Record Information
Version1.0
Creation date2010-04-08 22:10:11 UTC
Update date2019-11-26 03:06:51 UTC
Primary IDFDB012460
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). Phaseollin has been detected, but not quantified in, several different foods, such as green beans, cowpea, yellow wax beans, scarlet beans, and common beans. This could make phaseollin a potential biomarker for the consumption of these foods.
CAS Number13401-40-6
Structure
Thumb
Synonyms
SynonymSource
(-)-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
6b,12b-Dihydro-3,3-dimethyl-3H,7H-furo[3,2-c:5,4-f]bis[1]benzopyran-10-ol, 9CIdb_source
Predicted 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
Chemical FormulaC20H18O4
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
InChI IdentifierInChI=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
Isomeric SMILESCC1(C)OC2=C(C=C1)C1=C(C=C2)C2COC3=C(C=CC(O)=C3)C2O1
Average Molecular Weight322.3545
Monoisotopic Molecular Weight322.120509064
Classification
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

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 74.52%; H 5.63%; O 19.85%DFC
Melting PointMp 177-178°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 9.13DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -145 (c, 0.17 in EtOH)DFC
Spectroscopic UV Data377 (e 2880) (EtOH/NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPhaseollin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0pba-0986000000-ef26fd9f571cb19c6da7Spectrum
Predicted GC-MSPhaseollin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fr-4659000000-30489c44cd92abec518cSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1019000000-4bbab45d581bac2b73b0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-1095000000-dc691a3331d87151164dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-7390000000-d3aa381d2d66b3ecd240Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-eee8d60ede6b3ee25d06Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0069000000-190ffcf697fb9f20069bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0190000000-a6a942d005a9696cc3beSpectrum
NMRNot Available
ChemSpider ID3279224
ChEMBL IDNot Available
KEGG Compound IDC10514
Pubchem Compound ID4063834
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34173
CRC / DFC (Dictionary of Food Compounds) IDHHB31-I:HHB31-I
EAFUS IDNot Available
Dr. Duke IDPHASEOLLIN|PHASEOLIN
BIGG IDNot Available
KNApSAcK IDC00002559
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti feedantDUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.