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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:34:36 UTC

Update Date

2022-03-07 02:55:17 UTC

HMDB ID

HMDB0037339

Secondary Accession Numbers

HMDB37339

Metabolite Identification

Common Name

Luteolin 7-methyl ether

Description

Luteolin 7-methyl ether belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, luteolin 7-methyl ether is considered to be a flavonoid. Luteolin 7-methyl ether has been detected, but not quantified in, several different foods, such as herbs and spices, green tea, red tea, herbal tea, and black tea. This could make luteolin 7-methyl ether a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Luteolin 7-methyl ether.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0037339
     RDKit          3D
Luteolin 7-methyl ether
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.5579    2.1997   -0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651    0.8216   -0.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -0.0689   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046   -1.4030    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8680   -2.3421    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -3.6604    0.3592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890   -1.8091    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -2.6209    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6171   -3.8517    0.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834   -2.0299    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -0.6928    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -0.0359    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -0.7638    0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6345   -0.1079    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7135    1.2680    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313    1.9318    0.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    1.9995    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401    3.3772   -0.0964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    1.3298    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    0.0659    0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -0.4592    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208    0.4081   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5040    2.6417   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783    2.3647   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3253    2.6424    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -1.7952    0.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7031   -4.4890    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083   -2.6931    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203   -1.8464    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5674   -0.6376    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445    2.9202    0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    3.9289   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4555    1.9442   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226    1.4633   -0.1929 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061309432D          

 22 24  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  6  2  0  0  0  0
 16 12  2  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037339

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-7,17-19H,1H3

> <INCHI_KEY>
RRRSSAVLTCVNIQ-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.804855900068482

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.5490178679999995

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.941325463813527

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.327973213765677

> <JCHEM_PKA_STRONGEST_BASIC>
-4.745761850055501

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
79.37710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteolin 7-methyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037339
     RDKit          3D
Luteolin 7-methyl ether
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.5579    2.1997   -0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651    0.8216   -0.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -0.0689   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046   -1.4030    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8680   -2.3421    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -3.6604    0.3592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890   -1.8091    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -2.6209    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6171   -3.8517    0.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834   -2.0299    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -0.6928    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -0.0359    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -0.7638    0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6345   -0.1079    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7135    1.2680    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313    1.9318    0.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    1.9995    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401    3.3772   -0.0964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    1.3298    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    0.0659    0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -0.4592    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208    0.4081   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5040    2.6417   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783    2.3647   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3253    2.6424    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -1.7952    0.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7031   -4.4890    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083   -2.6931    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203   -1.8464    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5674   -0.6376    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445    2.9202    0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    3.9289   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4555    1.9442   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226    1.4633   -0.1929 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   10                                                       
CONECT    4    8   11                                                       
CONECT    5    9   12                                                       
CONECT    6    9   15                                                       
CONECT    7   13   14                                                       
CONECT    8    2    4   14                                                  
CONECT    9    5    6   21                                                  
CONECT   10    3   11   17                                                  
CONECT   11    4   10   18                                                  
CONECT   12    5   16   19                                                  
CONECT   13    7   16   20                                                  
CONECT   14    7    8   22                                                  
CONECT   15    6   16   22                                                  
CONECT   16   12   13   15                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21    1    9                                                       
CONECT   22   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0037339
HETATM    1  C1  UNL     1      -4.558   2.200  -0.408  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.765   0.822  -0.257  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.713  -0.069  -0.094  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.905  -1.403   0.052  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.868  -2.342   0.220  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.156  -3.660   0.359  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.589  -1.809   0.227  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.484  -2.621   0.384  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.617  -3.852   0.521  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.783  -2.030   0.384  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.949  -0.693   0.235  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.250  -0.036   0.229  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.401  -0.764   0.378  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.635  -0.108   0.369  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.713   1.268   0.211  1.00  0.00           C  
HETATM   16  O4  UNL     1       5.931   1.932   0.200  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.553   1.999   0.061  1.00  0.00           C  
HETATM   18  O5  UNL     1       3.640   3.377  -0.096  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.349   1.330   0.074  1.00  0.00           C  
HETATM   20  O6  UNL     1      -0.135   0.066   0.086  1.00  0.00           O  
HETATM   21  C15 UNL     1      -1.335  -0.459   0.082  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.421   0.408  -0.080  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.504   2.642  -0.781  1.00  0.00           H  
HETATM   24  H2  UNL     1      -3.778   2.365  -1.157  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.325   2.642   0.591  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.919  -1.795   0.043  1.00  0.00           H  
HETATM   27  H5  UNL     1      -2.703  -4.489   0.482  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.608  -2.693   0.507  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.420  -1.846   0.507  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.567  -0.638   0.482  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.945   2.920   0.084  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.798   3.929  -0.208  1.00  0.00           H  
HETATM   33  H11 UNL     1       1.456   1.944  -0.048  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.223   1.463  -0.193  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   21
CONECT    8    9    9   10
CONECT   10   11   11   28
CONECT   11   12   20
CONECT   12   13   13   19
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   19   19
CONECT   18   32
CONECT   19   33
CONECT   20   21
CONECT   21   22   22
CONECT   22   34
END

