Survey with prize
Record Information
Version1.0
Creation date2010-04-08 22:07:53 UTC
Update date2019-11-26 03:01:56 UTC
Primary IDFDB008012
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-(gamma,gamma-Dimethylallyl)-phaseollidin
Description4-(gamma,gamma-dimethylallyl)-phaseollidin, also known as 4-prenylphaseollidin, is a member of the class of compounds known as pterocarpans. Pterocarpans are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. 4-(gamma,gamma-dimethylallyl)-phaseollidin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 4-(gamma,gamma-dimethylallyl)-phaseollidin can be found in lima bean, which makes 4-(gamma,gamma-dimethylallyl)-phaseollidin a potential biomarker for the consumption of this food product.
CAS Number119269-76-0
Structure
Thumb
Synonyms
SynonymSource
(6AR,11ar-cis)-6a,11a-dihydro-4,10-bis(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-3,9-diolChEBI
4-PrenylphaseollidinChEBI
4-(g,g-Dimethylallyl)-phaseollidinGenerator
4-(Γ,γ-dimethylallyl)-phaseollidinGenerator
4-(GAMMA,GAMMA-DIMETHYLALLYL)PHASEOLLIDINdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.0029 g/LALOGPS
logP5.24ALOGPS
logP5.82ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)8.99ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity117.06 m³·mol⁻¹ChemAxon
Polarizability43.68 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H28O4
IUPAC name(1R,10R)-6,15-bis(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaene-5,14-diol
InChI IdentifierInChI=1S/C25H28O4/c1-14(2)5-7-17-21(26)12-10-19-23(17)28-13-20-16-9-11-22(27)18(8-6-15(3)4)24(16)29-25(19)20/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25-/m0/s1
InChI KeyHOGHBEDTLGAJAS-CPJSRVTESA-N
Isomeric SMILES[H][C@@]12COC3=C(CC=C(C)C)C(O)=CC=C3[C@]1([H])OC1=C2C=CC(O)=C1CC=C(C)C
Average Molecular Weight392.4874
Monoisotopic Molecular Weight392.198759384
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
  • 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0609000000-7f6eafcd3573353ef49dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-2629000000-98dd261731516b0f2592JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vi-5910000000-4ba38f879f50af3d25efJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-3fb281e63bf5492ae991JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0029000000-48e4c09ac77b7e4de95eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kvn-1963000000-d7f643af91d736e8c748JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID4-(GAMMA,GAMMA-DIMETHYLALLYL)PHASEOLLIDIN
BIGG IDNot Available
KNApSAcK IDNot Available
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
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
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Hitoshi Tanaka, Toshihiro Tanaka, Hideo Etoh, Three pterocarpans from Erythrina crista-galli, Phytochemistry, Vol. 45, No. 4, pp. 835-838, 1997 [No PubMed ID] DOI [Isolation of a similar compound]
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).