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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:46:08 UTC
Update Date2019-07-23 06:14:52 UTC
HMDB IDHMDB0033993
Secondary Accession Numbers
  • HMDB33993
Metabolite Identification
Common NameWairol
DescriptionWairol 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, wairol is considered to be a flavonoid lipid molecule. Wairol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Wairol has been detected, but not quantified in, alfalfa and pulses. This could make wairol a potential biomarker for the consumption of these foods.
Structure
Data?1563862492
Synonyms
ValueSource
3-Hydroxy-7,9-dimethoxycoumestanHMDB
7-Hydroxy-10,12-dimethoxycoumestanHMDB
Chemical FormulaC17H12O6
Average Molecular Weight312.2736
Monoisotopic Molecular Weight312.063388116
IUPAC Name5-hydroxy-12,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Namewairol
CAS Registry Number77331-73-8
SMILES
COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1
InChI Identifier
InChI=1S/C17H12O6/c1-20-9-6-12(21-2)14-13(7-9)22-16-10-4-3-8(18)5-11(10)23-17(19)15(14)16/h3-7,18H,1-2H3
InChI KeyGYNHMEBOILXPQT-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:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point292 - 294 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.48ALOGPS
logP2.39ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.16ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.56 m³·mol⁻¹ChemAxon
Polarizability31.35 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, Positivesplash10-00ls-0091000000-5d85530019f4920b724eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01b9-2429000000-6d3570acd18747099377Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-54baec802857fee21878Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-318256c07afe65ae6be3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-0090000000-2458e9700a1169091116Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-d8d58a8a68eaaaee361cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0049000000-0add473485d461dd0cdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014j-0090000000-c7d6b21ced36c6f74cc9Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012227
KNApSAcK IDC00009767
Chemspider ID4589918
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5488650
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.. .