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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:54:16 UTC

Update Date

2021-09-26 22:52:44 UTC

HMDB ID

HMDB0244768

Secondary Accession Numbers

None

Metabolite Identification

Common Name

17beta-Ethinylestradiol

Description

14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Based on a literature review very few articles have been published on 14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 17beta-ethinylestradiol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 17beta-Ethinylestradiol 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

HMDB0244768
     RDKit          3D
17beta-Ethinylestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.1288   -1.5716   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -0.7074    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3411    0.3454    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6628    0.8715    1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463    1.3979   -0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    1.4596   -1.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    1.0263   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    0.5256   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    1.4288   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    0.6183   -1.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.0928   -0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2517   -0.2296   -0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9446   -0.7145    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3046   -1.0362    0.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3326   -0.8829    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9787   -0.5503    1.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2651   -0.0635    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558    0.2666    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1116   -0.7769    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9556   -0.1827    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -1.3682   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436   -2.3197   -0.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1514    1.7950    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267   -0.4652   -1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8905   -1.2654    2.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603   -0.7079    2.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169    1.2346    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -1.8144    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234   -0.7111    2.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -1.3189    2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558    0.4423    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9509   -2.0199   -0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7168   -1.9985   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -1.0714   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
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 19 40  1  0
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 20 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
M  END


  Mrv1533004171514352D          

 22 25  0  0  0  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3074   -2.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9469   -3.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8255   -4.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  5 15  1  0  0  0  0
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  6 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244768

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2(O)C#C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3

> <INCHI_KEY>
BFPYWIDHMRZLRN-UHFFFAOYSA-N

> <FORMULA>
C20H24O2

> <MOLECULAR_WEIGHT>
296.41

> <EXACT_MASS>
296.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.50744658639819

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.897353088000001

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.594918895355708

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.327053739938252

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6637824751718564

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
87.3745

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethinyl estradiol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0244768
     RDKit          3D
17beta-Ethinylestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.1288   -1.5716   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -0.7074    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3411    0.3454    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6628    0.8715    1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463    1.3979   -0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    1.4596   -1.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    1.0263   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    0.5256   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    1.4288   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    0.6183   -1.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.0928   -0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2517   -0.2296   -0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9446   -0.7145    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3046   -1.0362    0.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3326   -0.8829    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9787   -0.5503    1.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2651   -0.0635    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558    0.2666    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1116   -0.7769    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -0.4753    1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556   -0.1827    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -1.3682   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436   -2.3197   -0.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352    0.0895    2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2185    1.1604   -1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596    2.4033   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7169    1.2346    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -1.8144    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234   -0.7111    2.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4558    0.4423    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7168   -1.9985   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -1.0714   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
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 21  3  1  0
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 17 11  1  0
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  4 24  1  0
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 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.307  -5.242   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.501  -6.170   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.274  -7.694   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    5    9                                                  
CONECT   16    6    2   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    2   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0244768
HETATM    1  C1  UNL     1       5.129  -1.572  -0.225  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.307  -0.707   0.035  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.341   0.345   0.349  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.663   0.871   1.590  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.446   1.398  -0.752  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.050   1.460  -1.385  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.191   1.026  -0.264  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.156   0.526  -0.607  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.020   1.429  -1.412  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.212   0.618  -1.879  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.912   0.093  -0.651  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.252  -0.230  -0.792  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.945  -0.715   0.293  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.305  -1.036   0.130  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.333  -0.883   1.506  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.979  -0.550   1.624  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.265  -0.064   0.552  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.856   0.267   0.735  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.112  -0.777   1.531  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.347  -0.475   1.630  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.956  -0.183   0.302  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.799  -1.368  -0.647  1.00  0.00           C  
HETATM   23  H1  UNL     1       5.844  -2.320  -0.469  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.935   0.090   2.163  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.219   1.160  -1.482  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.660   2.403  -0.302  1.00  0.00           H  
HETATM   27  H5  UNL     1       1.825   2.545  -1.604  1.00  0.00           H  
HETATM   28  H6  UNL     1       1.982   0.868  -2.298  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.151   1.795   0.514  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.127  -0.465  -1.120  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.365   2.332  -0.867  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.476   1.799  -2.308  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.892   1.262  -2.460  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.807  -0.228  -2.489  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.740  -0.092  -1.771  1.00  0.00           H  
HETATM   36  H14 UNL     1      -6.819  -1.392   0.919  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.891  -1.265   2.350  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.560  -0.708   2.608  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.717   1.235   1.303  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.341  -1.814   1.207  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.523  -0.711   2.581  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.844  -1.319   2.147  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.456   0.442   2.258  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.951  -2.020  -0.358  1.00  0.00           H  
HETATM   45  H23 UNL     1       2.717  -1.998  -0.492  1.00  0.00           H  
HETATM   46  H24 UNL     1       1.791  -1.071  -1.695  1.00  0.00           H  
CONECT    1    2    2    2   23
CONECT    2    3
CONECT    3    4    5   21
CONECT    4   24
CONECT    5    6   25   26
CONECT    6    7   27   28
CONECT    7    8   21   29
CONECT    8    9   18   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   12   17
CONECT   12   13   35
CONECT   13   14   15   15
CONECT   14   36
CONECT   15   16   37
CONECT   16   17   17   38
CONECT   17   18
CONECT   18   19   39
CONECT   19   20   40   41
CONECT   20   21   42   43
CONECT   21   22
CONECT   22   44   45   46
END

