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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:39 UTC
Update Date2019-07-23 06:06:44 UTC
HMDB IDHMDB0030562
Secondary Accession Numbers
  • HMDB30562
Metabolite Identification
Common Name3,8-Dihydroxy-9-methoxycoumestan
Description3,8-Dihydroxy-9-methoxycoumestan, also known as 3'-methoxycoumestrol (obsol.), belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, 3,8-dihydroxy-9-methoxycoumestan is considered to be a flavonoid lipid molecule. 3,8-Dihydroxy-9-methoxycoumestan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3,8-Dihydroxy-9-methoxycoumestan has been detected, but not quantified in, pulses. This could make 3,8-dihydroxy-9-methoxycoumestan a potential biomarker for the consumption of these foods.
Structure
Data?1563862004
Synonyms
ValueSource
3'-Methoxycoumestrol (obsol.)HMDB
8-MethoxycoumestrolHMDB
Chemical FormulaC16H10O6
Average Molecular Weight298.247
Monoisotopic Molecular Weight298.047738052
IUPAC Name5,14-dihydroxy-13-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Name3'-methoxycoumestrol
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C2OC3=C(C2=C1)C(=O)OC1=C3C=CC(O)=C1
InChI Identifier
InChI=1S/C16H10O6/c1-20-13-5-9-12(6-10(13)18)21-15-8-3-2-7(17)4-11(8)22-16(19)14(9)15/h2-6,17-18H,1H3
InChI KeyMQORJFLPGOCLDS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point329 - 329.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP2.58ALOGPS
logP2.24ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.11ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.08 m³·mol⁻¹ChemAxon
Polarizability29.47 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-0fza-0090000000-76df4a3bbd5cbf3d3521Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-01ea-2719400000-827a35e9748bd2ad1b5aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-81ccf2688b5b3be93b6fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-15f1e3c1bb77baa467f8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0arr-0090000000-8453f168e3c9246e9952Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-3ee8a6990521f9453d7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-62115a9a95e60433c1f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f8i-0190000000-f278d30e8f42c660f373Spectrum
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 IDFDB002446
KNApSAcK IDNot Available
Chemspider ID24843112
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44151023
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:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
3,8-Dihydroxy-9-methoxycoumestan → 3,4,5-trihydroxy-6-({14-hydroxy-13-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl}oxy)oxane-2-carboxylic aciddetails
3,8-Dihydroxy-9-methoxycoumestan → 3,4,5-trihydroxy-6-({5-hydroxy-13-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl}oxy)oxane-2-carboxylic aciddetails