| Common Name |
Eupatilin
| Description |
Eupatilin is found in herbs and spices. Eupatilin is isolated from Tanacetum vligare (tansy) Eupatilin has been shown to exhibit apoptotic, anti-proliferative and anti-inflammatory functions (PMID 19565564 , 15313404 , 19663482 ).Eupatilin belongs to the family of Flavonols. These are compounds that has the 3-hydroxyflavone backbone.
| Structure |
MOLSDFPDBSMILESInChI
Structure for HMDB29469 (Eupatilin)
| Synonyms |
| Value |
Source |
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 Formlia |
C18H16O7
| Average Molecliar Weight |
344.3154
| Monoisotopic Molecliar Weight |
344.089602866
| IUPAC Name |
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one
| Traditional Name |
eupatilin
| CAS Registry Number |
22368-21-4
| 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 Key |
DRRWBCNQOKKKOL-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound 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.
| Kingdom |
Organic compounds
| Super Class |
Phenylpropanoids and polyketides
| Class |
Flavonoids
| Sub Class |
O-methylated flavonoids
| Direct Parent |
6-O-methylated flavonoids
| Alternative Parents |
4-O-methylated flavonoids
3-O-methylated flavonoids
Flavones
7-hydroxyflavonoids
5-hydroxyflavonoids
Chromones
Methoxyphenols
Dimethoxybenzenes
Resorcinols
Anisoles
Pyranones and derivatives
Alkyl aryl ethers
Vinylogous acids
Heteroaromatic compounds
Oxacyclic compounds
Hydrocarbon derivatives
| Substituents |
6-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
3p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
7-hydroxyflavonoid
5-hydroxyflavonoid
Chromone
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Methoxyphenol
Benzopyran
Methoxybenzene
Resorcinol
Phenol ether
Anisole
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
dihydroxyflavone (CHEBI:4932 )
trimethoxyflavone (CHEBI:4932 )
Flavones and Flavonols (C10040 )
flavones (C10040 )
Flavones and Flavonols (LMPK12111228 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
anti-inflammatory
anti-proliferative
apoptotic
| Application |
Nutrient
| Cellliar locations |
Membrane
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point241 – 242 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility0.042 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.32 m3·mol-1ChemAxon
Polarizability34.96 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-004i-0009000000-49ab4bc3de4a48b20802View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-004i-0009000000-49ab4bc3de4a48b20802View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-00dl-0190000000-38950da50de81e298c12View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-00dl-0190000000-38950da50de81e298c12View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-03di-0029000000-97a3b9b712001536c733View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-03di-0029000000-97a3b9b712001536c733View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-01ot-0093000000-e9d84a364e774239b476View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-01ot-0093000000-e9d84a364e774239b476View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-0006-0009000000-ed31e8ea447863ac91b0View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – , negativesplash10-0006-0009000000-ed31e8ea447863ac91b0View in MoNA
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
809
| FoodDB ID |
FDB000591
| KNApSAcK ID |
C00003845
| Chemspider ID |
4438134
| KEGG Compound ID |
C10040
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB29469
| Metagene Link |
HMDB29469
| METLIN ID |
Not Available
| PubChem Compound |
5273755
| PDB ID |
Not Available
| ChEBI ID |
Not Available
Product: CGP 25454A
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- 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 ]
- 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 ]
- 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 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 2905001
