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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (1) Show 3 proteins XML

enzymes (2)transporters (1) Show 3 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2007-01-22 09:25:30 UTC

Update Date

2022-03-07 02:49:28 UTC

HMDB ID

HMDB0005782

Secondary Accession Numbers

HMDB05782

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 also seems to upregulate the LDL receptor. Hesperetin, in the form of its glycoside , is the predominant flavonoid in lemons and oranges. 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. Hesperetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hesperetin is a bitter tasting compound. 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 pummelo, welsh onions, and lemons. Hesperetin has also been detected, but not quantified, in several different foods, such as yellow bell peppers, carrots, rapinis, hazelnuts, and beers. Hesperetin is a biomarker for the consumption of citrus fruits. Hesperetin reduces or inhibits the activity of acyl-coenzyme A:cholesterol acyltransferase genes (ACAT1 and ACAT2) and it reduces microsomal triglyceride transfer protein (MTP) activity.

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>
HMDB0005782

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

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

520-33-2

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 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	227.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	2.60	PERRISSOUD,D & TESTA,B (1986)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	178.488	30932474
[M+H]+	Baker	176.544	30932474
[M-H]-	Not Available	178.488	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001935
[M+H]+	Not Available	176.544	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001935

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	172.182	31661259
DarkChem	[M-H]-	174.389	31661259
DeepCCS	[M+H]+	170.863	30932474
DeepCCS	[M-H]-	168.505	30932474
DeepCCS	[M-2H]-	202.489	30932474
DeepCCS	[M+Na]+	177.716	30932474
AllCCS	[M+H]+	170.6	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	170.7	32859911
AllCCS	[M+HCOO]-	170.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.44 minutes	32390414
Predicted by Siyang on May 30, 2022	11.6431 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.68 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2000.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	244.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	137.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	154.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	566.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	474.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	946.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	402.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1247.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	432.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	264.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	131.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hesperetin	COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1	4225.7	Standard polar	33892256
Hesperetin	COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1	2998.8	Standard non polar	33892256
Hesperetin	COC1=C(O)C=C(C=C1)[C@@H]1CC(=O)C2=C(O)C=C(O)C=C2O1	2989.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hesperetin,1TMS,isomer #1	COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	2928.7	Semi standard non polar	33892256
Hesperetin,1TMS,isomer #2	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O	2949.6	Semi standard non polar	33892256
Hesperetin,1TMS,isomer #3	COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O	2966.5	Semi standard non polar	33892256
Hesperetin,2TMS,isomer #1	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C	2867.3	Semi standard non polar	33892256
Hesperetin,2TMS,isomer #2	COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C	2884.8	Semi standard non polar	33892256
Hesperetin,2TMS,isomer #3	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O	2867.4	Semi standard non polar	33892256
Hesperetin,3TMS,isomer #1	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C	2856.0	Semi standard non polar	33892256
Hesperetin,1TBDMS,isomer #1	COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3214.6	Semi standard non polar	33892256
Hesperetin,1TBDMS,isomer #2	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O	3227.3	Semi standard non polar	33892256
Hesperetin,1TBDMS,isomer #3	COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O	3241.2	Semi standard non polar	33892256
Hesperetin,2TBDMS,isomer #1	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O[Si](C)(C)C(C)(C)C	3380.3	Semi standard non polar	33892256
Hesperetin,2TBDMS,isomer #2	COC1=CC=C([C@@H]2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3394.8	Semi standard non polar	33892256
Hesperetin,2TBDMS,isomer #3	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O	3392.6	Semi standard non polar	33892256
Hesperetin,3TBDMS,isomer #1	COC1=CC=C([C@@H]2CC(=O)C3=C(C=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O[Si](C)(C)C(C)(C)C	3537.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hesperetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0792000000-043d1ca82d4702349341	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hesperetin GC-MS (3 TMS) - 70eV, Positive	splash10-0udj-3860980000-a1715e067e13bbdada3e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hesperetin 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 - Hesperetin ESI-TOF 10V, Negative-QTOF	splash10-0udi-0009000000-da94c45c0a6bde515ea3	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin ESI-TOF 20V, Negative-QTOF	splash10-0udi-0169000000-5d9b7fba914d229018a6	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin ESI-TOF 40V, Negative-QTOF	splash10-053i-0920000000-b6ab2fed21176a341b28	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin ESI-TOF , Negative-QTOF	splash10-0udi-0009000000-b833c4c244a2461530ec	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin ESI-TOF 10V, Negative-QTOF	splash10-0udi-0009000000-32f8b49c4bc1df10782a	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin ESI-TOF 30V, Negative-QTOF	splash10-0iki-0930000000-20176d350f94ae4a84ed	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-qTof , Positive-QTOF	splash10-0udi-2910000000-54a5cf5acd3ca156389e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOF	splash10-0udi-0009000000-2a5462077f9208908972	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOF	splash10-0udi-0139000000-0c743a741d25379011aa	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOF	splash10-0w2i-0961000000-8406f0210238c955e23e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOF	splash10-0gw0-0920000000-b833f9a80eb4ea8d3b13	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOF	splash10-052r-0910000000-943c442894f2e6d36fe3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , negative-QTOF	splash10-0zfr-0925000000-20d9733844b315a5aac1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin Linear Ion Trap , negative-QTOF	splash10-0f7c-0092000000-df166f951c1d37996e32	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin Linear Ion Trap , negative-QTOF	splash10-0f79-0092000000-28f5918da43818b380bf	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , positive-QTOF	splash10-0udi-0009000000-fda4f743655d07e229dd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , positive-QTOF	splash10-0ufr-0906000000-4ff368578ae1225967b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , positive-QTOF	splash10-0ufr-0900000000-aaca372b112b1730d913	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Hesperetin LC-ESI-QTOF , positive-QTOF	splash10-0udi-0900000000-8857224e3cadbbf71a7d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hesperetin 10V, Positive-QTOF	splash10-0udi-0329000000-4364410cdc5a65b92032	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hesperetin 20V, Positive-QTOF	splash10-0udr-0944000000-edd7b755d11b9331e6c9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hesperetin 40V, Positive-QTOF	splash10-0uki-3910000000-9e449d46da8305c0b794	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hesperetin 10V, Negative-QTOF	splash10-0udi-0109000000-21473197ac3beced4628	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hesperetin 20V, Negative-QTOF	splash10-0udi-0569000000-1e4d2574c341d9d9124f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hesperetin 40V, Negative-QTOF	splash10-0pbl-4940000000-c9a717aa36bf4402e6c7	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.5 (0.033-1.0) uM	Adult (>18 years old)	Both	Normal	14751808	details
Blood	Detected and Quantified	0.35 (0.05-0.66) uM	Adult (>18 years old)	Both	Normal	17367568	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	20441150	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	18710603	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	16197573	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	10637051	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	16424119	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	15969493	details
Blood	Detected and Quantified	0.0222 +/- 0.0449 uM	Adult (>18 years old)	Female	Normal	12395214	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	0.03 +/- 0.09 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Detected and Quantified	1.0 +/- 0.48 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	20441150	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	18710603	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	16197573	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	10637051	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	16424119	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 203	15969493	details
Urine	Detected and Quantified	100 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	180 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17426744	details
Urine	Detected and Quantified	0.0667 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.246 +/- 0.359 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	0.0011 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20683461	details
Urine	Detected and Quantified	0.00154 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20683461	details
Urine	Detected and Quantified	0.0216 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21272408	details
Urine	Detected and Quantified	0.039 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	20683461	details
Urine	Detected and Quantified	0.180 +/- 0.510 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected and Quantified	0.200 +/- 1.0133 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	16870009	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB01094

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Hesperetin

METLIN ID

Not Available

PubChem Compound

72281

PDB ID

Not Available

ChEBI ID

28230

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000471

Good Scents ID

rw1594741

References

Synthesis Reference

Shinoda, J.; Kawagoye, M. Polyhydroxychalcones, polyhydroxyhydrochalcones and polyhydroxyflavanones. III. Synthesis of hesperetin. Yakugaku Zasshi (1928), 48 938-41.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Sterol O-acyltransferase 1

General function:: Involved in acyl-CoA binding
Specific function:: Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:: SOAT1
Uniprot ID:: P35610
Molecular weight:: 58130.665

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

Transporters

Enzyme Details

1. Microsomal triglyceride transfer protein large subunit

General function:: Involved in lipid transporter activity
Specific function:: Catalyzes the transport of triglyceride, cholesteryl ester, and phospholipid between phospholipid surfaces. Required for the secretion of plasma lipoproteins that contain apolipoprotein B
Gene Name:: MTTP
Uniprot ID:: P55157
Molecular weight:: 99350.3

Showing metabocard for Hesperetin (HMDB0005782)

MOL for HMDB0005782 (Hesperetin)

3D MOL for HMDB0005782 (Hesperetin)

3D SDF for HMDB0005782 (Hesperetin)

3D-SDF for HMDB0005782 (Hesperetin)

PDB for HMDB0005782 (Hesperetin)

3D PDB for HMDB0005782 (Hesperetin)

SMILES for HMDB0005782 (Hesperetin)

INCHI for HMDB0005782 (Hesperetin)

Structure for HMDB0005782 (Hesperetin)

3D Structure for HMDB0005782 (Hesperetin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Transporters