Record Information
Creation date2010-04-08 22:04:27 UTC
Update date2018-01-25 19:27:11 UTC
Primary IDFDB000133
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6-Geranylnaringenin
Description6-geranylnaringenin is a member of the class of compounds known as 6-prenylated flavanones. 6-prenylated flavanones are flavanones that features a C5-isoprenoid substituent at the 6-position. 6-geranylnaringenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 6-geranylnaringenin can be found in beer, which makes 6-geranylnaringenin a potential biomarker for the consumption of this food product.
CAS Number475207-59-1
Bonannione Adb_source
Predicted Properties
Water Solubility0.0034 g/LALOGPS
pKa (Strongest Acidic)7.73ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity119.34 m³·mol⁻¹ChemAxon
Polarizability44.6 ųChemAxon
Number of Rings3ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC25H28O5
IUPAC name(2S)-6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C25H28O5/c1-15(2)5-4-6-16(3)7-12-19-20(27)13-23-24(25(19)29)21(28)14-22(30-23)17-8-10-18(26)11-9-17/h5,7-11,13,22,26-27,29H,4,6,12,14H2,1-3H3/b16-7+/t22-/m0/s1
Isomeric SMILESCC(C)=CCC\C(C)=C\CC1=C(O)C=C2O[C@@H](CC(=O)C2=C1O)C1=CC=C(O)C=C1
Average Molecular Weight408.4868
Monoisotopic Molecular Weight408.193674006
DescriptionThis compound belongs to the class of organic compounds known as 6-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 6-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
Sub ClassFlavans
Direct Parent6-prenylated flavanones
Alternative Parents
  • 6-prenylated flavanone
  • Hydroxyflavonoid
  • Flavanone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Monoterpenoid
  • Bicyclic monoterpenoid
  • Benzopyran
  • Chromane
  • Aromatic monoterpenoid
  • Aryl alkyl ketone
  • Aryl ketone
  • Resorcinol
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0445900000-37ac1c951ae61d0e3fd5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05g0-2962100000-7fbaa2b4937372691e19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-6931000000-c1efd40b89535da80e30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0010900000-ee94c926d5ba482906b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1192700000-a7b5f928959b48502fc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4972000000-f24f024810202252f7e8View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5716903
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID223
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00008273
HET 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
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.