Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2019-11-26 03:07:09 UTC
Primary IDFDB012590
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlyceollin IV
DescriptionGlyceollin IV 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, glyceollin IV is considered to be a flavonoid lipid molecule. Glyceollin IV is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Glyceollin IV has been detected, but not quantified in, a few different foods, such as fats and oils, pulses, and soy beans. This could make glyceollin IV a potential biomarker for the consumption of these foods.
CAS Number69393-94-8
Structure
Thumb
Synonyms
SynonymSource
6a,9-Dihydroxy-3-methoxy-2-prenylpterocarpanHMDB
Glyceollin IVdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP3.23ALOGPS
logP3.58ChemAxon
logS-3.9ALOGPS
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 Count3ChemAxon
Refractivity98.39 m³·mol⁻¹ChemAxon
Polarizability38.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H22O5
IUPAC name5-methoxy-4-(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-10,14-diol
InChI IdentifierInChI=1S/C21H22O5/c1-12(2)4-5-13-8-15-18(10-17(13)24-3)25-11-21(23)16-7-6-14(22)9-19(16)26-20(15)21/h4,6-10,20,22-23H,5,11H2,1-3H3
InChI KeyWOKIXZBYDPTMJD-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=C1CC=C(C)C)C1OC3=C(C=CC(O)=C3)C1(O)CO2
Average Molecular Weight354.3964
Monoisotopic Molecular Weight354.146723814
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 71.17%; H 6.26%; O 22.57%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 Data[neutral] lmax 286 () (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-2339000000-2fdb6878fc8bdf2a507aJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-003r-2120900000-edfe0cf3412992f4a0cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2209000000-467ff670cf3951a248bcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0axr-4619000000-8240368038d16c88e0bfJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02td-9500000000-d9c6ec10795e4baad5d6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-469aef1a1d8300acefdeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0209000000-cf9d2669bd85d4acdfedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000j-2922000000-3a700b2499d36599d57eJSpectraViewer
ChemSpider ID4476501
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5317742
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34264
CRC / DFC (Dictionary of Food Compounds) IDKWB68-G:HJD85-Z
EAFUS IDNot Available
Dr. Duke IDGLYCEOLLIN-IV
BIGG IDNot Available
KNApSAcK IDC00009690
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.