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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:47:04 UTC
Update Date2019-07-23 06:10:03 UTC
HMDB IDHMDB0031993
Secondary Accession Numbers
  • HMDB31993
Metabolite Identification
Common NameGlyurallin A
DescriptionGlyurallin A, also known as arizonicanol e, 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. Glyurallin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, glyurallin a has been detected, but not quantified in, herbs and spices. This could make glyurallin a a potential biomarker for the consumption of these foods.
Structure
Data?1563862203
Synonyms
ValueSource
3,10-Dihydroxy-9-methoxy-8-(1,1-dimethyl-2-propenyl)pterocarpanHMDB
3,9-Dihydroxy-1-methoxy-2-prenylpterocarpeneHMDB
Arizonicanol eHMDB
Chemical FormulaC21H20O5
Average Molecular Weight352.3805
Monoisotopic Molecular Weight352.13107375
IUPAC Name3-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaene-5,14-diol
Traditional Name3-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaene-5,14-diol
CAS Registry Number213130-81-5
SMILES
COC1=C(CC=C(C)C)C(O)=CC2=C1C1=C(CO2)C2=C(O1)C=C(O)C=C2
InChI Identifier
InChI=1S/C21H20O5/c1-11(2)4-6-14-16(23)9-18-19(20(14)24-3)21-15(10-25-18)13-7-5-12(22)8-17(13)26-21/h4-5,7-9,22-23H,6,10H2,1-3H3
InChI KeyAEAIWNGAMDGGNB-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP3.86ALOGPS
logP4.26ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area72.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity99.6 m³·mol⁻¹ChemAxon
Polarizability38.61 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dr-1129000000-d1826d4ea1cafe132a90Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1002900000-43ea2f5935c72346b810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-4341afa67e07901f4027Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-3159000000-ce001b1701f4f76e811aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0671-4920000000-0a95facfbbd25a59ee7bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-b59c840c92359154fb9bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ik9-0917000000-ead352d16eee11dbe68eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ha-0912000000-65b21437e9dedb38947dSpectrum
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 IDFDB008686
KNApSAcK IDC00018916
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15818598
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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 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
Glyurallin A → 3,4,5-trihydroxy-6-{[5-hydroxy-3-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl]oxy}oxane-2-carboxylic aciddetails
Glyurallin A → 3,4,5-trihydroxy-6-{[14-hydroxy-3-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl]oxy}oxane-2-carboxylic aciddetails