Human Metabolome Database Version 3.5

Showing metabocard for 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid (HMDB06915)

Record Information
Version 3.5
Creation Date 2008-08-28 15:53:21 -0600
Update Date 2013-02-08 17:15:31 -0700
HMDB ID HMDB06915
Secondary Accession Numbers None
Metabolite Identification
Common Name 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
Description 2-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Hydroxy-3-(4-hydroxyphenyl)propenoate
  2. 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid
  3. 4-Hydroxy-enol-phenylpyruvate
Chemical Formula C9H8O4
Average Molecular Weight 180.1574
Monoisotopic Molecular Weight 180.042258744
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 Number Not 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 Key GQYBCIHRWMPOOF-YVMONPNESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Cinnamic Acid Derivatives
Sub Class Hydroxycinnamic Acid Derivatives
Other Descriptors
  • Cinnamic Acid Derivatives
  • Coumaric Acid Derivatives
  • Organic Compounds
Substituents
  • Allyl Alcohol
  • Carboxylic Acid
  • Enol
  • Enone
  • Phenol
  • Phenol Derivative
  • Phenylpropene
Direct Parent Hydroxycinnamic Acid Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
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 0.81 g/L ALOGPS
LogP 1.28 ALOGPS
LogP 1.31 ChemAxon
LogS -2.35 ALOGPS
pKa (strongest acidic) 3.16 ChemAxon
pKa (strongest basic) -6 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 77.76 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 47.01 ChemAxon
Polarizability 17.25 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Tyrosine Metabolism SMP00006 map00350 Link_out
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 FDB024152
KNApSAcK ID Not Available
Chemspider ID 552441 Link_out
KEGG Compound ID C05350 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06915 Link_out
Metagene Link HMDB06915 Link_out
METLIN ID Not Available
PubChem Compound 636708 Link_out
PDB ID Not Available
ChEBI ID 27683 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Macrophage migration inhibitory factor
Reactions:
4-Hydroxyphenylpyruvic acid unknown 2-Hydroxy-3-(4-hydroxyphenyl)propenoic acid details
Gene Name: MIF
Uniprot ID: P14174 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA