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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:52 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029512

Secondary Accession Numbers

HMDB29512

Metabolite Identification

Common Name

4',5-Dihydroxy-7-methoxy-6-methylflavone

Description

4',5-Dihydroxy-7-methoxy-6-methylflavone, also known as 8-demethylsideroxylin, 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-dihydroxy-7-methoxy-6-methylflavone is considered to be a flavonoid. 4',5-Dihydroxy-7-methoxy-6-methylflavone is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on 4',5-Dihydroxy-7-methoxy-6-methylflavone.

Structure

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

HMDB0029512
     RDKit          3D
4',5-Dihydroxy-7-methoxy-6-methylflavone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.9599    1.3938   -2.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2302    0.4052   -1.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331   -0.0626   -0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    0.3918   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -0.0816   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4485    0.3462   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973   -0.0914    0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8311    0.4377    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    0.0161    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074    0.5428    0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    1.4912   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6531    1.9909   -0.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2628    1.9126   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    1.3948   -0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.0332    1.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0144   -1.5150    1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189   -2.3934    2.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.0322    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420   -1.4996    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328   -2.4659    2.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774   -1.0075    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7682   -1.5194    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148    0.9027   -3.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919    1.7677   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    2.2393   -1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853    1.1367   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8866   -0.7243    1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0909    0.2177    1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2822    1.5823   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139    2.6593   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456    1.7237   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0597   -1.4193    2.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -2.8377    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9265   -1.5758    1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5060   -0.7817    0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691   -2.5118    0.2539 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21  3  1  0
 18  5  2  0
 14  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 20 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
M  END


  Mrv0541 02241210572D          

 22 24  0  0  0  0            999 V2000
    0.0004   -0.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    0.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269   -1.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844    2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    3.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4844   -2.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421   -2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -1.0307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -2.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0004   -3.5055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4020   -2.6806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2269   -2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4 15  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029512

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O5/c1-9-13(21-2)8-15-16(17(9)20)12(19)7-14(22-15)10-3-5-11(18)6-4-10/h3-8,18,20H,1-2H3

> <INCHI_KEY>
VQCXCCMCKDSXMQ-UHFFFAOYSA-N

> <FORMULA>
C17H14O5

> <MOLECULAR_WEIGHT>
298.2901

> <EXACT_MASS>
298.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.976991012378537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.51

> <JCHEM_LOGP>
3.3660045789999993

> <ALOGPS_LOGS>
-3.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.156605945672002

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.523415121109503

> <JCHEM_PKA_STRONGEST_BASIC>
-4.740434390299335

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
82.4374

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-demethylsideroxylin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029512
     RDKit          3D
4',5-Dihydroxy-7-methoxy-6-methylflavone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.9599    1.3938   -2.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2302    0.4052   -1.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331   -0.0626   -0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    0.3918   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -0.0816   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4485    0.3462   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973   -0.0914    0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8311    0.4377    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    0.0161    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074    0.5428    0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    1.4912   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6531    1.9909   -0.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2628    1.9126   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    1.3948   -0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.0332    1.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0144   -1.5150    1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189   -2.3934    2.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.0322    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420   -1.4996    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328   -2.4659    2.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774   -1.0075    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7682   -1.5194    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148    0.9027   -3.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919    1.7677   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    2.2393   -1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853    1.1367   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8866   -0.7243    1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0909    0.2177    1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2822    1.5823   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139    2.6593   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456    1.7237   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0597   -1.4193    2.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -2.8377    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9265   -1.5758    1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5060   -0.7817    0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691   -2.5118    0.2539 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21  3  1  0
 18  5  2  0
 14  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 20 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
M  END

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  O   UNK     0       0.001  -0.386   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.385   0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.771  -0.386   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.771  -1.924   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.157  -2.694   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.001   4.234   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.001   2.694   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.385   1.924   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.771   2.694   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.771   4.234   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.385   5.004   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.385   6.544   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.771  -5.004   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.385  -4.234   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.385  -2.694   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.001  -1.924   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.231  -2.694   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.231  -4.234   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.001  -5.004   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.001  -6.544   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.617  -5.004   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.157  -5.004   0.000  0.00  0.00           C+0
CONECT    1    2   16                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   13   15   19                                                  
CONECT   15    4   14   16                                                  
CONECT   16    1   15   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   14   18   20                                                  
CONECT   20   19                                                            
CONECT   21   18   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0029512
HETATM    1  C1  UNL     1      -3.960   1.394  -2.267  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.230   0.405  -1.261  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.133  -0.063  -0.529  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.851   0.392  -0.749  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.771  -0.082  -0.013  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.449   0.346  -0.217  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.497  -0.091   0.472  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.831   0.438   0.184  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.941   0.016   0.869  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.207   0.543   0.569  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.383   1.491  -0.414  1.00  0.00           C  
HETATM   12  O3  UNL     1       6.653   1.991  -0.684  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.263   1.913  -1.101  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.018   1.395  -0.806  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.249  -1.033   1.432  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.014  -1.515   1.685  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.219  -2.393   2.586  1.00  0.00           O  
HETATM   18  C14 UNL     1      -1.069  -1.032   0.945  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.342  -1.500   1.181  1.00  0.00           C  
HETATM   20  O5  UNL     1      -2.533  -2.466   2.179  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.377  -1.008   0.435  1.00  0.00           C  
HETATM   22  C17 UNL     1      -4.768  -1.519   0.694  1.00  0.00           C  
HETATM   23  H1  UNL     1      -3.315   0.903  -3.010  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.892   1.768  -2.714  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.467   2.239  -1.743  1.00  0.00           H  
HETATM   26  H4  UNL     1      -1.685   1.137  -1.514  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.887  -0.724   1.653  1.00  0.00           H  
HETATM   28  H6  UNL     1       6.091   0.218   1.103  1.00  0.00           H  
HETATM   29  H7  UNL     1       7.282   1.582  -1.360  1.00  0.00           H  
HETATM   30  H8  UNL     1       4.414   2.659  -1.872  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.146   1.724  -1.342  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.060  -1.419   2.017  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.441  -2.838   2.388  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.926  -1.576   1.786  1.00  0.00           H  
HETATM   35  H13 UNL     1      -5.506  -0.782   0.312  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.869  -2.512   0.254  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6   18   18
CONECT    6    7
CONECT    7    8   15   15
CONECT    8    9    9   14
CONECT    9   10   27
CONECT   10   11   11   28
CONECT   11   12   13
CONECT   12   29
CONECT   13   14   14   30
CONECT   14   31
CONECT   15   16   32
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   21   21
CONECT   20   33
CONECT   21   22
CONECT   22   34   35   36
END

HMDB0029512
     RDKit          3D
4',5-Dihydroxy-7-methoxy-6-methylflavone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.9599    1.3938   -2.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2302    0.4052   -1.2615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1331   -0.0626   -0.5290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8514    0.3918   -0.7485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7711   -0.0816   -0.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4485    0.3462   -0.2175 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973   -0.0914    0.4724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8311    0.4377    0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9407    0.0161    0.8691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2074    0.5428    0.5687 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    1.4912   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6531    1.9909   -0.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2628    1.9126   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185    1.3948   -0.8057 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2488   -1.0332    1.4322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0144   -1.5150    1.6851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189   -2.3934    2.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689   -1.0322    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420   -1.4996    1.1807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328   -2.4659    2.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3774   -1.0075    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7682   -1.5194    0.6935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3148    0.9027   -3.0105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8919    1.7677   -2.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4669    2.2393   -1.7433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6853    1.1367   -1.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8866   -0.7243    1.6534 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0909    0.2177    1.1032 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2822    1.5823   -1.3600 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139    2.6593   -1.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1456    1.7237   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0597   -1.4193    2.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4410   -2.8377    2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9265   -1.5758    1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5060   -0.7817    0.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8691   -2.5118    0.2539 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
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  7 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21  3  1  0
 18  5  2  0
 14  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  9 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
 20 33  1  0
 22 34  1  0
 22 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,4'-Dihydroxy-7-methoxy-6-methylflavone	ChEBI
5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-1-benzopyran-4-one	HMDB
8-Demethylsideroxylin	HMDB
8-Desmethyl-sideroxylin	HMDB
8-Desmethylsideroxylin	HMDB

Chemical Formula

C₁₇H₁₄O₅

Average Molecular Weight

298.2901

Monoisotopic Molecular Weight

298.084123558

IUPAC Name

5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-6-methyl-4H-chromen-4-one

Traditional Name

8-demethylsideroxylin

CAS Registry Number

80621-54-1

SMILES

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

InChI Identifier

InChI=1S/C17H14O5/c1-9-13(21-2)8-15-16(17(9)20)12(19)7-14(22-15)10-3-5-11(18)6-4-10/h3-8,18,20H,1-2H3

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:69917 )
monomethoxyflavone (CHEBI:69917 )
Flavones and Flavonols (LMPK12111017 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029512)
Cell membrane (HMDB: HMDB0029512)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029512)

Source

Endogenous

Endogenous (HMDB: HMDB0029512)

Plant

Plant (HMDB: HMDB0029512)

Exogenous

Food

Food (HMDB: HMDB0029512)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0029512)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	284 - 286 °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	0.032 g/L	ALOGPS
logP	3.51	ALOGPS
logP	3.37	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.52	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.44 m³·mol⁻¹	ChemAxon
Polarizability	30.98 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]+	172.21	31661259
DarkChem	[M-H]-	174.502	31661259
DeepCCS	[M+H]+	174.34	30932474
DeepCCS	[M-H]-	171.982	30932474
DeepCCS	[M-2H]-	206.048	30932474
DeepCCS	[M+Na]+	181.375	30932474
AllCCS	[M+H]+	168.3	32859911
AllCCS	[M+H-H2O]+	164.6	32859911
AllCCS	[M+NH4]+	171.7	32859911
AllCCS	[M+Na]+	172.7	32859911
AllCCS	[M-H]-	169.6	32859911
AllCCS	[M+Na-2H]-	168.8	32859911
AllCCS	[M+HCOO]-	168.0	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.	7.98 minutes	32390414
Predicted by Siyang on May 30, 2022	15.5486 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.0 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2589.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	424.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	197.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	233.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	501.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	654.1 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	762.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1384.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	521.9 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	1557.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	454.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	471.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	434.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	231.0 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	90.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4',5-Dihydroxy-7-methoxy-6-methylflavone	COC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1	4295.2	Standard polar	33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone	COC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1	3045.9	Standard non polar	33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone	COC1=C(C)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1	3169.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O)C=C1)O2	3111.0	Semi standard non polar	33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TMS,isomer #2	COC1=CC2=C(C(O)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C)C=C1)O2	3205.7	Semi standard non polar	33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,2TMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C)C=C1)O2	3194.8	Semi standard non polar	33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O)C=C1)O2	3363.5	Semi standard non polar	33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,1TBDMS,isomer #2	COC1=CC2=C(C(O)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O2	3442.8	Semi standard non polar	33892256
4',5-Dihydroxy-7-methoxy-6-methylflavone,2TBDMS,isomer #1	COC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1C)C(=O)C=C(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O2	3689.6	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-Dihydroxy-7-methoxy-6-methylflavone GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0390000000-96ed347dca125a37ab8b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone GC-MS (2 TMS) - 70eV, Positive	splash10-00vi-3359700000-39a3db4ae015d2759a4c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 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-Dihydroxy-7-methoxy-6-methylflavone 10V, Positive-QTOF	splash10-0002-0090000000-e1cc5ed174d56766f340	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Positive-QTOF	splash10-0002-0090000000-5de2f7f2587cc093e362	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 40V, Positive-QTOF	splash10-0fb9-3790000000-315fa43c144dda47386d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 10V, Negative-QTOF	splash10-0002-0090000000-cba666d2db9505376ec1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Negative-QTOF	splash10-0002-0090000000-08b338d59b21f8b65306	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 40V, Negative-QTOF	splash10-0170-4960000000-ce232a098b2d2f42f311	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 10V, Positive-QTOF	splash10-0002-0090000000-9b410a4cce68ead03b3b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Positive-QTOF	splash10-0002-0090000000-68753556a141556a2a95	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 40V, Positive-QTOF	splash10-0a4i-0290000000-c8e4a7bfee4317a1cf50	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 10V, Negative-QTOF	splash10-0002-0090000000-bfe4eca51ec0a2a32edf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4',5-Dihydroxy-7-methoxy-6-methylflavone 20V, Negative-QTOF	splash10-0f7k-0090000000-11f4cbb2469ab3dc4376	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

FDB000647

KNApSAcK ID

C00013597

Chemspider ID

24843977

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44258359

PDB ID

Not Available

ChEBI ID

69917

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 4',5-Dihydroxy-7-methoxy-6-methylflavone (HMDB0029512)

MOL for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

3D MOL for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

3D SDF for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

3D-SDF for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

PDB for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

3D PDB for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

SMILES for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

INCHI for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

Structure for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

3D Structure for HMDB0029512 (4',5-Dihydroxy-7-methoxy-6-methylflavone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra