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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015027

Secondary Accession Numbers

HMDB15027

Metabolite Identification

Common Name

Dienestrol

Description

Dienestrol is a synthetic, non-steroidal estrogen. It is an estrogen receptor agonist. Estrogens work partly by increasing a normal clear discharge from the vagina and making the vulva and urethra healthy. Using or applying an estrogen relieves or lessens: dryness and soreness in the vagina, itching, redness, or soreness of the vulva. Conditions that are treated with vaginal estrogens include a genital skin condition (vulvar atrophy), inflammation of the vagina (atrophic vaginitis), and inflammation of the urethra (atrophic urethritis).

Structure

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

HMDB0259978
     RDKit          3D
Z,Z-Dienestrol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.0466    3.5028    0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997    2.1406    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    1.6699    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    1.1324    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.0231    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    3.4598    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -0.2249    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -0.5028   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -1.7238   -0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5377   -2.7551   -0.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660   -4.0029   -0.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106   -2.5259    0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9085   -1.2722    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2110    0.1373    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -0.2665    0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823   -1.4405    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -2.0357   -0.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896   -3.1913   -1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -1.5538   -1.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -0.3757   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438    3.4551    1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665    3.8377   -0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    4.1567    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    1.5109    0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380    1.6572    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    3.9060    1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    4.0094   -0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315    3.7457    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7881    0.3179   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -1.9460   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540   -4.5797   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910   -3.3309    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544   -1.2075    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    0.2078    1.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773   -1.8407    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9241   -4.1263   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1279   -1.9818   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.0138   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  3
  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
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END


  Mrv0541 04191212152D          

 20 21  0  0  0  0            999 V2000
   -2.4455   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1600   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1600   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4455   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7311   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7311   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8745   -2.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4123   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0166   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1268    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4123   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1268   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8413   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8413   -0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7311    0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4123   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5558    0.2652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  3  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
  9 12  2  0  0  0  0
 14 10  2  0  0  0  0
 10 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 18  1  4  0  0  0
 12 19  1  4  0  0  0
 17 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015027

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3

> <INCHI_KEY>
NFDFQCUYFHCNBW-UHFFFAOYSA-N

> <FORMULA>
C18H18O2

> <MOLECULAR_WEIGHT>
266.3343

> <EXACT_MASS>
266.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.302238966883753

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol

> <ALOGPS_LOGP>
5.18

> <JCHEM_LOGP>
4.831961091333333

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.701624901640892

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.099340202888508

> <JCHEM_PKA_STRONGEST_BASIC>
-5.963491272451223

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
84.3572

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
di(p-oxyphenyl)-2,4-hexadiene

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259978
     RDKit          3D
Z,Z-Dienestrol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.0466    3.5028    0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997    2.1406    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    1.6699    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    1.1324    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.0231    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    3.4598    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -0.2249    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -0.5028   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -1.7238   -0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5377   -2.7551   -0.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660   -4.0029   -0.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106   -2.5259    0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9085   -1.2722    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2110    0.1373    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -0.2665    0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823   -1.4405    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -2.0357   -0.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896   -3.1913   -1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -1.5538   -1.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -0.3757   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438    3.4551    1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665    3.8377   -0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    4.1567    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    1.5109    0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380    1.6572    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    3.9060    1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    4.0094   -0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315    3.7457    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7881    0.3179   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -1.9460   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540   -4.5797   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910   -3.3309    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544   -1.2075    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    0.2078    1.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773   -1.8407    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9241   -4.1263   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1279   -1.9818   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.0138   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  3
  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
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0      -4.565  -1.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.899  -2.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.899  -4.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.565  -4.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.231  -4.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.231  -2.585   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.232  -4.895   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.898  -1.815   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.564  -2.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.770  -1.815   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.898  -0.275   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.564  -4.125   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.103   0.495   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.770  -0.275   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.103  -2.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.437  -1.815   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.437  -0.275   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.231   0.495   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.770  -4.895   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.771   0.495   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    3                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10   12                                                  
CONECT   10    9   14   15                                                  
CONECT   11    8   18                                                       
CONECT   12    9   19                                                       
CONECT   13   14   17                                                       
CONECT   14   10   13                                                       
CONECT   15   10   16                                                       
CONECT   16   15   17                                                       
CONECT   17   13   16   20                                                  
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   17                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0259978
HETATM    1  C1  UNL     1      -2.047   3.503   0.815  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.600   2.141   0.535  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.447   1.670   0.411  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.868   1.132   0.269  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.922   2.023   0.258  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.645   3.460   0.384  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.359  -0.225   0.125  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.435  -0.503  -0.753  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.019  -1.724  -0.873  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.538  -2.755  -0.102  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.166  -4.003  -0.260  1.00  0.00           O  
HETATM   12  C11 UNL     1       1.511  -2.526   0.744  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.909  -1.272   0.873  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.211   0.137   0.048  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.187  -0.267   0.837  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.882  -1.441   0.394  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.486  -2.036  -0.782  1.00  0.00           C  
HETATM   18  O2  UNL     1      -3.190  -3.191  -1.179  1.00  0.00           O  
HETATM   19  C17 UNL     1      -1.457  -1.554  -1.551  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.780  -0.376  -1.087  1.00  0.00           C  
HETATM   21  H1  UNL     1      -2.844   3.455   1.630  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.566   3.838  -0.134  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.286   4.157   1.194  1.00  0.00           H  
HETATM   24  H4  UNL     1      -2.555   1.511   0.382  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.938   1.657   0.172  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.891   3.906   1.359  1.00  0.00           H  
HETATM   27  H7  UNL     1       2.273   4.009  -0.407  1.00  0.00           H  
HETATM   28  H8  UNL     1       0.632   3.746   0.094  1.00  0.00           H  
HETATM   29  H9  UNL     1       2.788   0.318  -1.356  1.00  0.00           H  
HETATM   30  H10 UNL     1       3.849  -1.946  -1.531  1.00  0.00           H  
HETATM   31  H11 UNL     1       2.754  -4.580  -0.973  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.091  -3.331   1.363  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.154  -1.207   1.624  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.451   0.208   1.755  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.677  -1.841   0.968  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.924  -4.126  -0.893  1.00  0.00           H  
HETATM   37  H17 UNL     1      -1.128  -1.982  -2.439  1.00  0.00           H  
HETATM   38  H18 UNL     1      -0.021   0.014  -1.738  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   24
CONECT    3    4   14
CONECT    4    5    5    7
CONECT    5    6   25
CONECT    6   26   27   28
CONECT    7    8    8   13
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   12
CONECT   11   31
CONECT   12   13   13   32
CONECT   13   33
CONECT   14   15   15   20
CONECT   15   16   34
CONECT   16   17   17   35
CONECT   17   18   19
CONECT   18   36
CONECT   19   20   20   37
CONECT   20   38
END

HMDB0259978
     RDKit          3D
Z,Z-Dienestrol
 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.0466    3.5028    0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5997    2.1406    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4468    1.6699    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8683    1.1324    0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9219    2.0231    0.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6446    3.4598    0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3591   -0.2249    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4354   -0.5028   -0.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187   -1.7238   -0.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5377   -2.7551   -0.1022 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660   -4.0029   -0.2597 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106   -2.5259    0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9085   -1.2722    0.8732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2110    0.1373    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1866   -0.2665    0.8374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8823   -1.4405    0.3943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -2.0357   -0.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896   -3.1913   -1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -1.5538   -1.5510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803   -0.3757   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438    3.4551    1.6298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5665    3.8377   -0.1337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    4.1567    1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5554    1.5109    0.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9380    1.6572    0.1725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8905    3.9060    1.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2730    4.0094   -0.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6315    3.7457    0.0940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7881    0.3179   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -1.9460   -1.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7540   -4.5797   -0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0910   -3.3309    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1544   -1.2075    1.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4515    0.2078    1.7552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6773   -1.8407    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9241   -4.1263   -0.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1279   -1.9818   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    0.0138   -1.7382 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  3
  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
  5 25  1  0
  6 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,4'-Hydroxy-gamma,delta-diphenyl-beta,delta-hexadiene	ChEBI
Dehydrostilbestrol	ChEBI
Di(p-oxyphenyl)-2,4-hexadiene	ChEBI
p,P'-(diethylideneethylene)diphenol	ChEBI
4,4'-Hydroxy-g,delta-diphenyl-b,delta-hexadiene	Generator
4,4'-Hydroxy-γ,δ-diphenyl-β,δ-hexadiene	Generator
4,4'-Hydroxy-g,δ-diphenyl-b,δ-hexadiene	Generator, HMDB
Dehydrostilboestrol	HMDB
Dienesterol	HMDB
Dienoestrol	HMDB

Chemical Formula

C₁₈H₁₈O₂

Average Molecular Weight

266.3343

Monoisotopic Molecular Weight

266.13067982

IUPAC Name

4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol

Traditional Name

di(p-oxyphenyl)-2,4-hexadiene

CAS Registry Number

84-17-3

SMILES

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

InChI Identifier

InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3

InChI Key

NFDFQCUYFHCNBW-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
Styrene
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

phenols (CHEBI:4518 )
olefinic compound (CHEBI:4518 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	227.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.012 g/L	Not Available
LogP	5.9	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	5.18	ALOGPS
logP	4.83	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	9.1	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	3	ChemAxon
Refractivity	84.36 m³·mol⁻¹	ChemAxon
Polarizability	30.3 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.146	31661259
DarkChem	[M-H]-	166.552	31661259
DeepCCS	[M+H]+	168.272	30932474
DeepCCS	[M-H]-	165.914	30932474
DeepCCS	[M-2H]-	198.8	30932474
DeepCCS	[M+Na]+	174.366	30932474
AllCCS	[M+H]+	162.9	32859911
AllCCS	[M+H-H2O]+	159.0	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.6	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	166.6	32859911
AllCCS	[M+HCOO]-	166.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.29 minutes	32390414
Predicted by Siyang on May 30, 2022	14.6797 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.31 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dienestrol	CC=C(C(=CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	4048.4	Standard polar	33892256
Dienestrol	CC=C(C(=CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2549.3	Standard non polar	33892256
Dienestrol	CC=C(C(=CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1	2477.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dienestrol,1TMS,isomer #1	CC=C(C(=CC)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=C(O)C=C1	2678.2	Semi standard non polar	33892256
Dienestrol,2TMS,isomer #1	CC=C(C(=CC)C1=CC=C(O[Si](C)(C)C)C=C1)C1=CC=C(O[Si](C)(C)C)C=C1	2646.9	Semi standard non polar	33892256
Dienestrol,1TBDMS,isomer #1	CC=C(C(=CC)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)C1=CC=C(O)C=C1	2957.7	Semi standard non polar	33892256
Dienestrol,2TBDMS,isomer #1	CC=C(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	3150.1	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 - Dienestrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00li-0490000000-9822fe85c642c751ef7c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dienestrol GC-MS (2 TMS) - 70eV, Positive	splash10-0002-2129000000-85d4859c944ab60cda43	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dienestrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dienestrol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dienestrol 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 - Dienestrol 10V, Positive-QTOF	splash10-014i-0190000000-4e899b7d114c0d12ce05	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 20V, Positive-QTOF	splash10-014i-0390000000-e566be6b7c32827ae335	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 40V, Positive-QTOF	splash10-0ff0-1960000000-df6e60b979760bb8716b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 10V, Negative-QTOF	splash10-014i-0090000000-9f83049c943023145fc4	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 20V, Negative-QTOF	splash10-014i-0090000000-a561e18a5d83704153a8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 40V, Negative-QTOF	splash10-014v-2390000000-e667485e2f52b73a8c60	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 10V, Positive-QTOF	splash10-014r-0950000000-a83d76fab7650b74fa23	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 20V, Positive-QTOF	splash10-014i-0980000000-2dc0c991a1ec2189f1c0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 40V, Positive-QTOF	splash10-014i-1950000000-eb42188f3f31b28ea90a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 10V, Negative-QTOF	splash10-014i-0090000000-79681ca58867f351a3de	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 20V, Negative-QTOF	splash10-052r-0090000000-de5efb03350f2666b0b4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dienestrol 40V, Negative-QTOF	splash10-044j-0690000000-e90b31ad056043d005bc	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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 DB00890	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00890	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00890

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2941

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dienestrol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

4518

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

Enzymes

Enzyme Details

1. 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

Juriansz RL, Huseby RA, Wilcox RB: Interactions of putative estrogens with the intracellular receptor complex in mouse Leydig cells: relationship to preneoplastic hyperplasia. Cancer Res. 1988 Jan 1;48(1):14-8. [PubMed:3334987 ]
Grove RI, Korach KS: Estrogen stimulation of phosphatidylinositol metabolism in mouse uterine tissue. Endocrinology. 1987 Sep;121(3):1083-8. [PubMed:3622377 ]
Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. [PubMed:9048584 ]
Chae K, Lindzey J, McLachlan JA, Korach KS: Estrogen-dependent gene regulation by an oxidative metabolite of diethylstilbestrol, diethylstilbestrol-4',4"-quinone. Steroids. 1998 Mar;63(3):149-57. [PubMed:9558716 ]
Bovee TF, Helsdingen RJ, Rietjens IM, Keijer J, Hoogenboom RL: Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. J Steroid Biochem Mol Biol. 2004 Jul;91(3):99-109. [PubMed:15276617 ]
Maru BS, Tobias JH, Rivers C, Caunt CJ, Norman MR, McArdle CA: Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. Bone. 2009 Jan;44(1):102-12. doi: 10.1016/j.bone.2008.09.016. Epub 2008 Oct 11. [PubMed:18976723 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Dienestrol (HMDB0015027)

MOL for HMDB0015027 (Dienestrol)

3D MOL for HMDB0015027 (Dienestrol)

3D SDF for HMDB0015027 (Dienestrol)

3D-SDF for HMDB0015027 (Dienestrol)

PDB for HMDB0015027 (Dienestrol)

3D PDB for HMDB0015027 (Dienestrol)

SMILES for HMDB0015027 (Dienestrol)

INCHI for HMDB0015027 (Dienestrol)

Structure for HMDB0015027 (Dienestrol)

3D Structure for HMDB0015027 (Dienestrol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References