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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:18:03 UTC

Update Date

2021-09-14 15:19:03 UTC

HMDB ID

HMDB0061097

Secondary Accession Numbers

HMDB61097

Metabolite Identification

Common Name

17-alpha-ethinyl estradiol

Description

17-alpha-ethinyl estradiol is a metabolite of mestranol. Mestranol is the 3-methyl ether of ethinylestradiol. It was the estrogen used in many of the first oral contraceptives. It is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70% (50 µg of mestranol is pharmacokinetically bioequivalent to 35 µg of ethinylestradiol). (Wikipedia)

Structure

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

HMDB0061097
     RDKit          3D
17-alpha-ethinyl estradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
   -4.9760   -0.6165    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552   -0.1384    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3557    0.4388   -0.1876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8800    0.4068   -1.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    1.8539    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    2.0477   -0.4113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    0.7028   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    0.4601   -0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200    1.6798   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    1.5408   -0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    0.2555   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214    0.1424   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9062   -1.0114    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2918   -1.0901    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809   -2.0615    0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342   -1.9407    0.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405   -0.7906   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605   -0.7654   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426   -0.9229    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -0.3302    1.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0175   -0.2537   -0.2102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1806   -1.6000   -0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6283   -1.0539    2.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4361   -0.3819   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    2.0395    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6205    2.6088   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    2.8067   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9296    2.2837    0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    0.6831   -2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329    0.3204   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    1.7031    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    2.5935   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848    2.3530   -0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020    1.4851   -2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473    0.9851   -0.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8906   -0.3229    0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -2.9804    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -2.7777    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -1.6465   -0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -0.4282    1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051   -2.0138    1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -0.9726    1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.6658    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719   -1.8860   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911   -1.6942   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483   -2.3767   -0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  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  6
 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

  Mrv0541 07091309182D          

 22 25  0  0  0  0            999 V2000
   -0.0583    1.2570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7538    1.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5660    0.9666    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2632    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6255    1.7894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  3  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 13  4  1  0  0  0  0
 13 12  2  0  0  0  0
 14  5  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  2  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 16 15  1  0  0  0  0
 17  6  1  0  0  0  0
 17 16  1  0  0  0  0
 18  9  1  0  0  0  0
 18 17  1  0  0  0  0
 19  2  1  1  0  0  0
 19 10  1  0  0  0  0
 19 18  1  0  0  0  0
 20  3  1  6  0  0  0
 20 11  1  0  0  0  0
 20 19  1  0  0  0  0
 21 14  1  0  0  0  0
 20 22  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0061097

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(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/t16?,17?,18?,19-,20-/m1/s1

> <INCHI_KEY>
BFPYWIDHMRZLRN-YPKSLRHJSA-N

> <FORMULA>
C20H24O2

> <MOLECULAR_WEIGHT>
296.4034

> <EXACT_MASS>
296.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.391671105804114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(14S,15R)-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>
87.37449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.77e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(14S,15R)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-triene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061097
     RDKit          3D
17-alpha-ethinyl estradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
   -4.9760   -0.6165    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552   -0.1384    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3557    0.4388   -0.1876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8800    0.4068   -1.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    1.8539    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    2.0477   -0.4113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    0.7028   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    0.4601   -0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200    1.6798   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    1.5408   -0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    0.2555   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214    0.1424   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9062   -1.0114    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2918   -1.0901    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809   -2.0615    0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342   -1.9407    0.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405   -0.7906   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605   -0.7654   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426   -0.9229    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -0.3302    1.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0175   -0.2537   -0.2102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1806   -1.6000   -0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6283   -1.0539    2.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4361   -0.3819   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    2.0395    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6205    2.6088   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    2.8067   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9296    2.2837    0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    0.6831   -2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329    0.3204   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    1.7031    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    2.5935   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848    2.3530   -0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020    1.4851   -2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473    0.9851   -0.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8906   -0.3229    0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -2.9804    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -2.7777    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -1.6465   -0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -0.4282    1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051   -2.0138    1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -0.9726    1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.6658    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719   -1.8860   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911   -1.6942   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483   -2.3767   -0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  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  6
 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

