3,4-Dihydroxyphenacyl caffeate (CHEM026619)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:07:24 UTC
Update Date2016-11-09 01:18:18 UTC
Accession NumberCHEM026619
Identification
Common Name3,4-Dihydroxyphenacyl caffeate
ClassSmall Molecule
Description3,4-Dihydroxyphenacyl caffeate is found in green vegetables. 3,4-Dihydroxyphenacyl caffeate is a constituent of the rhizomes of Petasites japonicus (sweet coltsfoot)
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3,4-Dihydroxyphenacyl caffeic acidGenerator
PetasiphenoneHMDB
3,4-Dihydroxyphenacyl caffeate phenylpropanoid esterHMDB
2-(3,4-Dihydroxyphenyl)-2-oxoethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acidHMDB
Chemical FormulaC17H14O7
Average Molecular Mass330.289 g/mol
Monoisotopic Mass330.074 g/mol
CAS Registry Number162616-81-1
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
SMILESOC1=C(O)C=C(\C=C\C(=O)OCC(=O)C2=CC(O)=C(O)C=C2)C=C1
InChI IdentifierInChI=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
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-0ae47877e39b40f7ffd1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-0091012000-228cb4e71fac93b34f3cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gx0-0906000000-b1459bc849ae04a6cb0cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0901000000-cb6bf9791c712e815a89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pbi-2900000000-ce16e34487d82efdc6d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0903000000-eea1f6327d9fa7c9f5a4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-0900000000-43a0ae6a706d47e4399eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dr-1900000000-4e4e5542e0fd21644979Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-0905000000-9626493a6efb5b9cf1e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0910000000-1f4ba097bc174bd5378fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-fff9c576e807ebd5cc33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-c439c22de85c3cd6ef39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gwr-0945000000-4853c193de51a27ab656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02g9-0910000000-b666183b7e92ec76b45cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0031706
FooDB IDFDB008369
Phenol Explorer IDNot Available
KNApSAcK IDC00057125
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17226431
ChEBI ID174449
PubChem Compound ID16066851
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.