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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:38:47 UTC

Update Date

2022-03-07 02:52:41 UTC

HMDB ID

HMDB0030746

Secondary Accession Numbers

HMDB30746

Metabolite Identification

Common Name

5,7,3'-Trihydroxy-4'-methoxyflavanone

Description

5,7,3'-Trihydroxy-4'-methoxyflavanone 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. Based on a literature review a small amount of articles have been published on 5,7,3'-Trihydroxy-4'-methoxyflavanone.

Structure

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

HMDB0030746
     RDKit          3D
5,7,3'-Trihydroxy-4'-methoxyflavanone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.2383   -0.0642    0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837   -0.8581    0.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -0.4509    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.7418    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077    1.0802    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395    0.2502    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668    0.6701    0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554    1.2813   -1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.7117   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242    0.6325   -2.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594    0.2085   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022    0.2613   -0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844    0.8198   -2.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2087   -0.2520    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547   -0.8140    1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6157   -1.3390    2.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -0.8608    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -0.3652    0.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239   -0.3746    0.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548   -0.9416   -0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8886   -1.2784   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2715   -2.4839   -1.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2096   -0.0744    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1614    0.9868    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2085   -0.5325    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2156    1.4007    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8227    2.0257    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.4590    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1043    1.0888   -1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8113    2.3759   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    1.2349   -2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2577   -0.1991   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505   -0.7047    2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0055   -1.2971    2.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7715   -1.5743   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2404   -2.7646   -1.0535 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  0
  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

Hesperetin
  Mrv1572001071617292D          

 22 24  0  0  1  0            999 V2000
    3.8971    1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971    0.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971   -1.3500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4682   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4682    0.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0392   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -3.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -3.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8187   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8187   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5331   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1042   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -0.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
 10  7  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030746

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(C=C1)C1CC(=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

> <INCHI_KEY>
AIONOLUJZLIMTK-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.316274932427667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
hesperetine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030746
     RDKit          3D
5,7,3'-Trihydroxy-4'-methoxyflavanone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.2383   -0.0642    0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837   -0.8581    0.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -0.4509    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.7418    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077    1.0802    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395    0.2502    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668    0.6701    0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554    1.2813   -1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.7117   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242    0.6325   -2.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594    0.2085   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022    0.2613   -0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844    0.8198   -2.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2087   -0.2520    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547   -0.8140    1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6157   -1.3390    2.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -0.8608    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -0.3652    0.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239   -0.3746    0.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548   -0.9416   -0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8886   -1.2784   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2715   -2.4839   -1.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2096   -0.0744    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1614    0.9868    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2085   -0.5325    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2156    1.4007    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8227    2.0257    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.4590    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1043    1.0888   -1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8113    2.3759   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    1.2349   -2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2577   -0.1991   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505   -0.7047    2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0055   -1.2971    2.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7715   -1.5743   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2404   -2.7646   -1.0535 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  0
  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                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Hesperetin                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       7.275   2.100   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.275   0.560   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.941  -0.210   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.941  -1.750   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.275  -2.520   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.607  -2.520   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.274  -1.750   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.274  -0.210   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.607   0.560   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.940  -2.520   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.940  -4.060   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.606  -4.830   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.606  -6.370   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.727  -4.060   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.061  -4.830   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.061  -6.370   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.395  -4.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.395  -2.520   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.728  -1.750   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.061  -1.750   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.727  -2.520   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.606  -1.750   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3                                                       
CONECT   10    7   11   22                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   21                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   14   22                                                  
CONECT   22   21   10                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030746
HETATM    1  C1  UNL     1      -6.238  -0.064   0.522  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.184  -0.858   0.011  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.868  -0.451   0.084  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.461   0.742   0.648  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.108   1.080   0.682  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.139   0.250   0.161  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.267   0.670   0.231  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.655   1.281  -1.095  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.943   0.712  -1.599  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.224   0.633  -2.834  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.959   0.209  -0.686  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.302   0.261  -0.914  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.784   0.820  -2.068  1.00  0.00           O  
HETATM   14  C11 UNL     1       5.209  -0.252   0.026  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.755  -0.814   1.189  1.00  0.00           C  
HETATM   16  O4  UNL     1       5.616  -1.339   2.157  1.00  0.00           O  
HETATM   17  C13 UNL     1       3.389  -0.861   1.408  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.493  -0.365   0.502  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.124  -0.375   0.645  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.555  -0.942  -0.402  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.889  -1.278  -0.437  1.00  0.00           C  
HETATM   22  O6  UNL     1      -3.271  -2.484  -1.010  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.210  -0.074   1.649  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.161   0.987   0.206  1.00  0.00           H  
HETATM   25  H3  UNL     1      -7.208  -0.532   0.256  1.00  0.00           H  
HETATM   26  H4  UNL     1      -4.216   1.401   1.060  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.823   2.026   1.133  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.359   1.459   1.004  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.104   1.089  -1.881  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.811   2.376  -1.004  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.343   1.235  -2.830  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.258  -0.199  -0.176  1.00  0.00           H  
HETATM   33  H11 UNL     1       5.950  -0.705   2.900  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.006  -1.297   2.314  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.772  -1.574  -0.803  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.240  -2.765  -1.054  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

HMDB0030746
     RDKit          3D
5,7,3'-Trihydroxy-4'-methoxyflavanone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -6.2383   -0.0642    0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1837   -0.8581    0.0113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -0.4509    0.0838 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.7418    0.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1077    1.0802    0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1395    0.2502    0.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2668    0.6701    0.2311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6554    1.2813   -1.0952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9428    0.7117   -1.5989 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2242    0.6325   -2.8336 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9594    0.2085   -0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3022    0.2613   -0.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7844    0.8198   -2.0684 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2087   -0.2520    0.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7547   -0.8140    1.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6157   -1.3390    2.1572 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3891   -0.8608    1.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930   -0.3652    0.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1239   -0.3746    0.6455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548   -0.9416   -0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8886   -1.2784   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2715   -2.4839   -1.0099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2096   -0.0744    1.6494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1614    0.9868    0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2085   -0.5325    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2156    1.4007    1.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8227    2.0257    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3590    1.4590    1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1043    1.0888   -1.8810 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8113    2.3759   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3429    1.2349   -2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2577   -0.1991   -0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9505   -0.7047    2.9000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0055   -1.2971    2.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7715   -1.5743   -0.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2404   -2.7646   -1.0535 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  0
  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

Not Available

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.282

Monoisotopic Molecular Weight

302.079038171

IUPAC Name

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

Traditional Name

hesperetine

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1)C1CC(=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

InChI Key

AIONOLUJZLIMTK-UHFFFAOYSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030746)
Cell membrane (HMDB: HMDB0030746)

Source

Endogenous

Endogenous (HMDB: HMDB0030746)

Plant

Plant (HMDB: HMDB0030746)

Exogenous

Food

Food (HMDB: HMDB0030746)

Beverage

Other beverage

Fruit juice (FooDB: FOOD00763)

Fruit

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)

Exogenous (HMDB: HMDB0030746)

Process

Not Available

Role

Biological role

Pro-oxidant (HMDB: HMDB0030746)

Industrial application

Pharmaceutical industry

Antineoplastic agent

Anticancer agent (HMDB: HMDB0030746)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	30.32 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]+	170.825	31661259
DarkChem	[M-H]-	173.161	31661259
DeepCCS	[M+H]+	173.04	30932474
DeepCCS	[M-H]-	170.682	30932474
DeepCCS	[M-2H]-	203.921	30932474
DeepCCS	[M+Na]+	179.147	30932474
AllCCS	[M+H]+	170.6	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	170.8	32859911
AllCCS	[M+Na-2H]-	170.3	32859911
AllCCS	[M+HCOO]-	169.9	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.	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
5,7,3'-Trihydroxy-4'-methoxyflavanone	COC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	4274.3	Standard polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone	COC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	3013.0	Standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone	COC1=C(O)C=C(C=C1)C1CC(=O)C2=C(O)C=C(O)C=C2O1	2995.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TMS,isomer #1	COC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C	2962.5	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TMS,isomer #2	COC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O	2990.2	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TMS,isomer #3	COC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O	3002.5	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TMS,isomer #1	COC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C	2926.1	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TMS,isomer #2	COC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)C=C1O[Si](C)(C)C	2949.2	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TMS,isomer #3	COC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O	2953.2	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,3TMS,isomer #1	COC1=CC=C(C2CC(=O)C3=C(C=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)O2)C=C1O[Si](C)(C)C	2934.3	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TBDMS,isomer #1	COC1=CC=C(C2CC(=O)C3=C(O)C=C(O)C=C3O2)C=C1O[Si](C)(C)C(C)(C)C	3232.6	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TBDMS,isomer #2	COC1=CC=C(C2CC(=O)C3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)O2)C=C1O	3255.8	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,1TBDMS,isomer #3	COC1=CC=C(C2CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)C=C1O	3270.0	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TBDMS,isomer #1	COC1=CC=C(C2CC(=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	3429.5	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TBDMS,isomer #2	COC1=CC=C(C2CC(=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	3449.2	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,2TBDMS,isomer #3	COC1=CC=C(C2CC(=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	3448.8	Semi standard non polar	33892256
5,7,3'-Trihydroxy-4'-methoxyflavanone,3TBDMS,isomer #1	COC1=CC=C(C2CC(=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	3593.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)	splash10-052f-1971000000-56754303127301d1b2ea	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)	splash10-000l-2971100000-c6ded90239807f8bb898	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)	splash10-0a4l-1890100000-d023765b6d478c346388	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)	splash10-052f-1971000000-56754303127301d1b2ea	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)	splash10-000l-2971100000-c6ded90239807f8bb898	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-EI-TOF (Non-derivatized)	splash10-0a4l-1890100000-d023765b6d478c346388	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0792000000-043d1ca82d4702349341	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone GC-MS (3 TMS) - 70eV, Positive	splash10-0udj-3860980000-a1715e067e13bbdada3e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 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 - 5,7,3'-Trihydroxy-4'-methoxyflavanone DI-ESI-qTof , Negative-QTOF	splash10-0udi-0498000000-93e6bf74ac9acf6199dc	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone DI-ESI-qTof , Positive-QTOF	splash10-0udi-0900000000-3155fa8cf11cb598c7b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-qTof , Positive-QTOF	splash10-0udi-0910000000-950b0c394b2535d33d8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , negative-QTOF	splash10-0udi-0009000000-e068a12319d0bfd192f1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , negative-QTOF	splash10-0udi-0693000000-4d820f1d6dcf9d80fc41	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , negative-QTOF	splash10-0a4r-0910000000-3ba63f0018fc2d3146ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone Linear Ion Trap , negative-QTOF	splash10-000l-0190000000-5929a6a017c13b7d93e6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone Linear Ion Trap , negative-QTOF	splash10-000i-0190000000-eb01c4ad53e16b476f09	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOF	splash10-0udi-0169000000-5d9b7fba914d229018a6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOF	splash10-053i-0920000000-b6ab2fed21176a341b28	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOF	splash10-0udi-0009000000-32f8b49c4bc1df10782a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-TOF , negative-QTOF	splash10-0iki-0930000000-20176d350f94ae4a84ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , positive-QTOF	splash10-0udi-0907000000-36605ac798a9e373e56c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , positive-QTOF	splash10-0ufr-0900000000-de657b62f36904fa4d9e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone LC-ESI-QTOF , positive-QTOF	splash10-0udi-0900000000-aca6930de1cdc2b44ee3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone Linear Ion Trap , positive-QTOF	splash10-004i-0950000000-3910d5d1943ed6685f2c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone , positive-QTOF	splash10-0udi-0910000000-950b0c394b2535d33d8e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone , positive-QTOF	splash10-0udi-0901000000-21943a0770755ae8ec60	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 6V, Positive-QTOF	splash10-0udi-0859000000-8990f8b07e70df4050b5	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 10V, Positive-QTOF	splash10-0udi-0329000000-4364410cdc5a65b92032	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 20V, Positive-QTOF	splash10-0udr-0944000000-edd7b755d11b9331e6c9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 40V, Positive-QTOF	splash10-0uki-3910000000-9e449d46da8305c0b794	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 10V, Negative-QTOF	splash10-0udi-0109000000-21473197ac3beced4628	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 20V, Negative-QTOF	splash10-0udi-0569000000-1e4d2574c341d9d9124f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,7,3'-Trihydroxy-4'-methoxyflavanone 40V, Negative-QTOF	splash10-0pbl-4940000000-c9a717aa36bf4402e6c7	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB002676

KNApSAcK ID

C00014343

Chemspider ID

3467

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3593

PDB ID

Not Available

ChEBI ID

244674

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barreca D, Lagana G, Tellone E, Ficarra S, Leuzzi U, Galtieri A, Bellocco E: Influences of flavonoids on erythrocyte membrane and metabolic implication through anionic exchange modulation. J Membr Biol. 2009 Aug;230(3):163-71. doi: 10.1007/s00232-009-9197-x. [PubMed:19727922 ]
Choi EJ: Hesperetin induced G1-phase cell cycle arrest in human breast cancer MCF-7 cells: involvement of CDK4 and p21. Nutr Cancer. 2007;59(1):115-9. [PubMed:17927510 ]
De Clercq E: Potential antivirals and antiviral strategies against SARS coronavirus infections. Expert Rev Anti Infect Ther. 2006 Apr;4(2):291-302. [PubMed:16597209 ]
Jin YR, Han XH, Zhang YH, Lee JJ, Lim Y, Chung JH, Yun YP: Antiplatelet activity of hesperetin, a bioflavonoid, is mainly mediated by inhibition of PLC-gamma2 phosphorylation and cyclooxygenase-1 activity. Atherosclerosis. 2007 Sep;194(1):144-52. Epub 2006 Nov 7. [PubMed:17092506 ]
Kuppusamy UR, Das NP: Antilipolytic action of hesperetin in rat adipocytes. Planta Med. 1993 Dec;59(6):508-12. [PubMed:8302948 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

5,7,3'-Trihydroxy-4'-methoxyflavanone → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid	details
5,7,3'-Trihydroxy-4'-methoxyflavanone → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic acid	details
5,7,3'-Trihydroxy-4'-methoxyflavanone → 6-[5-(5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

5,7,3'-Trihydroxy-4'-methoxyflavanone → hesperetin 3'-O-sulfate	details

Showing metabocard for 5,7,3'-Trihydroxy-4'-methoxyflavanone (HMDB0030746)

MOL for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

3D MOL for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

3D SDF for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

3D-SDF for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

PDB for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

3D PDB for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

SMILES for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

INCHI for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

Structure for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

3D Structure for HMDB0030746 (5,7,3'-Trihydroxy-4'-methoxyflavanone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions