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Showing Compound Glyceollin II (FDB012347)

Record Information
Version1.0
Creation date2010-04-08 22:10:07 UTC
Update date2019-11-26 03:06:36 UTC
Primary IDFDB012347
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlyceollin II
DescriptionGlyceollin II 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. Glyceollin II is an extremely weak basic (essentially neutral) compound (based on its pKa). Glyceollin II has been detected, but not quantified in, a few different foods, such as fats and oils, pulses, and soy beans. This could make glyceollin II a potential biomarker for the consumption of these foods.
CAS Number67314-98-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-Glyceollin IIHMDB
3,3-Dimethyl-3H,7H-benzofuro[3,2-c]pyrano[3,2-g][1]benzopyran-7a,10(12ah)-diol, 9ciHMDB
3,3-Dimethyl-3H,7H-benzofuro[3,2-c]pyrano[3,2-g][1]benzopyran-7a,10(12aH)-diol, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.057 g/LALOGPS
logP3.26ALOGPS
logP2.91ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
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
Polarizability35.92 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H18O5
IUPAC name17,17-dimethyl-3,12,16-trioxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-1(13),4(9),5,7,14,18,20-heptaene-6,10-diol
InChI IdentifierInChI=1S/C20H18O5/c1-19(2)6-5-11-7-13-16(9-15(11)25-19)23-10-20(22)14-4-3-12(21)8-17(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3
InChI KeyDDJVLBCETGUEBO-UHFFFAOYSA-N
Isomeric SMILESCC1(C)OC2=CC3=C(C=C2C=C1)C1OC2=C(C=CC(O)=C2)C1(O)CO3
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
  • Pyranochromene
  • 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
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • 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 71.00%; H 5.36%; O 23.64%DFC
Melting PointMp 89-93°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data318 (e 5800) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-2529000000-2b3d952f809cbf001f1bJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9312700000-f2d19645877db9a07290JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1009000000-23033e803a8cb5fe5c8bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-1049000000-cd378d36fcd0a93afd0dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9110000000-04f1a650c737c9f09603JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-edb121303eeabbebf802JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-4773e07f96c778327e20JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-1093000000-04f44b04922eead7c975JSpectraViewer
ChemSpider ID3830080
ChEMBL IDNot Available
KEGG Compound IDC10422
Pubchem Compound ID4640119
Pubchem Substance IDNot Available
ChEBI ID52127
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34087
CRC / DFC (Dictionary of Food Compounds) IDHGM15-C:HGM15-C
EAFUS IDNot Available
Dr. Duke IDGLYCEOLLIN-II
BIGG IDNot Available
KNApSAcK IDC00002531
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
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).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.