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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:19:23 UTC

Update Date

2021-09-14 15:17:56 UTC

HMDB ID

HMDB0012111

Secondary Accession Numbers

HMDB12111

Metabolite Identification

Common Name

(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol

Description

(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol, also known as (1R,2R)-hydrobenzoin, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make (+)-(1R,2R)-1,2-diphenylethane-1,2-diol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol.

Structure

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

HMDB0012111
     RDKit          3D
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.3687   -2.5235   -0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -1.4604    0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5833   -0.3192    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    0.8860   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3509    1.8713   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    1.6756    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7652    0.4404    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976   -0.5386    0.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5672   -1.2356   -0.5948 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2806   -2.4600   -0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985   -0.3396    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    0.3831    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354    1.1748    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    1.2559    0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8534    0.5160   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7932   -0.2560   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -2.1628   -1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788   -1.7533    1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    1.0900   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    2.8424   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3272    2.4485    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7032    0.2685    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -1.4801    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688   -0.9065   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264   -3.1379   -1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795    0.3239    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838    1.7699    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546    1.8661    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7811    0.5879   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.8267   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8  3  1  0
 16 11  1  0
  1 17  1  0
  2 18  1  1
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  6
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv0541 02241203392D          

 16 17  0  0  1  0            999 V2000
   14.0136   -7.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6637  -10.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1887   -7.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4261   -7.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2511   -9.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2511  -10.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7762   -7.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0136   -8.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4261   -9.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4261  -10.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1887   -8.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0136  -10.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7762   -9.3228    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1887  -10.0368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9512   -9.3228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7762  -10.7514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  7 11  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  6  0  0  0
 13 14  1  0  0  0  0
 14 16  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0012111

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m1/s1

> <INCHI_KEY>
IHPDTPWNFBQHEB-ZIAGYGMSSA-N

> <FORMULA>
C14H14O2

> <MOLECULAR_WEIGHT>
214.2598

> <EXACT_MASS>
214.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.850432367361698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R)-1,2-diphenylethane-1,2-diol

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
2.3598012939999995

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.530859354576034

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.081236811022443

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5063964987553575

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
63.119200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-hydrobenzoin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012111
     RDKit          3D
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.3687   -2.5235   -0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -1.4604    0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5833   -0.3192    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    0.8860   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3509    1.8713   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    1.6756    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7652    0.4404    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976   -0.5386    0.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5672   -1.2356   -0.5948 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2806   -2.4600   -0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985   -0.3396    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    0.3831    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354    1.1748    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    1.2559    0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8534    0.5160   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7932   -0.2560   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -2.1628   -1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788   -1.7533    1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    1.0900   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    2.8424   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3272    2.4485    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7032    0.2685    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -1.4801    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688   -0.9065   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264   -3.1379   -1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795    0.3239    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838    1.7699    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546    1.8661    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7811    0.5879   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.8267   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8  3  1  0
 16 11  1  0
  1 17  1  0
  2 18  1  1
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  6
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      26.159 -13.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.239 -18.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.619 -13.401   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.929 -14.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.469 -17.403   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.469 -20.069   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.849 -14.735   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.159 -16.069   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.929 -17.403   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.929 -20.069   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.619 -16.069   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.159 -18.735   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.849 -17.403   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.619 -18.735   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.309 -17.403   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.849 -20.069   0.000  0.00  0.00           O+0
CONECT    1    3    4                                                       
CONECT    2    5    6                                                       
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3   11                                                       
CONECT    8    4   11                                                       
CONECT    9    5   12                                                       
CONECT   10    6   12                                                       
CONECT   11    7    8   13                                                  
CONECT   12    9   10   14                                                  
CONECT   13   11   15   14                                                  
CONECT   14   12   13   16                                                  
CONECT   15   13                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0012111
HETATM    1  O1  UNL     1      -1.369  -2.524  -0.276  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.603  -1.460   0.283  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.583  -0.319   0.267  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.378   0.886  -0.306  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.351   1.871  -0.250  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.565   1.676   0.386  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.765   0.440   0.968  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.798  -0.539   0.912  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.567  -1.236  -0.595  1.00  0.00           C  
HETATM   10  O2  UNL     1       1.281  -2.460  -0.738  1.00  0.00           O  
HETATM   11  C9  UNL     1       1.599  -0.340   0.002  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.484   0.383   1.135  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.535   1.175   1.547  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.716   1.256   0.835  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.853   0.516  -0.339  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.793  -0.256  -0.717  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.673  -2.163  -1.166  1.00  0.00           H  
HETATM   18  H2  UNL     1      -0.379  -1.753   1.306  1.00  0.00           H  
HETATM   19  H3  UNL     1      -0.458   1.090  -0.820  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.191   2.842  -0.708  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.327   2.449   0.430  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.703   0.269   1.467  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.001  -1.480   1.379  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.269  -0.907  -1.605  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.726  -3.138  -1.190  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.579   0.324   1.698  1.00  0.00           H  
HETATM   27  H11 UNL     1       2.484   1.770   2.450  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.555   1.866   1.132  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.781   0.588  -0.887  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.922  -0.827  -1.638  1.00  0.00           H  
CONECT    1    2   17
CONECT    2    3    9   18
CONECT    3    4    4    8
CONECT    4    5   19
CONECT    5    6    6   20
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8   23
CONECT    9   10   11   24
CONECT   10   25
CONECT   11   12   12   16
CONECT   12   13   26
CONECT   13   14   14   27
CONECT   14   15   28
CONECT   15   16   16   29
CONECT   16   30
END

HMDB0012111
     RDKit          3D
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.3687   -2.5235   -0.2756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6029   -1.4604    0.2832 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5833   -0.3192    0.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    0.8860   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3509    1.8713   -0.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5650    1.6756    0.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7652    0.4404    0.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7976   -0.5386    0.9117 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5672   -1.2356   -0.5948 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2806   -2.4600   -0.7376 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985   -0.3396    0.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4835    0.3831    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5354    1.1748    1.5473 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7158    1.2559    0.8346 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8534    0.5160   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7932   -0.2560   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -2.1628   -1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3788   -1.7533    1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4583    1.0900   -0.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    2.8424   -0.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3272    2.4485    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7032    0.2685    1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0011   -1.4801    1.3787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2688   -0.9065   -1.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7264   -3.1379   -1.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795    0.3239    1.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4838    1.7699    2.4498 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5546    1.8661    1.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7811    0.5879   -0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.8267   -1.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  2  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8  3  1  0
 16 11  1  0
  1 17  1  0
  2 18  1  1
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  6
 10 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Hydrobenzoin	ChEBI
(1R,2R)-Hydrobenzoin	ChEBI
(R,R)-(+)-Hydrobenzoin	ChEBI
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol	ChEBI

Chemical Formula

C₁₄H₁₄O₂

Average Molecular Weight

214.2598

Monoisotopic Molecular Weight

214.099379692

IUPAC Name

(1R,2R)-1,2-diphenylethane-1,2-diol

Traditional Name

(+)-hydrobenzoin

CAS Registry Number

52340-78-0

SMILES

O[C@@H]([C@H](O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C14H14O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13-16H/t13-,14-/m1/s1

InChI Key

IHPDTPWNFBQHEB-ZIAGYGMSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydrobenzoin (CHEBI:50014 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0012111)
Cell membrane (HMDB: HMDB0012111)

Source

Endogenous

Endogenous (HMDB: HMDB0012111)

Plant

Plant (HMDB: HMDB0012111)

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

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

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

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

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

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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	1.48 g/L	ALOGPS
logP	2.05	ALOGPS
logP	2.36	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	13.08	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.12 m³·mol⁻¹	ChemAxon
Polarizability	22.85 Å³	ChemAxon
Number of Rings	2	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]+	148.095	31661259
DarkChem	[M-H]-	148.542	31661259
DeepCCS	[M+H]+	152.499	30932474
DeepCCS	[M-H]-	150.103	30932474
DeepCCS	[M-2H]-	183.275	30932474
DeepCCS	[M+Na]+	158.411	30932474
AllCCS	[M+H]+	150.5	32859911
AllCCS	[M+H-H2O]+	146.1	32859911
AllCCS	[M+NH4]+	154.5	32859911
AllCCS	[M+Na]+	155.6	32859911
AllCCS	[M-H]-	151.2	32859911
AllCCS	[M+Na-2H]-	151.2	32859911
AllCCS	[M+HCOO]-	151.3	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.	6.27 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4287 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	27.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2293.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	383.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	130.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	457.1 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	648.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	74.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1068.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	390.5 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	1358.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	318.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	172.0 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol	O[C@@H]([C@H](O)C1=CC=CC=C1)C1=CC=CC=C1	3129.3	Standard polar	33892256
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol	O[C@@H]([C@H](O)C1=CC=CC=C1)C1=CC=CC=C1	1965.5	Standard non polar	33892256
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol	O[C@@H]([C@H](O)C1=CC=CC=C1)C1=CC=CC=C1	1848.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol,1TMS,isomer #1	C[Si](C)(C)O[C@H](C1=CC=CC=C1)[C@H](O)C1=CC=CC=C1	1826.6	Semi standard non polar	33892256
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol,2TMS,isomer #1	C[Si](C)(C)O[C@H](C1=CC=CC=C1)[C@H](O[Si](C)(C)C)C1=CC=CC=C1	1867.5	Semi standard non polar	33892256
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](C1=CC=CC=C1)[C@H](O)C1=CC=CC=C1	2078.0	Semi standard non polar	33892256
(+)-(1R,2R)-1,2-Diphenylethane-1,2-diol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](C1=CC=CC=C1)[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2305.1	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 - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-5900000000-394061468aba8a77892d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol GC-MS (2 TMS) - 70eV, Positive	splash10-004i-2920000000-fc1221353fb61e845a68	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 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 - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 10V, Positive-QTOF	splash10-014i-0290000000-a262606cc49f18a8a839	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 20V, Positive-QTOF	splash10-0aor-1940000000-fadcef7404e01b142764	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 40V, Positive-QTOF	splash10-0bt9-9300000000-95ff5df80e838be0f134	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 10V, Negative-QTOF	splash10-03di-0090000000-cdff589dfb8ea36de40c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 20V, Negative-QTOF	splash10-01t9-9360000000-66e82b42c9eca1c9961a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 40V, Negative-QTOF	splash10-004i-9200000000-05181718f5122f0c81f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 10V, Negative-QTOF	splash10-01ot-0960000000-a0a78e56e3571cd7ca87	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 20V, Negative-QTOF	splash10-01ot-3920000000-48ca05e5e1d0755cdced	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 40V, Negative-QTOF	splash10-00or-7900000000-95b629b0c904ea4b49d4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 10V, Positive-QTOF	splash10-002b-0920000000-e071a779a26566e55313	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 20V, Positive-QTOF	splash10-004j-0900000000-796a11bed9a0db34dbb2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol 40V, Positive-QTOF	splash10-002f-9200000000-45d257971bc1882043a1	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB028775

KNApSAcK ID

Not Available

Chemspider ID

745456

KEGG Compound ID

C16015

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

853019

PDB ID

Not Available

ChEBI ID

50014

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)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. Epoxide hydrolase 1

General function:: Involved in catalytic activity
Specific function:: Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:: EPHX1
Uniprot ID:: P07099
Molecular weight:: 52948.48

Reactions

Cis-stilbene oxide + Water → (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol	details

Showing metabocard for (+)-(1R,2R)-1,2-Diphenylethane-1,2-diol (HMDB0012111)

MOL for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D MOL for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D SDF for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D-SDF for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

PDB for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D PDB for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

SMILES for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

INCHI for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

Structure for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

3D Structure for HMDB0012111 ((+)-(1R,2R)-1,2-Diphenylethane-1,2-diol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions