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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 17:34:41 UTC

Update Date

2022-09-22 18:34:57 UTC

HMDB ID

HMDB0030090

Secondary Accession Numbers

HMDB30090

Metabolite Identification

Common Name

Sakuranetin

Description

Sakuranetin, also known as (2S)-sakuranetin, 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, sakuranetin is considered to be a flavonoid. Sakuranetin is found, on average, in the highest concentration within mexican oreganos (Lippia graveolens). Sakuranetin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), black walnuts (Juglans nigra), wild carrots (Daucus carota), walnuts (Juglans), and prunus (cherry, plum). This could make sakuranetin a potential biomarker for the consumption of these foods. Sakuranetin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Sakuranetin.

Structure

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

HMDB0030090
     RDKit          3D
Sakuranetin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4090    2.5557   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    1.1954   -0.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5611    0.2683   -0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7920   -1.0511   -0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634   -1.9352   -0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9143   -3.2782   -0.9818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297   -1.5126   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.1829    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    0.7128   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0722    0.2294    0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -0.6775    0.8555 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2537    0.0531    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.7788   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553    1.4547   -0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5808    1.3990    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847    2.0829   -0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4314    0.6654    1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723   -0.0080    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550   -1.8691   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -2.4336   -0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502   -3.6571    0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877    2.6171    0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436    3.0801   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036    3.0020   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7577   -1.4161   -1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7558   -3.6868   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    1.7515    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -0.9774    1.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770    0.8338   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    2.0231   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5280    2.0298    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.6188    1.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1696   -0.5796    2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243   -2.5827    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2203   -1.5038   -1.0896 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  1  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
  9  3  1  0
 18 12  1  0
 20  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  9 27  1  0
 11 28  1  1
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
M  END

SAK
  Mrv0541 02241214092D          

 22 24  0  0  0  0            999 V2000
   -2.0095   -0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240    0.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7240    1.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4385    1.5349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0095    1.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2950    1.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2950    0.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806   -0.1151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1339    0.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806   -0.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -1.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1339   -2.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8484   -0.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8484   -0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628    0.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773   -0.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918    0.2974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9918    1.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2773   -0.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628   -1.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5628   -2.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806    0.4688    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 22  1  6  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 20  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030090

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

> <INCHI_KEY>
DJOJDHGQRNZXQQ-AWEZNQCLSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.408587431441504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.9810021063333334

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.030780421501772

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.331411304247268

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9124888523211405

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sakuranetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030090
     RDKit          3D
Sakuranetin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4090    2.5557   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    1.1954   -0.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5611    0.2683   -0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7920   -1.0511   -0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634   -1.9352   -0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9143   -3.2782   -0.9818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297   -1.5126   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.1829    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    0.7128   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0722    0.2294    0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -0.6775    0.8555 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2537    0.0531    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.7788   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553    1.4547   -0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5808    1.3990    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847    2.0829   -0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4314    0.6654    1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723   -0.0080    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550   -1.8691   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -2.4336   -0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502   -3.6571    0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877    2.6171    0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436    3.0801   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036    3.0020   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7577   -1.4161   -1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7558   -3.6868   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    1.7515    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -0.9774    1.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770    0.8338   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    2.0231   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5280    2.0298    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.6188    1.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1696   -0.5796    2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243   -2.5827    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2203   -1.5038   -1.0896 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  1  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
  9  3  1  0
 18 12  1  0
 20  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  9 27  1  0
 11 28  1  1
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: SAK                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.751  -0.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.085   0.555   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.085   2.095   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -6.419   2.865   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.751   2.865   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.417   2.095   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.417   0.555   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.084  -0.215   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.250   0.555   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.084  -1.755   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.250  -2.525   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.250  -4.065   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.584  -1.755   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.584  -0.215   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.917   0.555   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.251  -0.215   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.585   0.555   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.585   2.095   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.251  -1.755   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.917  -2.525   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.917  -4.065   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -1.084   0.875   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7    9   10   22                                             
CONECT    9    8   14                                                       
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14    9   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   13   19   21                                                  
CONECT   21   20                                                            
CONECT   22    8                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030090
HETATM    1  C1  UNL     1      -4.409   2.556  -0.374  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.580   1.195  -0.675  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.561   0.268  -0.532  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.792  -1.051  -0.844  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.763  -1.935  -0.690  1.00  0.00           C  
HETATM    6  O2  UNL     1      -2.914  -3.278  -0.982  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.530  -1.513  -0.234  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.301  -0.183   0.080  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.340   0.713  -0.075  1.00  0.00           C  
HETATM   10  O3  UNL     1      -0.072   0.229   0.533  1.00  0.00           O  
HETATM   11  C8  UNL     1       0.979  -0.678   0.855  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.254   0.053   0.594  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.387   0.779  -0.563  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.555   1.455  -0.812  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.581   1.399   0.097  1.00  0.00           C  
HETATM   16  O4  UNL     1       5.785   2.083  -0.138  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.431   0.665   1.255  1.00  0.00           C  
HETATM   18  C14 UNL     1       3.272  -0.008   1.508  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.955  -1.869  -0.081  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.411  -2.434  -0.059  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.650  -3.657   0.103  1.00  0.00           O  
HETATM   22  H1  UNL     1      -4.288   2.617   0.746  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.344   3.080  -0.671  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.504   3.002  -0.814  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.758  -1.416  -1.207  1.00  0.00           H  
HETATM   26  H5  UNL     1      -3.756  -3.687  -1.315  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.211   1.752   0.154  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.884  -0.977   1.918  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.577   0.834  -1.300  1.00  0.00           H  
HETATM   30  H9  UNL     1       3.643   2.023  -1.731  1.00  0.00           H  
HETATM   31  H10 UNL     1       6.528   2.030   0.543  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.238   0.619   1.975  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.170  -0.580   2.420  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.724  -2.583   0.241  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.220  -1.504  -1.090  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8   20
CONECT    8    9    9   10
CONECT    9   27
CONECT   10   11
CONECT   11   12   19   28
CONECT   12   13   13   18
CONECT   13   14   29
CONECT   14   15   15   30
CONECT   15   16   17
CONECT   16   31
CONECT   17   18   18   32
CONECT   18   33
CONECT   19   20   34   35
CONECT   20   21   21
END

HMDB0030090
     RDKit          3D
Sakuranetin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -4.4090    2.5557   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5803    1.1954   -0.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5611    0.2683   -0.5316 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7920   -1.0511   -0.8439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7634   -1.9352   -0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9143   -3.2782   -0.9818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5297   -1.5126   -0.2335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3012   -0.1829    0.0799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3403    0.7128   -0.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0722    0.2294    0.5328 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -0.6775    0.8555 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2537    0.0531    0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3867    0.7788   -0.5627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553    1.4547   -0.8124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5808    1.3990    0.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7847    2.0829   -0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4314    0.6654    1.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2723   -0.0080    1.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9550   -1.8691   -0.0810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4112   -2.4336   -0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6502   -3.6571    0.1026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877    2.6171    0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3436    3.0801   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5036    3.0020   -0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7577   -1.4161   -1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7558   -3.6868   -1.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2108    1.7515    0.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8839   -0.9774    1.9179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5770    0.8338   -1.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6433    2.0231   -1.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5280    2.0298    0.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2383    0.6188    1.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1696   -0.5796    2.4205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7243   -2.5827    0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2203   -1.5038   -1.0896 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  1  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
  9  3  1  0
 18 12  1  0
 20  7  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
  9 27  1  0
 11 28  1  1
 13 29  1  0
 14 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-Sakuranetin	ChEBI
(S)-(-)-4',5-Dihydroxy-7-methoxyflavanone	ChEBI
(S)-2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one	ChEBI
4',5-Dihydroxy-7-methoxyflavanone	ChEBI
Naringenin 7-methyl ether	ChEBI
5,4'-Dihydroxy-7-methoxyflavanone	HMDB
7-O-Methylnaringenin	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

sakuranetin

CAS Registry Number

2957-21-3

SMILES

[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

InChI Key

DJOJDHGQRNZXQQ-AWEZNQCLSA-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
Flavanone
4'-hydroxyflavonoid
5-hydroxyflavonoid
Hydroxyflavonoid
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavanone (CHEBI:28927 )
dihydroxyflavanone (CHEBI:28927 )
flavonoid phytoalexin (CHEBI:28927 )
flavanones (C09833 )
Flavanones (LMPK12140571 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030090)
Cell membrane (HMDB: HMDB0030090)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030090)

Source

Exogenous

Exogenous (HMDB: HMDB0030090)

Food

Food (HMDB: HMDB0030090)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Fruit

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)

Berry

Blackcurrant (FooDB: FOOD00155)

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)

Nut

Walnut (FooDB: FOOD00608)
Black walnut (FooDB: FOOD00093)

Herb and spice

Herb

Mexican oregano (FooDB: FOOD00102)

Endogenous

Endogenous (HMDB: HMDB0030090)

Plant

Plant (HMDB: HMDB0030090)
Poaceae (HMDB: HMDB0030090)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0030090)

Agriculture

Pesticide

Fungicide (HMDB: HMDB0030090)

Pesticide (HMDB: HMDB0030090)

Biological role

Anti bacterial (HMDB: HMDB0030090)
Anti septic (HMDB: HMDB0030090)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	152 °C	Not Available
Boiling Point	555.90 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	109.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.370 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	2.86	ALOGPS
logP	2.98	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.9	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	75.77 m³·mol⁻¹	ChemAxon
Polarizability	29.41 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]+	166.515	31661259
DarkChem	[M-H]-	169.156	31661259
DeepCCS	[M+H]+	167.65	30932474
DeepCCS	[M-H]-	165.292	30932474
DeepCCS	[M-2H]-	199.44	30932474
DeepCCS	[M+Na]+	174.63	30932474
AllCCS	[M+H]+	167.2	32859911
AllCCS	[M+H-H2O]+	163.5	32859911
AllCCS	[M+NH4]+	170.7	32859911
AllCCS	[M+Na]+	171.7	32859911
AllCCS	[M-H]-	168.5	32859911
AllCCS	[M+Na-2H]-	167.9	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sakuranetin	[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1	3921.1	Standard polar	33892256
Sakuranetin	[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1	2839.3	Standard non polar	33892256
Sakuranetin	[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1	2820.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sakuranetin,1TMS,isomer #1	COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2750.6	Semi standard non polar	33892256
Sakuranetin,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)OC2=C1	2808.7	Semi standard non polar	33892256
Sakuranetin,2TMS,isomer #1	COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C)C=C3)O2)C(O[Si](C)(C)C)=C1	2800.3	Semi standard non polar	33892256
Sakuranetin,1TBDMS,isomer #1	COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3007.9	Semi standard non polar	33892256
Sakuranetin,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)OC2=C1	3072.0	Semi standard non polar	33892256
Sakuranetin,2TBDMS,isomer #1	COC1=CC2=C(C(=O)C[C@@H](C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3268.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)	splash10-0gdr-1950300000-a48312953ffcce6caa36	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)	splash10-056r-2951400000-d20272b440111f7a94e8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)	splash10-0gdr-1950300000-a48312953ffcce6caa36	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Sakuranetin GC-EI-TOF (Non-derivatized)	splash10-056r-2951400000-d20272b440111f7a94e8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sakuranetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1490000000-64eb4f6a24c41e1fbefa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sakuranetin GC-MS (2 TMS) - 70eV, Positive	splash10-06di-7948800000-c577b426dfaff9381d6b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sakuranetin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin LC-ESI-QFT 20V, positive-QTOF	splash10-014j-0900000000-54b50a99fb1941ecf021	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin LC-ESI-IT 20V, positive-QTOF	splash10-014j-0900000000-4702d57aa6a61bd59567	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOF	splash10-000i-0090000000-9cf4fa799bfdc4e4130b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOF	splash10-014i-0900000000-a8ce07e74597351565e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOF	splash10-00kr-0980000000-ad4f98ec1505fcea7278	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 30V, Positive-QTOF	splash10-014i-0900000000-2ac9f17f26389e03f793	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 50V, Positive-QTOF	splash10-00kf-9700000000-7510c0e1f415ab13f395	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 50V, Positive-QTOF	splash10-00kf-8900000000-890610439b8c00d535b8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 30V, Positive-QTOF	splash10-014i-0900000000-662e43a055eea0b8da6d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 50V, Positive-QTOF	splash10-00kf-8900000000-30c9f7d08bfa3bac40b3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 30V, Positive-QTOF	splash10-014i-0900000000-ff261837f1c0ee877f44	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOF	splash10-00kr-0980000000-2156366d1516097a79e8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOF	splash10-00kr-0980000000-dd5a370f9941d2861b69	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOF	splash10-000i-0090000000-72ef3a1b0a3a8e98b306	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOF	splash10-014i-0900000000-9c1d1e5a9b35f8821e91	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOF	splash10-00kr-0890000000-cf1b6b4990b6fefcaf01	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOF	splash10-000i-0090000000-e2d490f2b12fa6f624a7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOF	splash10-00kf-8900000000-bfd5bf6ff85e42769eb7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sakuranetin 6V, Positive-QTOF	splash10-014i-0900000000-4fadcc8d663cfc88b52b	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sakuranetin 10V, Positive-QTOF	splash10-000i-0290000000-5751ae9cb3dcf7cec01c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sakuranetin 20V, Positive-QTOF	splash10-014r-0890000000-32592494194e58ee1224	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sakuranetin 40V, Positive-QTOF	splash10-01ba-3910000000-cb744b8c05b1a8820085	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sakuranetin 10V, Negative-QTOF	splash10-000i-0090000000-1a79d429ac0d0568bc14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sakuranetin 20V, Negative-QTOF	splash10-00kr-0290000000-3868b08e8e2294ef0348	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sakuranetin 40V, Negative-QTOF	splash10-014i-5940000000-e495c14f115c39f42fae	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08517

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Sakuranetin

METLIN ID

Not Available

PubChem Compound

73571

PDB ID

SAK

ChEBI ID

28927

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1588731

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kim BG, Jung BR, Lee Y, Hur HG, Lim Y, Ahn JH: Regiospecific flavonoid 7-O-methylation with Streptomyces avermitilis O-methyltransferase expressed in Escherichia coli. J Agric Food Chem. 2006 Feb 8;54(3):823-8. [PubMed:16448189 ]
(). Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S. (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol. 2012 Feb;53(2):e1.. .

Showing metabocard for Sakuranetin (HMDB0030090)

MOL for HMDB0030090 (Sakuranetin)

3D MOL for HMDB0030090 (Sakuranetin)

3D SDF for HMDB0030090 (Sakuranetin)

3D-SDF for HMDB0030090 (Sakuranetin)

PDB for HMDB0030090 (Sakuranetin)

3D PDB for HMDB0030090 (Sakuranetin)

SMILES for HMDB0030090 (Sakuranetin)

INCHI for HMDB0030090 (Sakuranetin)

Structure for HMDB0030090 (Sakuranetin)

3D Structure for HMDB0030090 (Sakuranetin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra