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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:59 UTC

Update Date

2022-03-07 02:52:37 UTC

HMDB ID

HMDB0030617

Secondary Accession Numbers

HMDB30617

Metabolite Identification

Common Name

Pratensein

Description

Pratensein belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Pratensein has been detected, but not quantified in, a few different foods, such as chickpeas (Cicer arietinum), peanuts (Arachis hypogaea), and pulses. This could make pratensein a potential biomarker for the consumption of these foods. Pratensein 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 small amount of articles have been published on Pratensein.

Structure

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

HMDB0030617
     RDKit          3D
Pratensein
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.8190    0.9763   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8115    1.9618   -0.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    1.6026   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    0.3106    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160   -0.0441    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.9079    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5384    0.4858    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938    1.1831    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.7658    1.6463 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0933   -0.3298    1.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.7589    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135   -1.9041    0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255   -2.3032    1.0754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409   -2.6620   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -2.2712   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -3.0910   -1.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -1.1182    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0248   -0.6851    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950   -1.3704   -0.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1516    2.2087    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    2.5331   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831    3.8475   -0.5311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058    0.6999    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7352    1.3527   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400    0.0390   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919   -0.4759    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -1.0773    0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0119    2.1075    1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -0.1556    2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6047   -3.1287    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459   -3.5677   -0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590   -3.1426   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    2.9669   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326    4.1365   -0.7232 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  7  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061305232D          

 22 24  0  0  0  0            999 V2000
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13  3  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030617

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

> <INCHI_KEY>
FPIOBTBNRZPWJW-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.536486057173352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.9192011239999993

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.945644233854457

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.606885177302557

> <JCHEM_PKA_STRONGEST_BASIC>
-4.76562624760567

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pratensein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030617
     RDKit          3D
Pratensein
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.8190    0.9763   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8115    1.9618   -0.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    1.6026   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    0.3106    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160   -0.0441    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.9079    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5384    0.4858    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938    1.1831    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.7658    1.6463 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0933   -0.3298    1.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.7589    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135   -1.9041    0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255   -2.3032    1.0754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409   -2.6620   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -2.2712   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -3.0910   -1.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -1.1182    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0248   -0.6851    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950   -1.3704   -0.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1516    2.2087    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    2.5331   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831    3.8475   -0.5311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058    0.6999    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7352    1.3527   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400    0.0390   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919   -0.4759    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -1.0773    0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0119    2.1075    1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -0.1556    2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6047   -3.1287    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459   -3.5677   -0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590   -3.1426   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    2.9669   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326    4.1365   -0.7232 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  7  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   13                                                       
CONECT    4    8   11                                                       
CONECT    5    9   12                                                       
CONECT    6    9   14                                                       
CONECT    7   10   22                                                       
CONECT    8    2    4   10                                                  
CONECT    9    5    6   17                                                  
CONECT   10    7    8   16                                                  
CONECT   11    4   13   18                                                  
CONECT   12    5   15   19                                                  
CONECT   13    3   11   21                                                  
CONECT   14    6   15   22                                                  
CONECT   15   12   14   16                                                  
CONECT   16   10   15   20                                                  
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21    1   13                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0030617
HETATM    1  C1  UNL     1      -5.819   0.976  -0.391  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.812   1.962  -0.444  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.476   1.603  -0.183  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.143   0.311   0.120  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.816  -0.044   0.379  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.825   0.908   0.330  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.538   0.486   0.607  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.394   1.183   1.425  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.613   0.766   1.646  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.093  -0.330   1.110  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.385  -0.759   1.353  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.914  -1.904   0.804  1.00  0.00           C  
HETATM   13  O3  UNL     1       6.226  -2.303   1.075  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.141  -2.662  -0.021  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.817  -2.271  -0.302  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.126  -3.091  -1.135  1.00  0.00           O  
HETATM   17  C13 UNL     1       2.310  -1.118   0.261  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.025  -0.685   0.023  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.295  -1.370  -0.735  1.00  0.00           O  
HETATM   20  C15 UNL     1      -1.152   2.209   0.026  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.463   2.533  -0.225  1.00  0.00           C  
HETATM   22  O6  UNL     1      -2.783   3.847  -0.531  1.00  0.00           O  
HETATM   23  H1  UNL     1      -6.106   0.700   0.639  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.735   1.353  -0.908  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.540   0.039  -0.916  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.892  -0.476   0.171  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.611  -1.077   0.613  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.012   2.108   1.887  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.993  -0.156   2.007  1.00  0.00           H  
HETATM   30  H8  UNL     1       6.605  -3.129   0.678  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.546  -3.568  -0.461  1.00  0.00           H  
HETATM   32  H10 UNL     1       1.259  -3.143  -1.526  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.385   2.967  -0.016  1.00  0.00           H  
HETATM   34  H12 UNL     1      -3.733   4.137  -0.723  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    8   18
CONECT    8    9   28
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   29
CONECT   12   13   14   14
CONECT   13   30
CONECT   14   15   31
CONECT   15   16   17   17
CONECT   16   32
CONECT   17   18
CONECT   18   19   19
CONECT   20   21   21   33
CONECT   21   22
CONECT   22   34
END

HMDB0030617
     RDKit          3D
Pratensein
 34 36  0  0  0  0  0  0  0  0999 V2000
   -5.8190    0.9763   -0.3910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8115    1.9618   -0.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4764    1.6026   -0.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    0.3106    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8160   -0.0441    0.3790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    0.9079    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5384    0.4858    0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3938    1.1831    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6125    0.7658    1.6463 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0933   -0.3298    1.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.7589    1.3533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9135   -1.9041    0.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2255   -2.3032    1.0754 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409   -2.6620   -0.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -2.2712   -0.3025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259   -3.0910   -1.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3098   -1.1182    0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0248   -0.6851    0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2950   -1.3704   -0.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1516    2.2087    0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4629    2.5331   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7831    3.8475   -0.5311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1058    0.6999    0.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7352    1.3527   -0.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400    0.0390   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8919   -0.4759    0.1706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6105   -1.0773    0.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0119    2.1075    1.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9925   -0.1556    2.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6047   -3.1287    0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459   -3.5677   -0.4606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2590   -3.1426   -1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3848    2.9669   -0.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326    4.1365   -0.7232 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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  7  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
 20 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3',5,7-Trihydroxy-4'-methoxyisoflavone	ChEBI
3'-Hydroxy-biochanin a	ChEBI
3'-Hydroxybiochanin a	ChEBI
5,7,3'-Trihydroxy-4'-methoxyisoflavone	ChEBI
5,7-Dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
4776b Compound	MeSH, HMDB
4'-Methoxy-3',5,7-trihydroxyisoflavone	MeSH, HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

5,7-dihydroxy-3-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

pratensein

CAS Registry Number

2284-31-3

SMILES

COC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C16H12O6/c1-21-13-3-2-8(4-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

InChI Key

FPIOBTBNRZPWJW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:8359 )
7-hydroxyisoflavones (CHEBI:8359 )
isoflavones (C10520 )
Isoflavonoids (C10520 )
Isoflavonoids (LMPK12050265 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030617)
Cell membrane (HMDB: HMDB0030617)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030617)

Source

Endogenous

Endogenous (HMDB: HMDB0030617)

Plant

Plant (HMDB: HMDB0030617)
Fabaceae (HMDB: HMDB0030617)

Exogenous

Food

Food (HMDB: HMDB0030617)

Nut

Peanut (FooDB: FOOD00016)

Pulse

Pea

Chickpea (FooDB: FOOD00047)

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0030617)

Process

Not Available

Role

Biological role

Hypolipidemic (HMDB: HMDB0030617)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	272 - 273 °C	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	0.08 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.54 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]+	169.7	30932474
DeepCCS	[M-H]-	167.342	30932474
DeepCCS	[M-2H]-	200.619	30932474
DeepCCS	[M+Na]+	175.846	30932474
AllCCS	[M+H]+	168.5	32859911
AllCCS	[M+H-H2O]+	164.9	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	169.4	32859911
AllCCS	[M+Na-2H]-	168.8	32859911
AllCCS	[M+HCOO]-	168.2	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.	6.85 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8357 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2126.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	273.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	133.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	359.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	553.5 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	552.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	935.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	384.7 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	1412.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	399.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	439.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	232.1 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	136.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pratensein	COC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	4616.8	Standard polar	33892256
Pratensein	COC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	2976.8	Standard non polar	33892256
Pratensein	COC1=C(O)C=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	3113.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pratensein,1TMS,isomer #1	COC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	3205.3	Semi standard non polar	33892256
Pratensein,1TMS,isomer #2	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O	3239.0	Semi standard non polar	33892256
Pratensein,1TMS,isomer #3	COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3190.1	Semi standard non polar	33892256
Pratensein,2TMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C	3077.7	Semi standard non polar	33892256
Pratensein,2TMS,isomer #2	COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	3018.3	Semi standard non polar	33892256
Pratensein,2TMS,isomer #3	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O	3127.3	Semi standard non polar	33892256
Pratensein,3TMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C	2984.5	Semi standard non polar	33892256
Pratensein,1TBDMS,isomer #1	COC1=CC=C(C2=COC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3446.3	Semi standard non polar	33892256
Pratensein,1TBDMS,isomer #2	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O	3510.1	Semi standard non polar	33892256
Pratensein,1TBDMS,isomer #3	COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3455.5	Semi standard non polar	33892256
Pratensein,2TBDMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3620.7	Semi standard non polar	33892256
Pratensein,2TBDMS,isomer #2	COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3572.5	Semi standard non polar	33892256
Pratensein,2TBDMS,isomer #3	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O	3644.5	Semi standard non polar	33892256
Pratensein,3TBDMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3728.5	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 - Pratensein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fl0-0392000000-b33a9f600255a7645331	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pratensein GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-2180970000-37a9800477d82a62a0a2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pratensein GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pratensein 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 - Pratensein LC-ESI-QFT 21V, positive-QTOF	splash10-0udr-0096000000-f8f401a8a48dd8fb870d	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pratensein LC-ESI-IT 21V, positive-QTOF	splash10-00kr-0090000000-9331cc69724483ba671c	2020-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 10V, Positive-QTOF	splash10-0udi-0109000000-99b3ff2ff09032c77392	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 20V, Positive-QTOF	splash10-0udi-0329000000-07e3785d7c0ec0e32427	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 40V, Positive-QTOF	splash10-0fk9-6940000000-d65be68235fd05108d60	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 10V, Negative-QTOF	splash10-0002-0090000000-9bdb9b13d7148406dc38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 20V, Negative-QTOF	splash10-0002-0390000000-6f6b16a3d9e7b25e542d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 40V, Negative-QTOF	splash10-0ugi-2790000000-d080df272f8cc794ba14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 10V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 20V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 40V, Positive-QTOF	splash10-004i-0290000000-700da632aef4c754c8f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 10V, Negative-QTOF	splash10-0002-0090000000-fb4a565723d52a1e4624	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 20V, Negative-QTOF	splash10-0002-0090000000-185770323f5773ae368c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pratensein 40V, Negative-QTOF	splash10-0ufr-0090000000-d5386a1b1f88b835a298	2021-09-23	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Pratensein

METLIN ID

Not Available

PubChem Compound

5281803

PDB ID

Not Available

ChEBI ID

8359

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

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

Showing metabocard for Pratensein (HMDB0030617)

MOL for HMDB0030617 (Pratensein)

3D MOL for HMDB0030617 (Pratensein)

3D SDF for HMDB0030617 (Pratensein)

3D-SDF for HMDB0030617 (Pratensein)

PDB for HMDB0030617 (Pratensein)

3D PDB for HMDB0030617 (Pratensein)

SMILES for HMDB0030617 (Pratensein)

INCHI for HMDB0030617 (Pratensein)

Structure for HMDB0030617 (Pratensein)

3D Structure for HMDB0030617 (Pratensein)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra