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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:15:21 UTC
Update Date2019-07-23 06:16:00 UTC
HMDB IDHMDB0034414
Secondary Accession Numbers
  • HMDB34414
Metabolite Identification
Common Name3'-Hydroxy-4'-methoxyglabridin
Description3'-Hydroxy-4'-methoxyglabridin is found in herbs and spices. 3'-Hydroxy-4'-methoxyglabridin is isolated from Glycyrrhiza glabra (licorice
Structure
Data?1563862560
Synonyms
ValueSource
3'-MethoxyglabridinHMDB
Chemical FormulaC21H22O5
Average Molecular Weight354.3964
Monoisotopic Molecular Weight354.146723814
IUPAC Name3-{12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8,13-tetraen-5-yl}-6-methoxybenzene-1,2-diol
Traditional Name3-{12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8,13-tetraen-5-yl}-6-methoxybenzene-1,2-diol
CAS Registry Number74046-05-2
SMILES
COC1=C(O)C(O)=C(C=C1)C1COC2=C(C1)C=CC1=C2C=CC(C)(C)O1
InChI Identifier
InChI=1S/C21H22O5/c1-21(2)9-8-15-16(26-21)6-4-12-10-13(11-25-20(12)15)14-5-7-17(24-3)19(23)18(14)22/h4-9,13,22-23H,10-11H2,1-3H3
InChI KeyPPBISUGOQDBBEL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • 3'-hydroxy,4'-methoxyisoflavonoid
  • 4p-methoxyisoflavonoid
  • Hydroxyisoflavonoid
  • Isoflavanol
  • Isoflavan
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Benzopyran
  • Chromane
  • Methoxyphenol
  • 1-benzopyran
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point104 - 105 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP3.76ALOGPS
logP3.93ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)9.81ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity99.82 m³·mol⁻¹ChemAxon
Polarizability37.6 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f79-0869000000-6299a62cf75b9b237029JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1121900000-72a8015fc51c73ea80b3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1918000000-c556008430fe32443d00JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0944000000-1e08a8845b09767b6eacJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cdr-2930000000-48984bb4674ad632e32dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0319000000-45e2d49701cc2ebcc042JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fri-0978000000-6f8d39a31498fe33f531JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0931000000-09364c2c1a2b14c52517JSpectraViewer | MoNA
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
FoodDB IDFDB012809
KNApSAcK IDC00009730
Chemspider ID8513670
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10338211
PDB IDNot Available
ChEBI 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.. .

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
3'-Hydroxy-4'-methoxyglabridin → 6-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-2,3-dimethoxyphenoldetails
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
3'-Hydroxy-4'-methoxyglabridin → 6-(3-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-2-hydroxy-6-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3'-Hydroxy-4'-methoxyglabridin → 6-(6-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-2-hydroxy-3-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3'-Hydroxy-4'-methoxyglabridin → (3-{8,8-dimethyl-2H,3H,4H,8H-pyrano[2,3-f]chromen-3-yl}-2-hydroxy-6-methoxyphenyl)oxidanesulfonic aciddetails