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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:30:35 UTC
Update Date2020-02-26 21:43:42 UTC
HMDB IDHMDB0029469
Secondary Accession Numbers
  • HMDB29469
Metabolite Identification
Common 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. Eupatilin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Eupatilin.
Structure
Data?1582753422
Synonyms
ValueSource
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
Chemical FormulaC18H16O7
Average Molecular Weight344.3154
Monoisotopic Molecular Weight344.089602866
IUPAC Name2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
Traditional Nameeupatilin
CAS Registry Number22368-21-4
SMILES
COC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C=C(O)C(OC)=C2O
InChI Identifier
InChI=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
Chemical Taxonomy
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:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point241 - 242 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Eupatilin,1TMS,#13333.6812https://arxiv.org/abs/1905.12712
Eupatilin,1TMS,#23305.642https://arxiv.org/abs/1905.12712
Eupatilin,2TMS,#13242.2583https://arxiv.org/abs/1905.12712
Eupatilin,1TBDMS,#13560.5461https://arxiv.org/abs/1905.12712
Eupatilin,1TBDMS,#23554.8904https://arxiv.org/abs/1905.12712
Eupatilin,2TBDMS,#13727.595https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0400-0419000000-70483b200afe60275b2e2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1203900000-457b8f83215b0939194d2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0bt9-0095000000-af0abacc4b61c8c1f9992017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c122017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd22017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-49ab4bc3de4a48b208022017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c122017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c7332017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01ot-0093000000-e9d84a364e774239b4762017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0009000000-ed31e8ea447863ac91b02017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd22017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-49ab4bc3de4a48b208022017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00dl-0190000000-38950da50de81e298c122017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0029000000-97a3b9b712001536c7332017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-01ot-0093000000-e9d84a364e774239b4762017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0009000000-ed31e8ea447863ac91b02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0029000000-97a3b9b712001536c7332021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00dl-0190000000-38950da50de81e298c122021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-288d91e28ef5b4e11acb2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-407969684b55814341272016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-1692000000-e74a9b537956a2b7cc862016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-fb75c7de6bd1ce8bba912016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0049000000-acf62be5dec0cca783352016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-1490000000-4147079baefcf841dfef2016-08-03View Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID809
FooDB IDFDB000591
KNApSAcK IDC00003845
Chemspider ID4438134
KEGG Compound IDC10040
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEupatilin
METLIN IDNot Available
PubChem Compound5273755
PDB IDNot Available
ChEBI ID4932
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kim YD, Choi SC, Oh TY, Chun JS, Jun CD: Eupatilin inhibits T-cell activation by modulation of intracellular calcium flux and NF-kappaB and NF-AT activity. J Cell Biochem. 2009 Sep 1;108(1):225-36. doi: 10.1002/jcb.22244. [PubMed:19565564 ]
  2. Kim DH, Na HK, Oh TY, Kim WB, Surh YJ: Eupatilin, a pharmacologically active flavone derived from Artemisia plants, induces cell cycle arrest in ras-transformed human mammary epithelial cells. Biochem Pharmacol. 2004 Sep 15;68(6):1081-7. [PubMed:15313404 ]
  3. Giangaspero A, Ponti C, Pollastro F, Del Favero G, Della Loggia R, Tubaro A, Appendino G, Sosa S: Topical anti-inflammatory activity of Eupatilin, a lipophilic flavonoid from mountain wormwood ( Artemisia umbelliformis Lam.). J Agric Food Chem. 2009 Sep 9;57(17):7726-30. doi: 10.1021/jf901725p. [PubMed:19663482 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .