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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-28 21:53:21 UTC
Update Date2017-10-23 19:04:25 UTC
HMDB IDHMDB0006915
Secondary Accession Numbers
  • HMDB06915
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
ValueSource
4,alpha-Dihydroxycinnamic acidChEBI
4,a-DihydroxycinnamateGenerator
4,a-Dihydroxycinnamic acidGenerator
4,alpha-DihydroxycinnamateGenerator
4,α-dihydroxycinnamateGenerator
4,α-dihydroxycinnamic acidGenerator
2-Hydroxy-3-(4-hydroxyphenyl)propenoateGenerator
4-Hydroxy-enol-phenylpyruvateHMDB
Chemical FormulaC9H8O4
Average Molecular Weight180.1574
Monoisotopic Molecular Weight180.042258744
IUPAC Name(2Z)-2-hydroxy-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Name4,α-dihydroxycinnamic 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
DescriptionThis compound belongs to the class of chemical entities known as phenylpyruvic acid derivatives. These are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • Hydroxycinnamic acid or derivatives
  • Enol-phenylpyruvate
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Source:

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 Area77.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.01 m³·mol⁻¹ChemAxon
Polarizability17.25 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-1900000000-10c51d0329cb2a35dbb8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00gi-6259000000-cdf2744454615081e02fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0bu0-0900000000-a08730e02c84f43e7926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-2eb4f2eaa5d547249a3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-7900000000-63f2942443ac7bfdce48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-8576bdecf0b58e989df6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-46e515a63da5ddf92de9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0900000000-3c0a27f480b5bb59093cView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
AlkaptonuriaPw000180Pw000180 greyscalePw000180 simpleNot Available
Disulfiram PathwayPw000431Pw000431 greyscalePw000431 simpleNot Available
Dopamine beta-hydroxylase deficiencyPw000474Pw000474 greyscalePw000474 simpleNot Available
HawkinsinuriaPw000181Pw000181 greyscalePw000181 simpleNot Available
Monoamine oxidase-a deficiency (MAO-A)Pw000509Pw000509 greyscalePw000509 simpleNot Available
Displaying entries 1 - 5 of 8 in total
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
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