Record Information
Version1.0
Creation date2010-04-08 22:05:29 UTC
Update date2020-02-24 19:10:35 UTC
Primary IDFDB002706
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6alpha-Hydroxyphaseollin
Description6alpha-Hydroxyphaseollin 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. 6alpha-Hydroxyphaseollin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6alpha-Hydroxyphaseollin has been detected, but not quantified in, several different foods, such as common beans, green beans, pulses, soy beans, and yellow wax beans. This could make 6alpha-hydroxyphaseollin a potential biomarker for the consumption of these foods.
CAS Number34144-10-0
Structure
Thumb
Synonyms
SynonymSource
6a-HydroxyphaseollinGenerator
6Α-hydroxyphaseollinGenerator
3,3-Dimethyl-3H,7H-furo[3,2-c:5,4-f']bis[1]benzopyran-6b,10(12BH)-diol, 9ciHMDB
6a-HydroxyphaseolinHMDB
HydroxyphaseolinHMDB
3,3-Dimethyl-3H,7H-furo[3,2-c:5,4-f']bis[1]benzopyran-6b,10(12bH)-diol, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP3.25ALOGPS
logP2.91ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.08 m³·mol⁻¹ChemAxon
Polarizability35.76 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H18O5
IUPAC name6,6-dimethyl-5,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,7,9,14(19),15,17-heptaene-1,17-diol
InChI IdentifierInChI=1S/C20H18O5/c1-19(2)6-5-11-7-17-14(9-15(11)25-19)20(22)10-23-16-8-12(21)3-4-13(16)18(20)24-17/h3-9,18,21-22H,10H2,1-2H3
InChI KeyKVUZVBGGLCNPQI-UHFFFAOYSA-N
Isomeric SMILESCC1(C)OC2=CC3=C(OC4C5=C(OCC34O)C=C(O)C=C5)C=C2C=C1
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
Classification
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
  • Isoflavanol
  • Pterocarpan
  • Isoflavan
  • 2,2-dimethyl-1-benzopyran
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Benzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 71.00%; H 5.36%; O 23.64%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -207 (EtOAc)DFC
Spectroscopic UV Data318 (e 3100) (EtOH-NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0719000000-cf3c2e08ef3bd2364382JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9421800000-24030aa0a1bd1bf04638JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0119000000-9d0e8ebca7f968413587JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2179000000-f30cc34b053beadc9793JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0159-3930000000-23c01d50a8c57c7571b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-f60e3ca95575fcd65339JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029000000-e6e1cf7fd10e01016945JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gk9-0291000000-ad33ac8b7e4d4ad274b1JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3084583
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB30771
CRC / DFC (Dictionary of Food Compounds) IDCND49-Q:CND49-Q
EAFUS IDNot Available
Dr. Duke IDHYDROXYPHASEOLIN|6-ALPHA-HYDROXYPHASEOLLIN
BIGG IDNot Available
KNApSAcK IDC00020214
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.