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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:10:51 UTC
Update Date2022-03-07 02:55:34 UTC
HMDB IDHMDB0037922
Secondary Accession Numbers
  • HMDB37922
Metabolite Identification
Common NamePhaseol
DescriptionPhaseol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, phaseol is considered to be a flavonoid. Phaseol has been detected, but not quantified in, pulses and soy beans (Glycine max). This could make phaseol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Phaseol.
Structure
Data?1563863109
Synonyms
ValueSource
3,9-Dihydroxy-4-(3-methyl-2-butenyl)-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ciHMDB
3,9-Dihydroxy-4-prenylcoumestanHMDB
Phaseollidin hydrateHMDB
Chemical FormulaC20H16O5
Average Molecular Weight336.338
Monoisotopic Molecular Weight336.099773622
IUPAC Name5,14-dihydroxy-6-(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-9-one
Traditional Namephaseol
CAS Registry Number88478-02-8
SMILES
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C2
InChI Identifier
InChI=1S/C20H16O5/c1-10(2)3-5-12-15(22)8-7-14-18(12)25-20(23)17-13-6-4-11(21)9-16(13)24-19(14)17/h3-4,6-9,21-22H,5H2,1-2H3
InChI KeyFRXPSBUCIWPZMH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.98 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.068 g/LALOGPS
logP4.59ALOGPS
logP4.13ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)6.92ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.86 m³·mol⁻¹ChemAxon
Polarizability35.99 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]+182.17431661259
DarkChem[M-H]-177.47731661259
DeepCCS[M+H]+178.79630932474
DeepCCS[M-H]-176.43830932474
DeepCCS[M-2H]-210.34730932474
DeepCCS[M+Na]+185.57530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhaseolCC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C24426.3Standard polar33892256
PhaseolCC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C23185.5Standard non polar33892256
PhaseolCC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=C1C=CC(O)=C23384.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phaseol,1TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O)=CC=C213334.8Semi standard non polar33892256
Phaseol,1TMS,isomer #2CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C213376.7Semi standard non polar33892256
Phaseol,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C213362.6Semi standard non polar33892256
Phaseol,1TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O)=CC=C213546.8Semi standard non polar33892256
Phaseol,1TBDMS,isomer #2CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C213573.7Semi standard non polar33892256
Phaseol,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C213815.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phaseol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6u-4639000000-80b890faae18353528b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaseol GC-MS (2 TMS) - 70eV, Positivesplash10-06di-2021900000-3e59be6bbcc6090afaee2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaseol 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 - Phaseol 10V, Positive-QTOFsplash10-000i-0029000000-1b21ebd042fe669903352016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 20V, Positive-QTOFsplash10-00li-4097000000-35d782407e35cb768a502016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 40V, Positive-QTOFsplash10-014i-9260000000-27ea8869c3ebf9c3c0a12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 10V, Negative-QTOFsplash10-000i-0029000000-28986ccf750fc3fb6f102016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 20V, Negative-QTOFsplash10-000i-0059000000-e7b1828b4645bc1745a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 40V, Negative-QTOFsplash10-05gl-3691000000-7607411fdffd4e8e40dd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 10V, Negative-QTOFsplash10-000i-0009000000-dc81427ba733f47873d12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 20V, Negative-QTOFsplash10-000i-0029000000-3414aa7d4567ef62cdec2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 40V, Negative-QTOFsplash10-014l-1190000000-15d4a88f14d0d9d294cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 10V, Positive-QTOFsplash10-0019-0049000000-ed20812eeada82c0cb682021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 20V, Positive-QTOFsplash10-001i-0090000000-30908eb5a1e79c21ebed2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseol 40V, Positive-QTOFsplash10-004i-0090000000-1053c919d8eb7822a5722021-09-25Wishart 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 IDFDB017079
KNApSAcK IDC00010051
Chemspider ID24843105
KEGG Compound IDC05229
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257530
PDB IDNot Available
ChEBI ID17465
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1864231
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.. .