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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11)transporters (2) Show 13 proteins XML

enzymes (11)transporters (2) Show 13 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:36 UTC

HMDB ID

HMDB0014400

Secondary Accession Numbers

HMDB14400

Metabolite Identification

Common Name

Diethylstilbestrol

Description

Diethylstilbestrol, also known as DES, 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. Diethylstilbestrol is a drug which is used in the treatment of prostate cancer. previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery. A study of ovulation inhibition in women found that 5 mg/day oral DES was 92% effective, with ovulation occurring in only a single cycle. Diethylstilbestrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Diethylstilbestrol is found, on average, in the highest concentration within gram beans. This could make diethylstilbestrol a potential biomarker for the consumption of these foods. Diethylstilbestrol is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.

Structure

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

HMDB0014400
     RDKit          3D
Diethylstilbestrol
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.0471   -2.2005    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765   -0.8395   -0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -0.4593   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.5221    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6132    0.8600    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    0.7760    1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    1.3230    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5566    0.7987    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207    1.5941    2.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512    2.9852    2.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0274    3.7873    3.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3843    3.5154    1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287    2.7031    1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5563   -1.1391   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -0.3665   -2.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982   -0.8903   -3.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -2.2529   -3.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362   -2.8258   -4.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7008   -3.0277   -2.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -2.4868   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -2.2393    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3338   -2.4887    0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465   -3.0150   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -0.0478   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -0.9441   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2145    0.1858   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245    1.8965   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152   -0.3181    1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.4037    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.0636    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -0.2797    2.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    1.1933    3.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    4.1057    4.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054    4.5801    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    3.1151    0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    0.6991   -2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926   -0.2546   -4.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3877   -3.8206   -4.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8732   -4.0915   -2.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3165   -3.1202   -0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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

255
  Mrv0541 02231214332D          

 20 21  0  0  0  0            999 V2000
    3.7935    3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  2  3  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  2  0  0  0  0
  7 13  1  0  0  0  0
  8 12  2  0  0  0  0
  8 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 16  1  0  0  0  0
 13 17  2  0  0  0  0
 14 18  2  0  0  0  0
 15 19  2  0  0  0  0
 16 20  2  0  0  0  0
 17 19  1  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014400

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=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

> <INCHI_KEY>
RGLYKWWBQGJZGM-UHFFFAOYSA-N

> <FORMULA>
C18H20O2

> <MOLECULAR_WEIGHT>
268.3502

> <EXACT_MASS>
268.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.68848392059201

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[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>
9.731491526289267

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.12919852418957

> <JCHEM_PKA_STRONGEST_BASIC>
-5.956792337140983

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
83.24060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.09e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Stil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014400
     RDKit          3D
Diethylstilbestrol
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.0471   -2.2005    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765   -0.8395   -0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -0.4593   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.5221    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6132    0.8600    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    0.7760    1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    1.3230    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5566    0.7987    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207    1.5941    2.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512    2.9852    2.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0274    3.7873    3.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3843    3.5154    1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287    2.7031    1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5563   -1.1391   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -0.3665   -2.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982   -0.8903   -3.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -2.2529   -3.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362   -2.8258   -4.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7008   -3.0277   -2.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -2.4868   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -2.2393    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3338   -2.4887    0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465   -3.0150   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -0.0478   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -0.9441   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2145    0.1858   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245    1.8965   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152   -0.3181    1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.4037    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.0636    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -0.2797    2.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    1.1933    3.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    4.1057    4.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054    4.5801    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    3.1151    0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    0.6991   -2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926   -0.2546   -4.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3877   -3.8206   -4.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8732   -4.0915   -2.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3165   -3.1202   -0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 255                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       7.081   6.545   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.748  -6.545   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.081   0.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.748  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.415  -0.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.414   0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415   2.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414  -2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748   4.235   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081   5.005   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -5.005   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    5    7                                                  
CONECT    4    3    6    8                                                  
CONECT    5    3    9                                                       
CONECT    6    4   10                                                       
CONECT    7    3   11   13                                                  
CONECT    8    4   12   14                                                  
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    7   15                                                       
CONECT   12    8   16                                                       
CONECT   13    7   17                                                       
CONECT   14    8   18                                                       
CONECT   15   11   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   19                                                       
CONECT   18   14   20                                                       
CONECT   19    1   15   17                                                  
CONECT   20    2   16   18                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0014400
HETATM    1  C1  UNL     1       2.047  -2.200   0.028  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.777  -0.840  -0.548  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.327  -0.459  -0.543  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.139   0.522   0.193  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.613   0.860   0.161  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.092   0.776   1.631  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.697   1.323   1.112  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.557   0.799   2.034  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.321   1.594   2.855  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.251   2.985   2.782  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.027   3.787   3.616  1.00  0.00           O  
HETATM   12  C11 UNL     1       1.384   3.515   1.853  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.629   2.703   1.041  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.556  -1.139  -1.474  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.221  -0.367  -2.427  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.098  -0.890  -3.345  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.345  -2.253  -3.335  1.00  0.00           C  
HETATM   18  O2  UNL     1      -3.236  -2.826  -4.258  1.00  0.00           O  
HETATM   19  C17 UNL     1      -1.701  -3.028  -2.406  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.813  -2.487  -1.479  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.112  -2.239   0.431  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.334  -2.489   0.821  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.047  -3.015  -0.725  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.339  -0.048  -0.071  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.094  -0.944  -1.650  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.214   0.186  -0.432  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.725   1.896  -0.193  1.00  0.00           H  
HETATM   28  H8  UNL     1      -2.015  -0.318   1.870  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.463   1.404   2.270  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.143   1.064   1.682  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.654  -0.280   2.156  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.007   1.193   3.593  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.718   4.106   4.524  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.305   4.580   1.769  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.066   3.115   0.295  1.00  0.00           H  
HETATM   36  H16 UNL     1      -1.016   0.699  -2.429  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.593  -0.255  -4.068  1.00  0.00           H  
HETATM   38  H18 UNL     1      -3.388  -3.821  -4.213  1.00  0.00           H  
HETATM   39  H19 UNL     1      -1.873  -4.091  -2.374  1.00  0.00           H  
HETATM   40  H20 UNL     1      -0.316  -3.120  -0.747  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

HMDB0014400
     RDKit          3D
Diethylstilbestrol
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.0471   -2.2005    0.0280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7765   -0.8395   -0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -0.4593   -0.5428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1394    0.5221    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6132    0.8600    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    0.7760    1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6966    1.3230    1.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5566    0.7987    2.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3207    1.5941    2.8555 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2512    2.9852    2.7824 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0274    3.7873    3.6163 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3843    3.5154    1.8529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287    2.7031    1.0411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5563   -1.1391   -1.4742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2205   -0.3665   -2.4275 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0982   -0.8903   -3.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3448   -2.2529   -3.3352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2362   -2.8258   -4.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7008   -3.0277   -2.4058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8130   -2.4868   -1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117   -2.2393    0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3338   -2.4887    0.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0465   -3.0150   -0.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3393   -0.0478   -0.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0944   -0.9441   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2145    0.1858   -0.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245    1.8965   -0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0152   -0.3181    1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.4037    2.2699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1431    1.0636    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -0.2797    2.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0073    1.1933    3.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    4.1057    4.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3054    4.5801    1.7691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    3.1151    0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164    0.6991   -2.4292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5926   -0.2546   -4.0675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3877   -3.8206   -4.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8732   -4.0915   -2.3737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3165   -3.1202   -0.7474 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  3
  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
DES	HMDB
Diethylstilbesterol	HMDB
Diethylstilbestrol BP	HMDB
Diethylstilboesterol	HMDB
Dietilestilbestrol	HMDB
Percutatrine oestrogenique iscovesco	HMDB
Rcra waste number u089	HMDB
trans-Diethylstilbesterol	HMDB
trans-Diethylstilbestrol	HMDB
trans-Diethylstilboesterol	HMDB

Chemical Formula

C₁₈H₂₀O₂

Average Molecular Weight

268.3502

Monoisotopic Molecular Weight

268.146329884

IUPAC Name

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

Traditional Name

Stil

CAS Registry Number

56-53-1

SMILES

CCC(=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

InChI Key

RGLYKWWBQGJZGM-UHFFFAOYSA-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

Not Available

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0014400)
Nausea (HMDB: HMDB0014400)

Bleeding (HMDB: HMDB0014400)

Cancer

Cancer (HMDB: HMDB0014400)

Disposition

Biological location

Cell membrane (HMDB: HMDB0014400)

Biofluid or Excreta

Blood (HMDB: HMDB0014400)
Urine (HMDB: HMDB0014400)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0014400)

Source

Exogenous

Food

Food (HMDB: HMDB0014400)

Pulse

Bean

Gram bean (FooDB: FOOD00199)

Synthetic

Synthetic (HMDB: HMDB0014400)

Endogenous

Plant

Plant (HMDB: HMDB0014400)
Fabaceae (HMDB: HMDB0014400)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0014400)

Indirect biological role

Carcinogen (HMDB: HMDB0014400)

Environmental role

Air pollutant (HMDB: HMDB0014400)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	170.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.011 g/L	Not Available
LogP	5.07	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	4.62	ALOGPS
logP	5.19	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.13	ChemAxon
pKa (Strongest Basic)	-6	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	30.69 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
DarkChem	[M+H]+	167.976	31661259
DarkChem	[M-H]-	166.453	31661259
DeepCCS	[M+H]+	168.579	30932474
DeepCCS	[M-H]-	166.221	30932474
DeepCCS	[M-2H]-	199.107	30932474
DeepCCS	[M+Na]+	174.672	30932474
AllCCS	[M+H]+	164.8	32859911
AllCCS	[M+H-H2O]+	161.0	32859911
AllCCS	[M+NH4]+	168.4	32859911
AllCCS	[M+Na]+	169.4	32859911
AllCCS	[M-H]-	169.8	32859911
AllCCS	[M+Na-2H]-	169.5	32859911
AllCCS	[M+HCOO]-	169.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Diethylstilbestrol	CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	3889.4	Standard polar	33892256
Diethylstilbestrol	CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2434.2	Standard non polar	33892256
Diethylstilbestrol	CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2467.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Diethylstilbestrol,1TMS,isomer #1	CCC(=C(CC)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=C(O)C=C1	2624.7	Semi standard non polar	33892256
Diethylstilbestrol,2TMS,isomer #1	CCC(=C(CC)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1	2501.3	Semi standard non polar	33892256
Diethylstilbestrol,1TBDMS,isomer #1	CCC(=C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O)C=C1	2854.2	Semi standard non polar	33892256
Diethylstilbestrol,2TBDMS,isomer #1	CCC(=C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2889.1	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 - Diethylstilbestrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0390000000-d064f732675ea9894f2c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethylstilbestrol GC-MS (2 TMS) - 70eV, Positive	splash10-0awa-1019000000-1cc583dcfd41002dd339	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Diethylstilbestrol 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 - Diethylstilbestrol 10V, Positive-QTOF	splash10-014i-0290000000-f2a65d0f5428a0bf0096	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 20V, Positive-QTOF	splash10-0159-0690000000-6b39aa057a8cb6eb1def	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 40V, Positive-QTOF	splash10-001i-2950000000-4f5e80bdea64d9365cc7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 10V, Negative-QTOF	splash10-014i-0090000000-9bda79387111e5798094	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 20V, Negative-QTOF	splash10-014i-0090000000-7c62326707d11881c098	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 40V, Negative-QTOF	splash10-00ll-2490000000-de50c09ba9f659d1b047	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 10V, Negative-QTOF	splash10-014i-0090000000-e89c3535f3d6cda6ed7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 20V, Negative-QTOF	splash10-0ap0-0190000000-93dd0c6a4d49918f7fc7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 40V, Negative-QTOF	splash10-0300-0790000000-15fa3a704fd6a8d70eab	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 10V, Positive-QTOF	splash10-014r-0890000000-ce8b26781cf43b806840	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 20V, Positive-QTOF	splash10-00kr-0930000000-ff4502b2ae61ffdf7a9a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Diethylstilbestrol 40V, Positive-QTOF	splash10-052p-1950000000-6890970b5e5ae4ffaf87	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00255	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00255	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00255

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007498

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

DES

ChEBI ID

4531

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

Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. [PubMed:5171004 ]
Herbst AL, Ulfelder H, Poskanzer DC: Adenocarcinoma of the vagina. Association of maternal stilbestrol therapy with tumor appearance in young women. N Engl J Med. 1971 Apr 15;284(15):878-81. [PubMed:5549830 ]
Authors unspecified: Leuprolide versus diethylstilbestrol for metastatic prostate cancer. N Engl J Med. 1984 Nov 15;311(20):1281-6. [PubMed:6436700 ]
Ingle JN, Ahmann DL, Green SJ, Edmonson JH, Bisel HF, Kvols LK, Nichols WC, Creagan ET, Hahn RG, Rubin J, Frytak S: Randomized clinical trial of diethylstilbestrol versus tamoxifen in postmenopausal women with advanced breast cancer. N Engl J Med. 1981 Jan 1;304(1):16-21. [PubMed:7001242 ]
DIECKMANN WJ, DAVIS ME, RYNKIEWICZ LM, POTTINGER RE: Does the administration of diethylstilbestrol during pregnancy have therapeutic value? Am J Obstet Gynecol. 1953 Nov;66(5):1062-81. [PubMed:13104505 ]

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

References

Engel LL, Weidenfield J, Merriam GR: Metabolism of diethylstilbestrol by rat liver: a preliminary report. J Toxicol Environ Health Suppl. 1976;1:37-44. [PubMed:11352 ]

Enzyme Details

2. Estrogen receptor beta

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA- binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual
Gene Name:: ESR2
Uniprot ID:: Q92731
Molecular weight:: 59215.8

References

Authors unspecified: Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products. Int J Toxicol. 2008;27 Suppl 4:1-82. doi: 10.1080/10915810802548359. [PubMed:19101832 ]
Geistlinger TR, McReynolds AC, Guy RK: Ligand-selective inhibition of the interaction of steroid receptor coactivators and estrogen receptor isoforms. Chem Biol. 2004 Feb;11(2):273-81. [PubMed:15123288 ]

Enzyme Details

3. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Diethylstilbestrol → 3,4,5-trihydroxy-6-{4-[(3Z)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenoxy}oxane-2-carboxylic acid	details

Enzyme Details

4. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654 ]

Enzyme Details

5. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654 ]

Enzyme Details

6. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

References

Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654 ]

Enzyme Details

7. Cytochrome P450 19A1

General function:: Involved in monooxygenase activity
Specific function:: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name:: CYP19A1
Uniprot ID:: P11511
Molecular weight:: 57882.48

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

8. Cytochrome P450 2C8

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:: CYP2C8
Uniprot ID:: P10632
Molecular weight:: 55824.275

References

Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654 ]

Enzyme Details

9. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654 ]

Enzyme Details

10. Estrogen receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Can activate the transcriptional activity of TFF1
Gene Name:: ESR1
Uniprot ID:: P03372
Molecular weight:: 66215.4

References

Munoz G, Ovilo C, Estelle J, Silio L, Fernandez A, Rodriguez C: Association with litter size of new polymorphisms on ESR1 and ESR2 genes in a Chinese-European pig line. Genet Sel Evol. 2007 Mar-Apr;39(2):195-206. Epub 2007 Feb 17. [PubMed:17306201 ]
Dixon A, Wells CC, Singh S, Babayan R, Maric C: Renoprotective effects of a selective estrogen receptor modulator, raloxifene, in an animal model of diabetic nephropathy. Am J Nephrol. 2007;27(2):120-8. Epub 2007 Feb 15. [PubMed:17308373 ]
Hart SA, Snyder MA, Smejkalova T, Woolley CS: Estrogen mobilizes a subset of estrogen receptor-alpha-immunoreactive vesicles in inhibitory presynaptic boutons in hippocampal CA1. J Neurosci. 2007 Feb 21;27(8):2102-11. [PubMed:17314305 ]
Baron S, Escande A, Alberola G, Bystricky K, Balaguer P, Richard-Foy H: Estrogen receptor alpha and the activating protein-1 complex cooperate during insulin-like growth factor-I-induced transcriptional activation of the pS2/TFF1 gene. J Biol Chem. 2007 Apr 20;282(16):11732-41. Epub 2007 Feb 22. [PubMed:17317669 ]
Bains M, Cousins JC, Roberts JL: Neuroprotection by estrogen against MPP+-induced dopamine neuron death is mediated by ERalpha in primary cultures of mouse mesencephalon. Exp Neurol. 2007 Apr;204(2):767-76. Epub 2007 Jan 25. [PubMed:17320868 ]
Kwok KC, Cheung NH: Measuring binding kinetics of ligands with tethered receptors by fluorescence polarization and total internal reflection fluorescence. Anal Chem. 2010 May 1;82(9):3819-25. doi: 10.1021/ac1002245. [PubMed:20387803 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Sugimoto Y, Tsukahara S, Imai Y, Sugimoto Y, Ueda K, Tsuruo T: Reversal of breast cancer resistance protein-mediated drug resistance by estrogen antagonists and agonists. Mol Cancer Ther. 2003 Jan;2(1):105-12. [PubMed:12533678 ]

Only showing the first 10 proteins. There are 13 proteins in total.

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Showing metabocard for Diethylstilbestrol (HMDB0014400)

MOL for HMDB0014400 (Diethylstilbestrol)

3D MOL for HMDB0014400 (Diethylstilbestrol)

3D SDF for HMDB0014400 (Diethylstilbestrol)

3D-SDF for HMDB0014400 (Diethylstilbestrol)

PDB for HMDB0014400 (Diethylstilbestrol)

3D PDB for HMDB0014400 (Diethylstilbestrol)

SMILES for HMDB0014400 (Diethylstilbestrol)

INCHI for HMDB0014400 (Diethylstilbestrol)

Structure for HMDB0014400 (Diethylstilbestrol)

3D Structure for HMDB0014400 (Diethylstilbestrol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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Reactions

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Transporters

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