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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:42 UTC

Update Date

2021-10-13 04:38:12 UTC

HMDB ID

HMDB0002209

Secondary Accession Numbers

HMDB02209

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>
HMDB0002209

> <DATABASE_NAME>
hmdb

> <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

View in JSmol View Stereo Labels

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

Chemical Formula

C₁₅H₁₄O₃

Average Molecular Weight

242.2699

Monoisotopic Molecular Weight

242.094294314

IUPAC Name

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

Traditional Name

(-)-equol

CAS Registry Number

531-95-3

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 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Lower gastrointestinal disorder

Ileostomy (HMDB: HMDB0002209)

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 17449595)

Cellular substructure

Membrane (HMDB: HMDB0002209)
Cell membrane (HMDB: HMDB0002209)

Excreta

Biofluid or Excreta

Urine (PMID: 17413104)

Source

Exogenous

Exogenous (HMDB: HMDB0002209)

Food

Animal origin

Poultry

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)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Legumes (HMDB: HMDB0002209)

Soy

Soy (HMDB: HMDB0002209)

Endogenous

Endogenous (HMDB: HMDB0002209)

Plant

Plant (HMDB: HMDB0002209)

Microbe

Bifidobacterium (HMDB: HMDB0002209)
Enterococcus faecalis (HMDB: HMDB0002209)
Bacteroides ovatus (HMDB: HMDB0002209)
Lactobacillus mucosae (HMDB: HMDB0002209)
Eggerthella (HMDB: HMDB0002209)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002209)

Biomarker

Fruits Consumption (MarkerDB: MDB00000385)
Vegetables Consumption (MarkerDB: MDB00000385)
Soy Foods Consumption (MarkerDB: MDB00000385)
Fats Consumption (MarkerDB: MDB00000385)
Dietary Fibre Consumption (MarkerDB: MDB00000385)
Equol Exposure (MarkerDB: MDB00000385)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	189.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	72.3 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	0.044 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.979	31661259
DarkChem	[M-H]-	159.456	31661259
DeepCCS	[M+H]+	154.594	30932474
DeepCCS	[M-H]-	152.236	30932474
DeepCCS	[M-2H]-	185.142	30932474
DeepCCS	[M+Na]+	160.687	30932474
AllCCS	[M+H]+	156.5	32859911
AllCCS	[M+H-H2O]+	152.5	32859911
AllCCS	[M+NH4]+	160.2	32859911
AllCCS	[M+Na]+	161.3	32859911
AllCCS	[M-H]-	160.1	32859911
AllCCS	[M+Na-2H]-	159.6	32859911
AllCCS	[M+HCOO]-	159.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Equol	OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1	3233.6	Standard polar	33892256
Equol	OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1	2523.9	Standard non polar	33892256
Equol	OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1	2602.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Equol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O)=CC=C3C2)C=C1	2511.2	Semi standard non polar	33892256
Equol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C[C@@H](C3=CC=C(O)C=C3)COC2=C1	2505.5	Semi standard non polar	33892256
Equol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O[Si](C)(C)C)=CC=C3C2)C=C1	2484.9	Semi standard non polar	33892256
Equol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O)=CC=C3C2)C=C1	2782.8	Semi standard non polar	33892256
Equol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C[C@@H](C3=CC=C(O)C=C3)COC2=C1	2778.8	Semi standard non polar	33892256
Equol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)C=C1	3029.7	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 - Equol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-2590000000-de6943a0e29cb74d29c4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Equol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6439000000-bd3446db9a81b442105b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Equol 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 - Equol 10V, Positive-QTOF	splash10-006x-0890000000-7e7596ef550328bb2d8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 20V, Positive-QTOF	splash10-00di-0950000000-eb2fba880af94e2ffaa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 40V, Positive-QTOF	splash10-0adi-5910000000-ae99af1d6277808c807a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 10V, Negative-QTOF	splash10-0006-0390000000-9e81ff09baf049465955	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 20V, Negative-QTOF	splash10-0006-0390000000-23c63d12aef21bc1a2fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 40V, Negative-QTOF	splash10-0603-4930000000-18ce0b21dd8e144014a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 10V, Positive-QTOF	splash10-0005-0960000000-9edad7cf7d51f7a71fee	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 20V, Positive-QTOF	splash10-0006-0590000000-19e7c74a42b427564aac	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 40V, Positive-QTOF	splash10-056r-4930000000-a7500058dae2b15f912b	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 10V, Negative-QTOF	splash10-006x-0970000000-7b598fa2edd4a41a1f9b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 20V, Negative-QTOF	splash10-00kf-1970000000-4a2a37c7a8d430f4f164	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Equol 40V, Negative-QTOF	splash10-014i-3910000000-5790b5708e0e13e02c98	2021-09-25	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	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	0.0006 (0.00057 - 0.00066) uM	Adult (>18 years old)	Male	Normal	17449595	details
Blood	Detected and Quantified	0.0006 (0.00057 - 0.0007) uM	Adult (>18 years old)	Female	Normal	17449595	details
Blood	Detected and Quantified	0.0002 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.000413 uM	Adult (>18 years old)	Female	Normal	15159299	details
Blood	Detected and Quantified	0.00056 uM	Adult (>18 years old)	Female	Normal	9796633	details
Blood	Detected and Quantified	0.0006 uM	Adult (>18 years old)	Female	Normal	20332276	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	11410004	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	18469255	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	16920843	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	8017326	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	10798213	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	10952094	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	15506819	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	19776178	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	10527518	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	14698210	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	20164315	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	17579895	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	7662591	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	7722188	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 866	7930998	details
Urine	Detected and Quantified	0.06 (0.01-0.10) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23657156	details
Urine	Detected and Quantified	0.00333 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.00590 +/- 0.0120 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	0.00327 (0.00275-0.00388) umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	0.00625 (0.00504-0.00775) umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	National Health a...	details
Urine	Detected and Quantified	1.560 +/- 1.780 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	10778038	details
Urine	Detected and Quantified	0.00533 +/- 0.00600 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.00533 +/- 0.00533 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.440 +/- 0.807 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	17353586	details
Urine	Detected and Quantified	0.0393 +/- 0.128 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18791925	details
Urine	Detected and Quantified	0.0574 +/- 0.198 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	18791925	details
Urine	Detected and Quantified	0.000867 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19167951	details
Urine	Detected and Quantified	0.00686 umol/mmol creatinine	Children (1 - 13 years old)	Both	Normal	17976571	details
Urine	Detected and Quantified	0.0167 +/- 0.0680 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	10744130	details
Urine	Detected and Quantified	0.000413 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	15159299	details
Urine	Detected and Quantified	0.00433 umol/mmol creatinine	Children (1 - 13 years old)	Female	Normal	17366830	details
Urine	Detected and Quantified	0.00452 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	20332276	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0124 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	22493748	details
Urine	Detected and Quantified	0.0904 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.283 umol/mmol creatinine	Children (1-13 years old)	Female	Normal	20385037	details
Urine	Detected and Quantified	0.00288 +/- 0.0147 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.00320 +/- 0.0160 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0112 +/- 0.0368 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0144 +/- 0.0272 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0320 +/- 0.0880 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.13 +/- 0.12 (0.0061-0.623) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	17413104	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	0 - 36.7 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

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

VMH ID

Not Available

MarkerDB ID

MDB00000385

Good Scents ID

rw1732471

References

Synthesis Reference

Wang, Xiu-Ling; Hur, Hor-Gil; Lee, Je Hyeon; Kim, Ki Tae; Kim, Su-Il. Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium. Applied and Environmental Microbiology (2005), 71(1), 214-219

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [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. [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 (HMDB0002209)

MOL for HMDB0002209 (Equol)

3D MOL for HMDB0002209 (Equol)

3D SDF for HMDB0002209 (Equol)

3D-SDF for HMDB0002209 (Equol)

PDB for HMDB0002209 (Equol)

3D PDB for HMDB0002209 (Equol)

SMILES for HMDB0002209 (Equol)

INCHI for HMDB0002209 (Equol)

Structure for HMDB0002209 (Equol)

3D Structure for HMDB0002209 (Equol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra