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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:15 UTC

Update Date

2022-03-07 02:53:26 UTC

HMDB ID

HMDB0032696

Secondary Accession Numbers

HMDB32696

Metabolite Identification

Common Name

Cajanin

Description

Cajanin 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, cajanin is considered to be a flavonoid. Cajanin has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, pigeon peas (Cajanus cajan), pulses, and robusta coffees (Coffea canephora). This could make cajanin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cajanin.

Structure

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

HMDB0032696
     RDKit          3D
Cajanin
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9107   -1.2565   -1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2628   -0.0770   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9204    0.0810   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    1.3309   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228    1.6225   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466    2.8726    0.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2106    0.5827   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241    0.7506    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    1.8675    0.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567   -0.3690    0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736   -0.2018    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900   -0.1755   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6475   -0.0145   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091    0.1234    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4783    0.2790    1.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943    0.0966    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -0.0652    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -0.0931    2.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652   -1.6051   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138   -1.7334   -0.5103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354   -0.6784   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -0.9172   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5681   -1.0142   -2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2412   -2.0839   -1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181   -1.6283   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622    2.1671   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0131    3.4122    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9040   -0.2865   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3592    0.0036   -1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8864    1.2056    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5453    0.2022    2.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2258    0.0067    3.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -2.4868   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -1.9178   -0.9671 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
 17 18  1  0
 10 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061306382D          

 22 24  0  0  0  0            999 V2000
    0.0000    0.0000    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
    4.2868    3.3000    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
    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
    5.7158    3.3000    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
    4.2868    2.4750    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    2.0625    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
    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
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    0.0000    0.8250    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  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  0  0  0  0
 12 10  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032696

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1

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

> <INCHI_KEY>
ALFNTRJPGFNJQV-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.2629

> <EXACT_MASS>
300.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.527843152815638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.9192011239999993

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.811340459872458

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.220480818016382

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7379282267558676

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cajanin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032696
     RDKit          3D
Cajanin
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9107   -1.2565   -1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2628   -0.0770   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9204    0.0810   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    1.3309   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228    1.6225   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466    2.8726    0.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2106    0.5827   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241    0.7506    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    1.8675    0.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567   -0.3690    0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736   -0.2018    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900   -0.1755   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6475   -0.0145   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091    0.1234    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4783    0.2790    1.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943    0.0966    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -0.0652    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -0.0931    2.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652   -1.6051   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138   -1.7334   -0.5103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354   -0.6784   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -0.9172   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5681   -1.0142   -2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2412   -2.0839   -1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181   -1.6283   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622    2.1671   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0131    3.4122    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9040   -0.2865   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3592    0.0036   -1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8864    1.2056    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5453    0.2022    2.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2258    0.0067    3.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -2.4868   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -1.9178   -0.9671 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
 17 18  1  0
 10 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   4.620   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      10.669   6.160   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   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      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   2.310   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       0.000   1.540   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   10                                                       
CONECT    4    8   12                                                       
CONECT    5    9   13                                                       
CONECT    6    9   14                                                       
CONECT    7   11   22                                                       
CONECT    8    2    4   17                                                  
CONECT    9    5    6   21                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   16                                                  
CONECT   12    4   10   18                                                  
CONECT   13    5   15   19                                                  
CONECT   14    6   15   22                                                  
CONECT   15   13   14   16                                                  
CONECT   16   11   15   20                                                  
CONECT   17    8                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   16                                                            
CONECT   21    1    9                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0032696
HETATM    1  C1  UNL     1       5.911  -1.256  -1.278  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.263  -0.077  -0.930  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.920   0.081  -0.670  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.474   1.331  -0.341  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.123   1.623  -0.053  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.747   2.873   0.265  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.211   0.583  -0.108  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.124   0.751   0.151  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.561   1.867   0.452  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.957  -0.369   0.066  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.374  -0.202   0.338  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.290  -0.175  -0.687  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.648  -0.015  -0.420  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.109   0.123   0.881  1.00  0.00           C  
HETATM   15  O4  UNL     1      -6.478   0.279   1.051  1.00  0.00           O  
HETATM   16  C12 UNL     1      -4.194   0.097   1.893  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.831  -0.065   1.629  1.00  0.00           C  
HETATM   18  O5  UNL     1      -1.898  -0.093   2.651  1.00  0.00           O  
HETATM   19  C14 UNL     1      -0.465  -1.605  -0.268  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.814  -1.733  -0.510  1.00  0.00           O  
HETATM   21  C15 UNL     1       1.635  -0.678  -0.436  1.00  0.00           C  
HETATM   22  C16 UNL     1       2.984  -0.917  -0.713  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.568  -1.014  -2.165  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.241  -2.084  -1.552  1.00  0.00           H  
HETATM   25  H3  UNL     1       6.618  -1.628  -0.510  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.162   2.167  -0.290  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.013   3.412   0.516  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.904  -0.287  -1.697  1.00  0.00           H  
HETATM   29  H7  UNL     1      -5.359   0.004  -1.243  1.00  0.00           H  
HETATM   30  H8  UNL     1      -6.886   1.206   1.053  1.00  0.00           H  
HETATM   31  H9  UNL     1      -4.545   0.202   2.903  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.226   0.007   3.598  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.130  -2.487  -0.334  1.00  0.00           H  
HETATM   34  H12 UNL     1       3.296  -1.918  -0.967  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   26
CONECT    5    6    7    7
CONECT    6   27
CONECT    7    8   21
CONECT    8    9    9   10
CONECT   10   11   19   19
CONECT   11   12   12   17
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   16
CONECT   15   30
CONECT   16   17   17   31
CONECT   17   18
CONECT   18   32
CONECT   19   20   33
CONECT   20   21
CONECT   21   22   22
CONECT   22   34
END

HMDB0032696
     RDKit          3D
Cajanin
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9107   -1.2565   -1.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2628   -0.0770   -0.9297 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9204    0.0810   -0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4743    1.3309   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1228    1.6225   -0.0526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7466    2.8726    0.2651 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2106    0.5827   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241    0.7506    0.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5609    1.8675    0.4515 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9567   -0.3690    0.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3736   -0.2018    0.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2900   -0.1755   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6475   -0.0145   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091    0.1234    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4783    0.2790    1.0505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1943    0.0966    1.8929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8309   -0.0652    1.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8984   -0.0931    2.6511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4652   -1.6051   -0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138   -1.7334   -0.5103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354   -0.6784   -0.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9839   -0.9172   -0.7127 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5681   -1.0142   -2.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2412   -2.0839   -1.5525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6181   -1.6283   -0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1622    2.1671   -0.2904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0131    3.4122    0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9040   -0.2865   -1.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3592    0.0036   -1.2430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8864    1.2056    1.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5453    0.2022    2.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2258    0.0067    3.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1301   -2.4868   -0.3339 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -1.9178   -0.9671 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
 17 18  1  0
 10 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22  3  1  0
 21  7  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2',4',5-Trihydroxy-7-methoxyisoflavone	HMDB
Cajinin	HMDB

Chemical Formula

C₁₆H₁₂O₆

Average Molecular Weight

300.2629

Monoisotopic Molecular Weight

300.063388116

IUPAC Name

3-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-4H-chromen-4-one

Traditional Name

cajanin

CAS Registry Number

32884-36-9

SMILES

COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1

InChI Identifier

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

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:70036 )
isoflavones (C10203 )
Isoflavonoids (C10203 )
Isoflavonoids (LMPK12050326 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032696)
Cell membrane (HMDB: HMDB0032696)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032696)

Source

Endogenous

Endogenous (HMDB: HMDB0032696)

Plant

Exogenous

Food

Food (HMDB: HMDB0032696)

Pulse

Pea

Pigeon pea (FooDB: FOOD00037)

Pulses (FooDB: FOOD00867)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Exogenous (HMDB: HMDB0032696)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0032696)

Pesticide (HMDB: HMDB0032696)

Biological role

Phytoalexin (HMDB: HMDB0032696)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	208 - 210 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	147.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	3.01	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-4.7	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	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.53 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]+	174.082	30932474
DeepCCS	[M-H]-	171.724	30932474
DeepCCS	[M-2H]-	205.774	30932474
DeepCCS	[M+Na]+	181.001	30932474
AllCCS	[M+H]+	168.6	32859911
AllCCS	[M+H-H2O]+	164.9	32859911
AllCCS	[M+NH4]+	171.9	32859911
AllCCS	[M+Na]+	172.9	32859911
AllCCS	[M-H]-	169.5	32859911
AllCCS	[M+Na-2H]-	168.9	32859911
AllCCS	[M+HCOO]-	168.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.09 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3731 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2085.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	364.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	598.5 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	576.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	128.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	949.0 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	1465.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	443.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	243.6 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	124.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cajanin	COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1	4546.9	Standard polar	33892256
Cajanin	COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1	2859.5	Standard non polar	33892256
Cajanin	COC1=CC(O)=C2C(=O)C(=COC2=C1)C1=C(O)C=C(O)C=C1	2980.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cajanin,1TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C1	3084.8	Semi standard non polar	33892256
Cajanin,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C)=COC2=C1	3027.4	Semi standard non polar	33892256
Cajanin,1TMS,isomer #3	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O)=COC2=C1	3080.0	Semi standard non polar	33892256
Cajanin,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O)=COC2=C1	2955.6	Semi standard non polar	33892256
Cajanin,2TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C)=COC2=C1	2929.7	Semi standard non polar	33892256
Cajanin,2TMS,isomer #3	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)=COC2=C1	2962.3	Semi standard non polar	33892256
Cajanin,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)=COC2=C1	2891.1	Semi standard non polar	33892256
Cajanin,1TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O)=COC2=C1	3358.0	Semi standard non polar	33892256
Cajanin,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C1	3307.2	Semi standard non polar	33892256
Cajanin,1TBDMS,isomer #3	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)=COC2=C1	3342.2	Semi standard non polar	33892256
Cajanin,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=C3O)=COC2=C1	3484.7	Semi standard non polar	33892256
Cajanin,2TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C1	3440.6	Semi standard non polar	33892256
Cajanin,2TBDMS,isomer #3	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)=COC2=C1	3467.2	Semi standard non polar	33892256
Cajanin,3TBDMS,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=C3O[Si](C)(C)C(C)(C)C)=COC2=C1	3591.1	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 - Cajanin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-0591000000-2d725dedc079e3bf5cc4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cajanin GC-MS (3 TMS) - 70eV, Positive	splash10-0fkc-2170950000-8a37dcc2d7e2a3c24a67	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cajanin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 10V, Positive-QTOF	splash10-0udi-0009000000-9de62c366ea45b58088f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 20V, Positive-QTOF	splash10-0udi-0019000000-faebb53f0f824f475c3f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 40V, Positive-QTOF	splash10-0uy0-3790000000-1a6c3965725a8acc1921	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 10V, Negative-QTOF	splash10-0002-0090000000-f9e2a2f74f45fb1e1fe4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 20V, Negative-QTOF	splash10-0002-0090000000-85b3c09fa13b64ca415e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 40V, Negative-QTOF	splash10-0159-3690000000-fcc07e28e468be59704f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 10V, Negative-QTOF	splash10-0002-0090000000-fb4a565723d52a1e4624	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 20V, Negative-QTOF	splash10-0002-0090000000-fb4a565723d52a1e4624	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 40V, Negative-QTOF	splash10-00mo-0590000000-c12ad5716ba473535f98	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 10V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 20V, Positive-QTOF	splash10-0udi-0009000000-545fc7c692e0abcd7966	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanin 40V, Positive-QTOF	splash10-0a7i-0390000000-9e3fdcbbe9204f317f21	2021-09-24	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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281706

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1830961

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.. .

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

Cajanin → 3,4,5-trihydroxy-6-[3-hydroxy-4-(5-hydroxy-7-methoxy-4-oxo-4H-chromen-3-yl)phenoxy]oxane-2-carboxylic acid	details

Showing metabocard for Cajanin (HMDB0032696)

MOL for HMDB0032696 (Cajanin)

3D MOL for HMDB0032696 (Cajanin)

3D SDF for HMDB0032696 (Cajanin)

3D-SDF for HMDB0032696 (Cajanin)

PDB for HMDB0032696 (Cajanin)

3D PDB for HMDB0032696 (Cajanin)

SMILES for HMDB0032696 (Cajanin)

INCHI for HMDB0032696 (Cajanin)

Structure for HMDB0032696 (Cajanin)

3D Structure for HMDB0032696 (Cajanin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions