4-(gamma,gamma-Dimethylallyl)-phaseollidin (CHEM026518)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:02:03 UTC
Update Date2016-11-09 01:18:17 UTC
Accession NumberCHEM026518
Identification
Common Name4-(gamma,gamma-Dimethylallyl)-phaseollidin
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC25H28O4
Average Molecular Mass392.487 g/mol
Monoisotopic Mass392.199 g/mol
CAS Registry NumberNot Available
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
Traditional 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
SMILES[H][C@@]12COC3=C(CC=C(C)C)C(O)=CC=C3[C@]1([H])OC1=C2C=CC(O)=C1CC=C(C)C
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
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
  • 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0609000000-7f6eafcd3573353ef49dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004r-2629000000-98dd261731516b0f2592Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07vi-5910000000-4ba38f879f50af3d25efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-3fb281e63bf5492ae991Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0029000000-48e4c09ac77b7e4de95eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kvn-1963000000-d7f643af91d736e8c748Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0016-0039000000-3c32789b9567d481bf51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00nr-0096000000-19af337f8f533e3a9b5dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-2595000000-0333e8b9250587d11d09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-fc8307e58aa68e585da3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-8582e15307abd8d12928Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-0339000000-220bba4e20a04cb1b171Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0303158
FooDB IDFDB008012
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID20006335
ChEBI ID65862
PubChem Compound ID21141346
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15597305
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17055201
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18087807
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=20521535
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=8590641