Record Information
Version1.0
Creation date2010-04-08 22:12:49 UTC
Update date2019-11-26 03:14:09 UTC
Primary IDFDB017073
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlyceollidin II
DescriptionGlyceollidin II, also known as glyceocarpin, 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. Glyceollidin II is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceollidin II has been detected, but not quantified in, a few different foods, such as fats and oils, pulses, and soy beans. This could make glyceollidin II a potential biomarker for the consumption of these foods.
CAS Number77979-22-7
Structure
Thumb
Synonyms
SynonymSource
2-(3-Methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-3,6a,9(11ah)-triol, 9ciHMDB
GlyceocarpinHMDB
2-(3-Methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-3,6a,9(11aH)-triol, 9CIdb_source
Glyceollidin IIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.047 g/LALOGPS
logP2.83ALOGPS
logP3.44ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.99ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.91 m³·mol⁻¹ChemAxon
Polarizability36.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H20O5
IUPAC name4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,10,14-triol
InChI IdentifierInChI=1S/C20H20O5/c1-11(2)3-4-12-7-14-17(9-16(12)22)24-10-20(23)15-6-5-13(21)8-18(15)25-19(14)20/h3,5-9,19,21-23H,4,10H2,1-2H3
InChI KeyTUXXPRXOVFCNPC-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=CC2=C(OCC3(O)C2OC2=C3C=CC(O)=C2)C=C1O
Average Molecular Weight340.3698
Monoisotopic Molecular Weight340.13107375
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
  • Pterocarpan
  • Isoflavanol
  • Isoflavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Benzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.58%; H 5.92%; O 23.50%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGlyceollidin II, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0096-5839000000-50180bbfc9b76bea3f97Spectrum
Predicted GC-MSGlyceollidin II, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-3010390000-f6bb5546b4642330d785Spectrum
Predicted GC-MSGlyceollidin II, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlyceollidin II, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-3329000000-5aa9f134e06a45fe215c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n3-6798000000-49300595b1f75ca243dc2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ke-9300000000-8d8a47c3f8e46346decd2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-d8357dbca7239786c3932015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0219000000-4dfee9e063aaadabe4f52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-059b-1911000000-eac8f1938ce6de1309c62015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-dd4479d6058cdf87ccc72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0098000000-64891ab0f8bd69a95c042021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00m0-6951000000-0f5a3736b71f1535fed92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-fd63e399cebf431bd2892021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-99a1cffaed2aae0f92f12021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052g-8983000000-5bb20155a4a31e3a3f602021-09-23View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37916
CRC / DFC (Dictionary of Food Compounds) IDKWB68-G:KWB68-G
EAFUS IDNot Available
Dr. Duke IDGLYCEOCARPIN
BIGG IDNot Available
KNApSAcK IDC00009688
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
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.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.