Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:10:08 UTC
Update date2019-11-26 03:06:39 UTC
Primary IDFDB012378
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlyceofuran
DescriptionGlyceofuran 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, glyceofuran is considered to be a flavonoid lipid molecule. Glyceofuran is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Glyceofuran has been detected, but not quantified in, pulses and soy beans. This could make glyceofuran a potential biomarker for the consumption of these foods.
CAS Number78873-52-6
Structure
Thumb
Synonyms
SynonymSource
2-(1-Hydroxy-1-methylethyl)-6H-benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11ah)-diol, 9ciHMDB
2-(1-Hydroxy-1-methylethyl)-6H-benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11aH)-diol, 9CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP2.59ALOGPS
logP2.02ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)9.4ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.29 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.28 m³·mol⁻¹ChemAxon
Polarizability37.35 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H18O6
IUPAC name6-(2-hydroxypropan-2-yl)-7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-2(10),3,5,8,14(19),15,17-heptaene-13,17-diol
InChI IdentifierInChI=1S/C20H18O6/c1-19(2,22)17-6-10-5-12-15(8-14(10)25-17)24-9-20(23)13-4-3-11(21)7-16(13)26-18(12)20/h3-8,18,21-23H,9H2,1-2H3
InChI KeyFLURXOFTUKXKQN-UHFFFAOYSA-N
Isomeric SMILESCC(C)(O)C1=CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O1
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
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
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Coumaran
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Tertiary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Aromatic alcohol
  • Hydrocarbon derivative
  • Alcohol
  • 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 67.79%; H 5.12%; O 27.09%DFC
Melting PointMp 181° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -242 (c, 0.03 in MeOH)DFC
Spectroscopic UV Data362 () (HCl) (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-7239000000-cbb354a2f5e0465049d6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0adr-9321650000-ccccc6043f93ceb12437JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0009000000-fb8c3c3ed2b1a74ef37eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-0309000000-a2e24afb9472badcaf70JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aos-9600000000-6b402aa588d5c6253200JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-5827a5fdcff4bb07d377JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udj-0159000000-cb8c72007496c17093fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052s-2937000000-f96cd0208b55ca9cd852JSpectraViewer
ChemSpider ID546354
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID629096
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34111
CRC / DFC (Dictionary of Food Compounds) IDHGR48-N:HGR48-N
EAFUS IDNot Available
Dr. Duke IDGLYCEOFURAN
BIGG IDNot Available
KNApSAcK IDC00009691
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.