Record Information
Version1.0
Creation date2010-04-08 22:05:02 UTC
Update date2019-11-26 02:56:36 UTC
Primary IDFDB001601
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthoangelol
DescriptionXanthoangelol is a member of the class of compounds known as 3-prenylated chalcones. 3-prenylated chalcones are chalcones featuring a C5-isoprenoid unit at the 3-position. Thus, xanthoangelol is considered to be a flavonoid lipid molecule. Xanthoangelol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Xanthoangelol can be found in angelica, which makes xanthoangelol a potential biomarker for the consumption of this food product.
CAS Number62949-76-2
Structure
Thumb
Synonyms
SynonymSource
2',4,4'-Trihydroxy-3'-geranylchalconebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP5.29ALOGPS
logP7.02ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)7.57ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity120.87 m³·mol⁻¹ChemAxon
Polarizability44.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC25H28O4
IUPAC name(2E)-1-{3-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-2,4-dihydroxyphenyl}-3-(4-hydroxyphenyl)prop-2-en-1-one
InChI IdentifierInChI=1S/C25H28O4/c1-17(2)5-4-6-18(3)7-13-21-24(28)16-14-22(25(21)29)23(27)15-10-19-8-11-20(26)12-9-19/h5,7-12,14-16,26,28-29H,4,6,13H2,1-3H3/b15-10+,18-7+
InChI KeyLRSMBOSQWGHYCW-MDGZPELGSA-N
Isomeric SMILESCC(C)=CCC\C(C)=C\CC1=C(O)C(=CC=C1O)C(=O)\C=C\C1=CC=C(O)C=C1
Average Molecular Weight392.4874
Monoisotopic Molecular Weight392.198759384
Classification
Description Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent3-prenylated chalcones
Alternative Parents
Substituents
  • 3-prenylated chalcone
  • 2'-hydroxychalcone
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Aromatic monoterpenoid
  • Monocyclic monoterpenoid
  • Monoterpenoid
  • Benzoyl
  • Resorcinol
  • Styrene
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Enone
  • Acryloyl-group
  • Vinylogous acid
  • Alpha,beta-unsaturated ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0339000000-3eb277919860d2e4fdd1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0601-2952000000-73df19743994a0fa369cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-5900000000-e4cb5e04418a1afb6bd7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0119000000-290ed3def616d39463baSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-0559000000-c0809608b20870522a57Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-069a-1972000000-7769308132ae9fcc9110Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID643007
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 IDNot Available
BIGG IDNot Available
KNApSAcK IDC00007124
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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.