HMDB0244768
     RDKit          3D
17beta-Ethinylestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.1288   -1.5716   -0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069   -0.7074    0.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3411    0.3454    0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6628    0.8715    1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463    1.3979   -0.7525 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502    1.4596   -1.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1915    1.0263   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1564    0.5256   -0.6072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0198    1.4288   -1.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2116    0.6183   -1.8785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.0928   -0.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2517   -0.2296   -0.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9446   -0.7145    0.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3046   -1.0362    0.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3326   -0.8829    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9787   -0.5503    1.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2651   -0.0635    0.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8558    0.2666    0.7354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1116   -0.7769    1.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3468   -0.4753    1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9556   -0.1827    0.3019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7990   -1.3682   -0.6470 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436   -2.3197   -0.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9352    0.0895    2.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2185    1.1604   -1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596    2.4033   -0.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8247    2.5446   -1.6043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9818    0.8676   -2.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    1.7950    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267   -0.4652   -1.1199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3646    2.3318   -0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    1.7994   -2.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8924    1.2619   -2.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8075   -0.2276   -2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7400   -0.0922   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8193   -1.3918    0.9192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8905   -1.2654    2.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5603   -0.7079    2.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7169    1.2346    1.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3407   -1.8144    1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5234   -0.7111    2.5812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8442   -1.3189    2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4558    0.4423    2.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9509   -2.0199   -0.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7168   -1.9985   -0.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7911   -1.0714   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21  3  1  0
 21  7  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₂

Average Molecular Weight

296.41

Monoisotopic Molecular Weight

296.177630013

IUPAC Name

14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

Traditional Name

ethinyl estradiol

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2(O)C#C

InChI Identifier

InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3

InChI Key

BFPYWIDHMRZLRN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
3-hydroxysteroid
Hydroxysteroid
17-hydroxysteroid
Phenanthrene
Tetralin
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ynone
Cyclic alcohol
Tertiary alcohol
Acetylide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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	3.63	ALOGPS
logP	3.9	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-1.7	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	0	ChemAxon
Refractivity	87.37 m³·mol⁻¹	ChemAxon
Polarizability	34.51 Å³	ChemAxon
Number of Rings	4	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
DeepCCS	[M-2H]-	205.537	30932474
DeepCCS	[M+Na]+	181.102	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.6	32859911
AllCCS	[M+NH4]+	177.7	32859911
AllCCS	[M+Na]+	178.6	32859911
AllCCS	[M-H]-	179.1	32859911
AllCCS	[M+Na-2H]-	178.8	32859911
AllCCS	[M+HCOO]-	178.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17beta-Ethinylestradiol	CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2(O)C#C	4017.8	Standard polar	33892256
17beta-Ethinylestradiol	CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2(O)C#C	2738.5	Standard non polar	33892256
17beta-Ethinylestradiol	CC12CCC3C(CCC4=CC(O)=CC=C34)C1CCC2(O)C#C	2801.0	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 - 17beta-Ethinylestradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-06e9-1790000000-97e42defde6a5591ff4b	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17beta-Ethinylestradiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17beta-Ethinylestradiol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17beta-Ethinylestradiol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17beta-Ethinylestradiol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17beta-Ethinylestradiol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17beta-Ethinylestradiol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17beta-Ethinylestradiol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17beta-Ethinylestradiol 30V, Positive-QTOF	splash10-0a4i-1920000000-1f8770a9c48e2f91a041	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17beta-Ethinylestradiol 15V, Positive-QTOF	splash10-0002-0690000000-109ea8b9dd64262932c3	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17beta-Ethinylestradiol 45V, Positive-QTOF	splash10-0a4i-1900000000-15b8f7ed89788134a725	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17beta-Ethinylestradiol 60V, Positive-QTOF	splash10-0a4i-2900000000-410893f05949df268fef	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17beta-Ethinylestradiol 75V, Positive-QTOF	splash10-0a4i-3900000000-7bb336934b946274a1b1	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 17beta-Ethinylestradiol 90V, Positive-QTOF	splash10-0a4i-4900000000-1b9e3db9b9855338569f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17beta-Ethinylestradiol 10V, Positive-QTOF	splash10-0fb9-0090000000-140df4b7237411cfd0ce	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17beta-Ethinylestradiol 20V, Positive-QTOF	splash10-0ufs-0980000000-79591004571f5f0fec86	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17beta-Ethinylestradiol 40V, Positive-QTOF	splash10-0aor-2970000000-3e2f3da85a85341ca1b7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17beta-Ethinylestradiol 10V, Negative-QTOF	splash10-0002-0090000000-ebc6f53e480399549577	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17beta-Ethinylestradiol 20V, Negative-QTOF	splash10-0002-0090000000-d430c31e0747b683c198	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17beta-Ethinylestradiol 40V, Negative-QTOF	splash10-014l-2690000000-6e5b4a34072199f058cb	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

3170

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3285

PDB ID

Not Available

ChEBI ID

125402

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 17beta-Ethinylestradiol (HMDB0244768)

MOL for HMDB0244768 (17beta-Ethinylestradiol)

3D MOL for HMDB0244768 (17beta-Ethinylestradiol)

3D SDF for HMDB0244768 (17beta-Ethinylestradiol)

3D-SDF for HMDB0244768 (17beta-Ethinylestradiol)

PDB for HMDB0244768 (17beta-Ethinylestradiol)

3D PDB for HMDB0244768 (17beta-Ethinylestradiol)

SMILES for HMDB0244768 (17beta-Ethinylestradiol)

INCHI for HMDB0244768 (17beta-Ethinylestradiol)

Structure for HMDB0244768 (17beta-Ethinylestradiol)

3D Structure for HMDB0244768 (17beta-Ethinylestradiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra