Eupatilin (CHEM023189)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 20:53:36 UTC
Update Date2016-11-09 01:17:39 UTC
Accession NumberCHEM023189
Identification
Common NameEupatilin
ClassSmall Molecule
DescriptionA trimethoxyflavone that is flavone substituted by hydroxy groups at C-5 and C-7 and methoxy groups at C-6, C-3' and C-4' respectively. Isolated from Citrus reticulata and Salvia tomentosa, it exhibits anti-inflammatory, anti-ulcer and antineoplastic activities.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 Mass344.315 g/mol
Monoisotopic Mass344.090 g/mol
CAS Registry Number22368-21-4
IUPAC Name2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
Traditional Nameeupatilin
SMILESCOC1=CC=C(C=C1OC)C1=CC(=O)C2=C(O1)C=C(O)C(OC)=C2O
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
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0400-0419000000-70483b200afe60275b2eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1203900000-457b8f83215b0939194dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0bt9-0095000000-af0abacc4b61c8c1f999Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0009000000-49ab4bc3de4a48b20802Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-01ot-0093000000-e9d84a364e774239b476Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0009000000-ed31e8ea447863ac91b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0009000000-2dbf9806041cf0da0dd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0009000000-49ab4bc3de4a48b20802Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-01ot-0093000000-e9d84a364e774239b476Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0006-0009000000-ed31e8ea447863ac91b0Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-0029000000-97a3b9b712001536c733Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-00dl-0190000000-38950da50de81e298c12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-288d91e28ef5b4e11acbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0009000000-407969684b5581434127Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-067j-1692000000-e74a9b537956a2b7cc86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-fb75c7de6bd1ce8bba91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0049000000-acf62be5dec0cca78335Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00y0-1490000000-4147079baefcf841dfefSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029469
FooDB IDFDB000591
Phenol Explorer ID809
KNApSAcK IDC00003845
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEupatilin
Chemspider ID4438134
ChEBI ID4932
PubChem Compound ID5273755
Kegg Compound IDC10040
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17404061
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19663482
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23118554
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23292941
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=856983
6. 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.
7. 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.
8. 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.
9. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.