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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:21 UTC

Update Date

2022-03-07 02:52:43 UTC

HMDB ID

HMDB0030842

Secondary Accession Numbers

HMDB30842

Metabolite Identification

Common Name

4',5,7-Trimethoxyflavone

Description

4',5,7-Trimethoxyflavone, also known as trimethylapigenin, 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, 4',5,7-trimethoxyflavone is considered to be a flavonoid lipid molecule. 4',5,7-Trimethoxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4',5,7-trimethoxyflavone has been detected, but not quantified in, a few different foods, such as citrus, mandarin orange (clementine, tangerine), and sweet oranges. This could make 4',5,7-trimethoxyflavone a potential biomarker for the consumption of these foods.

Structure

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

HMDB0030842
     RDKit          3D
4',5,7-Trimethoxyflavone
 39 41  0  0  0  0  0  0  0  0999 V2000
    7.1942   -0.2032   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2217    0.7970   -0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    0.5117    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634   -0.8004   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.0912   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.0877    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.4046    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2710   -1.6795    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -1.9185    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -3.0876   -0.0075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730   -0.8617    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -1.1027    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614   -2.4101    0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0896   -2.8369    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728   -0.0001    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    1.2864    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5519    2.3503    0.1079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1887    3.6923    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3180    1.4754    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    0.3952    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415    0.5939    0.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    1.2209    0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9268    1.5146    0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792    0.2784   -0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3127   -0.6255    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9862   -0.9995   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791   -1.6187   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471   -2.1515   -0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -2.5121   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7465   -2.2024   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1698   -3.8847   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440   -2.8215    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2600   -0.1758    0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    3.9270   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9432    4.3261   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    4.0606    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660    2.4539    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683    2.0354    0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    2.5565    0.0401 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  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
  6 22  1  0
 22 23  2  0
 23  3  1  0
 21  7  1  0
 20 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 23 39  1  0
M  END


  Mrv1652304072020302D          

 23 25  0  0  0  0            999 V2000
    7.8592    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0012    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  7  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 12  1  0  0  0  0
 18 13  2  0  0  0  0
 19  1  1  0  0  0  0
 19 10  1  0  0  0  0
 20 11  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
 20 22  1  0  0  0  0
 17 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030842

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)15-10-14(19)18-16(22-3)8-13(21-2)9-17(18)23-15/h4-10H,1-3H3

> <INCHI_KEY>
ZXJJBDHPUHUUHD-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.3166

> <EXACT_MASS>
312.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.02673171392914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
2.494371301666667

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.54287180294915

> <JCHEM_PKA_STRONGEST_BASIC>
-4.343671577856831

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
86.36079999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030842
     RDKit          3D
4',5,7-Trimethoxyflavone
 39 41  0  0  0  0  0  0  0  0999 V2000
    7.1942   -0.2032   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2217    0.7970   -0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    0.5117    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634   -0.8004   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.0912   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.0877    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.4046    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2710   -1.6795    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -1.9185    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -3.0876   -0.0075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730   -0.8617    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -1.1027    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614   -2.4101    0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0896   -2.8369    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728   -0.0001    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    1.2864    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5519    2.3503    0.1079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1887    3.6923    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3180    1.4754    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    0.3952    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415    0.5939    0.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    1.2209    0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9268    1.5146    0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792    0.2784   -0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3127   -0.6255    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9862   -0.9995   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791   -1.6187   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471   -2.1515   -0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -2.5121   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7465   -2.2024   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1698   -3.8847   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440   -2.8215    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2600   -0.1758    0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    3.9270   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9432    4.3261   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    4.0606    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660    2.4539    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683    2.0354    0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    2.5565    0.0401 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  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
  6 22  1  0
 22 23  2  0
 23  3  1  0
 21  7  1  0
 20 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 07-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-APR-20         0                                  
HETATM    1  C   UNK     0      14.671   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.003   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003   3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.001  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.000   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.850   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6   11   12                                                       
CONECT    7   11   15                                                       
CONECT    8   13   14                                                       
CONECT    9    2    3   14                                                  
CONECT   10    4    5   19                                                  
CONECT   11    6    7   20                                                  
CONECT   12    6   16   17                                                  
CONECT   13    8   16   18                                                  
CONECT   14    8    9   21                                                  
CONECT   15    7   16   21                                                  
CONECT   16   12   13   15                                                  
CONECT   17   12   23                                                       
CONECT   18   13                                                            
CONECT   19    1   10                                                       
CONECT   20   11   22                                                       
CONECT   21   14   15                                                       
CONECT   22   20                                                            
CONECT   23   17                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0030842
HETATM    1  C1  UNL     1       7.194  -0.203  -0.030  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.222   0.797  -0.005  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.873   0.512   0.001  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.463  -0.800  -0.018  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.098  -1.091  -0.011  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.179  -0.088   0.013  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.741  -0.405   0.019  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.271  -1.679   0.002  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.092  -1.918   0.009  1.00  0.00           C  
HETATM   10  O2  UNL     1      -1.533  -3.088  -0.007  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.973  -0.862   0.033  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.347  -1.103   0.040  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.761  -2.410   0.022  1.00  0.00           O  
HETATM   14  C11 UNL     1      -5.090  -2.837   0.025  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.173  -0.000   0.065  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.673   1.286   0.083  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.552   2.350   0.108  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.189   3.692   0.127  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.318   1.475   0.075  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.432   0.395   0.050  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.142   0.594   0.043  1.00  0.00           O  
HETATM   22  C17 UNL     1       2.590   1.221   0.031  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.927   1.515   0.026  1.00  0.00           C  
HETATM   24  H1  UNL     1       8.179   0.278  -0.284  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.313  -0.625   0.983  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.986  -0.999  -0.784  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.179  -1.619  -0.037  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.847  -2.151  -0.027  1.00  0.00           H  
HETATM   29  H6  UNL     1       0.925  -2.512  -0.018  1.00  0.00           H  
HETATM   30  H7  UNL     1      -5.747  -2.202  -0.619  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.170  -3.885  -0.329  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.444  -2.821   1.082  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.260  -0.176   0.071  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.219   3.927  -0.320  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.943   4.326  -0.425  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.226   4.061   1.194  1.00  0.00           H  
HETATM   37  H14 UNL     1      -1.866   2.454   0.088  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.868   2.035   0.051  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.294   2.557   0.040  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   23
CONECT    4    5   27
CONECT    5    6    6   28
CONECT    6    7   22
CONECT    7    8    8   21
CONECT    8    9   29
CONECT    9   10   10   11
CONECT   11   12   12   20
CONECT   12   13   15
CONECT   13   14
CONECT   14   30   31   32
CONECT   15   16   16   33
CONECT   16   17   19
CONECT   17   18
CONECT   18   34   35   36
CONECT   19   20   20   37
CONECT   20   21
CONECT   22   23   23   38
CONECT   23   39
END

HMDB0030842
     RDKit          3D
4',5,7-Trimethoxyflavone
 39 41  0  0  0  0  0  0  0  0999 V2000
    7.1942   -0.2032   -0.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2217    0.7970   -0.0049 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8731    0.5117    0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4634   -0.8004   -0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0979   -1.0912   -0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1788   -0.0877    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.4046    0.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2710   -1.6795    0.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919   -1.9185    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5334   -3.0876   -0.0075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9730   -0.8617    0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3465   -1.1027    0.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7614   -2.4101    0.0218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0896   -2.8369    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1728   -0.0001    0.0655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6733    1.2864    0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5519    2.3503    0.1079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1887    3.6923    0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3180    1.4754    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4320    0.3952    0.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1415    0.5939    0.0429 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895    1.2209    0.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9268    1.5146    0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1792    0.2784   -0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3127   -0.6255    0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9862   -0.9995   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791   -1.6187   -0.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8471   -2.1515   -0.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9254   -2.5121   -0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7465   -2.2024   -0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1698   -3.8847   -0.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4440   -2.8215    1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2600   -0.1758    0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189    3.9270   -0.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9432    4.3261   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    4.0606    1.1936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8660    2.4539    0.0879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8683    2.0354    0.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2937    2.5565    0.0401 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  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 19 20  2  0
 20 21  1  0
  6 22  1  0
 22 23  2  0
 23  3  1  0
 21  7  1  0
 20 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  5 28  1  0
  8 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 18 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',5,7-Trimethyl-apigenin	MeSH
5,7,4'-Trimethylapigenin	MeSH
4'57-Trimethoxyflavone	ChEMBL, HMDB
4',5,7-Trimethoxy-flavone	HMDB
5,7,4'-Trimethoxyflavone	HMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-benzenopyran-4-one	HMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB
6-Hydroxy-4',5,7-trimethoxyflavone	HMDB
Apigenin 5,7,4'-trimethyl ether	HMDB
Apigenin trimethyl ether	HMDB
4',5,7-Trimethoxyflavone	MeSH
4’,5,7-Trimethoxyflavone	HMDB
5,7,4'-Tri-O-methylapigenin	HMDB
5,7,4'-Trimethoxyapigenin	HMDB
5,7,4’-Tri-O-methylapigenin	HMDB
5,7,4’-Trimethoxyapigenin	HMDB
5,7,4’-Trimethoxyflavone	HMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one	HMDB
5,7-Dimethoxy-2-(4-methoxyphenyl)chromone	HMDB
5,7-Dimethoxy-4-oxo-2-(4-methoxyphenyl)-4H-1-benzopyran	HMDB
Tri-O-methylapigenin	HMDB
Trimethylapigenin	HMDB

Chemical Formula

C₁₈H₁₆O₅

Average Molecular Weight

312.3166

Monoisotopic Molecular Weight

312.099773622

IUPAC Name

5,7-dimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

5,7-dimethoxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

5631-70-9

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1

InChI Identifier

InChI=1S/C18H16O5/c1-20-12-6-4-11(5-7-12)15-10-14(19)18-16(22-3)8-13(21-2)9-17(18)23-15/h4-10H,1-3H3

InChI Key

ZXJJBDHPUHUUHD-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

4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Flavone
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous ester
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111071 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030842)
Cell membrane (HMDB: HMDB0030842)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030842)

Source

Endogenous

Endogenous (HMDB: HMDB0030842)

Plant

Plant (HMDB: HMDB0030842)

Exogenous

Food

Food (HMDB: HMDB0030842)

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Exogenous (HMDB: HMDB0030842)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	156 - 157 °C	Not Available
Boiling Point	506.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	6.51 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.530 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.21	ALOGPS
logP	2.49	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	15.54	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.36 m³·mol⁻¹	ChemAxon
Polarizability	33.03 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
DarkChem	[M+H]+	175.27	31661259
DarkChem	[M-H]-	177.126	31661259
DeepCCS	[M+H]+	173.288	30932474
DeepCCS	[M-H]-	170.93	30932474
DeepCCS	[M-2H]-	204.093	30932474
DeepCCS	[M+Na]+	179.381	30932474
AllCCS	[M+H]+	172.8	32859911
AllCCS	[M+H-H2O]+	169.2	32859911
AllCCS	[M+NH4]+	176.2	32859911
AllCCS	[M+Na]+	177.1	32859911
AllCCS	[M-H]-	176.0	32859911
AllCCS	[M+Na-2H]-	175.4	32859911
AllCCS	[M+HCOO]-	174.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	9.32 minutes	32390414
Predicted by Siyang on May 30, 2022	15.6745 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.02 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2567.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	434.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	211.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	570.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	685.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	144.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1432.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	529.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1427.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	452.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	441.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	422.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	12.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4',5,7-Trimethoxyflavone	COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1	4298.7	Standard polar	33892256
4',5,7-Trimethoxyflavone	COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1	2895.2	Standard non polar	33892256
4',5,7-Trimethoxyflavone	COC1=CC=C(C=C1)C1=CC(=O)C2=C(OC)C=C(OC)C=C2O1	3134.5	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 - 4',5,7-Trimethoxyflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01qa-0691000000-7a823829ea08d5c44987	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5,7-Trimethoxyflavone 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 - 4',5,7-Trimethoxyflavone 10V, Positive-QTOF	splash10-03di-0009000000-5c2fa314b535098da3c3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Positive-QTOF	splash10-03di-0009000000-e66ded4021486610bfbe	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 40V, Positive-QTOF	splash10-053r-1490000000-a1ba798957d115c766da	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 10V, Negative-QTOF	splash10-03di-0009000000-6fd59ab6ee43b4030a5c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Negative-QTOF	splash10-03di-0029000000-1598e4635c488fb5e524	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 40V, Negative-QTOF	splash10-0kcr-1390000000-6872b99524899c8fbf57	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 10V, Positive-QTOF	splash10-03di-0009000000-0c9c5e8761c67e87c624	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Positive-QTOF	splash10-03di-0019000000-d5759b18375da517980a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 40V, Positive-QTOF	splash10-0g4j-0190000000-5d008847ec007268d4ec	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 10V, Negative-QTOF	splash10-03di-0009000000-70f2c2cfe29137281455	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5,7-Trimethoxyflavone 20V, Negative-QTOF	splash10-03xs-0097000000-951d276ce9092ed6732e	2021-09-24	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

FDB002800

KNApSAcK ID

C00003821

Chemspider ID

72029

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

79730

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1701731

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 4',5,7-Trimethoxyflavone (HMDB0030842)

MOL for HMDB0030842 (4',5,7-Trimethoxyflavone)

3D MOL for HMDB0030842 (4',5,7-Trimethoxyflavone)

3D SDF for HMDB0030842 (4',5,7-Trimethoxyflavone)

3D-SDF for HMDB0030842 (4',5,7-Trimethoxyflavone)

PDB for HMDB0030842 (4',5,7-Trimethoxyflavone)

3D PDB for HMDB0030842 (4',5,7-Trimethoxyflavone)

SMILES for HMDB0030842 (4',5,7-Trimethoxyflavone)

INCHI for HMDB0030842 (4',5,7-Trimethoxyflavone)

Structure for HMDB0030842 (4',5,7-Trimethoxyflavone)

3D Structure for HMDB0030842 (4',5,7-Trimethoxyflavone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra