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Showing Compound Axillarin (FDB002414)

Record Information
Version1.0
Creation date2010-04-08 22:05:22 UTC
Update date2020-02-24 19:11:07 UTC
Primary IDFDB002414
Secondary Accession Numbers
  • FDB005976
Chemical Information
FooDB NameAxillarin
Description2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one, also known as 3',4',5,7-tetrahydroxy-3,6-dimethoxyflavone or 3,6-dimethoxyquercetagetin, is a member of the class of compounds known as 6-o-methylated flavonoids. 6-o-methylated flavonoids are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one can be found in german camomile, which makes 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4h-chromen-4-one a potential biomarker for the consumption of this food product.
CAS Number5188-73-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3',4',5,7-Tetrahydroxy-3,6-dimethoxyflavoneChEBI
3,6-DimethoxyquercetagetinChEBI
Quercetagetin 3,6-dimethyl etherChEBI
DMQTMeSH
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4H-1-benzopyran-4-one, 9CIdb_source
Axillarindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.66ALOGPS
logP2.11ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.9ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.08 m³·mol⁻¹ChemAxon
Polarizability33.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC17H14O8
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,6-dimethoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C17H14O8/c1-23-16-10(20)6-11-12(13(16)21)14(22)17(24-2)15(25-11)7-3-4-8(18)9(19)5-7/h3-6,18-21H,1-2H3
InChI KeyKIGVXRGRNLQNNI-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C2=C(OC(=C(OC)C2=O)C2=CC(O)=C(O)C=C2)C=C1O
Average Molecular Weight346.2883
Monoisotopic Molecular Weight346.068867424
Classification
Description Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent6-O-methylated flavonoids
Alternative Parents
Substituents
  • 3-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 7-hydroxyflavonoid
  • 3'-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 58.96%; H 4.07%; O 36.96%DFC
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 Data369 (e 17800) (EtOH/NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAxillarin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-044j-1143195000-ef6e852b0fb445b85f27Spectrum
Predicted GC-MSAxillarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-0439000000-ac8c8e40c24b0ad21627Spectrum
Predicted GC-MSAxillarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-931bc81dc6845ae8bdb02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0109000000-ea22d6d990c5fcd681572016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-4922000000-60666c5d32df8f444ba72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-7ba67991d6c4bb1b57fc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0029000000-fb517d3332ab3b037f6c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-4941000000-fce546a0c270c82fc38f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-ec61fcb5ea3f5c984d692021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0419000000-37136757256ca6a2b4242021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01c0-1921000000-2ac43aecd3dfed3082e02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-24b80c82c41a998b9ea52021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-6bb94117a9648af67e8c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ls-1914000000-844cac53e0c6a48fb19b2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDCLR22-H:CLR22-H
EAFUS IDNot Available
Dr. Duke IDAXILLARIN
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 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 rhinoviral22587 A substance that destroys or inhibits replication of viruses.DUKE
anti viral22587 A substance that destroys or inhibits replication of viruses.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.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).