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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 10:39:22 UTC

Update Date

2021-09-26 23:05:25 UTC

HMDB ID

HMDB0252684

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Genkwanin

Description

Genkwanin, also known as 7-methylapigenin, 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, genkwanin is considered to be a flavonoid. Genkwanin is a bitter tasting compound. Genkwanin has been detected, but not quantified in, several different foods, such as common sages (Salvia officinalis), common thymes (Thymus vulgaris), rosemaries (Rosmarinus officinalis), sweet basils (Ocimum basilicum), and winter savories (Satureja montana). This could make genkwanin a potential biomarker for the consumption of these foods. Genkwanin 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 a significant number of articles have been published on Genkwanin. This compound has been identified in human blood as reported by (PMID: 31557052 ). Genkwanin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Genkwanin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0252684
     RDKit          3D
Genkwanin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.6297   -1.4309    0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393   -1.6667    0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   -0.7609    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7190    0.3993   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914    1.2905   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    2.4547   -1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4488    1.0195   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5263    1.9006   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    2.9579   -1.5843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    1.5924   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241    0.4284   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.0995   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    0.8636   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    0.4964   -0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3177   -0.6777    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6314   -1.1106    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.4784    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -1.1029    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -0.3833    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -0.1275    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -1.0031    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1908   -2.3392    1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8985   -1.0885   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465   -0.5912    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7881    0.6203   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1976    2.6445   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    2.2836   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549    1.7978   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899    1.1241   -0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0797   -0.8142    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4991   -2.4215    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -1.7649    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.9163    1.0627 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  2  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 20  7  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END


  Mrv0541 02241221522D          

 21 23  0  0  0  0            999 V2000
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
    3.5724    1.2375    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  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
 14 19  1  0  0  0  0
 17 20  1  0  0  0  0
  5 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0252684

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

> <INCHI_KEY>
JPMYFOBNRRGFNO-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.87293806969861

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
2.8525831896666665

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.953927091020219

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.336700889158914

> <JCHEM_PKA_STRONGEST_BASIC>
-4.74548958567233

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.39620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.59e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
genkwanin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0252684
     RDKit          3D
Genkwanin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.6297   -1.4309    0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393   -1.6667    0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   -0.7609    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7190    0.3993   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914    1.2905   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    2.4547   -1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4488    1.0195   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5263    1.9006   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    2.9579   -1.5843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    1.5924   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241    0.4284   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.0995   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    0.8636   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    0.4964   -0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3177   -0.6777    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6314   -1.1106    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.4784    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -1.1029    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -0.3833    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -0.1275    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -1.0031    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1908   -2.3392    1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8985   -1.0885   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465   -0.5912    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7881    0.6203   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1976    2.6445   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    2.2836   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549    1.7978   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899    1.1241   -0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0797   -0.8142    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4991   -2.4215    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -1.7649    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.9163    1.0627 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  2  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 20  7  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  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  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12                                                            
CONECT   14   10   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20   17                                                            
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0252684
HETATM    1  C1  UNL     1      -5.630  -1.431   0.895  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.239  -1.667   0.990  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.307  -0.761   0.479  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.719   0.399  -0.137  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.791   1.291  -0.640  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.213   2.455  -1.258  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.449   1.020  -0.525  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.526   1.901  -1.022  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.880   2.958  -1.584  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.821   1.592  -0.888  1.00  0.00           C  
HETATM   11  C8  UNL     1       1.224   0.428  -0.270  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.632   0.099  -0.126  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.675   0.864  -0.563  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.001   0.496  -0.396  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.318  -0.678   0.230  1.00  0.00           C  
HETATM   16  O4  UNL     1       6.631  -1.111   0.432  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.270  -1.478   0.687  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.954  -1.103   0.515  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.284  -0.383   0.190  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.995  -0.128   0.083  1.00  0.00           C  
HETATM   21  C16 UNL     1      -1.958  -1.003   0.578  1.00  0.00           C  
HETATM   22  H1  UNL     1      -6.191  -2.339   1.127  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.898  -1.089  -0.146  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.946  -0.591   1.557  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.788   0.620  -0.231  1.00  0.00           H  
HETATM   26  H5  UNL     1      -4.198   2.645  -1.337  1.00  0.00           H  
HETATM   27  H6  UNL     1       1.554   2.284  -1.278  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.455   1.798  -1.062  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.790   1.124  -0.753  1.00  0.00           H  
HETATM   30  H9  UNL     1       7.080  -0.814   1.310  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.499  -2.421   1.190  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.186  -1.765   0.891  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.644  -1.916   1.063  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8   20
CONECT    8    9    9   10
CONECT   10   11   11   27
CONECT   11   12   19
CONECT   12   13   13   18
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16   17
CONECT   16   30
CONECT   17   18   18   31
CONECT   18   32
CONECT   19   20
CONECT   20   21   21
CONECT   21   33
END

HMDB0252684
     RDKit          3D
Genkwanin
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.6297   -1.4309    0.8952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2393   -1.6667    0.9895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3069   -0.7609    0.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7190    0.3993   -0.1371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7914    1.2905   -0.6398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    2.4547   -1.2577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4488    1.0195   -0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5263    1.9006   -1.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    2.9579   -1.5843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8206    1.5924   -0.8881 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2241    0.4284   -0.2698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    0.0995   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    0.8636   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0010    0.4964   -0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3177   -0.6777    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6314   -1.1106    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702   -1.4784    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9537   -1.1029    0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2839   -0.3833    0.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9951   -0.1275    0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -1.0031    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1908   -2.3392    1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8985   -1.0885   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9465   -0.5912    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7881    0.6203   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1976    2.6445   -1.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    2.2836   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4549    1.7978   -1.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7899    1.1241   -0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0797   -0.8142    1.3099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4991   -2.4215    1.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862   -1.7649    0.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6439   -1.9163    1.0627 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  2  0
 11 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 20  7  1  0
 18 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,4'-Dihydroxy-7-methoxyflavone	ChEBI
7-Methylapigenin	ChEBI
Apigenin 7-methyl ether	ChEBI
5,4'-Dihydroxy-7-methoxy-flavone	MeSH
Gengkwanin	MeSH

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.2635

Monoisotopic Molecular Weight

284.068473494

IUPAC Name

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

Traditional Name

genkwanin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H12O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChI Key

JPMYFOBNRRGFNO-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:75718 )
monomethoxyflavone (CHEBI:75718 )
flavones (C10046 )
Flavones and Flavonols (C10046 )
Flavones and Flavonols (LMPK12111018 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0252684)

Not Available

Anti bacterial (HMDB: HMDB0252684)
Purgative (HMDB: HMDB0252684)

Industrial application

Agriculture

Pesticide (HMDB: HMDB0252684)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.39	ALOGPS
logP	2.85	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.34	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	77.4 m³·mol⁻¹	ChemAxon
Polarizability	28.87 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]+	168.314	30932474
DeepCCS	[M-H]-	165.956	30932474
DeepCCS	[M-2H]-	198.954	30932474
DeepCCS	[M+Na]+	174.407	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.0	32859911
AllCCS	[M+NH4]+	168.4	32859911
AllCCS	[M+Na]+	169.5	32859911
AllCCS	[M-H]-	165.8	32859911
AllCCS	[M+Na-2H]-	165.1	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	13.5473 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.16 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2434.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	351.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	171.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	202.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	481.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	585.5 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	621.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1189.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.3 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	1434.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	411.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	403.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	207.2 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	106.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Genkwanin	COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1	4447.2	Standard polar	33892256
Genkwanin	COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1	2929.6	Standard non polar	33892256
Genkwanin	COC1=CC(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1	3060.7	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Genkwanin

METLIN ID

Not Available

PubChem Compound

5281617

PDB ID

Not Available

ChEBI ID

75718

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1588971

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Genkwanin (HMDB0252684)

MOL for HMDB0252684 (Genkwanin)

3D MOL for HMDB0252684 (Genkwanin)

3D SDF for HMDB0252684 (Genkwanin)

3D-SDF for HMDB0252684 (Genkwanin)

PDB for HMDB0252684 (Genkwanin)

3D PDB for HMDB0252684 (Genkwanin)

SMILES for HMDB0252684 (Genkwanin)

INCHI for HMDB0252684 (Genkwanin)

Structure for HMDB0252684 (Genkwanin)

3D Structure for HMDB0252684 (Genkwanin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized