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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:55:24 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034127

Secondary Accession Numbers

HMDB34127

Metabolite Identification

Common Name

Prunetin

Description

Prunetin, also known as padmakastein, belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone. Thus, prunetin is considered to be a flavonoid. Prunetin is a bitter tasting compound. Prunetin has been detected, but not quantified in, several different foods, such as green tea, prunus (cherry, plum), red tea, black tea, and herbs and spices. This could make prunetin a potential biomarker for the consumption of these foods. Prunetin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Prunetin.

Structure

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

HMDB0034127
     RDKit          3D
Prunetin
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.1505   -0.1521   -0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489    0.7607   -0.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8301    0.4316   -0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062   -0.7387    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595   -1.0573    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547   -2.2211    0.9052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196   -0.1529   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358   -0.3952    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -1.4398    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119    0.5041   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    0.2127   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434    1.2104    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6643    1.0165    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2047   -0.2238    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5436   -0.4273    0.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4218   -1.2417   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -1.0173   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880    1.6549   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    1.8862   -1.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    1.0431   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640    1.3300   -1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0949   -1.0879   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646   -0.3812    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1705    0.2619   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481   -1.4588    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0736   -2.6873    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266    2.1977    0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3064    1.7917    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2206   -0.2482    0.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8714   -2.2077   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -1.7895   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    2.3655   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0973    2.2610   -1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 20  7  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

Prunetin
  Mrv1652305062021512D          

 21 23  0  0  0  0            999 V2000
   10.7820   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7820   -6.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0675   -5.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4965   -5.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4965   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0675   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2109   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2109   -6.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4965   -8.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531   -6.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0675   -8.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9254   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6398   -6.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9254   -8.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3543   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6398   -8.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3543   -8.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0688   -8.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6386   -5.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9241   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 11  2  0  0  0  0
  6 12  1  0  0  0  0
  7 20  1  0  0  0  0
  9 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 15 17  2  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
 17 18  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034127

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

> <INCHI_KEY>
KQMVAGISDHMXJJ-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.70535120292798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
3.2227664456666663

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.974426058464246

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.323399360483996

> <JCHEM_PKA_STRONGEST_BASIC>
-4.737551646594349

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
prunetin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034127
     RDKit          3D
Prunetin
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.1505   -0.1521   -0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489    0.7607   -0.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8301    0.4316   -0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062   -0.7387    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595   -1.0573    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547   -2.2211    0.9052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196   -0.1529   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358   -0.3952    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -1.4398    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119    0.5041   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    0.2127   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434    1.2104    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6643    1.0165    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2047   -0.2238    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5436   -0.4273    0.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4218   -1.2417   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -1.0173   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880    1.6549   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    1.8862   -1.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    1.0431   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640    1.3300   -1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0949   -1.0879   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646   -0.3812    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1705    0.2619   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481   -1.4588    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0736   -2.6873    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266    2.1977    0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3064    1.7917    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2206   -0.2482    0.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8714   -2.2077   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -1.7895   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    2.3655   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0973    2.2610   -1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 20  7  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Prunetin                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-20         0                                  
HETATM    1  C   UNK     0      20.126 -11.404   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.126 -12.944   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.793 -10.634   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      21.460 -10.634   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      21.460 -13.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.793 -13.714   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.459 -11.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.794 -11.404   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.794 -12.944   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      21.460 -15.254   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.459 -12.944   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      18.793 -15.254   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      24.127 -13.714   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.461 -12.944   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.127 -15.254   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.795 -13.714   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.461 -16.024   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.795 -15.254   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      28.128 -16.024   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.125 -10.634   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      14.792 -11.404   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    2   11   12                                                  
CONECT    7    3   20   11                                                  
CONECT    8    4    9                                                       
CONECT    9    5   13    8                                                  
CONECT   10    5                                                            
CONECT   11    6    7                                                       
CONECT   12    6                                                            
CONECT   13    9   14   15                                                  
CONECT   14   13   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   18                                                       
CONECT   17   15   18                                                       
CONECT   18   16   19   17                                                  
CONECT   19   18                                                            
CONECT   20    7   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0034127
HETATM    1  C1  UNL     1       6.151  -0.152  -0.489  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.149   0.761  -0.888  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.830   0.432  -0.618  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.506  -0.739   0.013  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.159  -1.057   0.279  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.855  -2.221   0.905  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.220  -0.153  -0.120  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.136  -0.395   0.107  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.552  -1.440   0.680  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.112   0.504  -0.286  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.514   0.213  -0.030  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.343   1.210   0.482  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.664   1.017   0.748  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.205  -0.224   0.498  1.00  0.00           C  
HETATM   15  O4  UNL     1      -6.544  -0.427   0.766  1.00  0.00           O  
HETATM   16  C12 UNL     1      -4.422  -1.242  -0.009  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.090  -1.017  -0.268  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.688   1.655  -0.915  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.587   1.886  -1.130  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.527   1.043  -0.763  1.00  0.00           C  
HETATM   21  C16 UNL     1       2.864   1.330  -1.012  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.095  -1.088  -1.067  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.965  -0.381   0.600  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.170   0.262  -0.617  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.248  -1.459   0.331  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.074  -2.687   1.205  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.927   2.198   0.684  1.00  0.00           H  
HETATM   28  H7  UNL     1      -5.306   1.792   1.146  1.00  0.00           H  
HETATM   29  H8  UNL     1      -7.221  -0.248   0.047  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.871  -2.208  -0.196  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.433  -1.789  -0.669  1.00  0.00           H  
HETATM   32  H11 UNL     1      -1.469   2.365  -1.225  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.097   2.261  -1.512  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    7    7
CONECT    6   26
CONECT    7    8   20
CONECT    8    9    9   10
CONECT   10   11   18   18
CONECT   11   12   12   17
CONECT   12   13   27
CONECT   13   14   14   28
CONECT   14   15   16
CONECT   15   29
CONECT   16   17   17   30
CONECT   17   31
CONECT   18   19   32
CONECT   19   20
CONECT   20   21   21
CONECT   21   33
END

HMDB0034127
     RDKit          3D
Prunetin
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.1505   -0.1521   -0.4892 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1489    0.7607   -0.8876 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8301    0.4316   -0.6183 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062   -0.7387    0.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595   -1.0573    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547   -2.2211    0.9052 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2196   -0.1529   -0.1200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358   -0.3952    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -1.4398    0.6800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1119    0.5041   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5143    0.2127   -0.0304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434    1.2104    0.4822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6643    1.0165    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2047   -0.2238    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5436   -0.4273    0.7659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4218   -1.2417   -0.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0904   -1.0173   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880    1.6549   -0.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5871    1.8862   -1.1303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    1.0431   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640    1.3300   -1.0120 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0949   -1.0879   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9646   -0.3812    0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1705    0.2619   -0.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481   -1.4588    0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0736   -2.6873    1.2054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9266    2.1977    0.6843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3064    1.7917    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2206   -0.2482    0.0469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8714   -2.2077   -0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4327   -1.7895   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    2.3655   -1.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0973    2.2610   -1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 10 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 20  7  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',5-Dihydroxy-7-methoxygenistein	ChEBI
4',5-Dihydroxy-7-methoxyisoflavone	ChEBI
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone	ChEBI
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one	ChEBI
7-O-Methyl-genistein	ChEBI
Padmakastein	ChEBI
Prunusetin	ChEBI
5,4'-Dihydroxy-7-methoxyisoflavone	HMDB, MeSH
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one, 9ci	HMDB
5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one	HMDB
Isoflavone, 4',5-dihydroxy-7-methoxy- (7ci,8ci)	HMDB

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.267

Monoisotopic Molecular Weight

284.068473486

IUPAC Name

5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one

Traditional Name

prunetin

CAS Registry Number

552-59-0

SMILES

COC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H12O5/c1-20-11-6-13(18)15-14(7-11)21-8-12(16(15)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3

InChI Key

KQMVAGISDHMXJJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C7 atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylisoflavones

Alternative Parents

Substituents

7-o-methylisoflavone
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Ether
Oxacycle
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:8600 )
methoxyisoflavone (CHEBI:8600 )
isoflavones (C10521 )
Isoflavonoids (C10521 )
Isoflavonoids (LMPK12050353 )
a small molecule (CPD-3521 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034127)
Cell membrane (HMDB: HMDB0034127)

Excreta

Biofluid or Excreta

Urine (PMID: 15506819)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034127)

Source

Exogenous

Exogenous (HMDB: HMDB0034127)

Food

Food (HMDB: HMDB0034127)

Fruit

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Sour cherry (FooDB: FOOD00146)

Confectionery

Candy

Liquorice (FooDB: FOOD00627)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Herb

Red clover (FooDB: FOOD00930)

Endogenous

Plant

Plant (HMDB: HMDB0034127)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034127)

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0034127)

Pesticide (HMDB: HMDB0034127)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	246 - 248 °C	Not Available
Boiling Point	546.50 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	71.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.530 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	175.17	30932474
[M+H]+	Baker	166.256	30932474
[M-H]-	Not Available	175.17	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001944
[M+H]+	Not Available	166.256	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001944

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.059 g/L	ALOGPS
logP	3.36	ALOGPS
logP	3.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.32	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.71 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
DeepCCS	[M+H]+	169.736	30932474
DeepCCS	[M-H]-	167.378	30932474
DeepCCS	[M-2H]-	201.178	30932474
DeepCCS	[M+Na]+	176.405	30932474
AllCCS	[M+H]+	165.1	32859911
AllCCS	[M+H-H2O]+	161.3	32859911
AllCCS	[M+NH4]+	168.6	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	166.3	32859911
AllCCS	[M+HCOO]-	165.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Prunetin	COC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1	4168.6	Standard polar	33892256
Prunetin	COC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1	2793.8	Standard non polar	33892256
Prunetin	COC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C=C1	2902.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Prunetin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1	3043.9	Semi standard non polar	33892256
Prunetin,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3)=COC2=C1	3082.4	Semi standard non polar	33892256
Prunetin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3)=COC2=C1	3001.9	Semi standard non polar	33892256
Prunetin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3)=COC2=C1	3287.3	Semi standard non polar	33892256
Prunetin,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=COC2=C1	3324.4	Semi standard non polar	33892256
Prunetin,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)=COC2=C1	3484.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Prunetin GC-EI-TOF (Non-derivatized)	splash10-03di-1932800000-7ba8925a2b1306b10b50	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Prunetin GC-EI-TOF (Non-derivatized)	splash10-03di-1932800000-7ba8925a2b1306b10b50	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prunetin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0490000000-568458ba8831c097f5c5	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prunetin GC-MS (2 TMS) - 70eV, Positive	splash10-08ml-3439700000-90e7b4e47d986f3bfb5f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prunetin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Prunetin 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 - Prunetin ESI-TOF 10V, Negative-QTOF	splash10-0udi-0190000000-b6ecb3ccb54bdeacbe00	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF 20V, Negative-QTOF	splash10-0udi-0190000000-b6ecb3ccb54bdeacbe00	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF , Negative-QTOF	splash10-001i-0090000000-11b97ad586d2e24e7115	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF 40V, Negative-QTOF	splash10-014r-0090000000-fb797f4684174e26b1d0	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF 30V, Negative-QTOF	splash10-014i-0090000000-6db4d2441911d696b121	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF 10V, Negative-QTOF	splash10-001i-0090000000-306c2baf58cc6c40c407	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF 20V, Negative-QTOF	splash10-0159-0090000000-a85c6c3392aa2541b48c	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF , Negative-QTOF	splash10-001i-0090000000-11b97ad586d2e24e7115	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF 40V, Negative-QTOF	splash10-014r-0090000000-fb797f4684174e26b1d0	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin ESI-TOF 30V, Negative-QTOF	splash10-014i-0090000000-6db4d2441911d696b121	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin LC-ESI-TOF , negative-QTOF	splash10-001i-0090000000-306c2baf58cc6c40c407	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin LC-ESI-TOF , negative-QTOF	splash10-0159-0090000000-a85c6c3392aa2541b48c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin LC-ESI-TOF , negative-QTOF	splash10-014r-0090000000-fb797f4684174e26b1d0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin LC-ESI-TOF , negative-QTOF	splash10-014i-0090000000-6db4d2441911d696b121	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin LC-ESI-QFT 19V, positive-QTOF	splash10-002r-0290000000-e0d4e56550195007ab89	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin LC-ESI-IT 19V, positive-QTOF	splash10-0690-0690000000-292dcb6a0c7801e87353	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin 10V, Positive-QTOF	splash10-001i-0090000000-306c2baf58cc6c40c407	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin 20V, Positive-QTOF	splash10-0159-0090000000-a85c6c3392aa2541b48c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Prunetin 30V, Positive-QTOF	splash10-014i-0090000000-6db4d2441911d696b121	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prunetin 10V, Positive-QTOF	splash10-000i-0090000000-280a25523108ad3de6f1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prunetin 20V, Positive-QTOF	splash10-000i-0090000000-8512eb234e9b55c8fabc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prunetin 40V, Positive-QTOF	splash10-0gbi-2790000000-911d7dc4d9e528af001b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prunetin 10V, Negative-QTOF	splash10-001i-0090000000-3539a40fa0eaf6326969	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prunetin 20V, Negative-QTOF	splash10-001i-0090000000-bb3562f94d2cef4ead46	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Prunetin 40V, Negative-QTOF	splash10-0gb9-3980000000-4d720fa6bb02944fb579	2015-04-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 881	15506819	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 881	20067656	details

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Prunetin

METLIN ID

Not Available

PubChem Compound

5281804

PDB ID

Not Available

ChEBI ID

8600

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1504561

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Prunetin (HMDB0034127)

MOL for HMDB0034127 (Prunetin)

3D MOL for HMDB0034127 (Prunetin)

3D SDF for HMDB0034127 (Prunetin)

3D-SDF for HMDB0034127 (Prunetin)

PDB for HMDB0034127 (Prunetin)

3D PDB for HMDB0034127 (Prunetin)

SMILES for HMDB0034127 (Prunetin)

INCHI for HMDB0034127 (Prunetin)

Structure for HMDB0034127 (Prunetin)

3D Structure for HMDB0034127 (Prunetin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra