Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:58:56 UTC
Update Date2022-09-22 18:34:25 UTC
HMDB IDHMDB0034188
Secondary Accession Numbers
  • HMDB34188
Metabolite Identification
Common Name(R)-Glabridin
Description(R)-Glabridin 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 (R)-Glabridin has been detected, but not quantified in, several different foods, such as green tea, black tea, herbal tea, red tea, and herbs and spices. This could make (R)-glabridin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (R)-Glabridin.
Structure
Data?1563862524
Synonyms
ValueSource
GlabridinHMDB
Chemical FormulaC20H20O4
Average Molecular Weight324.3704
Monoisotopic Molecular Weight324.136159128
IUPAC Name4-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}benzene-1,3-diol
Traditional Name4-{8,8-dimethyl-2H,3H,4H-pyrano[2,3-f]chromen-3-yl}benzene-1,3-diol
CAS Registry Number59870-68-7
SMILES
CC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C2
InChI Identifier
InChI=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
InChI KeyLBQIJVLKGVZRIW-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
  • 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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point154 - 155 °CNot Available
Boiling Point518.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.93 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.260 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Polarizability34.7 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]+177.66331661259
DarkChem[M-H]-178.16231661259
DeepCCS[M+H]+184.18830932474
DeepCCS[M-H]-181.8330932474
DeepCCS[M-2H]-216.0330932474
DeepCCS[M+Na]+191.4430932474
AllCCS[M+H]+179.932859911
AllCCS[M+H-H2O]+176.532859911
AllCCS[M+NH4]+183.132859911
AllCCS[M+Na]+184.032859911
AllCCS[M-H]-183.532859911
AllCCS[M+Na-2H]-183.032859911
AllCCS[M+HCOO]-182.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-GlabridinCC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C23766.4Standard polar33892256
(R)-GlabridinCC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C22896.0Standard non polar33892256
(R)-GlabridinCC1(C)OC2=C(C=C1)C1=C(CC(CO1)C1=C(O)C=C(O)C=C1)C=C23173.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Glabridin,1TMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O)C=C2O[Si](C)(C)C)C3)O12859.1Semi standard non polar33892256
(R)-Glabridin,1TMS,isomer #2CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C)C=C2O)C3)O12894.1Semi standard non polar33892256
(R)-Glabridin,2TMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C)C=C2O[Si](C)(C)C)C3)O12774.8Semi standard non polar33892256
(R)-Glabridin,1TBDMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O)C=C2O[Si](C)(C)C(C)(C)C)C3)O13124.7Semi standard non polar33892256
(R)-Glabridin,1TBDMS,isomer #2CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O)C3)O13168.2Semi standard non polar33892256
(R)-Glabridin,2TBDMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OCC(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)C3)O13232.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Glabridin GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fr-0986000000-a402c5b6e8c58929f3c92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Glabridin GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-3459800000-a946a115c0381a5145412017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Glabridin 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 - (R)-Glabridin 10V, Positive-QTOFsplash10-004r-1829000000-4f7978527f8f0227426e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Positive-QTOFsplash10-000i-1954000000-3100d85b046e6a2b3d972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Positive-QTOFsplash10-00kr-3920000000-63380871cd9494383eb42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 10V, Negative-QTOFsplash10-00di-0319000000-aa71f3a8c3f10d8f00672016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Negative-QTOFsplash10-05fr-1967000000-16a39bd697ce2e0387362016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Negative-QTOFsplash10-0a4r-1930000000-c0c1123cde5ce60280802016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 10V, Negative-QTOFsplash10-00di-0009000000-b64caba2598a2db6662e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Negative-QTOFsplash10-05gi-2069000000-4c00c7aa5fb9df7307f62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Negative-QTOFsplash10-0as0-4592000000-252b77c9d4eace96e92a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 10V, Positive-QTOFsplash10-004i-0039000000-1f47f6bebdc38361425c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 20V, Positive-QTOFsplash10-004i-0069000000-04dcce05f2db2252e85d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Glabridin 40V, Positive-QTOFsplash10-0abj-1692000000-f247596537c4ed45bb1f2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012481
KNApSAcK IDC00002529
Chemspider ID3682058
KEGG Compound IDC10421
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4484219
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1700451
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
(R)-Glabridin → 6-(4-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-3-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
(R)-Glabridin → 6-(2-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-5-hydroxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails