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Showing Compound 8-Methoxycirsilineol (FDB007325)

Record Information
Version1.0
Creation date2010-04-08 22:07:33 UTC
Update date2025-11-18 23:04:36 UTC
Primary IDFDB007325
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name8-Methoxycirsilineol
Description8-methoxycirsilineol, also known as 4',5-dihydroxy-3',6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, 8-methoxycirsilineol is considered to be a flavonoid lipid molecule. 8-methoxycirsilineol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 8-methoxycirsilineol can be found in common thyme and mandarin orange (clementine, tangerine), which makes 8-methoxycirsilineol a potential biomarker for the consumption of these food products.
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
4',5-Dihydroxy-3',6,7,8-tetramethoxyflavoneMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.049 g/LALOGPS
logP2.5ALOGPS
logP2.38ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.39ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area103.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity96.79 m³·mol⁻¹ChemAxon
Polarizability37.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC19H18O8
IUPAC name5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C19H18O8/c1-23-13-7-9(5-6-10(13)20)12-8-11(21)14-15(22)17(24-2)19(26-4)18(25-3)16(14)27-12/h5-8,20,22H,1-4H3
InChI KeyUBZBPKARIHPOEC-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1
Average Molecular Weight374.3414
Monoisotopic Molecular Weight374.100167552
Classification
Description Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 7-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 3p-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • Flavone
  • Hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Methoxyphenol
  • Methoxybenzene
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Pyranone
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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-MS
TypeDescriptionSplash KeyView
Predicted GC-MS8-Methoxycirsilineol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a4m-0119000000-4d729ed5b40be87c837eSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-88eeaa041c0341fda9222016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-1208521393a6520d9fe92016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0249000000-5cd254dd993868fece6e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-47561a80cd759f3faddb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0009000000-9748404246f3879610a12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-0194000000-cf977e9fd970b2a297f42016-08-03View Spectrum
NMRNot Available
ChemSpider ID157560
ChEMBL IDCHEMBL74272
KEGG Compound IDNot Available
Pubchem Compound ID181092
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 ID8-METHOXY-CIRSILINEOL
BIGG IDNot Available
KNApSAcK IDNot Available
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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.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).