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Showing Compound Chrysosplenol (FDB005990)

Record Information
Version1.0
Creation date2010-04-08 22:06:56 UTC
Update date2019-11-26 03:00:54 UTC
Primary IDFDB005990
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChrysosplenol
DescriptionChrysosplenol, also known as quercetagetin 3,7,3'-trimethyl ether or 4',5,6-trihydroxy-3,3',7-trimethoxyflavone, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, chrysosplenol is considered to be a flavonoid lipid molecule. Chrysosplenol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Chrysosplenol can be found in german camomile, which makes chrysosplenol a potential biomarker for the consumption of this food product.
CAS Number23370-16-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4',5,6-Trihydroxy-3,3',7-trimethoxyflavoneChEBI
Quercetagetin 3,7,3'-trimethyl etherChEBI
3, 7, 3-O-trimethylquercetagetinbiospider
3,7,3'-tri-methylquercetagetinbiospider
Chrysosplenol Cbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.07 g/LALOGPS
logP2.9ALOGPS
logP2.26ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.44ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.56 m³·mol⁻¹ChemAxon
Polarizability35.61 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H16O8
IUPAC name5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C18H16O8/c1-23-10-6-8(4-5-9(10)19)17-18(25-3)16(22)13-11(26-17)7-12(24-2)14(20)15(13)21/h4-7,19-21H,1-3H3
InChI KeyQQBSPLCHDUCBNM-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=C(OC)C(=O)C2=C(O)C(O)=C(OC)C=C2O1
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
Classification
Description Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent7-O-methylated flavonoids
Alternative Parents
Substituents
  • 3p-methoxyflavonoid-skeleton
  • 3-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
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, Positivesplash10-03di-0009000000-5170e7840ad4ffef7fcd2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-535620010cfb75744da82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0rl0-0944000000-9d3700c202fea36fdbb72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-db4d16df96abc4c642d42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0119000000-15f3573902c1c49b4d062016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06ri-2984000000-c23ed70880e88757005d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-ef0e36da9abfe27aa0762021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-97d15839107665ea85c92021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02ai-2914000000-0c7f0d74550e6932a4072021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-f8e67485e1c0a329c3152021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0309000000-544d04d93dc0400e76d02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06e9-1912000000-3cec27af837a13ad4dcf2021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC10031
Pubchem Compound ID189065
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 IDCHRYSOSPLENOL
BIGG IDNot Available
KNApSAcK IDC00001031
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
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).