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 (2S)-hesperetin, 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. 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 exists in all living organisms, ranging from bacteria to humans. Hesperetin is a bitter tasting compound. Hesperetin is found, on average, in the highest concentration within a few different foods, such as limes (Citrus aurantiifolia), persian limes (Citrus latifolia), and sweet oranges (Citrus sinensis) and in a lower concentration in welsh onions (Allium fistulosum), mandarin orange (clementine, tangerine), and pummelos (Citrus maxima). Hesperetin has also been detected, but not quantified in, several different foods, such as red raspberries (Rubus idaeus), kiwis (Actinidia chinensis), garden onion (var.), common thymes (Thymus vulgaris), and cashew nuts (Anacardium occidentale). This could make hesperetin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Hesperetin.

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
(2S)-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
Hesperitin	MeSH
5,7, 3'-Trihydroxy-4'-methoxyflavanone	HMDB
5,7,3'-Trihydroxy-4'-methoxyflavanone	HMDB
Cyanidanon 4'-methyl ether 1626	HMDB
Hesperin	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

Description

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

4'-O-methylated flavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

3'-hydroxyflavanones (CHEBI:28230 )
trihydroxyflavanone (CHEBI:28230 )
monomethoxyflavanone (CHEBI:28230 )
flavanones (C01709 )
Flavanones (LMPK12140003 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.52	ALOGPS
logP	2.68	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.86	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	77.75 m³·mol⁻¹	ChemAxon
Polarizability	29.3 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

Spectra

Not Available

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192159	Sterol O-acyltransferase 1	Enzyme	P35610	Homo sapiens
MMDBp0193115	Cytochrome P450 1A2	Unknown	P05177	Homo sapiens
MMDBp0193163	Microsomal triglyceride transfer protein large subunit	Transporter	P55157	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Food Exposures

Other Exposures

Source Type	Data Source	Reference
General Exposome	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

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