MiMeDB: Showing metabocard for Hesperetin (MMDBc0000610)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:51:03 UTC

Update Date

2024-09-27 19:09:01 UTC

Metabolite ID

MMDBc0000610

Metabolite Identification

Common Name

Hesperetin

Description

Hesperetin, also known as prestwick_908 or YSO2, belongs to the class of organic compounds known as 4'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C4' atom of the flavonoid backbone. Thus, hesperetin is considered to be a flavonoid lipid molecule. Hesperetin is a drug which is used for lowering cholesterol and, possibly, otherwise favorably affecting lipids. in vitro research also suggests the possibility that hesperetin might have some anticancer effects and that it might have some anti-aromatase activity, as well as activity again. Hesperetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Hesperetin exists in all living organisms, ranging from bacteria to humans. Hesperetin is a bitter tasting compound. Outside of the human body, Hesperetin is found, on average, in the highest concentration within a few different foods, such as limes, persian limes, and sweet oranges and in a lower concentration in grape wines, lemons, and pummelo. Hesperetin has also been detected, but not quantified in, several different foods, such as kiwis, nectarines, pears, alliums, and rosemaries. This could make hesperetin a potential biomarker for the consumption of these foods. A trihydroxyflavanone having the three hydroxy gropus located at the 3'-, 5- and 7-positions and an additional methoxy substituent at the 4'-position.

Structure

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

HMDB0005782
     RDKit          3D
Hesperetin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.2275   -0.0917    0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2335   -0.9442    0.2372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777   -0.5936    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943    0.6281    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419    0.9371    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836    0.0754    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278    0.5143    0.2284 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5903    0.8563   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659    1.4690   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    2.5796   -1.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9520    0.6591   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2943    0.8463   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828    1.7819   -1.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976    0.0400    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7562   -0.8959    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6894   -1.6928    1.6037 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4071   -1.0611    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4669   -0.2961    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -0.4560    0.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999   -1.1378   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453   -1.4836   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197   -2.7424   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220   -0.1180    1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1312    0.9555    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165   -0.4401    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2376    1.3161    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579    1.9087    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.4582    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -0.0585   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.5579   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256    2.4140   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    0.1908   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6735   -1.5700    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0926   -1.8174    1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -1.8152   -0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920   -2.9737   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  1
  8 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 22 36  1  0
M  END

1094
  Mrv1652305271900152D          

 22 24  0  0  1  0            999 V2000
    5.9369    0.2231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -2.2519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3793   -2.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3644    1.4606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    2.2856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8492    0.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2223   -0.1894    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2223   -1.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -1.0144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9369   -1.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    1.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3888   -1.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3888    0.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934    1.4606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1363   -1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1363   -0.1723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    0.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790    1.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.0481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2 11  2  0  0  0  0
  3 15  1  0  0  0  0
  4 21  1  0  0  0  0
  4 22  1  0  0  0  0
  5 17  1  0  0  0  0
  6 19  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  1  0  0  0
  8 11  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 15  2  0  0  0  0
 12 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 20  2  0  0  0  0
 15 18  1  0  0  0  0
 16 19  1  0  0  0  0
 17 21  2  0  0  0  0
 18 19  2  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000610

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1

> <INCHI_KEY>
AIONOLUJZLIMTK-AWEZNQCLSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
29.30120362969032

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
2.6774367846666665

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.332001059420389

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8617015285745655

> <JCHEM_PKA_STRONGEST_BASIC>
-4.618662915893278

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
77.75300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hesperetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005782
     RDKit          3D
Hesperetin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.2275   -0.0917    0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2335   -0.9442    0.2372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777   -0.5936    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943    0.6281    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419    0.9371    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836    0.0754    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278    0.5143    0.2284 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5903    0.8563   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659    1.4690   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    2.5796   -1.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9520    0.6591   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2943    0.8463   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828    1.7819   -1.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976    0.0400    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7562   -0.8959    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6894   -1.6928    1.6037 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4071   -1.0611    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4669   -0.2961    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -0.4560    0.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999   -1.1378   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453   -1.4836   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197   -2.7424   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220   -0.1180    1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1312    0.9555    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165   -0.4401    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2376    1.3161    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579    1.9087    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.4582    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -0.0585   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.5579   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256    2.4140   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    0.1908   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6735   -1.5700    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0926   -1.8174    1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -1.8152   -0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920   -2.9737   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  1
  8 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 22 36  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1094                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      11.082   0.416   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      11.082  -4.204   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.775  -4.257   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.414   2.726   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.081   4.266   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      16.519   0.454   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.748  -0.354   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748  -1.894   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   0.416   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.416  -1.894   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.082  -2.664   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.416  -0.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   1.956   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -0.354   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.792  -2.717   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.792   0.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.081   2.726   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.188  -1.926   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.188  -0.322   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747   0.416   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.747   1.956   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   1.956   0.000  0.00  0.00           C+0
CONECT    1    7   12                                                       
CONECT    2   11                                                            
CONECT    3   15                                                            
CONECT    4   21   22                                                       
CONECT    5   17                                                            
CONECT    6   19                                                            
CONECT    7    1    8    9                                                  
CONECT    8    7   11                                                       
CONECT    9    7   13   14                                                  
CONECT   10   11   12   15                                                  
CONECT   11    2    8   10                                                  
CONECT   12    1   10   16                                                  
CONECT   13    9   17                                                       
CONECT   14    9   20                                                       
CONECT   15    3   10   18                                                  
CONECT   16   12   19                                                       
CONECT   17    5   13   21                                                  
CONECT   18   15   19                                                       
CONECT   19    6   16   18                                                  
CONECT   20   14   21                                                       
CONECT   21    4   17   20                                                  
CONECT   22    4                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0005782
HETATM    1  C1  UNL     1      -6.227  -0.092   0.717  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.233  -0.944   0.237  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.878  -0.594   0.230  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.494   0.628   0.708  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.142   0.937   0.683  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.184   0.075   0.204  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.228   0.514   0.228  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.590   0.856  -1.224  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.966   1.469  -1.112  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.235   2.580  -1.575  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.952   0.659  -0.420  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.294   0.846  -0.658  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.783   1.782  -1.542  1.00  0.00           O  
HETATM   14  C11 UNL     1       5.198   0.040   0.038  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.756  -0.896   0.918  1.00  0.00           C  
HETATM   16  O4  UNL     1       5.689  -1.693   1.604  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.407  -1.061   1.135  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.467  -0.296   0.479  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.104  -0.456   0.693  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.600  -1.138  -0.266  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.945  -1.484  -0.258  1.00  0.00           C  
HETATM   22  O6  UNL     1      -3.320  -2.742  -0.753  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.322  -0.118   1.830  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.131   0.955   0.421  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.217  -0.440   0.302  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.238   1.316   1.088  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.858   1.909   1.066  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.336   1.458   0.786  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.718  -0.059  -1.834  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.131   1.558  -1.657  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.326   2.414  -2.115  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.250   0.191  -0.151  1.00  0.00           H  
HETATM   33  H11 UNL     1       6.673  -1.570   1.443  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.093  -1.817   1.844  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.854  -1.815  -0.642  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.292  -2.974  -0.739  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    6   27
CONECT    6    7   20
CONECT    7    8   19   28
CONECT    8    9   29   30
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   31
CONECT   14   15   15   32
CONECT   15   16   17
CONECT   16   33
CONECT   17   18   18   34
CONECT   18   19
CONECT   20   21   21   35
CONECT   21   22
CONECT   22   36
END

HMDB0005782
     RDKit          3D
Hesperetin
 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.2275   -0.0917    0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2335   -0.9442    0.2372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8777   -0.5936    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4943    0.6281    0.7080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1419    0.9371    0.6834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1836    0.0754    0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2278    0.5143    0.2284 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5903    0.8563   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9659    1.4690   -1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2354    2.5796   -1.5750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9520    0.6591   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2943    0.8463   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7828    1.7819   -1.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976    0.0400    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7562   -0.8959    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6894   -1.6928    1.6037 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4071   -1.0611    1.1350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4669   -0.2961    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1041   -0.4560    0.6929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999   -1.1378   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9453   -1.4836   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3197   -2.7424   -0.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3220   -0.1180    1.8303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1312    0.9555    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2165   -0.4401    0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2376    1.3161    1.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8579    1.9087    1.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.4582    0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -0.0585   -1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1311    1.5579   -1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3256    2.4140   -2.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500    0.1908   -0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6735   -1.5700    1.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0926   -1.8174    1.8437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8539   -1.8152   -0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2920   -2.9737   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 19  7  1  0
 18 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  1
  8 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 17 34  1  0
 20 35  1  0
 22 36  1  0
M  END

Synonyms

Value	Source
(-)-(S)-Hesperetin	ChEBI
(-)-Hesperetin	ChEBI
(S)-2,3-Dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
3',5,7-Trihydroxy-4'-methoxyflavanone	ChEBI
5,7, 3'-Trihydroxy-4'-methoxyflavanone	HMDB
5,7,3'-Trihydroxy-4'-methoxyflavanone	HMDB
Cyanidanon 4'-methyl ether 1626	HMDB
Hesperin	HMDB
Hesperitin	HMDB
Prestwick_908	HMDB
YSO2	HMDB

Molecular Formula

C₁₆H₁₄O₆

Average Mass

302.2788

Monoisotopic Mass

302.07903818

IUPAC Name

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

Traditional Name

hesperetin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1

InChI Identifier

InChI=1S/C16H14O6/c1-21-13-3-2-8(4-10(13)18)14-7-12(20)16-11(19)5-9(17)6-15(16)22-14/h2-6,14,17-19H,7H2,1H3/t14-/m0/s1

InChI Key

AIONOLUJZLIMTK-AWEZNQCLSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0792000000-043d1ca82d4702349341	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0udj-3860980000-a1715e067e13bbdada3e	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-da94c45c0a6bde515ea3	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0169000000-5d9b7fba914d229018a6	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 40V, Negative	splash10-053i-0920000000-b6ab2fed21176a341b28	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0009000000-b833c4c244a2461530ec	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-32f8b49c4bc1df10782a	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-0iki-0930000000-20176d350f94ae4a84ed	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0udi-2910000000-54a5cf5acd3ca156389e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0009000000-2a5462077f9208908972	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0139000000-0c743a741d25379011aa	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0w2i-0961000000-8406f0210238c955e23e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0gw0-0920000000-b833f9a80eb4ea8d3b13	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-052r-0910000000-943c442894f2e6d36fe3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0zfr-0925000000-20d9733844b315a5aac1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0f7c-0092000000-df166f951c1d37996e32	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0f79-0092000000-28f5918da43818b380bf	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0009000000-fda4f743655d07e229dd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ufr-0906000000-4ff368578ae1225967b0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0ufr-0900000000-aaca372b112b1730d913	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0900000000-8857224e3cadbbf71a7d	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0329000000-4364410cdc5a65b92032	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udr-0944000000-edd7b755d11b9331e6c9	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uki-3910000000-9e449d46da8305c0b794	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0109000000-21473197ac3beced4628	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0569000000-1e4d2574c341d9d9124f	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pbl-4940000000-c9a717aa36bf4402e6c7	2017-07-26	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.23 MHz, DMSO-d6, experimental)		2015-03-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	0.0011				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	20683461
Human Urine	Detected and Quantified	0.00154				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	20683461
Human Urine	Detected and Quantified	0.0216				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	21272408
Human Urine	Detected and Quantified	0.039				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	20683461
Human Urine	Detected and Quantified	0.0667				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	27273479
Human Urine	Detected and Quantified	100				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Urine	Detected and Quantified	180				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	17426744
Human Blood	Detected and Quantified	0.0222	0.0449			uM	Adult (>18 years old)	Female	Normal	HMDB	12395214
Human Urine	Detected and Quantified	0.03	0.09			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Urine	Detected and Quantified	0.180	0.510			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.200	1.0133			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16870009
Human Urine	Detected and Quantified	0.246	0.359			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	26814424
Human Blood	Detected and Quantified	0.35		0.05	0.66	uM	Adult (>18 years old)	Both	Normal	HMDB	17367568
Human Blood	Detected and Quantified	0.5		0.033	1.0	uM	Adult (>18 years old)	Both	Normal	HMDB	14751808
Human Urine	Detected and Quantified	1.0	0.48			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	16197573
Human Feces	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	20809621
Human Feces	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	20809621
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

References

Showing metabocard for Hesperetin (MMDBc0000610)

MOL for #<Metabolite:0x00007fb7ab86f3c0>

3D MOL for #<Metabolite:0x00007fb7ab86f3c0>

3D SDF for #<Metabolite:0x00007fb7ab86f3c0>

3D-SDF for #<Metabolite:0x00007fb7ab86f3c0>

PDB for #<Metabolite:0x00007fb7ab86f3c0>

3D PDB for #<Metabolite:0x00007fb7ab86f3c0>

SMILES for #<Metabolite:0x00007fb7ab86f3c0>

INCHI for #<Metabolite:0x00007fb7ab86f3c0>

Structure for #<Metabolite:0x00007fb7ab86f3c0>

3D Structure for #<Metabolite:0x00007fb7ab86f3c0>