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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:14 UTC
Update Date2019-07-23 06:06:35 UTC
HMDB IDHMDB0030503
Secondary Accession Numbers
  • HMDB30503
Metabolite Identification
Common Name(2S,4S,6S)-2-[2-(4-Hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetate
Description(2S,4S,6S)-2-[2-(4-Hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetate belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain (2S,4S,6S)-2-[2-(4-Hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (2S,4S,6S)-2-[2-(4-Hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetate has been detected, but not quantified in, herbs and spices. This could make (2S,4S,6S)-2-[2-(4-hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetate a potential biomarker for the consumption of these foods.
Structure
Data?1563861995
Synonyms
ValueSource
(2S,4S,6S)-2-[2-(4-Hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetic acidGenerator
2-(3,4-Dihydroxy-5-methoxyphenyl)-6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]oxan-4-yl acetic acidGenerator
(2S,4R,6S)-2-[2-(4-Hydroxy-3-methoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetic acidGenerator
Chemical FormulaC23H28O8
Average Molecular Weight432.4636
Monoisotopic Molecular Weight432.178417872
IUPAC Name2-(3,4-dihydroxy-5-methoxyphenyl)-6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]oxan-4-yl acetate
Traditional Name2-(3,4-dihydroxy-5-methoxyphenyl)-6-[2-(4-hydroxy-3-methoxyphenyl)ethyl]oxan-4-yl acetate
CAS Registry Number182227-92-5
SMILES
COC1=CC(CCC2CC(CC(O2)C2=CC(OC)=C(O)C(O)=C2)OC(C)=O)=CC=C1O
InChI Identifier
InChI=1S/C23H28O8/c1-13(24)30-17-11-16(6-4-14-5-7-18(25)21(8-14)28-2)31-20(12-17)15-9-19(26)23(27)22(10-15)29-3/h5,7-10,16-17,20,25-27H,4,6,11-12H2,1-3H3
InChI KeyPCHXAHPLKORHMW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Catechol
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Ether
  • Dialkyl ether
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

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
Water Solubility0.011 g/LALOGPS
logP2.76ALOGPS
logP2.96ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.35ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity112.68 m³·mol⁻¹ChemAxon
Polarizability46.19 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udl-1912000000-145b3d188c87ea40b775Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-001i-3056069000-d0b28ebfa12745a0a8d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-0905600000-a666ac50193eda88e7e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00vu-0925300000-60e9b1271326e8a9340aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rl-4911000000-afb74e1f8977db632782Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2245900000-a878a06e2d388b025fa8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05gr-4019400000-ceb518f41e5bfcd3f34cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9722000000-aa535729b487497a2462Spectrum
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
FooDB IDFDB002372
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751038
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.. .

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
(2S,4S,6S)-2-[2-(4-Hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-yl 4-acetate → (2S,4S,6S)-2-[2-(4-Hydroxy-3-meyhoxyphenyl)ethyl]tetrahydro-6-(4,5-dihydroxy-3-methoxyphenyl)-2H-pyran-4-oldetails