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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:28:47 UTC
Update Date2019-07-23 06:14:10 UTC
HMDB IDHMDB0033722
Secondary Accession Numbers
  • HMDB33722
Metabolite Identification
Common NameSativol
Description6alpha-Hydroxymaackiain, also known as 6a-hydroxyinermin, belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 6alpha-hydroxymaackiain is considered to be a flavonoid lipid molecule. 6alpha-Hydroxymaackiain is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6alpha-Hydroxymaackiain has been detected, but not quantified in, several different foods, such as common pea, herbs and spices, pulses, and tea. This could make 6alpha-hydroxymaackiain a potential biomarker for the consumption of these foods.
Structure
Data?1563862450
Synonyms
ValueSource
6a-HydroxymaackiainGenerator
6Α-hydroxymaackiainGenerator
3,6a-Dihydroxy-8,9-methylenedioxypterocarpanHMDB
6a-HydroxyinerminHMDB
4,9-Dihydroxy-3-methoxycoumestanHMDB
8,12-Dihydroxy-7-methoxycoumestanHMDB
Chemical FormulaC16H10O6
Average Molecular Weight298.247
Monoisotopic Molecular Weight298.047738052
IUPAC Name6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
Traditional Name6,14-dihydroxy-5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one
CAS Registry Number7331-58-0
SMILES
COC1=C(O)C2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2
InChI Identifier
InChI=1S/C16H10O6/c1-20-10-5-4-9-14-12(16(19)22-15(9)13(10)18)8-3-2-7(17)6-11(8)21-14/h2-6,17-18H,1H3
InChI KeyYLRNDYZYIUVEDH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Pterocarpan
  • Isoflavanol
  • Isoflavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Coumaran
  • Benzodioxole
  • Benzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organooxygen compound
  • 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 Point303 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP2.48ALOGPS
logP2.89ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.08ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.08 m³·mol⁻¹ChemAxon
Polarizability29.44 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, Positivesplash10-000i-0790000000-8463a2699ea35ddc8f35Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05i1-2019300000-e978a2229c6916f190d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-1c2655c0874df2c777abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0090000000-0c32dcdf67d63237b7dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00pj-1090000000-c46fed3bc46b4bc5af33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-833559a945ff2bea2313Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-c98d267548cdbf45b286Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-0090000000-74dca69cf78e048d00c1Spectrum
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 IDFDB011839
KNApSAcK IDC00009677
Chemspider ID24785132
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257487
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.. .