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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:29:31 UTC
Update Date2019-07-23 06:23:20 UTC
HMDB IDHMDB0037252
Secondary Accession Numbers
  • HMDB37252
Metabolite Identification
Common Name5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate
Description5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5,8-dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate has been detected, but not quantified in, herbs and spices. This could make 5,8-dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate a potential biomarker for the consumption of these foods.
Structure
Data?1563863000
Synonyms
ValueSource
5-Hydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl acetic acidGenerator
Chemical FormulaC19H18O7
Average Molecular Weight358.342
Monoisotopic Molecular Weight358.10525293
IUPAC Name5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl acetate
Traditional Name5-hydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-4-oxo-2,3-dihydro-1-benzopyran-8-yl acetate
CAS Registry Number99877-75-5
SMILES
COC1=C(OC(C)=O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2
InChI Identifier
InChI=1S/C19H18O7/c1-10(20)26-18-15(24-2)8-14(22)16-17(23)12(9-25-19(16)18)7-11-3-5-13(21)6-4-11/h3-6,8,12,21-22H,7,9H2,1-2H3
InChI KeyNXGGYXKVAVMQLL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassHomoisoflavonoids
Sub ClassHomoisoflavans
Direct ParentHomoisoflavanones
Alternative Parents
Substituents
  • Homoisoflavanone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point155 - 156 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.12ALOGPS
logP2.93ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.38ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity91.89 m³·mol⁻¹ChemAxon
Polarizability35.66 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-1419000000-b0ecf8a1f92634443b59Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-054w-4300900000-aa72cd4374b7c15736bbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0249000000-7aea38e5e85b74b335d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ar0-0965000000-63c8850b7c91af750093Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-1910000000-4c71e9a133fac5f16c4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1129000000-a88901a1764bac53a984Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-6297000000-4ae5e6abc49e76f6de7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-d06977ddba9aa7418f30Spectrum
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 IDFDB016263
KNApSAcK IDNot Available
Chemspider ID10254761
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21627907
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. (). 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
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 8-acetate → 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanonedetails