Record Information
Version1.0
Creation date2010-04-08 22:13:15 UTC
Update date2019-11-26 03:15:03 UTC
Primary IDFDB017693
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSideritiflavone
DescriptionSideritiflavone 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. Thus, sideritiflavone is considered to be a flavonoid lipid molecule. Sideritiflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sideritiflavone has been detected, but not quantified in, a few different foods, such as herbs and spices, peppermints, and spearmints. This could make sideritiflavone a potential biomarker for the consumption of these foods.
CAS Number70360-12-2
Structure
Thumb
Synonyms
SynonymSource
2-(3,4-Dihydroxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-1-benzopyran-4-oneHMDB
3',4',5-Trihydroxy-6,7,8-trimethoxyflavoneHMDB
5,3',4'-Trihydroxy-6,7,8-trimethoxyflavoneHMDB
SideritoflavoneHMDB
Sideritiflavonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.067 g/LALOGPS
logP2.65ALOGPS
logP2.23ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)8.66ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.3 m³·mol⁻¹ChemAxon
Polarizability35.59 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H16O8
IUPAC name2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C18H16O8/c1-23-16-14(22)13-11(21)7-12(8-4-5-9(19)10(20)6-8)26-15(13)17(24-2)18(16)25-3/h4-7,19-20,22H,1-3H3
InChI KeyUWNUJPINKMRKKR-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC(O)=C(O)C=C1
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
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
  • 6-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • Phenol
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 60.00%; H 4.48%; O 35.52%DFC
Melting PointMp 197-198°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data348 (e 77624) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSSideritiflavone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-0119000000-d661f929d6e7c6e1e2a6Spectrum
Predicted GC-MSSideritiflavone, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-1030190000-da25a150ef664eff6f06Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-341009b391d78207b8afSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-0f73369acc39d5f93764Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0cfr-2977000000-3274aff2824af897c04aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-9bdb314df607331460dcSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-0019000000-4a242a4a1e57df1b5552Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9271000000-f83431b833cacf2df46eSpectrum
NMRNot Available
ChemSpider ID136978
ChEMBL IDCHEMBL312790
KEGG Compound IDNot Available
Pubchem Compound ID155493
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB38356
CRC / DFC (Dictionary of Food Compounds) IDHBZ77-A:KZB66-Z
EAFUS IDNot Available
Dr. Duke IDSIDERITOFLAVONE
BIGG IDNot Available
KNApSAcK IDC00003927
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 arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cataract52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.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— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).