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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:57 UTC
Update Date2019-07-23 06:09:19 UTC
HMDB IDHMDB0031706
Secondary Accession Numbers
  • HMDB31706
Metabolite Identification
Common Name3,4-Dihydroxyphenacyl caffeate
Description3,4-Dihydroxyphenacyl caffeate is found in green vegetables. 3,4-Dihydroxyphenacyl caffeate is a constituent of the rhizomes of Petasites japonicus (sweet coltsfoot)
Structure
Data?1563862159
Synonyms
ValueSource
PetasiphenoneHMDB
3,4-Dihydroxyphenacyl caffeate phenylpropanoid esterMeSH
Chemical FormulaC17H14O7
Average Molecular Weight330.2889
Monoisotopic Molecular Weight330.073952802
IUPAC Name2-(3,4-dihydroxyphenyl)-2-oxoethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Traditional Name2-(3,4-dihydroxyphenyl)-2-oxoethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
CAS Registry Number162616-81-1
SMILES
OC1=C(O)C=C(\C=C\C(=O)OCC(=O)C2=CC(O)=C(O)C=C2)C=C1
InChI Identifier
InChI=1S/C17H14O7/c18-12-4-1-10(7-14(12)20)2-6-17(23)24-9-16(22)11-3-5-13(19)15(21)8-11/h1-8,18-21H,9H2/b6-2+
InChI KeyDPMVCMFEBYVTFB-QHHAFSJGSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Cinnamic acid or derivatives
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid ester
  • Benzoyl
  • Catechol
  • Styrene
  • Aryl alkyl ketone
  • Phenol
  • Fatty acid ester
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alpha-acyloxy ketone
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point236 - 238 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP2.79ALOGPS
logP2.53ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.65 m³·mol⁻¹ChemAxon
Polarizability32.21 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-0ae47877e39b40f7ffd1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-0091012000-228cb4e71fac93b34f3cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gx0-0906000000-b1459bc849ae04a6cb0cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0901000000-cb6bf9791c712e815a89JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-2900000000-ce16e34487d82efdc6d7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0903000000-eea1f6327d9fa7c9f5a4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0900000000-43a0ae6a706d47e4399eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dr-1900000000-4e4e5542e0fd21644979JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008369
KNApSAcK IDNot Available
Chemspider ID17226431
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16066851
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .