Record Information
Version1.0
Creation date2010-04-08 22:10:05 UTC
Update date2019-11-26 03:06:32 UTC
Primary IDFDB012291
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-4',5,7-Trihydroxy-8-prenylflavanone
Description(s)-4',5,7-trihydroxy-8-prenylflavanone is a member of the class of compounds known as 8-prenylated flavanones. 8-prenylated flavanones are flavanones that features a C5-isoprenoid substituent at the 8-position. Thus, (s)-4',5,7-trihydroxy-8-prenylflavanone is considered to be a flavonoid lipid molecule (s)-4',5,7-trihydroxy-8-prenylflavanone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (s)-4',5,7-trihydroxy-8-prenylflavanone can be found in beer, which makes (s)-4',5,7-trihydroxy-8-prenylflavanone a potential biomarker for the consumption of this food product.
CAS Number53846-50-7
Structure
Thumb
Synonyms
SynonymSource
Sophoraflavanone Bbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.015 g/LALOGPS
logP3.23ALOGPS
logP4.56ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)7.69ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.53 m³·mol⁻¹ChemAxon
Polarizability36.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H20O5
IUPAC name5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
InChI IdentifierInChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3
InChI KeyLPEPZZAVFJPLNZ-UHFFFAOYSA-N
Isomeric SMILESCC(C)=CCC1=C2OC(CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1
Average Molecular Weight340.375
Monoisotopic Molecular Weight340.131073744
Classification
Description belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct Parent8-prenylated flavanones
Alternative Parents
Substituents
  • 8-prenylated flavanone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 CompositionC 70.58%; H 5.92%; O 23.50%DFC
Melting PointMp 202-204° (195.5-196°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]22D -25 (c, 0.1 in EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-7589000000-886e0b6df480ecaba958JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0249000000-fbed0c40cf3c13b84733JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0603-2593000000-f1a2c0c2007bf89e2ab5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-4911000000-726f9f81100de40c4037JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0109000000-6d859e5b3387eac061c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1559000000-b662b86e3b7e05a8b1fbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bf-2910000000-1d038b393b58014f3a01JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID221
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDKRN34-S:HFR46-E
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00008245
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 / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
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.