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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:57:59 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034173
Secondary Accession Numbers
  • HMDB34173
Metabolite Identification
Common NamePhaseollin
DescriptionPhaseollin 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. Phaseollin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, phaseollin has been detected, but not quantified in, several different foods, such as cowpea, scarlet beans, pulses, soy beans, and green beans. This could make phaseollin a potential biomarker for the consumption of these foods. Phaseolin is a prenylated pterocarpan found in French bean (Phaseolus vulgaris) seeds and in the stems of Erythrina subumbrans.
Structure
Data?1563862522
Synonyms
ValueSource
(-)-PhaseollinHMDB
6b,12b-Dihydro-3,3-dimethyl-3H,7H-furo[3,2-c:5,4-F]bis[1]benzopyran-10-ol, 9ciHMDB
PhaseolinHMDB
Phaseolin fungicideHMDB
Chemical FormulaC20H18O4
Average Molecular Weight322.3545
Monoisotopic Molecular Weight322.120509064
IUPAC Name17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol
Traditional Name17,17-dimethyl-4,12,18-trioxapentacyclo[11.8.0.0²,¹¹.0⁵,¹⁰.0¹⁴,¹⁹]henicosa-1(13),5(10),6,8,14(19),15,20-heptaen-7-ol
CAS Registry Number13401-40-6
SMILES
CC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1
InChI Identifier
InChI=1S/C20H18O4/c1-20(2)8-7-14-16(24-20)6-5-12-15-10-22-17-9-11(21)3-4-13(17)19(15)23-18(12)14/h3-9,15,19,21H,10H2,1-2H3
InChI KeyLWTDZKXXJRRKDG-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
  • Benzofuran
  • Coumaran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point177 - 178 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.007 g/LALOGPS
logP4.14ALOGPS
logP3.57ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)9.42ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area47.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity90.99 m³·mol⁻¹ChemAxon
Polarizability34.66 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]+174.33231661259
DarkChem[M-H]-174.52331661259
DeepCCS[M+H]+181.79930932474
DeepCCS[M-H]-179.44130932474
DeepCCS[M-2H]-213.66230932474
DeepCCS[M+Na]+188.88930932474
AllCCS[M+H]+179.032859911
AllCCS[M+H-H2O]+175.532859911
AllCCS[M+NH4]+182.232859911
AllCCS[M+Na]+183.232859911
AllCCS[M-H]-184.032859911
AllCCS[M+Na-2H]-183.332859911
AllCCS[M+HCOO]-182.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PhaseollinCC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O13808.3Standard polar33892256
PhaseollinCC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O12754.2Standard non polar33892256
PhaseollinCC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O12964.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Phaseollin,1TMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OC2C4=CC=C(O[Si](C)(C)C)C=C4OCC32)O12822.4Semi standard non polar33892256
Phaseollin,1TBDMS,isomer #1CC1(C)C=CC2=C(C=CC3=C2OC2C4=CC=C(O[Si](C)(C)C(C)(C)C)C=C4OCC32)O13087.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phaseollin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pba-0986000000-ef26fd9f571cb19c6da72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaseollin GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-4659000000-30489c44cd92abec518c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaseollin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phaseollin 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 - Phaseollin 10V, Positive-QTOFsplash10-00di-1019000000-4bbab45d581bac2b73b02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 20V, Positive-QTOFsplash10-01b9-1095000000-dc691a3331d87151164d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 40V, Positive-QTOFsplash10-014i-7390000000-d3aa381d2d66b3ecd2402016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 10V, Negative-QTOFsplash10-00di-0009000000-eee8d60ede6b3ee25d062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 20V, Negative-QTOFsplash10-00di-0069000000-190ffcf697fb9f20069b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 40V, Negative-QTOFsplash10-000i-0190000000-a6a942d005a9696cc3be2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 10V, Negative-QTOFsplash10-00di-0009000000-a4f58630e05faac231a52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 20V, Negative-QTOFsplash10-00fr-0098000000-6433a047af8ecc8e05c12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 40V, Negative-QTOFsplash10-0a6r-1982000000-aef35370b06f5bbbb8e32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 10V, Positive-QTOFsplash10-00di-0009000000-17eb34705e2ef23f703b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 20V, Positive-QTOFsplash10-00di-0029000000-9d0ae020608ee5e985d12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phaseollin 40V, Positive-QTOFsplash10-0avj-0932000000-f87d4a45a8e512e4f2722021-09-24Wishart 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 IDFDB012460
KNApSAcK IDC00002559
Chemspider ID3279224
KEGG Compound IDC10514
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhaseolin (pterocarpan)
METLIN IDNot Available
PubChem Compound4063834
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.. .