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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:59 UTC
Update Date2022-03-07 02:52:11 UTC
HMDB IDHMDB0029533
Secondary Accession Numbers
  • HMDB29533
Metabolite Identification
Common NameGlabrone
DescriptionGlabrone, also known as eurycarpin b, belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. Thus, glabrone is considered to be a flavonoid. Based on a literature review very few articles have been published on Glabrone.
Structure
Data?1582753432
Synonyms
ValueSource
7-Hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-4H-1-benzopyran-4-one, 9ciHMDB
Eurycarpin bHMDB
Morusin hydroperoxideHMDB
7,2'-Dihydroxy-6'',6''-dimethylpyrano-(2'',3''-4',3')isoflavoneHMDB
Chemical FormulaC20H16O5
Average Molecular Weight336.338
Monoisotopic Molecular Weight336.099773622
IUPAC Name7-hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-4H-chromen-4-one
Traditional Nameglabrone
CAS Registry Number60008-02-8
SMILES
CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O
InChI Identifier
InChI=1S/C20H16O5/c1-20(2)8-7-14-16(25-20)6-5-12(18(14)22)15-10-24-17-9-11(21)3-4-13(17)19(15)23/h3-10,21-22H,1-2H3
InChI KeyCOLMVFWKLOZOOP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassPyranoisoflavonoids
Direct ParentPyranoisoflavonoids
Alternative Parents
Substituents
  • Pyranoisoflavonoid
  • Isoflavone
  • Hydroxyisoflavonoid
  • 2,2-dimethyl-1-benzopyran
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point224 - 226 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.22 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.37ALOGPS
logP3.63ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)6.47ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.1 m³·mol⁻¹ChemAxon
Polarizability35.43 ųChemAxon
Number of Rings4ChemAxon
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]+179.01831661259
DarkChem[M-H]-177.90331661259
DeepCCS[M+H]+182.57730932474
DeepCCS[M-H]-180.21930932474
DeepCCS[M-2H]-214.22230932474
DeepCCS[M+Na]+189.4530932474
AllCCS[M+H]+180.932859911
AllCCS[M+H-H2O]+177.532859911
AllCCS[M+NH4]+184.132859911
AllCCS[M+Na]+185.032859911
AllCCS[M-H]-181.632859911
AllCCS[M+Na-2H]-180.932859911
AllCCS[M+HCOO]-180.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
GlabroneCC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O4006.6Standard polar33892256
GlabroneCC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O2877.2Standard non polar33892256
GlabroneCC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O3270.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Glabrone,1TMS,isomer #1CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O)=CC=C4C3=O)=C2O[Si](C)(C)C)O13166.1Semi standard non polar33892256
Glabrone,1TMS,isomer #2CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C)=CC=C4C3=O)=C2O)O13151.4Semi standard non polar33892256
Glabrone,2TMS,isomer #1CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C)=CC=C4C3=O)=C2O[Si](C)(C)C)O13016.9Semi standard non polar33892256
Glabrone,1TBDMS,isomer #1CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O)=CC=C4C3=O)=C2O[Si](C)(C)C(C)(C)C)O13390.7Semi standard non polar33892256
Glabrone,1TBDMS,isomer #2CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3=O)=C2O)O13384.5Semi standard non polar33892256
Glabrone,2TBDMS,isomer #1CC1(C)C=CC2=C(C=CC(C3=COC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3=O)=C2O[Si](C)(C)C(C)(C)C)O13513.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Glabrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0239000000-02cdbb828adf59f8e9ea2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glabrone GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-2253900000-f6bfe8e93085c4a375172017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glabrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glabrone 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 - Glabrone 10V, Positive-QTOFsplash10-000i-0009000000-fc949cee3880d9c2ab1f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 20V, Positive-QTOFsplash10-000i-0039000000-1edd6131ef24c47e48062016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 40V, Positive-QTOFsplash10-0fts-5691000000-ad71d104a59d05ec8c592016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 10V, Negative-QTOFsplash10-000i-0009000000-4afa58f64fe760256bc12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 20V, Negative-QTOFsplash10-000i-0009000000-e43df9b15069f6af971f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 40V, Negative-QTOFsplash10-014r-2895000000-e8a10eca75882be562552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 10V, Negative-QTOFsplash10-000i-0009000000-dc81427ba733f47873d12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 20V, Negative-QTOFsplash10-000i-0019000000-c2ab3766f57ecce69cb82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 40V, Negative-QTOFsplash10-0006-0091000000-759b8e8f1fed3a4e82b82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 10V, Positive-QTOFsplash10-000i-0009000000-515a0c5934a26e5d5bd92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 20V, Positive-QTOFsplash10-000i-0039000000-38059c03312539ee043e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glabrone 40V, Positive-QTOFsplash10-004i-1191000000-5158d69189a52fff5aec2021-09-25Wishart 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 IDFDB000674
KNApSAcK IDC00009434
Chemspider ID4476468
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5317652
PDB IDNot Available
ChEBI ID698651
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1810261
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.. .