  • Carboxylic Acid
  • Enol
  • Enone
  • Phenylpropene
Direct Parent Cinnamic Acid Derivatives
Status Expected and Not Quantified
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.05 g/L ALOGPS
LogP 1.55 ALOGPS
LogP 1.62 ChemAxon
LogS -2.20 ALOGPS
pKa (strongest acidic) 3.59 ChemAxon
pKa (strongest basic) -6.1 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 45.03 ChemAxon
Polarizability 16.22 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB028869
KNApSAcK ID Not Available
Chemspider ID 556910 Link_out
KEGG Compound ID C02763 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12225 Link_out
Metagene Link HMDB12225 Link_out
METLIN ID Not Available
PubChem Compound 641637 Link_out
PDB ID Not Available
ChEBI ID 16815 Link_out
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Name: Macrophage migration inhibitory factor
Phenylpyruvic acid unknown Enol-phenylpyruvate details
Phenylpyruvic acid unknown Enol-phenylpyruvate details
Gene Name: MIF
Uniprot ID: P14174 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA