Record Information
Version1.0
Creation date2010-04-08 22:04:38 UTC
Update date2020-02-24 19:10:10 UTC
Primary IDFDB000591
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEupatilin
DescriptionEupatilin 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. Thus, eupatilin is considered to be a flavonoid. Eupatilin has been detected, but not quantified in, herbs and spices and mandarin orange (clementine, tangerine). This could make eupatilin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Eupatilin.
CAS Number22368-21-4
Structure
Thumb
Synonyms
SynonymSource
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-oneChEBI
5,7-Dihydroxy-3',4',6-trimethoxyflavoneChEBI
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one, 9ciHMDB
EuptailinHMDB
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one, 9CIdb_source
Eupatilindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP2.89ALOGPS
logP2.54ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)7.15ChemAxon
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
Polarizability34.96 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H16O7
IUPAC name2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C18H16O7/c1-22-12-5-4-9(6-14(12)23-2)13-7-10(19)16-15(25-13)8-11(20)18(24-3)17(16)21/h4-8,20-21H,1-3H3
InChI KeyDRRWBCNQOKKKOL-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C=C(O)C(OC)=C2O
Average Molecular Weight344.3154
Monoisotopic Molecular Weight344.089602866
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
  • 3p-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

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 241-242° (234-236°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data340 (e 26300) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEupatilin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0400-0419000000-70483b200afe60275b2eSpectrum
Predicted GC-MSEupatilin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-1203900000-457b8f83215b0939194dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0bt9-0095000000-af0abacc4b61c8c1f999Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd2Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-49ab4bc3de4a48b20802Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01ot-0093000000-e9d84a364e774239b476Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0009000000-ed31e8ea447863ac91b0Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd2Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-49ab4bc3de4a48b20802Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-01ot-0093000000-e9d84a364e774239b476Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0009000000-ed31e8ea447863ac91b0Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-288d91e28ef5b4e11acbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-407969684b5581434127Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-1692000000-e74a9b537956a2b7cc86Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-fb75c7de6bd1ce8bba91Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0049000000-acf62be5dec0cca78335Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-1490000000-4147079baefcf841dfefSpectrum
NMRNot Available
ChemSpider ID4438134
ChEMBL IDCHEMBL312750
KEGG Compound IDC10040
Pubchem Compound ID5273755
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID809
DrugBank IDNot Available
HMDB IDHMDB29469
CRC / DFC (Dictionary of Food Compounds) IDBDZ27-L:BDZ27-L
EAFUS IDNot Available
Dr. Duke IDEUPATILIN
BIGG IDNot Available
KNApSAcK IDC00003845
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
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.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.