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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:41:54 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033924

Secondary Accession Numbers

HMDB33924

Metabolite Identification

Common Name

Cajanol

Description

Cajanol belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, cajanol is considered to be a flavonoid. Cajanol has been detected, but not quantified in, pigeon peas (Cajanus cajan) and pulses. This could make cajanol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Cajanol.

Structure

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

HMDB0033924
     RDKit          3D
Cajanol
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.6097    0.7311   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6822   -0.2722   -0.1198 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3234   -0.1245   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596    1.0775   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635    1.2515   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084    2.4898   -0.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5363    0.2000   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450   -1.0234    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5153   -1.1832    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3291   -2.0880    0.5146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -2.0789    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.7605    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -0.8074    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6630   -1.8761   -0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0051   -1.8948   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382   -0.8455   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1993   -0.8671   -0.7847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767    0.2261    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9252    0.2495    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    1.3234    1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894    2.4103    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    0.3051   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737    1.2608   -0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594    1.4033   -1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5390    0.2205   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836    1.3583    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3707    1.9589   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893    2.7932   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260   -2.1414    0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -2.1858   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143   -2.9225    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4770   -0.6992    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -2.7177   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4345   -2.7393   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8931   -1.2593   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9114    1.0805    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0493    2.0787    2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429    2.8721    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528    3.1964    2.0940 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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  2  0
  9  3  1  0
 19 13  1  0
 22  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
M  END


  Mrv0541 05061307272D          

 23 25  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
    4.2868    0.8250    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
    1.4289    2.4750    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
    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
    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
    5.0013    1.2375    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
  4  3  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  2  0  0  0  0
 15  7  2  0  0  0  0
 16 13  2  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 19 13  1  0  0  0  0
 20 17  2  0  0  0  0
 21  1  1  0  0  0  0
 21 10  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  8  1  0  0  0  0
 23 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033924

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-21-10-6-13(19)16-15(7-10)23-8-12(17(16)20)11-4-3-9(18)5-14(11)22-2/h3-7,12,18-19H,8H2,1-2H3

> <INCHI_KEY>
RYYWWFXWFMYKJM-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.679675755521107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-3-(4-hydroxy-2-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.715880904333333

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.01110401359322

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.30803744653241

> <JCHEM_PKA_STRONGEST_BASIC>
-3.916073047021457

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
82.622

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cajanol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033924
     RDKit          3D
Cajanol
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.6097    0.7311   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6822   -0.2722   -0.1198 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3234   -0.1245   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596    1.0775   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635    1.2515   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084    2.4898   -0.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5363    0.2000   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450   -1.0234    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5153   -1.1832    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3291   -2.0880    0.5146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -2.0789    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.7605    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -0.8074    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6630   -1.8761   -0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0051   -1.8948   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382   -0.8455   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1993   -0.8671   -0.7847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767    0.2261    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9252    0.2495    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    1.3234    1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894    2.4103    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    0.3051   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737    1.2608   -0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594    1.4033   -1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5390    0.2205   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836    1.3583    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3707    1.9589   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893    2.7932   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260   -2.1414    0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -2.1858   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143   -2.9225    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4770   -0.6992    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -2.7177   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4345   -2.7393   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8931   -1.2593   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9114    1.0805    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0493    2.0787    2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429    2.8721    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528    3.1964    2.0940 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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  2  0
  9  3  1  0
 19 13  1  0
 22  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   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      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   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       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003   6.930   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       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    9   14                                                       
CONECT    6   10   13                                                       
CONECT    7   10   15                                                       
CONECT    8   12   23                                                       
CONECT    9    3    5   18                                                  
CONECT   10    6    7   21                                                  
CONECT   11    4   12   14                                                  
CONECT   12    8   11   17                                                  
CONECT   13    6   16   19                                                  
CONECT   14    5   11   22                                                  
CONECT   15    7   16   23                                                  
CONECT   16   13   15   17                                                  
CONECT   17   12   16   20                                                  
CONECT   18    9                                                            
CONECT   19   13                                                            
CONECT   20   17                                                            
CONECT   21    1   10                                                       
CONECT   22    2   14                                                       
CONECT   23    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0033924
HETATM    1  C1  UNL     1       6.610   0.731  -0.422  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.682  -0.272  -0.120  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.323  -0.124  -0.116  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.760   1.078  -0.423  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.363   1.252  -0.425  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.908   2.490  -0.744  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.536   0.200  -0.114  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.145  -1.023   0.198  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.515  -1.183   0.197  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.329  -2.088   0.515  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.017  -2.079   0.102  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.665  -0.760   0.561  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.090  -0.807   0.205  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.663  -1.876  -0.456  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.005  -1.895  -0.779  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.838  -0.845  -0.456  1.00  0.00           C  
HETATM   17  O4  UNL     1      -6.199  -0.867  -0.785  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.277   0.226   0.204  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.925   0.249   0.532  1.00  0.00           C  
HETATM   20  O5  UNL     1      -2.350   1.323   1.196  1.00  0.00           O  
HETATM   21  C16 UNL     1      -3.189   2.410   1.537  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.085   0.305  -0.107  1.00  0.00           C  
HETATM   23  O6  UNL     1      -0.474   1.261  -0.649  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.259   1.403  -1.224  1.00  0.00           H  
HETATM   25  H2  UNL     1       7.539   0.221  -0.795  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.884   1.358   0.451  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.371   1.959  -0.681  1.00  0.00           H  
HETATM   28  H5  UNL     1       0.989   2.793  -0.784  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.926  -2.141   0.444  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.037  -2.186  -0.984  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.514  -2.923   0.635  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.477  -0.699   1.648  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.022  -2.718  -0.722  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.435  -2.739  -1.296  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.893  -1.259  -0.130  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.911   1.080   0.478  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.049   2.079   2.135  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.543   2.872   0.583  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.653   3.196   2.094  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8   22
CONECT    8    9    9   10
CONECT    9   29
CONECT   10   11
CONECT   11   12   30   31
CONECT   12   13   22   32
CONECT   13   14   14   19
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   18
CONECT   17   35
CONECT   18   19   19   36
CONECT   19   20
CONECT   20   21
CONECT   21   37   38   39
CONECT   22   23   23
END

HMDB0033924
     RDKit          3D
Cajanol
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.6097    0.7311   -0.4217 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6822   -0.2722   -0.1198 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3234   -0.1245   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596    1.0775   -0.4230 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3635    1.2515   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9084    2.4898   -0.7435 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5363    0.2000   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1450   -1.0234    0.1983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5153   -1.1832    0.1974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3291   -2.0880    0.5146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0168   -2.0789    0.1016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -0.7605    0.5606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898   -0.8074    0.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6630   -1.8761   -0.4560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0051   -1.8948   -0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382   -0.8455   -0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1993   -0.8671   -0.7847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2767    0.2261    0.2044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9252    0.2495    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3496    1.3234    1.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1894    2.4103    1.5367 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0845    0.3051   -0.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4737    1.2608   -0.6490 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2594    1.4033   -1.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5390    0.2205   -0.7948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8836    1.3583    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3707    1.9589   -0.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9893    2.7932   -0.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9260   -2.1414    0.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0367   -2.1858   -0.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5143   -2.9225    0.6355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4770   -0.6992    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0216   -2.7177   -0.7217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4345   -2.7393   -1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8931   -1.2593   -0.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9114    1.0805    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0493    2.0787    2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5429    2.8721    0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6528    3.1964    2.0940 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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 12 22  1  0
 22 23  2  0
  9  3  1  0
 19 13  1  0
 22  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 21 37  1  0
 21 38  1  0
 21 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',5-Dihydroxy-2',7-dimethoxyisoflavanone	HMDB

Chemical Formula

C₁₇H₁₆O₆

Average Molecular Weight

316.3053

Monoisotopic Molecular Weight

316.094688244

IUPAC Name

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

Traditional Name

cajanol

CAS Registry Number

61020-70-0

SMILES

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

InChI Identifier

InChI=1S/C17H16O6/c1-21-10-6-13(19)16-15(7-10)23-8-12(17(16)20)11-4-3-9(18)5-14(11)22-2/h3-7,12,18-19H,8H2,1-2H3

InChI Key

RYYWWFXWFMYKJM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C7 atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

7-O-methylated isoflavonoids

Alternative Parents

Substituents

2p-methoxyisoflavonoid-skeleton
7-methoxyisoflavonoid-skeleton
Hydroxyisoflavonoid
Isoflavanol
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoflavanones (C10204 )
Isoflavonoids (C10204 )
Isoflavonoids (LMPK12050499 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033924)
Cell membrane (HMDB: HMDB0033924)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033924)

Source

Exogenous

Exogenous (HMDB: HMDB0033924)

Food

Food (HMDB: HMDB0033924)

Pulse

Pea

Pigeon pea (FooDB: FOOD00037)

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033924)
Fabaceae (HMDB: HMDB0033924)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033924)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	62.2 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	0.08 g/L	ALOGPS
logP	2.78	ALOGPS
logP	2.72	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.31	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.62 m³·mol⁻¹	ChemAxon
Polarizability	31.68 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	174.249	31661259
DarkChem	[M-H]-	174.458	31661259
DeepCCS	[M+H]+	178.821	30932474
DeepCCS	[M-H]-	176.463	30932474
DeepCCS	[M-2H]-	210.516	30932474
DeepCCS	[M+Na]+	185.743	30932474
AllCCS	[M+H]+	173.7	32859911
AllCCS	[M+H-H2O]+	170.3	32859911
AllCCS	[M+NH4]+	177.0	32859911
AllCCS	[M+Na]+	177.9	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	176.0	32859911
AllCCS	[M+HCOO]-	175.8	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.	7.82 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2581 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2347.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	295.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	159.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	191.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	646.2 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	643.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1172.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	464.0 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	1469.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	412.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	418.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	355.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	210.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	97.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cajanol	COC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C1	4092.7	Standard polar	33892256
Cajanol	COC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C1	2890.1	Standard non polar	33892256
Cajanol	COC1=CC(O)=C2C(=O)C(COC2=C1)C1=C(OC)C=C(O)C=C1	3005.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cajanol,1TMS,isomer #1	COC1=CC2=C(C(=O)C(C3=CC=C(O)C=C3OC)CO2)C(O[Si](C)(C)C)=C1	2894.3	Semi standard non polar	33892256
Cajanol,1TMS,isomer #2	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3OC)COC2=C1	2848.0	Semi standard non polar	33892256
Cajanol,2TMS,isomer #1	COC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C)C=C3OC)CO2)C(O[Si](C)(C)C)=C1	2791.4	Semi standard non polar	33892256
Cajanol,1TBDMS,isomer #1	COC1=CC2=C(C(=O)C(C3=CC=C(O)C=C3OC)CO2)C(O[Si](C)(C)C(C)(C)C)=C1	3146.0	Semi standard non polar	33892256
Cajanol,1TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC)COC2=C1	3103.4	Semi standard non polar	33892256
Cajanol,2TBDMS,isomer #1	COC1=CC2=C(C(=O)C(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC)CO2)C(O[Si](C)(C)C(C)(C)C)=C1	3290.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cajanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0962000000-1f286a9d768f17f227ba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cajanol GC-MS (2 TMS) - 70eV, Positive	splash10-006t-5743900000-66dcacacf6409e3d921b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cajanol 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 - Cajanol 10V, Positive-QTOF	splash10-014i-0439000000-9178972eb0df1ac5bbd9	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 20V, Positive-QTOF	splash10-014r-0943000000-a6bbc67ee5ad791006a6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 40V, Positive-QTOF	splash10-014r-1910000000-4d36e1a0c0db818e2b5a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 10V, Negative-QTOF	splash10-014i-0019000000-bc5ce896443d7ccab549	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 20V, Negative-QTOF	splash10-014i-0897000000-c3f885ce66d3c32a9950	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 40V, Negative-QTOF	splash10-00xr-8970000000-c9ad7f726a2934c55a66	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 10V, Positive-QTOF	splash10-014i-0209000000-ee2b84d4fd0a849d586a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 20V, Positive-QTOF	splash10-014m-0902000000-cf023e624af01c6e8958	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 40V, Positive-QTOF	splash10-014i-0920000000-ee180313b1e9aad8cb5e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 10V, Negative-QTOF	splash10-014i-0009000000-57e0edfe40e4094c309a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 20V, Negative-QTOF	splash10-016s-0896000000-33081233015da57b7a0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cajanol 40V, Negative-QTOF	splash10-014i-0390000000-d3f68146d89e03e730aa	2021-09-22	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

442670

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1839281

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Liu XL, Zhang XJ, Fu YJ, Zu YG, Wu N, Liang L, Efferth T: Cajanol inhibits the growth of Escherichia coli and Staphylococcus aureus by acting on membrane and DNA damage. Planta Med. 2011 Jan;77(2):158-63. doi: 10.1055/s-0030-1250146. Epub 2010 Aug 27. [PubMed:20803417 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Cajanol (HMDB0033924)

MOL for HMDB0033924 (Cajanol)

3D MOL for HMDB0033924 (Cajanol)

3D SDF for HMDB0033924 (Cajanol)

3D-SDF for HMDB0033924 (Cajanol)

PDB for HMDB0033924 (Cajanol)

3D PDB for HMDB0033924 (Cajanol)

SMILES for HMDB0033924 (Cajanol)

INCHI for HMDB0033924 (Cajanol)

Structure for HMDB0033924 (Cajanol)

3D Structure for HMDB0033924 (Cajanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra