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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:22:20 UTC

Update Date

2021-09-26 23:06:11 UTC

HMDB ID

HMDB0253156

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dihydrodiethylstilbestrol

Description

Hexestrol 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 Hexestrol. This compound has been identified in human blood as reported by (PMID: 31557052 ). Dihydrodiethylstilbestrol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dihydrodiethylstilbestrol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0253158
     RDKit          3D
Phenol, 4,4'-(1,2-diethyl-1,2-ethanediyl)bis-, (R*,S*)-
 42 43  0  0  0  0  0  0  0  0999 V2000
    1.6243   -3.2102    1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -1.8219    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524   -0.7974    0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052    0.5129    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.5821   -0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027    1.7978   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714    2.8479   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    4.0700   -0.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553    2.7403    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5586    1.5405    1.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -1.0842   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -2.3735    0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416   -2.4724   -0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2996   -0.0375   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    0.6175   -1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    1.6177   -1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098    1.9086   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1856    2.9024   -0.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    1.2501    0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0365    0.2735    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257   -3.3147    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547   -3.5670    1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -3.9699    0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747   -1.4836    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328   -1.9165   -0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4905   -0.7494    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736   -0.2178   -1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    1.9046   -2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667    4.2319   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2181    3.5722    1.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1550    1.4671    2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -1.1835   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -2.4829    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3714   -3.2830   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -2.3379   -1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -3.4767   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095   -1.7360   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507    0.4100   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382    2.1311   -2.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803    3.8433   -0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098    1.5250    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818   -0.2306    1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 11 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
 10  4  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
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END


  Mrv0541 05281414452D          

 20 21  0  0  0  0            999 V2000
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    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
    0.7144    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7144    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7144   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    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  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253156

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3

> <INCHI_KEY>
PBBGSZCBWVPOOL-UHFFFAOYSA-N

> <FORMULA>
C18H22O2

> <MOLECULAR_WEIGHT>
270.3661

> <EXACT_MASS>
270.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
31.28976394482296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(4-hydroxyphenyl)hexan-3-yl]phenol

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
5.365653387333333

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.528838560353584

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.92658743011141

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4484876357871075

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
82.65719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrodiethylstilbestrol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253158
     RDKit          3D
Phenol, 4,4'-(1,2-diethyl-1,2-ethanediyl)bis-, (R*,S*)-
 42 43  0  0  0  0  0  0  0  0999 V2000
    1.6243   -3.2102    1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -1.8219    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524   -0.7974    0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052    0.5129    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.5821   -0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027    1.7978   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714    2.8479   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    4.0700   -0.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553    2.7403    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5586    1.5405    1.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -1.0842   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -2.3735    0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416   -2.4724   -0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2996   -0.0375   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    0.6175   -1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    1.6177   -1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098    1.9086   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1856    2.9024   -0.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    1.2501    0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0365    0.2735    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257   -3.3147    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547   -3.5670    1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -3.9699    0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747   -1.4836    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328   -1.9165   -0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4905   -0.7494    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736   -0.2178   -1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    1.9046   -2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667    4.2319   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2181    3.5722    1.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1550    1.4671    2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -1.1835   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -2.4829    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3714   -3.2830   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -2.3379   -1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -3.4767   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095   -1.7360   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507    0.4100   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382    2.1311   -2.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803    3.8433   -0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098    1.5250    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818   -0.2306    1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 11 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
 10  4  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
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

HEADER    PROTEIN                                 28-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-MAY-14         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000  10.780   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    HMDB0253645
HETATM    1  C1  UNL     1       0.682  -3.282   0.493  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.272  -1.934   0.433  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.957  -0.996  -0.648  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.758   0.239  -0.390  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.692   0.696  -1.272  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.440   1.842  -1.026  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.209   2.531   0.171  1.00  0.00           C  
HETATM    8  O1  UNL     1       3.949   3.682   0.433  1.00  0.00           O  
HETATM    9  C8  UNL     1       2.276   2.088   1.068  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.546   0.928   0.778  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.417  -0.706  -1.070  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.187  -1.882  -1.585  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.600  -1.463  -2.012  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.239   0.108  -0.143  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.538   1.429  -0.364  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.313   2.163   0.505  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.826   1.591   1.650  1.00  0.00           C  
HETATM   18  O2  UNL     1      -3.618   2.330   2.543  1.00  0.00           O  
HETATM   19  C17 UNL     1      -2.548   0.281   1.898  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.764  -0.441   1.007  1.00  0.00           C  
HETATM   21  H1  UNL     1       1.398  -3.888   1.165  1.00  0.00           H  
HETATM   22  H2  UNL     1       0.753  -3.877  -0.460  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.268  -3.402   1.030  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.172  -1.491   1.463  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.407  -2.101   0.384  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.449  -1.441  -1.583  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.841   0.143  -2.177  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.184   2.221  -1.712  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.784   4.172   1.284  1.00  0.00           H  
HETATM   30  H10 UNL     1       2.104   2.620   1.982  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.836   0.649   1.540  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.319  -0.044  -2.006  1.00  0.00           H  
HETATM   33  H13 UNL     1      -1.216  -2.770  -0.969  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.701  -2.195  -2.558  1.00  0.00           H  
HETATM   35  H15 UNL     1      -2.947  -2.225  -2.739  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.609  -0.496  -2.508  1.00  0.00           H  
HETATM   37  H17 UNL     1      -3.200  -1.417  -1.094  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.173   1.947  -1.237  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.552   3.210   0.334  1.00  0.00           H  
HETATM   40  H20 UNL     1      -3.130   2.826   3.304  1.00  0.00           H  
HETATM   41  H21 UNL     1      -2.949  -0.187   2.804  1.00  0.00           H  
HETATM   42  H22 UNL     1      -1.598  -1.458   1.280  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   11   26
CONECT    4    5    5   10
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8    9
CONECT    8   29
CONECT    9   10   10   30
CONECT   10   31
CONECT   11   12   14   32
CONECT   12   13   33   34
CONECT   13   35   36   37
CONECT   14   15   15   20
CONECT   15   16   38
CONECT   16   17   17   39
CONECT   17   18   19
CONECT   18   40
CONECT   19   20   20   41
CONECT   20   42
END

HMDB0253158
     RDKit          3D
Phenol, 4,4'-(1,2-diethyl-1,2-ethanediyl)bis-, (R*,S*)-
 42 43  0  0  0  0  0  0  0  0999 V2000
    1.6243   -3.2102    1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9332   -1.8219    0.6922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524   -0.7974    0.7653 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5052    0.5129    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0064    0.5821   -0.9198 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6027    1.7978   -1.2786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6714    2.8479   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2628    4.0700   -0.7312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553    2.7403    0.8807 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5586    1.5405    1.2567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2607   -1.0842   -0.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -2.3735    0.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1416   -2.4724   -0.9740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2996   -0.0375   -0.2214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5105    0.6175   -1.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    1.6177   -1.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098    1.9086   -0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1856    2.9024   -0.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969    1.2501    0.7925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0365    0.2735    0.8740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7257   -3.3147    1.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4547   -3.5670    1.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092   -3.9699    0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8747   -1.4836    1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3328   -1.9165   -0.3802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4905   -0.7494    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9736   -0.2178   -1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0153    1.9046   -2.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6667    4.2319   -1.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2181    3.5722    1.5603 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1550    1.4671    2.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2373   -1.1835   -1.1923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4146   -2.4829    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3714   -3.2830   -0.2614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7249   -2.3379   -1.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5615   -3.4767   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9095   -1.7360   -0.7411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9507    0.4100   -2.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6382    2.1311   -2.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8803    3.8433   -0.2711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6098    1.5250    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818   -0.2306    1.8035 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 11 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
 10  4  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
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 15 38  1  0
 16 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Exestrol	Kegg
Dihydrodiethylstilbestrol	MeSH
Hexestrol, (r,r)-(+-)-isomer	MeSH
Hexestrol, (r,s)-isomer	MeSH
Hexestrol, (R-(r,r))-isomer	MeSH
Hexestrol, (S-(r,r))-isomer	MeSH

Chemical Formula

C₁₈H₂₂O₂

Average Molecular Weight

270.3661

Monoisotopic Molecular Weight

270.161979948

IUPAC Name

4-[4-(4-hydroxyphenyl)hexan-3-yl]phenol

Traditional Name

dihydrodiethylstilbestrol

CAS Registry Number

Not Available

SMILES

CCC(C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3

InChI Key

PBBGSZCBWVPOOL-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

stilbenoid (CHEBI:31669 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.98	ALOGPS
logP	5.37	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-5.4	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	5	ChemAxon
Refractivity	82.66 m³·mol⁻¹	ChemAxon
Polarizability	31.29 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
DeepCCS	[M+H]+	170.747	30932474
DeepCCS	[M-H]-	168.389	30932474
DeepCCS	[M-2H]-	201.275	30932474
DeepCCS	[M+Na]+	176.841	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	162.3	32859911
AllCCS	[M+NH4]+	169.6	32859911
AllCCS	[M+Na]+	170.6	32859911
AllCCS	[M-H]-	171.6	32859911
AllCCS	[M+Na-2H]-	171.8	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihydrodiethylstilbestrol,1TMS,isomer #1	CCC(C1=CC=C(O)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C)C=C1	2402.6	Semi standard non polar	33892256
Dihydrodiethylstilbestrol,1TMS,isomer #1	CCC(C1=CC=C(O)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C)C=C1	2043.2	Standard non polar	33892256
Dihydrodiethylstilbestrol,1TMS,isomer #1	CCC(C1=CC=C(O)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C)C=C1	2776.8	Standard polar	33892256
Dihydrodiethylstilbestrol,2TMS,isomer #1	CCC(C1=CC=C(O[Si](C)(C)C)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C)C=C1	2295.1	Semi standard non polar	33892256
Dihydrodiethylstilbestrol,2TMS,isomer #1	CCC(C1=CC=C(O[Si](C)(C)C)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C)C=C1	2007.9	Standard non polar	33892256
Dihydrodiethylstilbestrol,2TMS,isomer #1	CCC(C1=CC=C(O[Si](C)(C)C)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C)C=C1	2564.1	Standard polar	33892256
Dihydrodiethylstilbestrol,1TBDMS,isomer #1	CCC(C1=CC=C(O)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2660.5	Semi standard non polar	33892256
Dihydrodiethylstilbestrol,1TBDMS,isomer #1	CCC(C1=CC=C(O)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2281.0	Standard non polar	33892256
Dihydrodiethylstilbestrol,1TBDMS,isomer #1	CCC(C1=CC=C(O)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2887.0	Standard polar	33892256
Dihydrodiethylstilbestrol,2TBDMS,isomer #1	CCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2823.2	Semi standard non polar	33892256
Dihydrodiethylstilbestrol,2TBDMS,isomer #1	CCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2482.6	Standard non polar	33892256
Dihydrodiethylstilbestrol,2TBDMS,isomer #1	CCC(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C(CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2789.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrodiethylstilbestrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-1930000000-6a1adfdbcb3abda20a52	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrodiethylstilbestrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrodiethylstilbestrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrodiethylstilbestrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihydrodiethylstilbestrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-000i-1900000000-fe382bb3152ab42cd695	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 10V, Positive-QTOF	splash10-00di-0190000000-8f8d59584b0b0cea9ac0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 20V, Positive-QTOF	splash10-00di-0490000000-c4d6493ceeb60d503349	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 40V, Positive-QTOF	splash10-0kci-2980000000-ae03d5aca3238c8ebadd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 10V, Negative-QTOF	splash10-014i-0090000000-6b24ab83eea5558633e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 20V, Negative-QTOF	splash10-014i-0090000000-d44b82720a04d68e4545	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 40V, Negative-QTOF	splash10-0frl-2390000000-88a03be7f0f2c97056b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 10V, Positive-QTOF	splash10-00di-0590000000-b8c3b65112f8b8996e29	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 20V, Positive-QTOF	splash10-007a-2920000000-7c7efd262e5ac7c42273	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 40V, Positive-QTOF	splash10-0002-2920000000-d8ae3809572afd0f275e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 10V, Negative-QTOF	splash10-014i-0090000000-a3d9c28ab975a7b818e3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 20V, Negative-QTOF	splash10-014i-0090000000-f6ff5a3f99889207c20f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihydrodiethylstilbestrol 40V, Negative-QTOF	splash10-0hfy-1980000000-1822d34b81398fb0cd72	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3480

KEGG Compound ID

C13101

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hexestrol

METLIN ID

Not Available

PubChem Compound

3606

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Dihydrodiethylstilbestrol (HMDB0253156)

MOL for HMDB0253156 (Dihydrodiethylstilbestrol)

3D MOL for HMDB0253156 (Dihydrodiethylstilbestrol)

3D SDF for HMDB0253156 (Dihydrodiethylstilbestrol)

3D-SDF for HMDB0253156 (Dihydrodiethylstilbestrol)

PDB for HMDB0253156 (Dihydrodiethylstilbestrol)

3D PDB for HMDB0253156 (Dihydrodiethylstilbestrol)

SMILES for HMDB0253156 (Dihydrodiethylstilbestrol)

INCHI for HMDB0253156 (Dihydrodiethylstilbestrol)

Structure for HMDB0253156 (Dihydrodiethylstilbestrol)

3D Structure for HMDB0253156 (Dihydrodiethylstilbestrol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra