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Showing Compound Eupatilin (FDB000591)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
Physico-Chemical Properties - Experimental
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
Predicted GC-MSEupatilin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSEupatilin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0bt9-0095000000-af0abacc4b61c8c1f9992017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c122017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-49ab4bc3de4a48b208022017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c122017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01ot-0093000000-e9d84a364e774239b4762017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0009000000-ed31e8ea447863ac91b02017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd22017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-49ab4bc3de4a48b208022017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00dl-0190000000-38950da50de81e298c122017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0029000000-97a3b9b712001536c7332017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-01ot-0093000000-e9d84a364e774239b4762017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0009000000-ed31e8ea447863ac91b02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0029000000-97a3b9b712001536c7332021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00dl-0190000000-38950da50de81e298c122021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-288d91e28ef5b4e11acb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-407969684b55814341272016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-1692000000-e74a9b537956a2b7cc862016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-fb75c7de6bd1ce8bba912016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0049000000-acf62be5dec0cca783352016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-1490000000-4147079baefcf841dfef2016-08-03View Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
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.