Record Information
Version1.0
Creation date2010-04-08 22:12:36 UTC
Update date2019-11-26 03:13:40 UTC
Primary IDFDB016712
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameXanthomicrol
DescriptionXanthomicrol 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, xanthomicrol is considered to be a flavonoid lipid molecule. Xanthomicrol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Xanthomicrol is found, on average, in the highest concentration within sweet basils. Xanthomicrol has also been detected, but not quantified in, several different foods, such as citrus, herbs and spices, peppermints, and winter savories. This could make xanthomicrol a potential biomarker for the consumption of these foods.
CAS Number16545-23-6
Structure
Thumb
Synonyms
SynonymSource
4',5-Dihydroxy-6,7,8-trimethoxyflavoneChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-oneHMDB
Xanthomicroldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.89ALOGPS
logP2.54ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)8.67ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area94.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability34.64 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H16O7
IUPAC name5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C18H16O7/c1-22-16-14(21)13-11(20)8-12(9-4-6-10(19)7-5-9)25-15(13)17(23-2)18(16)24-3/h4-8,19,21H,1-3H3
InChI KeySAMBWAJRKKEEOR-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(OC)C(OC)=C2OC(=CC(=O)C2=C1O)C1=CC=C(O)C=C1
Average Molecular Weight344.3154
Monoisotopic Molecular Weight344.089602866
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
  • 8-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 62.79%; H 4.68%; O 32.53%DFC
Melting PointMp 227-230°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data402 (e 32500) (MeOH-NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSXanthomicrol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-02vi-0119000000-0c0e3709b7f79d4ca206Spectrum
Predicted GC-MSXanthomicrol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-1111900000-21e3d411a6a5821413b0Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-444df5d8e4a6a98b29e2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-17bd95784ea2af1d207bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mk-2393000000-dde4b83302a1581e7635Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7123f771ed6080c1a185Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0019000000-7d461a8e7316b5241de2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05r4-1491000000-f7bf40ad7c31df0b7feaSpectrum
NMRNot Available
ChemSpider ID65965
ChEMBL IDCHEMBL476121
KEGG Compound IDC14476
Pubchem Compound ID73207
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37600
CRC / DFC (Dictionary of Food Compounds) IDCNL42-X:KSN57-I
EAFUS IDNot Available
Dr. Duke IDXANTHOMICROL| 4'5-DIHYDROXY-6,7,8-TRIMETHOXYFLAVONE
BIGG IDNot Available
KNApSAcK IDC00003879
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 neoplastic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.