Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:48:59 UTC
Update Date2022-03-07 02:53:57 UTC
HMDB IDHMDB0034041
Secondary Accession Numbers
  • HMDB34041
Metabolite Identification
Common NameGlyceollin III
DescriptionGlyceollin III 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 III has been detected, but not quantified in, a few different foods, such as fats and oils, pulses, and soy beans (Glycine max). This could make glyceollin III a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Glyceollin III.
Structure
Data?1563862500
Synonyms
ValueSource
1,2-dihydro-2-(1-Methylethenyl)-6H-benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11ah)-diol, 9ciHMDB
Chemical FormulaC20H18O5
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
IUPAC Name6-(prop-1-en-2-yl)-7,11,20-trioxapentacyclo[11.7.0.0²,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-2(10),3,8,14(19),15,17-hexaene-13,17-diol
Traditional Nameglyceollin III
CAS Registry Number61080-23-7
SMILES
CC(=C)C1CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O1
InChI Identifier
InChI=1S/C20H18O5/c1-10(2)15-6-11-5-13-17(8-16(11)24-15)23-9-20(22)14-4-3-12(21)7-18(14)25-19(13)20/h3-5,7-8,15,19,21-22H,1,6,9H2,2H3
InChI KeyMIYTVBARXCVVHZ-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
  • Coumaran
  • Benzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • 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 Point149 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.57ALOGPS
logP2.93ChemAxon
logS-3.3ALOGPS
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 Count1ChemAxon
Refractivity90.57 m³·mol⁻¹ChemAxon
Polarizability35.88 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]+180.29531661259
DarkChem[M-H]-176.77531661259
DeepCCS[M+H]+179.96130932474
DeepCCS[M-H]-177.60330932474
DeepCCS[M-2H]-211.53930932474
DeepCCS[M+Na]+186.76630932474
AllCCS[M+H]+182.832859911
AllCCS[M+H-H2O]+179.532859911
AllCCS[M+NH4]+185.932859911
AllCCS[M+Na]+186.732859911
AllCCS[M-H]-186.132859911
AllCCS[M+Na-2H]-185.532859911
AllCCS[M+HCOO]-185.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glyceollin IIICC(=C)C1CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O14178.1Standard polar33892256
Glyceollin IIICC(=C)C1CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O12786.8Standard non polar33892256
Glyceollin IIICC(=C)C1CC2=CC3=C(OCC4(O)C3OC3=C4C=CC(O)=C3)C=C2O13157.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glyceollin III,1TMS,isomer #1C=C(C)C1CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C)C2=CC=C(O)C=C2OC312934.8Semi standard non polar33892256
Glyceollin III,1TMS,isomer #2C=C(C)C1CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O[Si](C)(C)C)C=C2OC313002.5Semi standard non polar33892256
Glyceollin III,2TMS,isomer #1C=C(C)C1CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2OC312979.0Semi standard non polar33892256
Glyceollin III,1TBDMS,isomer #1C=C(C)C1CC2=CC3=C(C=C2O1)OCC1(O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2OC313176.4Semi standard non polar33892256
Glyceollin III,1TBDMS,isomer #2C=C(C)C1CC2=CC3=C(C=C2O1)OCC1(O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC313260.3Semi standard non polar33892256
Glyceollin III,2TBDMS,isomer #1C=C(C)C1CC2=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=C2OC313457.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glyceollin III GC-MS (Non-derivatized) - 70eV, Positivesplash10-059l-9748000000-0c8f6f42b908caad29562017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceollin III GC-MS (2 TMS) - 70eV, Positivesplash10-01bl-9302700000-4a761389ba0b47aab22e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glyceollin III 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 - Glyceollin III 10V, Positive-QTOFsplash10-000i-1209000000-36787a23fcfd732f51442015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 20V, Positive-QTOFsplash10-0a4r-1819000000-4d66b9b9a426ed6600f22015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 40V, Positive-QTOFsplash10-05mo-9500000000-7c7ec4875763a3f0c8412015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 10V, Negative-QTOFsplash10-000i-0009000000-133c641ded1401e9d55b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 20V, Negative-QTOFsplash10-000i-0219000000-ba2ad87e769092cd90b72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 40V, Negative-QTOFsplash10-05mt-3901000000-020981508ab46f0dc5f42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 10V, Negative-QTOFsplash10-000i-0009000000-fba49930c01349472a4d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 20V, Negative-QTOFsplash10-000i-0019000000-af0b7835583d543b96342021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 40V, Negative-QTOFsplash10-0573-4495000000-264588e0a82f1e6313ba2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 10V, Positive-QTOFsplash10-000i-0009000000-2b8ef97f349df851f3ad2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 20V, Positive-QTOFsplash10-000i-0009000000-e6d501831916ec1e2f4e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glyceollin III 40V, Positive-QTOFsplash10-00kb-8975000000-67f7754206e4f58245be2021-09-24Wishart 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 IDFDB012283
KNApSAcK IDC00009685
Chemspider ID10174551
KEGG Compound IDC15511
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlyceollin III
METLIN IDNot Available
PubChem Compound12002084
PDB IDNot Available
ChEBI ID52086
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.. .