Glabridin (CHEM021049)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 02:53:28 UTC
Update Date2026-04-04 06:43:24 UTC
Accession NumberCHEM021049
Identification
Common NameGlabridin
ClassSmall Molecule
DescriptionA member of the class of hydroxyisoflavans that is (R)-isoflavan substituted by hydroxy groups at positions 2' and 4' and a 2,2-dimethyl-2H-pyran group across positions 7 and 8 respectively.
Contaminant Sources
  • Cosmetic Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
4-(3,4-dihydro-8,8-Dimethyl-2H,8H-benzo(1,2-b:3,4-b')dipyran-3-yl)-1,3-benzenediolMeSH
Chemical FormulaC20H20O4
Average Molecular Mass324.370 g/mol
Monoisotopic Mass324.136 g/mol
CAS Registry NumberNot Available
IUPAC Name4-[(3R)-8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl]benzene-1,3-diol
Traditional Nameglabridin
SMILES[H][C@]1(COC2=C(C1)C=CC1=C2C=CC(C)(C)O1)C1=C(O)C=C(O)C=C1
InChI IdentifierInChI=1S/C20H20O4/c1-20(2)8-7-16-18(24-20)6-3-12-9-13(11-23-19(12)16)15-5-4-14(21)10-17(15)22/h3-8,10,13,21-22H,9,11H2,1-2H3/t13-/m0/s1
InChI KeyLBQIJVLKGVZRIW-ZDUSSCGKSA-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
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavan
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0093 g/LALOGPS
logP3.81ALOGPS
logP4.09ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.52ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity93.35 m³·mol⁻¹ChemAxon
Polarizability35.92 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-1829000000-4f7978527f8f0227426eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1954000000-3100d85b046e6a2b3d97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-3920000000-63380871cd9494383eb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0319000000-aa71f3a8c3f10d8f0067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-1967000000-16a39bd697ce2e038736Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-1930000000-c0c1123cde5ce6028080Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00002529
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlabridin
Chemspider IDNot Available
ChEBI ID5369
PubChem Compound ID124052
Kegg Compound IDC10421
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=24361284
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25737160