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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:55:16 UTC

Update Date

2021-09-26 22:50:51 UTC

HMDB ID

HMDB0243678

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(R)-Equol

Description

(R)-Equol, also known as rac-equol or 3' hydroxy equol, belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Thus, (R)-equol is considered to be a flavonoid. Based on a literature review a significant number of articles have been published on (R)-Equol. This compound has been identified in human blood as reported by (PMID: 31557052 ). (r)-equol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (R)-Equol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0243678
     RDKit          3D
(R)-Equol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.8359   -0.0227   -1.0768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -0.1374   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    0.2392    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623    0.1296    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132   -0.3828   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -0.5200   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.3929    1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337   -1.0689    1.7448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -0.3450    1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713   -0.5756    1.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099    0.1818    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8604   -0.0580    0.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717    1.1696   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7289    1.4339   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8348    0.6525    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704    0.8600    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2681   -0.7639   -1.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194   -0.6451   -1.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3913   -0.8390   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5689    0.6369    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.4275    1.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1982   -0.9474   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283   -1.3839    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -2.4335    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.3561    1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3003   -0.7323    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7887    1.7875   -0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4082    2.2219   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    1.3624    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1407    1.4139   -0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335   -1.1748   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741   -0.9437   -2.7337 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  0
  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


  Mrv1652308221900062D          

 18 20  0  0  0  0            999 V2000
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  4  2  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14  8  2  0  0  0  0
 15  8  1  0  0  0  0
 15 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0243678

> <DATABASE_NAME>
hmdb

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

> <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

> <INCHI_KEY>
ADFCQWZHKCXPAJ-UHFFFAOYSA-N

> <FORMULA>
C15H14O3

> <MOLECULAR_WEIGHT>
242.274

> <EXACT_MASS>
242.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.27504316404469

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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

$$$$

HMDB0243678
     RDKit          3D
(R)-Equol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.8359   -0.0227   -1.0768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -0.1374   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    0.2392    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623    0.1296    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132   -0.3828   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -0.5200   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.3929    1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337   -1.0689    1.7448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -0.3450    1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713   -0.5756    1.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099    0.1818    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8604   -0.0580    0.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717    1.1696   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7289    1.4339   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8348    0.6525    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704    0.8600    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2681   -0.7639   -1.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194   -0.6451   -1.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3913   -0.8390   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5689    0.6369    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.4275    1.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1982   -0.9474   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283   -1.3839    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -2.4335    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.3561    1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3003   -0.7323    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7887    1.7875   -0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4082    2.2219   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    1.3624    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1407    1.4139   -0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335   -1.1748   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741   -0.9437   -2.7337 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  0
  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                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    4   10                                                       
CONECT    2    5   10                                                       
CONECT    3    6   11                                                       
CONECT    4    1   13                                                       
CONECT    5    2   13                                                       
CONECT    6    3   14                                                       
CONECT    7   11   12                                                       
CONECT    8   14   15                                                       
CONECT    9   12   18                                                       
CONECT   10    1    2   12                                                  
CONECT   11    3    7   15                                                  
CONECT   12    7    9   10                                                  
CONECT   13    4    5   16                                                  
CONECT   14    6    8   17                                                  
CONECT   15    8   11   18                                                  
CONECT   16   13                                                            
CONECT   17   14                                                            
CONECT   18    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0243678
HETATM    1  O1  UNL     1      -5.836  -0.023  -1.077  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.461  -0.137  -0.816  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.909   0.239   0.376  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.562   0.130   0.637  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.713  -0.383  -0.337  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.253  -0.520  -0.100  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.001  -1.393   1.107  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.234  -1.069   1.745  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.229  -0.345   1.090  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.571  -0.576   1.266  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.510   0.182   0.582  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.860  -0.058   0.767  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.072   1.170  -0.277  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.729   1.434  -0.482  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.835   0.652   0.221  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.370   0.860   0.068  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.268  -0.764  -1.542  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.619  -0.645  -1.782  1.00  0.00           C  
HETATM   19  H1  UNL     1      -6.391  -0.839  -0.826  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.569   0.637   1.132  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.125   0.428   1.580  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.198  -0.947  -1.017  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.828  -1.384   1.826  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.118  -2.433   0.729  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.868  -1.356   1.946  1.00  0.00           H  
HETATM   26  H8  UNL     1       6.300  -0.732   0.152  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.789   1.787  -0.833  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.408   2.222  -1.168  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.012   1.362   0.974  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.141   1.414  -0.863  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.634  -1.175  -2.342  1.00  0.00           H  
HETATM   32  H14 UNL     1      -4.074  -0.944  -2.734  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

HMDB0243678
     RDKit          3D
(R)-Equol
 32 34  0  0  0  0  0  0  0  0999 V2000
   -5.8359   -0.0227   -1.0768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4612   -0.1374   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    0.2392    0.3755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623    0.1296    0.6373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7132   -0.3828   -0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2533   -0.5200   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0012   -1.3929    1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2337   -1.0689    1.7448 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2286   -0.3450    1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5713   -0.5756    1.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5099    0.1818    0.5824 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8604   -0.0580    0.7666 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0717    1.1696   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7289    1.4339   -0.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8348    0.6525    0.2213 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3704    0.8600    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2681   -0.7639   -1.5417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6194   -0.6451   -1.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3913   -0.8390   -0.8256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5689    0.6369    1.1315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1251    0.4275    1.5801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1982   -0.9474   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8283   -1.3839    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1184   -2.4335    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8679   -1.3561    1.9455 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3003   -0.7323    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7887    1.7875   -0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4082    2.2219   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0122    1.3624    0.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1407    1.4139   -0.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6335   -1.1748   -2.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741   -0.9437   -2.7337 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  0
  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
rac-Equol	HMDB
(+-)-Isomer OF equol	HMDB
3' Hydroxy equol	HMDB
3'-Hydroxy-equol	HMDB
4'-O-Methyl equol	HMDB
4'-Methoxy-7-isoflavanol	HMDB
6' Hydroxy equol	HMDB
Equol, 4'-O-methyl	HMDB
4' O Methyl equol	HMDB
4' Methoxy 7 isoflavanol	HMDB
6'-Hydroxy-equol	HMDB
Equol	HMDB

Chemical Formula

C₁₅H₁₄O₃

Average Molecular Weight

242.274

Monoisotopic Molecular Weight

242.094294311

IUPAC Name

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

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

InChI Key

ADFCQWZHKCXPAJ-UHFFFAOYSA-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

Isoflavans (LMPK12080003 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	26.28 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	158.538	30932474
DeepCCS	[M-H]-	156.18	30932474
DeepCCS	[M-2H]-	189.083	30932474
DeepCCS	[M+Na]+	164.631	30932474
AllCCS	[M+H]+	156.3	32859911
AllCCS	[M+H-H2O]+	152.3	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.2	32859911
AllCCS	[M-H]-	159.8	32859911
AllCCS	[M+Na-2H]-	159.3	32859911
AllCCS	[M+HCOO]-	158.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	6.12 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4259 minutes	33406817
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1736.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	331.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	192.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	369.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	609.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	459.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	115.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1154.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	441.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1279.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	351.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	381.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	219.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	66.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Equol	OC1=CC=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	3277.1	Standard polar	33892256
(R)-Equol	OC1=CC=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	2430.7	Standard non polar	33892256
(R)-Equol	OC1=CC=C(C=C1)C1COC2=C(C1)C=CC(O)=C2	2582.3	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 - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-6439000000-bd3446db9a81b442105b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-2590000000-de6943a0e29cb74d29c4	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Equol 35V, Positive-QTOF	splash10-0ac0-0900000000-3192dc4c13fb215c586a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Equol 35V, Negative-QTOF	splash10-000i-0900000000-251406d93e191ace934e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 10V, Positive-QTOF	splash10-00dl-0970000000-1381c23a65be7114f63d	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 20V, Positive-QTOF	splash10-00di-0940000000-869abb7fd54f38d87829	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 40V, Positive-QTOF	splash10-0aor-5910000000-fff6d3a44eaa4686d906	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 10V, Negative-QTOF	splash10-0006-0290000000-8a5661f0cbec13fdd246	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 20V, Negative-QTOF	splash10-0006-0290000000-bdecaab71eff8da66d92	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 40V, Negative-QTOF	splash10-06dl-4930000000-9276319b719bf0d7d4fd	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 10V, Negative-QTOF	splash10-0006-0390000000-e16211e2bb6219c985c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 20V, Negative-QTOF	splash10-0006-0890000000-bb6990c985428199e7b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 40V, Negative-QTOF	splash10-014l-5930000000-0e4c38eb16c2b9ade7d7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 10V, Positive-QTOF	splash10-0006-0090000000-a810a7788942d2c00b91	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 20V, Positive-QTOF	splash10-0006-0790000000-71a7d70c2e4a22202365	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Equol 40V, Positive-QTOF	splash10-0573-6920000000-ad41dea2e22e2e0db859	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

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	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB089308

KNApSAcK ID

Not Available

Chemspider ID

339332

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

382975

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (R)-Equol (HMDB0243678)

MOL for HMDB0243678 ((R)-Equol)

3D MOL for HMDB0243678 ((R)-Equol)

3D SDF for HMDB0243678 ((R)-Equol)

3D-SDF for HMDB0243678 ((R)-Equol)

PDB for HMDB0243678 ((R)-Equol)

3D PDB for HMDB0243678 ((R)-Equol)

SMILES for HMDB0243678 ((R)-Equol)

INCHI for HMDB0243678 ((R)-Equol)

Structure for HMDB0243678 ((R)-Equol)

3D Structure for HMDB0243678 ((R)-Equol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra