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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-04-06 16:21:19 UTC
Update Date2020-02-26 21:37:09 UTC
HMDB IDHMDB0012225
Secondary Accession Numbers
  • HMDB12225
Metabolite Identification
Common NameEnol-phenylpyruvate
DescriptionEnol-phenylpyruvate belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Enol-phenylpyruvate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Enol-phenylpyruvate has been detected, but not quantified in, several different foods, such as pepper (spice), chinese water chestnuts, vanilla, giant butterburs, and chives. This could make enol-phenylpyruvate a potential biomarker for the consumption of these foods.
Structure
Data?1582753029
Synonyms
ValueSource
enol-Phenylpyruvic acidKegg
enol-alpha-Ketohydrocinnamic acidKegg
enol-a-KetohydrocinnamateGenerator
enol-a-Ketohydrocinnamic acidGenerator
enol-alpha-KetohydrocinnamateGenerator
enol-Α-ketohydrocinnamateGenerator
enol-Α-ketohydrocinnamic acidGenerator
2-Hydroxy-3-phenylpropenoateHMDB
2-Hydroxy-3-phenylpropenoic acidHMDB
PhenylpyruvateHMDB
enol-PhenylpyruvateKEGG
Chemical FormulaC9H8O3
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
IUPAC Name(2Z)-2-hydroxy-3-phenylprop-2-enoic acid
Traditional NameDL-α-hydroxycinnamic 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
Description Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
Substituents
  • Enol-phenylpyruvate
  • Cinnamic acid or derivatives
  • Cinnamic acid
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

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 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 Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.03 m³·mol⁻¹ChemAxon
Polarizability16.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-5900000000-07a9ccc24b7ad66a59682017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0006-9670000000-d024b973929302194fed2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-014l-5900000000-07a9ccc24b7ad66a59682021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-1900000000-f12b39c1d374881c9d922017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014m-3900000000-a34acb2eaa08f8dd34f42017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-0a8c8446d21d68f2bc422017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-b2326bee6ab6a67c10db2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02tc-4900000000-6653ccc39bf1df275eb02017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-8900000000-8729ced74e114658afa62017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0900000000-984ecdf21cdafac77fb02021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kf-9800000000-11fdfc299dc6de7cf6982021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-6e597f6e10d803f677902021-09-06View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014l-5900000000-986457b755b06e8364752021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9500000000-16341ab51a4f4937a3352021-09-07View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-6c4342e7a7da48b645f72021-09-07View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028869
KNApSAcK IDNot Available
Chemspider ID556910
KEGG Compound IDC02763
BioCyc IDENOL-PHENYLPYRUVATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound641637
PDB IDNot Available
ChEBI ID16815
Food Biomarker OntologyNot Available
VMH IDM00647
MarkerDB IDNot Available
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 ]