HMDB0037339
     RDKit          3D
Luteolin 7-methyl ether
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.5579    2.1997   -0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7651    0.8216   -0.2570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132   -0.0689   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046   -1.4030    0.0522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8680   -2.3421    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1556   -3.6604    0.3592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5890   -1.8091    0.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4836   -2.6209    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6171   -3.8517    0.5212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834   -2.0299    0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9487   -0.6928    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2503   -0.0359    0.2293 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4010   -0.7638    0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6345   -0.1079    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7135    1.2680    0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313    1.9318    0.1998 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5527    1.9995    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6401    3.3772   -0.0964 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3485    1.3298    0.0738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1353    0.0659    0.0862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -0.4592    0.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208    0.4081   -0.0796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5040    2.6417   -0.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7783    2.3647   -1.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3253    2.6424    0.5912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9189   -1.7952    0.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7031   -4.4890    0.4817 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6083   -2.6931    0.5069 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4203   -1.8464    0.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5674   -0.6376    0.4824 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9445    2.9202    0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7978    3.9289   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4555    1.9442   -0.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2226    1.4633   -0.1929 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 11 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 19 12  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one	HMDB
2-(3,4-Dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
5,3',4'-Trihydroxy-7-methoxyflavone	HMDB
7-O-Methylluteolin	HMDB
Hydroxygenkwanin	MeSH

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

Traditional Name

luteolin 7-methyl ether

CAS Registry Number

20243-59-8

SMILES

COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O6/c1-21-9-5-12(19)16-13(20)7-14(22-15(16)6-9)8-2-3-10(17)11(18)4-8/h2-7,17-19H,1H3

InChI Key

RRRSSAVLTCVNIQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
Flavone
3'-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Catechol
Anisole
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111045 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037339)

Cellular substructure

Membrane (HMDB: HMDB0037339)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037339)

Source

Exogenous

Food

Food (HMDB: HMDB0037339)

Tea

Herb and spice

Herb

Common sage (FooDB: FOOD00165)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037339)

Not Available

Nutrient (HMDB: HMDB0037339)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	306 - 308 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	3.08	ALOGPS
logP	2.55	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.33	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.38 m³·mol⁻¹	ChemAxon
Polarizability	29.8 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	172.958	30932474
DeepCCS	[M-H]-	170.6	30932474
DeepCCS	[M-2H]-	204.617	30932474
DeepCCS	[M+Na]+	179.844	30932474
AllCCS	[M+H]+	168.2	32859911
AllCCS	[M+H-H2O]+	164.5	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.6	32859911
AllCCS	[M-H]-	167.8	32859911
AllCCS	[M+Na-2H]-	167.0	32859911
AllCCS	[M+HCOO]-	166.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Luteolin 7-methyl ether	COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1	4784.8	Standard polar	33892256
Luteolin 7-methyl ether	COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1	3120.4	Standard non polar	33892256
Luteolin 7-methyl ether	COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC(O)=C(O)C=C1	3157.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Luteolin 7-methyl ether,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C1	3293.4	Semi standard non polar	33892256
Luteolin 7-methyl ether,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3318.4	Semi standard non polar	33892256
Luteolin 7-methyl ether,1TMS,isomer #3	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3354.6	Semi standard non polar	33892256
Luteolin 7-methyl ether,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C1	3292.4	Semi standard non polar	33892256
Luteolin 7-methyl ether,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C1	3269.0	Semi standard non polar	33892256
Luteolin 7-methyl ether,2TMS,isomer #3	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3225.1	Semi standard non polar	33892256
Luteolin 7-methyl ether,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C1	3154.3	Semi standard non polar	33892256
Luteolin 7-methyl ether,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O)=C3)OC2=C1	3577.6	Semi standard non polar	33892256
Luteolin 7-methyl ether,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3578.1	Semi standard non polar	33892256
Luteolin 7-methyl ether,1TBDMS,isomer #3	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3611.1	Semi standard non polar	33892256
Luteolin 7-methyl ether,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C1	3780.9	Semi standard non polar	33892256
Luteolin 7-methyl ether,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3749.2	Semi standard non polar	33892256
Luteolin 7-methyl ether,2TBDMS,isomer #3	COC1=CC(O)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3728.8	Semi standard non polar	33892256
Luteolin 7-methyl ether,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C1	3872.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin 7-methyl ether GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fl0-0590000000-fe91bcd17d90efeea961	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin 7-methyl ether GC-MS (3 TMS) - 70eV, Positive	splash10-0ukc-2161960000-7bc9092b67b6d695ebc9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin 7-methyl ether GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Luteolin 7-methyl ether GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 10V, Positive-QTOF	splash10-0udi-0029000000-606b4cb8ba1d122f1377	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 20V, Positive-QTOF	splash10-0udi-0189000000-3b7dd23ed7603c6a2382	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 40V, Positive-QTOF	splash10-0zir-2490000000-f3e287f3d78aa8da00ad	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 10V, Negative-QTOF	splash10-0002-0090000000-7809e9ae65d2112a1ffd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 20V, Negative-QTOF	splash10-0002-0090000000-afdd1a1cb4493a0415e5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 40V, Negative-QTOF	splash10-00lr-2490000000-b0e365edc50ace3d87cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 10V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 20V, Positive-QTOF	splash10-0udi-0019000000-db7633ef115eab893fbb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 40V, Positive-QTOF	splash10-0a4r-0290000000-3fdbd8f853e60934e093	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 10V, Negative-QTOF	splash10-0002-0090000000-ea8480b3ca37fc485b0e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Luteolin 7-methyl ether 20V, Negative-QTOF	splash10-0532-0090000000-27686460288b02aa6d56	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016361

KNApSAcK ID

C00003865

Chemspider ID

4476827

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318214

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Luteolin 7-methyl ether (HMDB0037339)

MOL for HMDB0037339 (Luteolin 7-methyl ether)

3D MOL for HMDB0037339 (Luteolin 7-methyl ether)

3D SDF for HMDB0037339 (Luteolin 7-methyl ether)

3D-SDF for HMDB0037339 (Luteolin 7-methyl ether)

PDB for HMDB0037339 (Luteolin 7-methyl ether)

3D PDB for HMDB0037339 (Luteolin 7-methyl ether)

SMILES for HMDB0037339 (Luteolin 7-methyl ether)

INCHI for HMDB0037339 (Luteolin 7-methyl ether)

Structure for HMDB0037339 (Luteolin 7-methyl ether)

3D Structure for HMDB0037339 (Luteolin 7-methyl ether)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra