NP-MRD: Showing NP-Card for Eupatilin (NP0045377)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:54 UTC

Updated at

2024-09-03 04:15:35 UTC

NP-MRD ID

NP0045377

Natural Product DOI

https://doi.org/10.57994/0321

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eupatilin

Description

Eupatilin 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 lipid molecule. Eupatilin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 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 found in Achillea setacea, Ageratina calophylla, Artemisia argyi, Artemisia austriaca, Artemisia dubia, Artemisia fragrans, Artemisia frigida, Artemisia giraldii, Artemisia judaica, Artemisia leucodes, Artemisia ludoviciana, Artemisia ludoviciana var. mexicana, Artemisia mongolica, Artemisia monosperma, Artemisia nitida, Artemisia oliveriana, Artemisia porrecta, Artemisia princeps, Artemisia roxburghiana, Artemisia rubripes, Artemisia umbelliformis, Artemisia verlotiorum, Artemisia vulgaris , Baccharis gaudichaudiana, Baccharis gaudichaudiana DC, Centaurea arenaria, Centaurea cineraria, Centaurea cuneifolia, Centaurea sulphurea, Centaurea tougourensis, Chromolaena odorata, Chrysanthemum indicum , Eriocephalus punctulatus, Eupatorium capillifolium, Eupatorium semiserratum, Layia hieracioides, Monoclea gottschei, Ononis vaginalis, Inula britannica , Phyla dulcis, Psilostrophe cooperi, Salvia cardiophylla, Salvia limbata, Salvia palaestina, Salvia sclarea , Salvia tomentosa, Salvia sylvestris, Sideritis gomeraea, Sideritis tomentosa, Tanacetum polycephalum, Tanacetum vulgare , Teucrium divaricatum, Veratrum dahuricum, Veronica officinalis , Veronica orchidea and Veronica teucrium. Eupatilin was first documented in 2004 (PMID: 15313404). Isolated from Citrus reticulata and Salvia tomentosa, it exhibits anti-inflammatory, anti-ulcer and antineoplastic activities (PMID: 17404061) (PMID: 19663482) (PMID: 23118554) (PMID: 23292941) (PMID: 19565564).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -5.9943    0.2846    2.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5708    0.3009    1.4728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2470    0.1982    1.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2658    0.0709    2.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9593   -0.0285    1.5506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6639    0.0007    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2518   -0.1102   -0.2169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488   -0.0923   -1.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975   -0.1997   -1.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.1833   -3.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3969   -0.3230   -0.8593 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7495   -0.4314   -1.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1536   -0.4135   -2.5190 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6858   -0.5571   -0.1922 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0364   -0.6665   -0.4977 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8170    0.4917   -0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665   -0.5736    1.1348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2362   -0.7009    2.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9250   -0.4644    1.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599   -0.3374    0.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6839   -0.2325    0.7043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6880    0.1305   -0.7182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0180    0.2332   -0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0472    0.3637   -1.2082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8811    0.4053   -2.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3858   -0.3159    3.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0476    1.3200    3.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0316   -0.1526    2.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4220    0.0418    3.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1351   -0.1313    2.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5794    0.0059   -2.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1270   -0.4929   -2.7261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3260    1.3767   -0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9843    0.6770   -1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8442    0.3523   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0493   -0.7248    3.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6225   -0.4793    2.4546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4993    0.1566   -1.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7612    1.4421   -2.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0884   -0.2624   -2.9783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8363    0.0212   -3.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 20  2  0
 20 21  1  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14 12  2  0
 12 13  1  0
 23  3  1  0
 21  7  1  0
 12 11  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
 22 38  1  0
 25 39  1  0
 25 40  1  0
 25 41  1  0
  8 31  1  0
 19 37  1  0
 18 36  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 13 32  1  0
M  END

  Mrv0541 02241219372D          

 25 27  0  0  0  0            999 V2000
    0.7008    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0408    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4433   -2.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1033   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457   -1.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5882   -1.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5882    2.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457    2.4745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    2.4745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    2.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7008    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457    0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8457    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  2 21  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045377

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.3154

> <EXACT_MASS>
344.089602866

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
34.96485549698378

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.5372406583333333

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.82888411144905

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.15491096709655

> <JCHEM_PKA_STRONGEST_BASIC>
-4.317512637276356

> <JCHEM_POLAR_SURFACE_AREA>
94.45000000000002

> <JCHEM_REFRACTIVITY>
90.3226

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
eupatilin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.308   2.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.076   1.539   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.076   0.001   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.926   2.309   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.694   1.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.694   0.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.308  -0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.308  -2.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.694  -3.079   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.694  -4.619   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.312   0.001   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.926  -0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.926  -2.309   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.312  -3.079   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.698  -2.463   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.698   4.003   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.312   4.619   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -4.080   3.849   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.694   4.619   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.308   3.849   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.308   2.309   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.694   1.539   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.080   2.309   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.312   1.539   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.312   0.001   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3   21                                                  
CONECT    3    2    7                                                       
CONECT    4    5                                                            
CONECT    5    1    4    6                                                  
CONECT    6    5    7   12                                                  
CONECT    7    3    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9                                                            
CONECT   11   12                                                            
CONECT   12    6   11   13                                                  
CONECT   13    9   12   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   17                                                            
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21    2   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23   18   22   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one	ChEBI
5,7-Dihydroxy-3',4',6-trimethoxyflavone	ChEBI
2-(3,4-Dimethoxyphenyl)-5,7-dihydroxy-6-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
Euptailin	HMDB

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3154 Da

Monoisotopic Mass

344.08960 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C2D6OS, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 500 MHz, C2D6OS, experimental)	eliane.garo@unibas.ch	Not Available	Not Available	2022-12-23	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea setacea	LOTUS Database	35616633
Ageratina calophylla	LOTUS Database	35616633
Artemisia argyi	LOTUS Database	35616633
Artemisia austriaca	LOTUS Database	35616633
Artemisia dubia	LOTUS Database	35616633
Artemisia fragrans	LOTUS Database	35616633
Artemisia frigida	LOTUS Database	35616633
Artemisia giraldii	Plant	KNApSAcK
Artemisia judaica	LOTUS Database	35616633
Artemisia leucodes	LOTUS Database	35616633
Artemisia ludoviciana	LOTUS Database	35616633
Artemisia ludoviciana var. mexicana	Plant	KNApSAcK
Artemisia mongolica	Plant	KNApSAcK
Artemisia monosperma	LOTUS Database	35616633
Artemisia nitida	Plant	KNApSAcK
Artemisia oliveriana	Plant	KNApSAcK
Artemisia porrecta	Plant	KNApSAcK
Artemisia princeps	LOTUS Database	35616633
Artemisia roxburghiana	LOTUS Database	35616633
Artemisia rubripes	LOTUS Database	35616633
Artemisia umbelliformis	Plant	KNApSAcK
Artemisia verlotiorum	Plant	KNApSAcK
Artemisia vulgaris	Plant	KNApSAcK
Baccharis gaudichaudiana	Plant	KNApSAcK
Baccharis gaudichaudiana DC	Plant	KNApSAcK
Centaurea arenaria	LOTUS Database	35616633
Centaurea cineraria	LOTUS Database	35616633
Centaurea cuneifolia	LOTUS Database	35616633
Centaurea sulphurea	LOTUS Database	35616633
Centaurea tougourensis	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Chrysanthemum indicum	Plant	KNApSAcK
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Eriocephalus punctulatus	Plant	KNApSAcK
Eupatorium capillifolium	Plant	KNApSAcK
Eupatorium semiserratum	Plant	KNApSAcK
Layia hieracioides	LOTUS Database	35616633
Monoclea gottschei	Plant	KNApSAcK
Ononis vaginalis	Plant	KNApSAcK
Pentanema britannicum	Plant	KNApSAcK
Phyla dulcis	LOTUS Database	35616633
Psilostrophe cooperi	LOTUS Database	35616633
Salvia cardiophylla	Plant	KNApSAcK
Salvia limbata	LOTUS Database	35616633
Salvia palaestina	Plant	KNApSAcK
Salvia sclarea	Plant	KNApSAcK
Salvia tomentosa	Plant	KNApSAcK
Salvia x sylvestris	LOTUS Database	35616633
Sideritis gomerae	Plant	KNApSAcK
Sideritis tomentosa	Plant	KNApSAcK
Tanacetum polycephalum	Plant	KNApSAcK
Tanacetum vulgare	Plant	KNApSAcK
Teucrium divaricatum	LOTUS Database	35616633
Veratrum dahuricum	LOTUS Database	35616633
Veronica officinalis	Plant	KNApSAcK
Veronica orchidea	Plant	KNApSAcK
Veronica teucrium	Plant	KNApSAcK

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:4932 )
trimethoxyflavone (CHEBI:4932 )
flavones (C10040 )
Flavones and Flavonols (C10040 )
Flavones and Flavonols (LMPK12111228 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.89	ALOGPS
logP	2.54	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.45 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	34.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029469

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Eupatilin

METLIN ID

Not Available

PubChem Compound

5273755

PDB ID

Not Available

ChEBI ID

4932

Good Scents ID

Not Available

References

General References

Kim MJ, Kim DH, Lee KW, Yoon DY, Surh YJ: Jaceosidin induces apoptosis in ras-transformed human breast epithelial cells through generation of reactive oxygen species. Ann N Y Acad Sci. 2007 Jan;1095:483-95. doi: 10.1196/annals.1397.052. [PubMed:17404061 ]
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 ]
Lim JC, Park SY, Nam Y, Nguyen TT, Sohn UD: The Protective Effect of Eupatilin against Hydrogen Peroxide-Induced Injury Involving 5-Lipoxygenase in Feline Esophageal Epithelial Cells. Korean J Physiol Pharmacol. 2012 Oct;16(5):313-20. doi: 10.4196/kjpp.2012.16.5.313. Epub 2012 Oct 18. [PubMed:23118554 ]
Park BB, Yoon Js, Kim Es, Choi J, Won Yw, Choi Jh, Lee YY: Inhibitory effects of eupatilin on tumor invasion of human gastric cancer MKN-1 cells. Tumour Biol. 2013 Apr;34(2):875-85. doi: 10.1007/s13277-012-0621-y. Epub 2013 Jan 8. [PubMed:23292941 ]
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. doi: 10.1016/j.bcp.2004.04.027. [PubMed:15313404 ]

Showing NP-Card for Eupatilin (NP0045377)

MOL for NP0045377 (Eupatilin)

3D MOL for NP0045377 (Eupatilin)

3D SDF for NP0045377 (Eupatilin)

3D-SDF for NP0045377 (Eupatilin)

PDB for NP0045377 (Eupatilin)

3D PDB for NP0045377 (Eupatilin)

SMILES for NP0045377 (Eupatilin)

INCHI for NP0045377 (Eupatilin)

Structure for NP0045377 (Eupatilin)

3D Structure for NP0045377 (Eupatilin)