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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 21:13:27 UTC

Update Date

2021-09-23 21:13:27 UTC

HMDB ID

HMDB0302859

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Estrogen

Description

diethylstilbestrol, also known as DES or distilbene, 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. Based on a literature review a significant number of articles have been published on diethylstilbestrol.

Structure

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

HMDB0302859
     RDKit          3D
Estrogen
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6872    0.3739    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -0.5869    1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427   -0.2559    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    0.0112   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    0.3320   -1.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043   -0.2962   -2.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    0.0331    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9976   -0.7120   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284   -0.7228   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7309    0.0169    0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646    0.0147    1.2765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7953    0.7675    1.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4723    0.7517    1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7665   -0.1819   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131    0.9398   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    1.0405   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873   -0.0159   -0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8258    0.0575   -0.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.1565   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.2656    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192    0.7990    3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046    1.2668    2.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928   -0.0634    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -0.8736    1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416   -1.5591    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790    1.4570   -1.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.0739   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1960   -0.8314   -3.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -1.1144   -2.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3727    0.3996   -3.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7371   -1.3166   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624   -1.2957   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6647    0.7262    0.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995    1.3564    2.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    1.3521    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633    1.8090   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9917    1.9773   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2430    0.8705   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5890   -2.0065    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -2.1724    0.6821 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  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  7  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END


  Mrv1533007131513462D          

 20 21  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    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
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    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
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17  3  1  0  0  0  0
 17 13  1  0  0  0  0
 18  4  1  0  0  0  0
 18 14  1  0  0  0  0
 18 17  2  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302859

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C(=C(\CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

> <INCHI_KEY>
RGLYKWWBQGJZGM-ISLYRVAYSA-N

> <FORMULA>
C18H20O2

> <MOLECULAR_WEIGHT>
268.356

> <EXACT_MASS>
268.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.683957430730576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
5.193882748

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.231491526289268

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.629198524189572

> <JCHEM_PKA_STRONGEST_BASIC>
-6.456792337140983

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
83.2406

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
estrogen

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302859
     RDKit          3D
Estrogen
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6872    0.3739    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -0.5869    1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427   -0.2559    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    0.0112   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    0.3320   -1.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043   -0.2962   -2.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    0.0331    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9976   -0.7120   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284   -0.7228   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7309    0.0169    0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646    0.0147    1.2765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7953    0.7675    1.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4723    0.7517    1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7665   -0.1819   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131    0.9398   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    1.0405   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873   -0.0159   -0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8258    0.0575   -0.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.1565   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.2656    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192    0.7990    3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046    1.2668    2.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928   -0.0634    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -0.8736    1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416   -1.5591    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790    1.4570   -1.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.0739   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1960   -0.8314   -3.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -1.1144   -2.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3727    0.3996   -3.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7371   -1.3166   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624   -1.2957   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6647    0.7262    0.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995    1.3564    2.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    1.3521    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633    1.8090   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9917    1.9773   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2430    0.8705   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5890   -2.0065    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -2.1724    0.6821 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  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  7  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001   8.470   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1   17                                                       
CONECT    4    2   18                                                       
CONECT    5    9   13                                                       
CONECT    6   10   13                                                       
CONECT    7   11   14                                                       
CONECT    8   12   14                                                       
CONECT    9    5   15                                                       
CONECT   10    6   15                                                       
CONECT   11    7   16                                                       
CONECT   12    8   16                                                       
CONECT   13    5    6   17                                                  
CONECT   14    7    8   18                                                  
CONECT   15    9   10   19                                                  
CONECT   16   11   12   20                                                  
CONECT   17    3   13   18                                                  
CONECT   18    4   14   17                                                  
CONECT   19   15                                                            
CONECT   20   16                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0302859
HETATM    1  C1  UNL     1      -0.687   0.374   2.690  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.045  -0.587   1.743  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.343  -0.256   0.291  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.659   0.011  -0.489  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.498   0.332  -1.927  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.604  -0.296  -2.669  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.055   0.033   0.048  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.998  -0.712  -0.633  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.328  -0.723  -0.232  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.731   0.017   0.862  1.00  0.00           C  
HETATM   11  O1  UNL     1       6.065   0.015   1.276  1.00  0.00           O  
HETATM   12  C11 UNL     1       3.795   0.768   1.552  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.472   0.752   1.118  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.767  -0.182  -0.027  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.313   0.940  -0.584  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.642   1.041  -0.896  1.00  0.00           C  
HETATM   17  C16 UNL     1      -4.487  -0.016  -0.648  1.00  0.00           C  
HETATM   18  O2  UNL     1      -5.826   0.058  -0.952  1.00  0.00           O  
HETATM   19  C17 UNL     1      -3.950  -1.156  -0.084  1.00  0.00           C  
HETATM   20  C18 UNL     1      -2.614  -1.266   0.232  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.119   0.799   3.333  1.00  0.00           H  
HETATM   22  H2  UNL     1      -1.105   1.267   2.138  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.493  -0.063   3.315  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.972  -0.874   1.924  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.642  -1.559   1.877  1.00  0.00           H  
HETATM   26  H6  UNL     1       0.379   1.457  -1.951  1.00  0.00           H  
HETATM   27  H7  UNL     1       1.458   0.074  -2.481  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.196  -0.831  -3.618  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.113  -1.114  -2.140  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.373   0.400  -3.064  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.737  -1.317  -1.508  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.062  -1.296  -0.752  1.00  0.00           H  
HETATM   33  H13 UNL     1       6.665   0.726   0.865  1.00  0.00           H  
HETATM   34  H14 UNL     1       4.100   1.356   2.414  1.00  0.00           H  
HETATM   35  H15 UNL     1       1.775   1.352   1.666  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.663   1.809  -0.792  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.992   1.977  -1.340  1.00  0.00           H  
HETATM   38  H18 UNL     1      -6.243   0.871  -1.363  1.00  0.00           H  
HETATM   39  H19 UNL     1      -4.589  -2.006   0.123  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.183  -2.172   0.682  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4    4   14
CONECT    4    5    7
CONECT    5    6   26   27
CONECT    6   28   29   30
CONECT    7    8    8   13
CONECT    8    9   31
CONECT    9   10   10   32
CONECT   10   11   12
CONECT   11   33
CONECT   12   13   13   34
CONECT   13   35
CONECT   14   15   15   20
CONECT   15   16   36
CONECT   16   17   17   37
CONECT   17   18   19
CONECT   18   38
CONECT   19   20   20   39
CONECT   20   40
END

HMDB0302859
     RDKit          3D
Estrogen
 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.6872    0.3739    2.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0452   -0.5869    1.7427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3427   -0.2559    0.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6593    0.0112   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4984    0.3320   -1.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6043   -0.2962   -2.6688 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0549    0.0331    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9976   -0.7120   -0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3284   -0.7228   -0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7309    0.0169    0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646    0.0147    1.2765 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7953    0.7675    1.5522 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4723    0.7517    1.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7665   -0.1819   -0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3131    0.9398   -0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6417    1.0405   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873   -0.0159   -0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8258    0.0575   -0.9522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9497   -1.1565   -0.0842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -1.2656    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192    0.7990    3.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046    1.2668    2.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4928   -0.0634    3.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9721   -0.8736    1.9238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6416   -1.5591    1.8774 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3790    1.4570   -1.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.0739   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1960   -0.8314   -3.6179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1135   -1.1144   -2.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3727    0.3996   -3.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7371   -1.3166   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0624   -1.2957   -0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6647    0.7262    0.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0995    1.3564    2.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7750    1.3521    1.6661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6633    1.8090   -0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9917    1.9773   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2430    0.8705   -1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5890   -2.0065    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -2.1724    0.6821 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  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 13  7  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 15 36  1  0
 16 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-3,4-Bis(4-hydroxyphenyl)-3-hexene	ChEBI
(e)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenol	ChEBI
4,4'-Dihydroxy-alpha,beta-diethylstilbene	ChEBI
alpha,Alpha'-diethyl-(e)-4,4'-stilbenediol	ChEBI
DES	ChEBI
Diethylstilbestrolum	ChEBI
Dietilestilbestrol	ChEBI
Distilbene	ChEBI
trans-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenol	ChEBI
trans-Diethylstilbesterol	ChEBI
trans-Diethylstilbestrol	ChEBI
trans-Diethylstilboesterol	ChEBI
Stilbestrol	Kegg
4,4'-Dihydroxy-a,b-diethylstilbene	Generator
4,4'-Dihydroxy-α,β-diethylstilbene	Generator
a,Alpha'-diethyl-(e)-4,4'-stilbenediol	Generator
Α,alpha'-diethyl-(e)-4,4'-stilbenediol	Generator
Agostilben	MeSH
Apstil	MeSH
Diethylstilbestrol, (Z)-isomer	MeSH
Diethylstilbestrol, disodium salt	MeSH
Distilbène	MeSH
Estrogen, stilbene	MeSH
Stilbene estrogen	MeSH
Tampovagan	MeSH
co Pharma brand OF diethylstilbestrol	MeSH
Gerda brand OF diethylstilbestrol	MeSH
APS brand OF diethylstilbestrol	MeSH
CO-Pharma brand OF diethylstilbestrol	MeSH

Chemical Formula

C₁₈H₂₀O₂

Average Molecular Weight

268.356

Monoisotopic Molecular Weight

268.146329884

IUPAC Name

4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol

Traditional Name

estrogen

CAS Registry Number

Not Available

SMILES

CC\C(=C(\CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

InChI Key

RGLYKWWBQGJZGM-ISLYRVAYSA-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
Phenylpropane
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

polyphenol (CHEBI:41922 )

Ontology

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	4.62	ALOGPS
logP	5.19	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.63	ChemAxon
pKa (Strongest Basic)	-6.5	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	4	ChemAxon
Refractivity	83.24 m³·mol⁻¹	ChemAxon
Polarizability	30.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
AllCCS	[M+H]+	164.822	32859911
AllCCS	[M+H-H2O]+	161.004	32859911
AllCCS	[M+Na]+	169.392	32859911
AllCCS	[M+NH4]+	168.371	32859911
AllCCS	[M-H]-	169.763	32859911
AllCCS	[M+Na-2H]-	169.529	32859911
AllCCS	[M+HCOO]-	169.403	32859911
DeepCCS	[M+H]+	173.988	30932474
DeepCCS	[M-H]-	171.63	30932474
DeepCCS	[M-2H]-	204.516	30932474
DeepCCS	[M+Na]+	180.081	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 10V, Positive-QTOF	splash10-014i-0290000000-f2a65d0f5428a0bf0096	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 20V, Positive-QTOF	splash10-0159-0690000000-6b39aa057a8cb6eb1def	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 40V, Positive-QTOF	splash10-001i-2950000000-4f5e80bdea64d9365cc7	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 10V, Negative-QTOF	splash10-014i-0090000000-9bda79387111e5798094	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 20V, Negative-QTOF	splash10-014i-0090000000-7c62326707d11881c098	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 40V, Negative-QTOF	splash10-00ll-2490000000-de50c09ba9f659d1b047	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 10V, Positive-QTOF	splash10-014r-0890000000-ce8b26781cf43b806840	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 20V, Positive-QTOF	splash10-00kr-0930000000-ff4502b2ae61ffdf7a9a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 40V, Positive-QTOF	splash10-052p-1950000000-6890970b5e5ae4ffaf87	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 10V, Negative-QTOF	splash10-014i-0090000000-e89c3535f3d6cda6ed7d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 20V, Negative-QTOF	splash10-0ap0-0190000000-93dd0c6a4d49918f7fc7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Estrogen 40V, Negative-QTOF	splash10-0300-0790000000-15fa3a704fd6a8d70eab	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB006560

KNApSAcK ID

Not Available

Chemspider ID

395306

KEGG Compound ID

C07620

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Diethylstilbestrol

METLIN ID

Not Available

PubChem Compound

448537

PDB ID

Not Available

ChEBI ID

41922

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1023561

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Estrogen (HMDB0302859)

MOL for HMDB0302859 (Estrogen)

3D MOL for HMDB0302859 (Estrogen)

3D SDF for HMDB0302859 (Estrogen)

3D-SDF for HMDB0302859 (Estrogen)

PDB for HMDB0302859 (Estrogen)

3D PDB for HMDB0302859 (Estrogen)

SMILES for HMDB0302859 (Estrogen)

INCHI for HMDB0302859 (Estrogen)

Structure for HMDB0302859 (Estrogen)

3D Structure for HMDB0302859 (Estrogen)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra