MiMeDB: Showing metabocard for Equol (MMDBc0057093)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-10-05 15:38:43 UTC

Update Date

2024-10-09 22:40:16 UTC

Metabolite ID

MMDBc0057093

Metabolite Identification

Common Name

Equol

Description

Equol is a metabolite of daidzein, a phytoestrogen common in the human diet and abundant in soy. Intestinal bacteria in humans can reduce daidzein to equol, and can be found in normal human urine. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. (PMID: 17579895 , 17579894 ). Equol can be found in Bacteroides, Bifidobacterium, Enterococcus, Lactobacillus and Eggerthella (PMID: 20519412 ; PMID: 18838805 ).

Structure

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

HMDB0002209
     RDKit          3D
Equol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.0398    0.8708    1.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    0.3167    1.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    1.0480    1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    0.5216    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -0.7836    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993   -1.4022   -0.5534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1308   -0.8171   -1.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4408    0.4682   -1.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    0.5205   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.4938   -1.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378    1.5568   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6939    2.5181   -0.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064    0.6535    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690   -0.3027    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756   -0.3876   -0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7943   -1.4322    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7399   -1.5170    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8881   -0.9982    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9971    1.8293    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7445    2.0785    1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7539    1.1837    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -2.4830   -0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920   -1.5175   -2.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -0.8046   -2.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858    2.1821   -2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    3.4302   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8241    0.7257    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.0239    1.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -1.3361    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971   -2.4303    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8166   -2.5672   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7845   -1.5943    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
 17 18  2  0
 18  2  1  0
 16  6  1  0
 15  9  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END


  Mrv1652310011709232D          

 18 20  0  0  1  0            999 V2000
   14.5096   -8.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5096   -9.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2239  -10.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9385   -9.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9385   -8.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2239   -8.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6529  -10.1765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3673   -9.7640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.3673   -8.9390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6529   -8.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0833  -10.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7949   -8.5264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0833  -11.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978  -11.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5123  -11.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5123  -10.1774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -9.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2284  -11.4149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  6  0  0  0
  1 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 11 17  1  0  0  0  0
 15 18  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0057093

> <DATABASE_NAME>
MIME

> <SMILES>
OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1

> <INCHI_KEY>
ADFCQWZHKCXPAJ-GFCCVEGCSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.2699

> <EXACT_MASS>
242.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
25.814472608961456

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
3.1916778773333334

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.310681940578428

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.632070985862319

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855539683956429

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
68.96020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-equol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002209
     RDKit          3D
Equol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.0398    0.8708    1.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    0.3167    1.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    1.0480    1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    0.5216    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -0.7836    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993   -1.4022   -0.5534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1308   -0.8171   -1.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4408    0.4682   -1.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    0.5205   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.4938   -1.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378    1.5568   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6939    2.5181   -0.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064    0.6535    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690   -0.3027    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756   -0.3876   -0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7943   -1.4322    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7399   -1.5170    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8881   -0.9982    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9971    1.8293    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7445    2.0785    1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7539    1.1837    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -2.4830   -0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920   -1.5175   -2.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -0.8046   -2.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858    2.1821   -2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    3.4302   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8241    0.7257    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.0239    1.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -1.3361    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971   -2.4303    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8166   -2.5672   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7845   -1.5943    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
 17 18  2  0
 18  2  1  0
 16  6  1  0
 15  9  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

HEADER    PROTEIN                                 01-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-OCT-17         0                                  
HETATM    1  C   UNK     0      27.085 -16.686   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.085 -18.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.418 -18.996   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.752 -18.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.752 -16.686   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.418 -15.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.085 -18.996   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.419 -18.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      32.419 -16.686   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      31.085 -15.916   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      33.756 -18.998   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      25.751 -15.916   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      33.756 -20.536   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.089 -21.306   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.423 -20.536   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.423 -18.998   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.089 -18.228   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      37.760 -21.308   0.000  0.00  0.00           O+0
CONECT    1    2    6   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    8   13   17                                                  
CONECT   12    1                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   11                                                       
CONECT   18   15                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0002209
HETATM    1  O1  UNL     1      -5.040   0.871   1.839  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.900   0.317   1.253  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.746   1.048   1.080  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.595   0.522   0.500  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.590  -0.784   0.073  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.399  -1.402  -0.553  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.131  -0.817  -1.923  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.441   0.468  -1.803  1.00  0.00           O  
HETATM    9  C7  UNL     1       1.614   0.521  -1.037  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.581   1.494  -1.327  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.738   1.557  -0.583  1.00  0.00           C  
HETATM   12  O3  UNL     1       4.694   2.518  -0.868  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.906   0.653   0.429  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.969  -0.303   0.723  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.776  -0.388  -0.025  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.794  -1.432   0.330  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.740  -1.517   0.244  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.888  -0.998   0.821  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.997   1.829   2.135  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.745   2.078   1.415  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.754   1.184   0.417  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.677  -2.483  -0.748  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.592  -1.517  -2.417  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.068  -0.805  -2.518  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.386   2.182  -2.143  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.660   3.430  -0.415  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.824   0.726   0.997  1.00  0.00           H  
HETATM   28  H10 UNL     1       3.103  -1.024   1.530  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.495  -1.336   1.414  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.297  -2.430   0.283  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.817  -2.567  -0.070  1.00  0.00           H  
HETATM   32  H14 UNL     1      -4.784  -1.594   0.946  1.00  0.00           H  
CONECT    1    2   19
CONECT    2    3    3   18
CONECT    3    4   20
CONECT    4    5    5   21
CONECT    5    6   17
CONECT    6    7   16   22
CONECT    7    8   23   24
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   25
CONECT   11   12   13   13
CONECT   12   26
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16
CONECT   16   29   30
CONECT   17   18   18   31
CONECT   18   32
END

HMDB0002209
     RDKit          3D
Equol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.0398    0.8708    1.8387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    0.3167    1.2530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7455    1.0480    1.0802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5953    0.5216    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899   -0.7836    0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3993   -1.4022   -0.5534 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1308   -0.8171   -1.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4408    0.4682   -1.8033 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6143    0.5205   -1.0371 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5808    1.4938   -1.3270 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378    1.5568   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6939    2.5181   -0.8683 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9064    0.6535    0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9690   -0.3027    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7756   -0.3876   -0.0251 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7943   -1.4322    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7399   -1.5170    0.2441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8881   -0.9982    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9971    1.8293    2.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7445    2.0785    1.4150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7539    1.1837    0.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6769   -2.4830   -0.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5920   -1.5175   -2.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0678   -0.8046   -2.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858    2.1821   -2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    3.4302   -0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8241    0.7257    0.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1028   -1.0239    1.5302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4949   -1.3361    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971   -2.4303    0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8166   -2.5672   -0.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7845   -1.5943    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
  5 17  1  0
 17 18  2  0
 18  2  1  0
 16  6  1  0
 15  9  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  6 22  1  6
  7 23  1  0
  7 24  1  0
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END

Synonyms

Value	Source
(+-)-Isomer OF equol	MeSH
3' Hydroxy equol	MeSH
3'-Hydroxy-equol	MeSH
4' O Methyl equol	MeSH
4' Methoxy 7 isoflavanol	MeSH
4'-O-Methyl equol	MeSH
4'-Methoxy-7-isoflavanol	MeSH
6' Hydroxy equol	MeSH
6'-Hydroxy-equol	MeSH
Equol, 4'-O-methyl	MeSH
AUS-131(S)-equol	ChEMBL, HMDB
(-)-(S)-Equol	HMDB
(-)-Equol	HMDB
(S)-(-)-4',7-Isoflavandiol	HMDB
(S)-3,4-dihydro-3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol	HMDB
(S)-Equol	HMDB
4',7-Dihydroxyisoflavan	HMDB
4',7-Isoflavandiol	HMDB

Molecular Formula

C₁₅H₁₄O₃

Average Mass

242.2699

Monoisotopic Mass

242.094294314

IUPAC Name

(3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol

Traditional Name

(-)-equol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1

InChI Identifier

InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1

InChI Key

ADFCQWZHKCXPAJ-GFCCVEGCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavans (CHEBI:34741 )
isoflavans (C14131 )
Isoflavanes (C14131 )

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.044 g/L	ALOGPS
logP	2.91	ALOGPS
logP	3.19	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.96 m³·mol⁻¹	ChemAxon
Polarizability	25.81 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-2590000000-de6943a0e29cb74d29c4	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6439000000-bd3446db9a81b442105b	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-0890000000-7e7596ef550328bb2d8b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0950000000-eb2fba880af94e2ffaa4	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adi-5910000000-ae99af1d6277808c807a	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0390000000-9e81ff09baf049465955	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0390000000-23c63d12aef21bc1a2fe	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0603-4930000000-18ce0b21dd8e144014a5	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0005-0960000000-9edad7cf7d51f7a71fee	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0590000000-19e7c74a42b427564aac	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-4930000000-a7500058dae2b15f912b	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0970000000-7b598fa2edd4a41a1f9b	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kf-1970000000-4a2a37c7a8d430f4f164	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3910000000-5790b5708e0e13e02c98	2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links

Exposure Sources

Source Type	Activity	Data Source	Reference
General Exposome	Not Available	U.S. Environmental Protection Agency	CompTox
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0002209

DrugBank ID

DB11674

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

Equol

METLIN ID

Not Available

PubChem Compound

91469

PDB ID

Not Available

ChEBI ID

428126

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1093/ajcn/85.4.1050. [PubMed:17413104 ]
Yuan JP, Wang JH, Liu X: Metabolism of dietary soy isoflavones to equol by human intestinal microflora--implications for health. Mol Nutr Food Res. 2007 Jul;51(7):765-81. doi: 10.1002/mnfr.200600262. [PubMed:17579894 ]
Moors S, Blaszkewicz M, Bolt HM, Degen GH: Simultaneous determination of daidzein, equol, genistein and bisphenol A in human urine by a fast and simple method using SPE and GC-MS. Mol Nutr Food Res. 2007 Jul;51(7):787-98. doi: 10.1002/mnfr.200600289. [PubMed:17579895 ]
Setchell KD, Clerici C: Equol: history, chemistry, and formation. J Nutr. 2010 Jul;140(7):1355S-62S. doi: 10.3945/jn.109.119776. Epub 2010 Jun 2. [PubMed:20519412 ]
Yokoyama S, Suzuki T: Isolation and characterization of a novel equol-producing bacterium from human feces. Biosci Biotechnol Biochem. 2008 Oct;72(10):2660-6. doi: 10.1271/bbb.80329. Epub 2008 Oct 7. [PubMed:18838805 ]

Showing metabocard for Equol (MMDBc0057093)

MOL for #<Metabolite:0x00007fdb4c44f4b0>

3D MOL for #<Metabolite:0x00007fdb4c44f4b0>

3D SDF for #<Metabolite:0x00007fdb4c44f4b0>

3D-SDF for #<Metabolite:0x00007fdb4c44f4b0>

PDB for #<Metabolite:0x00007fdb4c44f4b0>

3D PDB for #<Metabolite:0x00007fdb4c44f4b0>

SMILES for #<Metabolite:0x00007fdb4c44f4b0>

INCHI for #<Metabolite:0x00007fdb4c44f4b0>

Structure for #<Metabolite:0x00007fdb4c44f4b0>

3D Structure for #<Metabolite:0x00007fdb4c44f4b0>