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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:37:42 UTC

Update Date

2022-03-07 02:57:09 UTC

HMDB ID

HMDB0041710

Secondary Accession Numbers

HMDB41710

Metabolite Identification

Common Name

cis-4-Hydroxyequol

Description

cis-4-Hydroxyequol belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Based on a literature review very few articles have been published on cis-4-Hydroxyequol.

Structure

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

HMDB0041710
     RDKit          3D
cis-4-Hydroxyequol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.9342   -0.3241    0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5389   -0.4053    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840   -0.2618   -0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.3384   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7271   -0.5585    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745   -0.6475    0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3062   -1.6869   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -1.3449   -1.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892   -0.3765   -0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7820   -0.4764   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4887    0.5334    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8739    0.4621    0.1943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8146    1.6228    0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282    1.7295    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444    0.7253   -0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2595    0.7550   -0.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0591    0.9838   -1.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139   -0.7003    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902   -0.6267    1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3806    0.5801    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -0.0859   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174   -0.2248   -1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0902   -0.8473    1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -1.8948   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970   -2.6353   -0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -1.3515   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4409    0.8479   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3287    2.4448    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8820    2.5711    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    1.4752    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    1.6705   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581   -0.8780    2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291   -0.7366    2.2697 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
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  6  1  0
 15  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  1
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv0541 02271201302D          

 19 21  0  0  0  0            999 V2000
    0.9336   -1.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481   -1.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -1.1020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6481    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9336   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2191    0.1355    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2191    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954    1.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243    1.3730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    0.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6388    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9243   -0.2770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2098    0.1355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -0.2770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0770   -1.5145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3532    1.3730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4954   -1.1020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  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
  7  6  1  6  0  0  0
 16 19  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0041710

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@H]1[C@H](COC2=CC(O)=CC=C12)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,15-18H,8H2/t13-,15-/m1/s1

> <INCHI_KEY>
YOSDNAMJVOLJKI-UKRRQHHQSA-N

> <FORMULA>
C15H14O4

> <MOLECULAR_WEIGHT>
258.2693

> <EXACT_MASS>
258.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.891012997657786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.82

> <JCHEM_LOGP>
2.0024235373333337

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.110935583559284

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.32215650280372

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3011826075856723

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
70.3769

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.82e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041710
     RDKit          3D
cis-4-Hydroxyequol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.9342   -0.3241    0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5389   -0.4053    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840   -0.2618   -0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.3384   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7271   -0.5585    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745   -0.6475    0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3062   -1.6869   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -1.3449   -1.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892   -0.3765   -0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7820   -0.4764   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4887    0.5334    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8739    0.4621    0.1943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8146    1.6228    0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282    1.7295    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444    0.7253   -0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2595    0.7550   -0.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0591    0.9838   -1.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139   -0.7003    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902   -0.6267    1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3806    0.5801    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -0.0859   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174   -0.2248   -1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0902   -0.8473    1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -1.8948   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970   -2.6353   -0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -1.3515   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4409    0.8479   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3287    2.4448    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8820    2.5711    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    1.4752    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    1.6705   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581   -0.8780    2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291   -0.7366    2.2697 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
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  6  1  0
 15  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  1
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0       1.743  -2.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.076  -2.827   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.410  -2.057   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.410  -0.517   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.076   0.253   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.743  -0.517   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.409   0.253   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.409   1.793   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.925   2.563   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.258   1.793   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.592   2.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.926   1.793   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.926   0.253   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.592  -0.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.258   0.253   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.925  -0.517   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.744  -2.827   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.259   2.563   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -0.925  -2.057   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    8   16    6                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16    7   15   19                                                  
CONECT   17    3                                                            
CONECT   18   12                                                            
CONECT   19   16                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0041710
HETATM    1  O1  UNL     1      -5.934  -0.324   0.236  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.539  -0.405   0.206  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.884  -0.262  -0.987  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.509  -0.338  -1.039  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.727  -0.558   0.076  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.274  -0.647   0.077  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.306  -1.687  -0.820  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.621  -1.345  -1.233  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.389  -0.377  -0.630  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.782  -0.476  -0.535  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.489   0.533   0.084  1.00  0.00           C  
HETATM   12  O3  UNL     1       5.874   0.462   0.194  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.815   1.623   0.598  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.428   1.729   0.507  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.744   0.725  -0.106  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.260   0.755  -0.249  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.059   0.984  -1.587  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.414  -0.700   1.269  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.790  -0.627   1.342  1.00  0.00           C  
HETATM   20  H1  UNL     1      -6.381   0.580   0.382  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.481  -0.086  -1.888  1.00  0.00           H  
HETATM   22  H3  UNL     1      -2.017  -0.225  -1.975  1.00  0.00           H  
HETATM   23  H4  UNL     1       0.090  -0.847   1.104  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.264  -1.895  -1.725  1.00  0.00           H  
HETATM   25  H6  UNL     1       0.397  -2.635  -0.250  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.260  -1.352  -0.954  1.00  0.00           H  
HETATM   27  H8  UNL     1       6.441   0.848  -0.531  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.329   2.445   1.096  1.00  0.00           H  
HETATM   29  H10 UNL     1       1.882   2.571   0.902  1.00  0.00           H  
HETATM   30  H11 UNL     1      -0.220   1.475   0.423  1.00  0.00           H  
HETATM   31  H12 UNL     1       0.574   1.670  -1.963  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.858  -0.878   2.200  1.00  0.00           H  
HETATM   33  H14 UNL     1      -4.329  -0.737   2.270  1.00  0.00           H  
CONECT    1    2   20
CONECT    2    3    3   19
CONECT    3    4   21
CONECT    4    5    5   22
CONECT    5    6   18
CONECT    6    7   16   23
CONECT    7    8   24   25
CONECT    8    9
CONECT    9   10   10   15
CONECT   10   11   26
CONECT   11   12   13   13
CONECT   12   27
CONECT   13   14   28
CONECT   14   15   15   29
CONECT   15   16
CONECT   16   17   30
CONECT   17   31
CONECT   18   19   19   32
CONECT   19   33
END

HMDB0041710
     RDKit          3D
cis-4-Hydroxyequol
 33 35  0  0  0  0  0  0  0  0999 V2000
   -5.9342   -0.3241    0.2361 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5389   -0.4053    0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8840   -0.2618   -0.9867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5086   -0.3384   -1.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7271   -0.5585    0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2745   -0.6475    0.0772 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3062   -1.6869   -0.8197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -1.3449   -1.2334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892   -0.3765   -0.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7820   -0.4764   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4887    0.5334    0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8739    0.4621    0.1943 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8146    1.6228    0.5984 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282    1.7295    0.5073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444    0.7253   -0.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2595    0.7550   -0.2492 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0591    0.9838   -1.5870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139   -0.7003    1.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902   -0.6267    1.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3806    0.5801    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4808   -0.0859   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0174   -0.2248   -1.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0902   -0.8473    1.1043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643   -1.8948   -1.7248 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970   -2.6353   -0.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2601   -1.3515   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4409    0.8479   -0.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3287    2.4448    1.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8820    2.5711    0.9017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2201    1.4752    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5741    1.6705   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581   -0.8780    2.1999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291   -0.7366    2.2697 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
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19  2  1  0
 16  6  1  0
 15  9  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  1
  7 24  1  0
  7 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 16 30  1  1
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₄O₄

Average Molecular Weight

258.2693

Monoisotopic Molecular Weight

258.089208936

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](COC2=CC(O)=CC=C12)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,15-18H,8H2/t13-,15-/m1/s1

InChI Key

YOSDNAMJVOLJKI-UKRRQHHQSA-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
Secondary alcohol
Ether
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0041710)

Excreta

Biofluid or Excreta

Urine (PMID: 10527518)

Cellular substructure

Extracellular (HMDB: HMDB0041710)
Cytoplasm (HMDB: HMDB0041710)

Source

Exogenous

Food

Food (HMDB: HMDB0041710)

Endogenous

Plant

Plant (HMDB: HMDB0041710)

Not Available

Nutrient (HMDB: HMDB0041710)

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
Water Solubility	0.18 g/L	ALOGPS
logP	1.82	ALOGPS
logP	2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.38 m³·mol⁻¹	ChemAxon
Polarizability	26.89 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]+	158.838	31661259
DarkChem	[M-H]-	161.901	31661259
DeepCCS	[M-2H]-	194.109	30932474
DeepCCS	[M+Na]+	169.336	30932474
AllCCS	[M+H]+	160.7	32859911
AllCCS	[M+H-H2O]+	156.8	32859911
AllCCS	[M+NH4]+	164.4	32859911
AllCCS	[M+Na]+	165.4	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	161.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
cis-4-Hydroxyequol	O[C@H]1[C@H](COC2=CC(O)=CC=C12)C1=CC=C(O)C=C1	3594.5	Standard polar	33892256
cis-4-Hydroxyequol	O[C@H]1[C@H](COC2=CC(O)=CC=C12)C1=CC=C(O)C=C1	2754.0	Standard non polar	33892256
cis-4-Hydroxyequol	O[C@H]1[C@H](COC2=CC(O)=CC=C12)C1=CC=C(O)C=C1	2775.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
cis-4-Hydroxyequol,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C2=CC=C(O)C=C2OC[C@@H]1C1=CC=C(O)C=C1	2634.5	Semi standard non polar	33892256
cis-4-Hydroxyequol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)OC[C@H](C1=CC=C(O)C=C1)[C@@H]2O	2630.4	Semi standard non polar	33892256
cis-4-Hydroxyequol,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O)=CC=C3[C@H]2O)C=C1	2656.3	Semi standard non polar	33892256
cis-4-Hydroxyequol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC[C@H](C1=CC=C(O)C=C1)[C@@H]2O[Si](C)(C)C	2593.6	Semi standard non polar	33892256
cis-4-Hydroxyequol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O)=CC=C3[C@H]2O[Si](C)(C)C)C=C1	2587.1	Semi standard non polar	33892256
cis-4-Hydroxyequol,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O[Si](C)(C)C)=CC=C3[C@H]2O)C=C1	2614.5	Semi standard non polar	33892256
cis-4-Hydroxyequol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O[Si](C)(C)C)=CC=C3[C@H]2O[Si](C)(C)C)C=C1	2611.7	Semi standard non polar	33892256
cis-4-Hydroxyequol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C2=CC=C(O)C=C2OC[C@@H]1C1=CC=C(O)C=C1	2905.6	Semi standard non polar	33892256
cis-4-Hydroxyequol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC[C@H](C1=CC=C(O)C=C1)[C@@H]2O	2916.6	Semi standard non polar	33892256
cis-4-Hydroxyequol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O)=CC=C3[C@H]2O)C=C1	2939.4	Semi standard non polar	33892256
cis-4-Hydroxyequol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC[C@H](C1=CC=C(O)C=C1)[C@@H]2O[Si](C)(C)C(C)(C)C	3075.2	Semi standard non polar	33892256
cis-4-Hydroxyequol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O)=CC=C3[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3090.5	Semi standard non polar	33892256
cis-4-Hydroxyequol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3[C@H]2O)C=C1	3178.6	Semi standard non polar	33892256
cis-4-Hydroxyequol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([C@H]2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3[C@H]2O[Si](C)(C)C(C)(C)C)C=C1	3288.0	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 - cis-4-Hydroxyequol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2970000000-5ef7ff154f3d2b0eaeca	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-4-Hydroxyequol GC-MS (3 TMS) - 70eV, Positive	splash10-0rr9-2423900000-c8d36a9be87cd4ce77f0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - cis-4-Hydroxyequol 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 - cis-4-Hydroxyequol 10V, Positive-QTOF	splash10-052f-0390000000-38475a6e039494b610f2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 20V, Positive-QTOF	splash10-0079-0930000000-8c016cee3525520653c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 40V, Positive-QTOF	splash10-066r-6910000000-4b914a0652272d427d13	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 10V, Negative-QTOF	splash10-0a4i-0390000000-3b98721e2cd2e7e1e351	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 20V, Negative-QTOF	splash10-0a4r-0290000000-80e6b4b20a9c28af0704	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 40V, Negative-QTOF	splash10-0aor-3910000000-8620b2f70091e5cb908c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 10V, Positive-QTOF	splash10-0a4i-0090000000-3c3c73d5929ea8ef6006	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 20V, Positive-QTOF	splash10-0a4l-0890000000-14454bc6e15213bce60b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 40V, Positive-QTOF	splash10-00di-4900000000-ddb5a8fe01967f646dc3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 10V, Negative-QTOF	splash10-0a4i-0090000000-fa57a8abfe4b74e797b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 20V, Negative-QTOF	splash10-0a4i-0590000000-cc8f2c5c1801f1bc00a4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-4-Hydroxyequol 40V, Negative-QTOF	splash10-0acc-1920000000-99a39b8ca173332865fa	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 907	10527518	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

FDB029875

KNApSAcK ID

Not Available

Chemspider ID

30777607

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

40424401

PDB ID

Not Available

ChEBI ID

174382

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

Neveu V, Perez-Jimenez J, Vos F, Crespy V, du Chaffaut L, Mennen L, Knox C, Eisner R, Cruz J, Wishart D, Scalbert A: Phenol-Explorer: an online comprehensive database on polyphenol contents in foods. Database (Oxford). 2010;2010:bap024. doi: 10.1093/database/bap024. Epub 2010 Jan 8. [PubMed:20428313 ]

Showing metabocard for cis-4-Hydroxyequol (HMDB0041710)

MOL for HMDB0041710 (cis-4-Hydroxyequol)

3D MOL for HMDB0041710 (cis-4-Hydroxyequol)

3D SDF for HMDB0041710 (cis-4-Hydroxyequol)

3D-SDF for HMDB0041710 (cis-4-Hydroxyequol)

PDB for HMDB0041710 (cis-4-Hydroxyequol)

3D PDB for HMDB0041710 (cis-4-Hydroxyequol)

SMILES for HMDB0041710 (cis-4-Hydroxyequol)

INCHI for HMDB0041710 (cis-4-Hydroxyequol)

Structure for HMDB0041710 (cis-4-Hydroxyequol)

3D Structure for HMDB0041710 (cis-4-Hydroxyequol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra