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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-18 15:59:15 UTC
Update Date2019-11-12 17:23:27 UTC
HMDB IDHMDB0135790
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-(3,4-dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Description2-(3,4-dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 2-(3,4-dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 2-hydroxy-2-(4-hydroxyphenyl)ethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate. This hydroxylation-of-benzene-ortho-to-edg occurs in humans. It is generated by cyp1a2 enzyme via a hydroxylation-of-benzene-ortho-to-edg reaction.
Structure
Data?1563876418
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acidGenerator
Chemical FormulaC18H18O7
Average Molecular Weight346.335
Monoisotopic Molecular Weight346.10525292
IUPAC Name2-(3,4-dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Traditional Name2-(3,4-dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(C=CC(=O)OCC(O)C2=CC(O)=C(O)C=C2)=C1
InChI Identifier
InChI=1S/C18H18O7/c1-24-17-8-11(2-5-14(17)20)3-7-18(23)25-10-16(22)12-4-6-13(19)15(21)9-12/h2-9,16,19-22H,10H2,1H3
InChI KeyGWDNVPPHEOAZCL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Catechol
  • Phenol ether
  • Methoxybenzene
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Aromatic alcohol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.05ALOGPS
logP2.54ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.12ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity90.81 m³·mol⁻¹ChemAxon
Polarizability34.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-6063039000-22f7912cb19e355fd6d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-0900000000-81b7333aeb002435ffccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f92-0905000000-e912e9e7c461713ce4c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ug0-0901000000-4bc01aa2bb08838e1856Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-c883a09697bfac65d6b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002e-0904000000-a73e68d22fbfc982a191Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056u-0900000000-7c4692e1f3e018c45973Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-0900000000-c569f8460149566126caSpectrum
Biological Properties
Cellular LocationsNot Available
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
2-(3,4-dihydroxyphenyl)-2-hydroxyethyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate → 3,4-Dihydroxyphenylglycoldetails