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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:56 UTC
Update Date2022-03-07 02:52:41 UTC
HMDB IDHMDB0030771
Secondary Accession Numbers
  • HMDB30771
Metabolite Identification
Common Name6alpha-Hydroxyphaseollin
Description6alpha-Hydroxyphaseollin 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. 6alpha-Hydroxyphaseollin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 6alpha-hydroxyphaseollin has been detected, but not quantified in, several different foods, such as common beans, green beans, pulses, soy beans, and yellow wax beans. This could make 6alpha-hydroxyphaseollin a potential biomarker for the consumption of these foods.
Structure
Data?1563862035
Synonyms
ValueSource
6a-HydroxyphaseollinGenerator
6Α-hydroxyphaseollinGenerator
3,3-Dimethyl-3H,7H-furo[3,2-c:5,4-f']bis[1]benzopyran-6b,10(12BH)-diol, 9ciHMDB
6a-HydroxyphaseolinHMDB
HydroxyphaseolinHMDB
Chemical FormulaC20H18O5
Average Molecular Weight338.3539
Monoisotopic Molecular Weight338.115423686
IUPAC Name6,6-dimethyl-5,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,7,9,14(19),15,17-heptaene-1,17-diol
Traditional Name6,6-dimethyl-5,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,7,9,14(19),15,17-heptaene-1,17-diol
CAS Registry Number34144-10-0
SMILES
CC1(C)OC2=CC3=C(OC4C5=C(OCC34O)C=C(O)C=C5)C=C2C=C1
InChI Identifier
InChI=1S/C20H18O5/c1-19(2)6-5-11-7-17-14(9-15(11)25-19)20(22)10-23-16-8-12(21)3-4-13(16)18(20)24-17/h3-9,18,21-22H,10H2,1-2H3
InChI KeyKVUZVBGGLCNPQI-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
  • 2,2-dimethyl-1-benzopyran
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Benzofuran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Tertiary alcohol
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.058 g/LALOGPS
logP3.25ALOGPS
logP2.91ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.41ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area68.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity92.08 m³·mol⁻¹ChemAxon
Polarizability35.76 ųChemAxon
Number of Rings5ChemAxon
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]+179.19631661259
DarkChem[M-H]-180.73131661259
DeepCCS[M-2H]-220.12530932474
DeepCCS[M+Na]+195.3630932474
AllCCS[M+H]+182.632859911
AllCCS[M+H-H2O]+179.232859911
AllCCS[M+NH4]+185.832859911
AllCCS[M+Na]+186.632859911
AllCCS[M-H]-186.732859911
AllCCS[M+Na-2H]-186.132859911
AllCCS[M+HCOO]-185.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
6alpha-HydroxyphaseollinCC1(C)OC2=CC3=C(OC4C5=C(OCC34O)C=C(O)C=C5)C=C2C=C14186.1Standard polar33892256
6alpha-HydroxyphaseollinCC1(C)OC2=CC3=C(OC4C5=C(OCC34O)C=C(O)C=C5)C=C2C=C12715.4Standard non polar33892256
6alpha-HydroxyphaseollinCC1(C)OC2=CC3=C(OC4C5=C(OCC34O)C=C(O)C=C5)C=C2C=C13083.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6alpha-Hydroxyphaseollin,1TMS,isomer #1CC1(C)C=CC2=CC3=C(C=C2O1)C1(O[Si](C)(C)C)COC2=CC(O)=CC=C2C1O32895.8Semi standard non polar33892256
6alpha-Hydroxyphaseollin,1TMS,isomer #2CC1(C)C=CC2=CC3=C(C=C2O1)C1(O)COC2=CC(O[Si](C)(C)C)=CC=C2C1O32943.8Semi standard non polar33892256
6alpha-Hydroxyphaseollin,2TMS,isomer #1CC1(C)C=CC2=CC3=C(C=C2O1)C1(O[Si](C)(C)C)COC2=CC(O[Si](C)(C)C)=CC=C2C1O32922.2Semi standard non polar33892256
6alpha-Hydroxyphaseollin,1TBDMS,isomer #1CC1(C)C=CC2=CC3=C(C=C2O1)C1(O[Si](C)(C)C(C)(C)C)COC2=CC(O)=CC=C2C1O33153.2Semi standard non polar33892256
6alpha-Hydroxyphaseollin,1TBDMS,isomer #2CC1(C)C=CC2=CC3=C(C=C2O1)C1(O)COC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C1O33190.3Semi standard non polar33892256
6alpha-Hydroxyphaseollin,2TBDMS,isomer #1CC1(C)C=CC2=CC3=C(C=C2O1)C1(O[Si](C)(C)C(C)(C)C)COC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2C1O33392.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxyphaseollin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0719000000-cf3c2e08ef3bd23643822017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxyphaseollin GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-9421800000-24030aa0a1bd1bf046382017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 6alpha-Hydroxyphaseollin 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 - 6alpha-Hydroxyphaseollin 10V, Positive-QTOFsplash10-000i-0119000000-9d0e8ebca7f9684135872015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 20V, Positive-QTOFsplash10-000i-2179000000-f30cc34b053beadc97932015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 40V, Positive-QTOFsplash10-0159-3930000000-23c01d50a8c57c7571b62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 10V, Negative-QTOFsplash10-000i-0009000000-f60e3ca95575fcd653392015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 20V, Negative-QTOFsplash10-000i-0029000000-e6e1cf7fd10e010169452015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 40V, Negative-QTOFsplash10-0gk9-0291000000-ad33ac8b7e4d4ad274b12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 10V, Positive-QTOFsplash10-000i-0009000000-2b8ef97f349df851f3ad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 20V, Positive-QTOFsplash10-000i-0029000000-d05b5990aa58cc0a95ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 40V, Positive-QTOFsplash10-00s2-1495000000-29b08f31042c3c70b30a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 10V, Negative-QTOFsplash10-000i-0009000000-fba49930c01349472a4d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 20V, Negative-QTOFsplash10-000i-0009000000-1fd324b854bd3d9f5ddc2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6alpha-Hydroxyphaseollin 40V, Negative-QTOFsplash10-05tr-0149000000-711f552084263e83749e2021-09-24Wishart LabView Spectrum
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 IDFDB002706
KNApSAcK IDC00020214
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751081
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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
6alpha-Hydroxyphaseollin → 3,4,5-trihydroxy-6-({1-hydroxy-6,6-dimethyl-5,12,20-trioxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁴,¹⁹]henicosa-2(11),3,7,9,14(19),15,17-heptaen-17-yl}oxy)oxane-2-carboxylic aciddetails