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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:54:23 UTC
Update Date2022-03-07 02:53:59 UTC
HMDB IDHMDB0034111
Secondary Accession Numbers
  • HMDB34111
Metabolite Identification
Common 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. Outside of the human body, 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.
Structure
Data?1563862512
Synonyms
ValueSource
2-(1-Hydroxy-1-methylethyl)-6H-benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11ah)-diol, 9ciHMDB
Chemical FormulaC20H18O6
Average Molecular Weight354.3533
Monoisotopic Molecular Weight354.110338308
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
Traditional 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
CAS Registry Number78873-52-6
SMILES
CC(C)(O)C1=CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O1
InChI Identifier
InChI=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
Chemical Taxonomy
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point181 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.26 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+181.35731661259
DarkChem[M-H]-181.38831661259
DeepCCS[M+H]+185.54430932474
DeepCCS[M-H]-183.18630932474
DeepCCS[M-2H]-217.41230932474
DeepCCS[M+Na]+192.6430932474
AllCCS[M+H]+184.832859911
AllCCS[M+H-H2O]+181.632859911
AllCCS[M+NH4]+187.732859911
AllCCS[M+Na]+188.632859911
AllCCS[M-H]-189.232859911
AllCCS[M+Na-2H]-188.832859911
AllCCS[M+HCOO]-188.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlyceofuranCC(C)(O)C1=CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O14385.8Standard polar33892256
GlyceofuranCC(C)(O)C1=CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O12920.0Standard non polar33892256
GlyceofuranCC(C)(O)C1=CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O13248.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glyceofuran,1TMS,isomer #1CC(C)(O[Si](C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O)C=C2OC313205.1Semi standard non polar33892256
Glyceofuran,1TMS,isomer #2CC(C)(O)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C)C2=CC=C(O)C=C2OC313164.9Semi standard non polar33892256
Glyceofuran,1TMS,isomer #3CC(C)(O)C1=CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O[Si](C)(C)C)C=C2OC313223.1Semi standard non polar33892256
Glyceofuran,2TMS,isomer #1CC(C)(O[Si](C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C)C2=CC=C(O)C=C2OC313158.8Semi standard non polar33892256
Glyceofuran,2TMS,isomer #2CC(C)(O[Si](C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O[Si](C)(C)C)C=C2OC313218.0Semi standard non polar33892256
Glyceofuran,2TMS,isomer #3CC(C)(O)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC313179.5Semi standard non polar33892256
Glyceofuran,3TMS,isomer #1CC(C)(O[Si](C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC313215.0Semi standard non polar33892256
Glyceofuran,1TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O)C=C2OC313474.2Semi standard non polar33892256
Glyceofuran,1TBDMS,isomer #2CC(C)(O)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2OC313449.0Semi standard non polar33892256
Glyceofuran,1TBDMS,isomer #3CC(C)(O)C1=CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC313484.8Semi standard non polar33892256
Glyceofuran,2TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2OC313657.3Semi standard non polar33892256
Glyceofuran,2TBDMS,isomer #2CC(C)(O[Si](C)(C)C(C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC313726.7Semi standard non polar33892256
Glyceofuran,2TBDMS,isomer #3CC(C)(O)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC313679.1Semi standard non polar33892256
Glyceofuran,3TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)C1=CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC313919.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glyceofuran GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-7239000000-cbb354a2f5e0465049d62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceofuran GC-MS (3 TMS) - 70eV, Positivesplash10-0adr-9321650000-ccccc6043f93ceb124372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceofuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceofuran GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 10V, Positive-QTOFsplash10-0a4r-0009000000-fb8c3c3ed2b1a74ef37e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 20V, Positive-QTOFsplash10-0a4r-0309000000-a2e24afb9472badcaf702015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 40V, Positive-QTOFsplash10-0aos-9600000000-6b402aa588d5c62532002015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 10V, Negative-QTOFsplash10-0udi-0009000000-5827a5fdcff4bb07d3772015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 20V, Negative-QTOFsplash10-0udj-0159000000-cb8c72007496c17093fd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 40V, Negative-QTOFsplash10-052s-2937000000-f96cd0208b55ca9cd8522015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 10V, Negative-QTOFsplash10-0udi-0009000000-b3503695056246b53ddc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 20V, Negative-QTOFsplash10-0udi-0019000000-399d97f6327be6bdb8eb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 40V, Negative-QTOFsplash10-0006-9071000000-c07cfac9b83b049661952021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 10V, Positive-QTOFsplash10-0a4i-0009000000-aa2af3dc1d62c35046d02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 20V, Positive-QTOFsplash10-052r-0009000000-8d358ebedf37c248b1ce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceofuran 40V, Positive-QTOFsplash10-0pdr-0689000000-c317721f319a7ff236a12021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012378
KNApSAcK IDC00009691
Chemspider ID546354
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound629096
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .