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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:34 UTC

Update Date

2021-10-13 04:47:12 UTC

HMDB ID

HMDB0005760

Secondary Accession Numbers

HMDB05760

Metabolite Identification

Common Name

Dihydrodaidzein

Description

Dihydrodaidzein belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Thus, dihydrodaidzein is considered to be a flavonoid. Dihydrodaidzein has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make dihydrodaidzein a potential biomarker for the consumption of these foods. Dihydrodaidzein is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on Dihydrodaidzein.

Structure

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

HMDB0005760
     RDKit          3D
Dihydrodaidzein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.2079   -0.2166   -2.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    0.1001   -0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -0.1083   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507   -0.3298   -1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2623   -0.5271   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889   -0.5050    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9263   -0.7063    0.7255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -0.2864    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -0.0901    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    0.1332    1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    0.0731    1.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3771    0.6811    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7905    0.4214   -0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.4761   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    1.2623   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4975   -0.0156   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8433   -0.2082   -1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -1.0700   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085   -0.8410   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.3514   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0503   -0.7006   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.1570    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8150   -0.2627    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -1.0107    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    0.6527    2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1741    1.7476    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329    2.5040   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6802    2.0979   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5668   -0.3015   -0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -2.0879   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.6870   -0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 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
 12  2  1  0
 19 13  1  0
  9  3  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

  Mrv0541 02231220282D          

 19 21  0  0  0  0            999 V2000
   17.8603   -3.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8603   -5.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7725   -3.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2881   -6.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1458   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1458   -3.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8603   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4315   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5748   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5748   -3.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4315   -5.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7171   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3122   -5.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3122   -3.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0596   -4.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0596   -3.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7171   -6.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0026   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0026   -5.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  2  7  2  0  0  0  0
  3 16  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 18  2  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005760

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2

> <INCHI_KEY>
JHYXBPPMXZIHKG-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.761430116176626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.3812234356666666

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.501081398648399

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.775319135909201

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9060041662312335

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.69560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+/-)-dihydrodaidzein

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0005760
     RDKit          3D
Dihydrodaidzein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.2079   -0.2166   -2.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    0.1001   -0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -0.1083   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507   -0.3298   -1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2623   -0.5271   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889   -0.5050    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9263   -0.7063    0.7255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -0.2864    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -0.0901    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    0.1332    1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    0.0731    1.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3771    0.6811    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7905    0.4214   -0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.4761   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    1.2623   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4975   -0.0156   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8433   -0.2082   -1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -1.0700   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085   -0.8410   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.3514   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0503   -0.7006   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.1570    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8150   -0.2627    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -1.0107    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    0.6527    2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1741    1.7476    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329    2.5040   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6802    2.0979   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5668   -0.3015   -0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -2.0879   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.6870   -0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 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
 12  2  1  0
 19 13  1  0
  9  3  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      33.339  -6.468   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      33.339 -11.088   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      38.775  -6.431   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      26.671 -11.858   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      32.005  -8.778   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.005  -7.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.339  -9.548   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.672  -9.548   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.673  -8.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.673  -7.238   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.672 -11.088   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.339  -8.778   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.049  -9.602   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.049  -6.415   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.445  -8.810   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.445  -7.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.339 -11.858   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.005  -9.548   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.005 -11.088   0.000  0.00  0.00           C+0
CONECT    1    6   10                                                       
CONECT    2    7                                                            
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5    6    7    8                                                  
CONECT    6    1    5                                                       
CONECT    7    2    5    9                                                  
CONECT    8    5   11   12                                                  
CONECT    9    7   10   13                                                  
CONECT   10    1    9   14                                                  
CONECT   11    8   17                                                       
CONECT   12    8   18                                                       
CONECT   13    9   15                                                       
CONECT   14   10   16                                                       
CONECT   15   13   16                                                       
CONECT   16    3   14   15                                                  
CONECT   17   11   19                                                       
CONECT   18   12   19                                                       
CONECT   19    4   17   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0005760
HETATM    1  O1  UNL     1       0.208  -0.217  -2.050  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.553   0.100  -0.883  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.939  -0.108  -0.476  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.951  -0.330  -1.393  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.262  -0.527  -1.009  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.589  -0.505   0.335  1.00  0.00           C  
HETATM    7  O2  UNL     1       5.926  -0.706   0.725  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.594  -0.286   1.254  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.287  -0.090   0.862  1.00  0.00           C  
HETATM   10  O3  UNL     1       1.277   0.133   1.818  1.00  0.00           O  
HETATM   11  C8  UNL     1      -0.095   0.073   1.477  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.377   0.681   0.120  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.791   0.421  -0.208  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.655   1.476  -0.384  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.003   1.262  -0.695  1.00  0.00           C  
HETATM   16  C13 UNL     1      -4.498  -0.016  -0.834  1.00  0.00           C  
HETATM   17  O4  UNL     1      -5.843  -0.208  -1.144  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.631  -1.070  -0.657  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.308  -0.841  -0.351  1.00  0.00           C  
HETATM   20  H1  UNL     1       2.719  -0.351  -2.451  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.050  -0.701  -1.741  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.472   0.157   0.787  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.815  -0.263   2.316  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.372  -1.011   1.472  1.00  0.00           H  
HETATM   25  H6  UNL     1      -0.654   0.653   2.235  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.174   1.748   0.187  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.333   2.504  -0.290  1.00  0.00           H  
HETATM   28  H9  UNL     1      -4.680   2.098  -0.833  1.00  0.00           H  
HETATM   29  H10 UNL     1      -6.567  -0.301  -0.453  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.029  -2.088  -0.768  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.633  -1.687  -0.214  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   12
CONECT    3    4    4    9
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7    8
CONECT    7   22
CONECT    8    9    9   23
CONECT    9   10
CONECT   10   11
CONECT   11   12   24   25
CONECT   12   13   26
CONECT   13   14   14   19
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   18
CONECT   17   29
CONECT   18   19   19   30
CONECT   19   31
END

HMDB0005760
     RDKit          3D
Dihydrodaidzein
 31 33  0  0  0  0  0  0  0  0999 V2000
    0.2079   -0.2166   -2.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533    0.1001   -0.8826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9388   -0.1083   -0.4761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9507   -0.3298   -1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2623   -0.5271   -1.0090 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5889   -0.5050    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9263   -0.7063    0.7255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5944   -0.2864    1.2535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865   -0.0901    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770    0.1332    1.8179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0951    0.0731    1.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3771    0.6811    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7905    0.4214   -0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6548    1.4761   -0.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0033    1.2623   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4975   -0.0156   -0.8337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8433   -0.2082   -1.1444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6308   -1.0700   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3085   -0.8410   -0.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7193   -0.3514   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0503   -0.7006   -1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4724    0.1570    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8150   -0.2627    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3721   -1.0107    1.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6539    0.6527    2.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1741    1.7476    0.1874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3329    2.5040   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6802    2.0979   -0.8331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5668   -0.3015   -0.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0291   -2.0879   -0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6331   -1.6870   -0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 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
 12  2  1  0
 19 13  1  0
  9  3  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
 11 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 17 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+/-)-dihydrodaidzein	ChEBI
2,3-Dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
7,4'-Dihydroxyisoflavanone	ChEBI
4',7-Dihydroxy-isoflavanone	HMDB

Chemical Formula

C₁₅H₁₂O₄

Average Molecular Weight

256.2534

Monoisotopic Molecular Weight

256.073558872

IUPAC Name

7-hydroxy-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(+/-)-dihydrodaidzein

CAS Registry Number

17238-05-0

SMILES

OC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2

InChI Key

JHYXBPPMXZIHKG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavanol
Isoflavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Aryl alkyl ketone
Aryl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavanone (CHEBI:75842 )
Isoflavonoids (LMPK12050447 )
an isoflavone (CPD-12609 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18469255)

Excreta

Biofluid or Excreta

Urine (PMID: 17413104)

Cellular substructure

Membrane (HMDB: HMDB0005760)

Source

Endogenous

Endogenous (HMDB: HMDB0005760)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Soy Foods Consumption (MarkerDB: MDB00000469)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	250 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	873.5 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	0.14 g/L	ALOGPS
logP	2.77	ALOGPS
logP	2.38	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	25.76 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]+	160.144	31661259
DarkChem	[M-H]-	160.405	31661259
DeepCCS	[M+H]+	160.839	30932474
DeepCCS	[M-H]-	158.481	30932474
DeepCCS	[M-2H]-	191.367	30932474
DeepCCS	[M+Na]+	166.932	30932474
AllCCS	[M+H]+	158.8	32859911
AllCCS	[M+H-H2O]+	154.9	32859911
AllCCS	[M+NH4]+	162.5	32859911
AllCCS	[M+Na]+	163.6	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	160.4	32859911
AllCCS	[M+HCOO]-	159.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihydrodaidzein	OC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O	3770.5	Standard polar	33892256
Dihydrodaidzein	OC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O	2665.8	Standard non polar	33892256
Dihydrodaidzein	OC1=CC=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O	2752.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrodaidzein,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C=C1	2703.6	Semi standard non polar	33892256
Dihydrodaidzein,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)COC2=C1	2672.5	Semi standard non polar	33892256
Dihydrodaidzein,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1	2726.2	Semi standard non polar	33892256
Dihydrodaidzein,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2=O)C=C1	2951.0	Semi standard non polar	33892256
Dihydrodaidzein,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=O)C(C3=CC=C(O)C=C3)COC2=C1	2935.3	Semi standard non polar	33892256
Dihydrodaidzein,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1	3229.5	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 - Dihydrodaidzein GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a6r-2790000000-5c32d81fea587727221d	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrodaidzein GC-MS (2 TMS) - 70eV, Positive	splash10-00fr-7936000000-b483e2a442556fb427d9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrodaidzein 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 - Dihydrodaidzein LC-ESI-QFT 17V, positive-QTOF	splash10-03di-0900000000-f3ddb99bf79f26ab077e	2020-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihydrodaidzein LC-ESI-IT 17V, positive-QTOF	splash10-03k9-0900000000-790a36fdcf35d00b97de	2020-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Negative-QTOF	splash10-0a4i-0090000000-baed821bce01fea923c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Negative-QTOF	splash10-0a4i-0290000000-2fcebdf6ef2c3dc568ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Negative-QTOF	splash10-014l-7920000000-9009639f6e531f9f33d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Negative-QTOF	splash10-0a4i-0090000000-82e226df9342cd67d796	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Negative-QTOF	splash10-0a4i-0290000000-99d6d002cfbacfc07cf1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Negative-QTOF	splash10-0j7r-1980000000-ce78cc93955eeefee01f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Positive-QTOF	splash10-0a4i-0290000000-5103dee7bd918c7b6c9e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Positive-QTOF	splash10-0a4r-0970000000-a12e6d9523183e1efc4a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Positive-QTOF	splash10-05ts-6910000000-83db00f15de1477dcc4f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 10V, Positive-QTOF	splash10-0a4i-0090000000-b46e3a63d530434294a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 20V, Positive-QTOF	splash10-0a4i-0590000000-dc00d36993e2435d676f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodaidzein 40V, Positive-QTOF	splash10-0a6r-5920000000-4238c2fb09b7ca171b68	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	18469255	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	10952094	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	15506819	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	15113171	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	10527518	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	14698210	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	10509897	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	20164315	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	7662591	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	17499260	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	18469255	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	10952094	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	15506819	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	15113171	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	10527518	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	14698210	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	10509897	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	20164315	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	7662591	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 861	17499260	details
Urine	Detected and Quantified	0.114 +/- 0.03 (0.05 - 0.23) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17413104	details
Urine	Detected and Quantified	0.0791 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.0916 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22493748	details
Urine	Detected and Quantified	0.192 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0.0007 +/- 0.0003 (0.0001 - 0.002) umol/mmol creatinine	Adult (>18 years old)	Both	Soy consumption (ileostomies)	17413104	details

Associated Disorders and Diseases

Disease References

Ileostomy
Walsh KR, Haak SJ, Bohn T, Tian Q, Schwartz SJ, Failla ML: Isoflavonoid glucosides are deconjugated and absorbed in the small intestine of human subjects with ileostomies. Am J Clin Nutr. 2007 Apr;85(4):1050-6. [PubMed:17413104 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023752

KNApSAcK ID

C00009533

Chemspider ID

154076

KEGG Compound ID

Not Available

BioCyc ID

2-HYDROXY-23-DIHYDRODAIDZEIN

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176907

PDB ID

Not Available

ChEBI ID

75842

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000469

Good Scents ID

rw1134981

References

Synthesis Reference

Jain, Amolak C.; Nayyar, Naresh K. Synthesis of (±)-sativanone and (±)-dihydrodaidzein. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1987), 26B(2), 136-9.

Material Safety Data Sheet (MSDS)

Not Available

General References

Franke AA, Custer LJ, Wilkens LR, Le Marchand LL, Nomura AM, Goodman MT, Kolonel LN: Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):45-59. [PubMed:12270199 ]

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

Dihydrodaidzein → 3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic acid	details
Dihydrodaidzein → 3,4,5-trihydroxy-6-[4-(7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]oxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

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

Reactions

Dihydrodaidzein → [4-(7-hydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl)phenyl]oxidanesulfonic acid	details

Showing metabocard for Dihydrodaidzein (HMDB0005760)

MOL for HMDB0005760 (Dihydrodaidzein)

3D MOL for HMDB0005760 (Dihydrodaidzein)

3D SDF for HMDB0005760 (Dihydrodaidzein)

3D-SDF for HMDB0005760 (Dihydrodaidzein)

PDB for HMDB0005760 (Dihydrodaidzein)

3D PDB for HMDB0005760 (Dihydrodaidzein)

SMILES for HMDB0005760 (Dihydrodaidzein)

INCHI for HMDB0005760 (Dihydrodaidzein)

Structure for HMDB0005760 (Dihydrodaidzein)

3D Structure for HMDB0005760 (Dihydrodaidzein)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions