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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:25:18 UTC
Update Date2019-07-23 06:14:02 UTC
HMDB IDHMDB0033669
Secondary Accession Numbers
  • HMDB33669
Metabolite Identification
Common NamePhaseollidin
DescriptionPhaseollidin 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. Phaseollidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, phaseollidin has been detected, but not quantified in, several different foods, such as fruits, cowpea, yellow wax beans, common beans, and lima beans. This could make phaseollidin a potential biomarker for the consumption of these foods.
Structure
Data?1563862442
Synonyms
ValueSource
(-)-PhaseollidinHMDB
6a,11a-Dihydro-10-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-3,9-diol, 9ciHMDB
Chemical FormulaC20H20O4
Average Molecular Weight324.3704
Monoisotopic Molecular Weight324.136159128
IUPAC Name15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol
Traditional Name15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,14-diol
CAS Registry Number37831-70-2
SMILES
CC(C)=CCC1=C(O)C=CC2=C1OC1C2COC2=C1C=CC(O)=C2
InChI Identifier
InChI=1S/C20H20O4/c1-11(2)3-5-14-17(22)8-7-13-16-10-23-18-9-12(21)4-6-15(18)20(16)24-19(13)14/h3-4,6-9,16,20-22H,5,10H2,1-2H3
InChI KeyOFWYIUYVHYPQNX-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 Parents
Substituents
  • Isoflavanol
  • Pterocarpan
  • Isoflavan
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Coumaran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point67 - 69 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.028 g/LALOGPS
logP3.79ALOGPS
logP4.09ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.09ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.82 m³·mol⁻¹ChemAxon
Polarizability35.42 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, Positivesplash10-0a4l-6594000000-8b5b4b73f84f06975696Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-4233900000-c266017f6caebe727b88Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1139000000-0516bafeac70b7f3307bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016r-4395000000-3bab6345ec8bef02793dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-9220000000-7b01887f18b52a30201cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-e5c925628b63acda0106Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0049000000-f683037041131d6a52a1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-3960000000-8b4bbee7eb29375ba3ddSpectrum
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 IDFDB011772
KNApSAcK IDC00002558
Chemspider ID4292653
KEGG Compound IDC05230
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5117820
PDB IDNot Available
ChEBI ID17556
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
Phaseollidin → 3,4,5-trihydroxy-6-{[14-hydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-yl]oxy}oxane-2-carboxylic aciddetails
Phaseollidin → 3,4,5-trihydroxy-6-{[5-hydroxy-15-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-14-yl]oxy}oxane-2-carboxylic aciddetails