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -0.109   2.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.791   3.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.407   2.075   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.541  -1.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.519   1.947   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025  -1.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.003   2.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.971   2.761   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.770  -0.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.455   3.032   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.495   0.325   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.049  -0.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.533  -0.407   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.042   0.499   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.010   1.041   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.494   1.312   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.502   0.135   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.985   0.406   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.462   1.854   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.923   1.804   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.558   0.228   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.034   3.340   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   19                                                            
CONECT    3    1   20                                                       
CONECT    4    6   13                                                       
CONECT    5    7   14                                                       
CONECT    6    4   17                                                       
CONECT    7    5   15                                                       
CONECT    8   10   16                                                       
CONECT    9   11   18                                                       
CONECT   10    8   19                                                       
CONECT   11    9   20                                                       
CONECT   12   13   14                                                       
CONECT   13    4   12   15                                                  
CONECT   14    5   12   21                                                  
CONECT   15    7   13   16                                                  
CONECT   16    8   15   17                                                  
CONECT   17    6   16   18                                                  
CONECT   18    9   17   19                                                  
CONECT   19    2   10   18   20                                             
CONECT   20    3   11   19   22                                             
CONECT   21   14                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0061097
HETATM    1  C1  UNL     1      -4.976  -0.616   1.634  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.255  -0.138   0.808  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.356   0.439  -0.188  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.880   0.407  -1.469  1.00  0.00           O  
HETATM    5  C4  UNL     1      -2.982   1.854   0.136  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.582   2.048  -0.411  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.196   0.703  -1.029  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.267   0.460  -0.961  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.020   1.680  -0.447  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.442   1.541  -0.948  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.969   0.256  -0.368  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.321   0.142  -0.175  1.00  0.00           C  
HETATM   13  C12 UNL     1       4.906  -1.011   0.358  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.292  -1.090   0.541  1.00  0.00           O  
HETATM   15  C13 UNL     1       4.081  -2.062   0.694  1.00  0.00           C  
HETATM   16  C14 UNL     1       2.734  -1.941   0.498  1.00  0.00           C  
HETATM   17  C15 UNL     1       2.140  -0.791  -0.034  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.661  -0.765  -0.206  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.043  -0.923   1.115  1.00  0.00           C  
HETATM   20  C18 UNL     1      -1.404  -0.330   1.163  1.00  0.00           C  
HETATM   21  C19 UNL     1      -2.017  -0.254  -0.210  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.181  -1.600  -0.829  1.00  0.00           C  
HETATM   23  H1  UNL     1      -5.628  -1.054   2.373  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.436  -0.382  -1.656  1.00  0.00           H  
HETATM   25  H3  UNL     1      -3.043   2.039   1.216  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.621   2.609  -0.361  1.00  0.00           H  
HETATM   27  H5  UNL     1      -1.535   2.807  -1.206  1.00  0.00           H  
HETATM   28  H6  UNL     1      -0.930   2.284   0.464  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.593   0.683  -2.060  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.633   0.320  -2.020  1.00  0.00           H  
HETATM   31  H9  UNL     1       1.067   1.703   0.657  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.605   2.593  -0.896  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.085   2.353  -0.562  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.402   1.485  -2.047  1.00  0.00           H  
HETATM   35  H13 UNL     1       4.947   0.985  -0.448  1.00  0.00           H  
HETATM   36  H14 UNL     1       6.891  -0.323   0.295  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.517  -2.980   1.114  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.101  -2.778   0.768  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.428  -1.646  -0.873  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.565  -0.428   1.929  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.105  -2.014   1.377  1.00  0.00           H  
HETATM   42  H20 UNL     1      -2.077  -0.973   1.794  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.423   0.666   1.619  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.272  -1.886  -0.893  1.00  0.00           H  
HETATM   45  H23 UNL     1      -1.791  -1.694  -1.847  1.00  0.00           H  
HETATM   46  H24 UNL     1      -1.748  -2.377  -0.132  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

HMDB0061097
     RDKit          3D
17-alpha-ethinyl estradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
   -4.9760   -0.6165    1.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552   -0.1384    0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3557    0.4388   -0.1876 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8800    0.4068   -1.4688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9818    1.8539    0.1356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819    2.0477   -0.4113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    0.7028   -1.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    0.4601   -0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0200    1.6798   -0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4419    1.5408   -0.9477 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9686    0.2555   -0.3683 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3214    0.1424   -0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9062   -1.0114    0.3577 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2918   -1.0901    0.5409 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0809   -2.0615    0.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7342   -1.9407    0.4977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1405   -0.7906   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6605   -0.7654   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0426   -0.9229    1.1152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4042   -0.3302    1.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0175   -0.2537   -0.2102 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1806   -1.6000   -0.8291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6283   -1.0539    2.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4361   -0.3819   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0430    2.0395    1.2156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6205    2.6088   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    2.8067   -1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9296    2.2837    0.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5932    0.6831   -2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6329    0.3204   -2.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667    1.7031    0.6570 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6047    2.5935   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848    2.3530   -0.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4020    1.4851   -2.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9473    0.9851   -0.4483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8906   -0.3229    0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5165   -2.9804    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008   -2.7777    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -1.6465   -0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5650   -0.4282    1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051   -2.0138    1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0769   -0.9726    1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    0.6658    1.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719   -1.8860   -0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7911   -1.6942   -1.8471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483   -2.3767   -0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  3  2  1  1
  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  6
 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

Value	Source
17-a-Ethinyl estradiol	Generator
17-Α-ethinyl estradiol	Generator

Chemical Formula

C₂₀H₂₄O₂

Average Molecular Weight

296.4034

Monoisotopic Molecular Weight

296.177630012

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(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/t16?,17?,18?,19-,20-/m1/s1

InChI Key

BFPYWIDHMRZLRN-YPKSLRHJSA-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 (HMDB: HMDB0061097)

Organ

Kidney (HMDB: HMDB0061097)
Liver (HMDB: HMDB0061097)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061097)

Cellular substructure

Cytoplasm (HMDB: HMDB0061097)
Membrane (HMDB: HMDB0061097)

Source

Endogenous

Endogenous (HMDB: HMDB0061097)

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
Water Solubility	0.0068 g/L	ALOGPS
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	34.39 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
DarkChem	[M+H]+	169.602	31661259
DarkChem	[M-H]-	167.332	31661259
DeepCCS	[M-2H]-	205.902	30932474
DeepCCS	[M+Na]+	181.129	30932474
AllCCS	[M+H]+	174.8	32859911
AllCCS	[M+H-H2O]+	171.5	32859911
AllCCS	[M+NH4]+	177.9	32859911
AllCCS	[M+Na]+	178.7	32859911
AllCCS	[M-H]-	181.5	32859911
AllCCS	[M+Na-2H]-	181.3	32859911
AllCCS	[M+HCOO]-	181.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17-alpha-ethinyl estradiol	C[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(O)C#C	4017.8	Standard polar	33892256
17-alpha-ethinyl estradiol	C[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(O)C#C	2738.4	Standard non polar	33892256
17-alpha-ethinyl estradiol	C[C@@]12CCC3C(CCC4=CC(O)=CC=C34)C1CC[C@]2(O)C#C	2801.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17-alpha-ethinyl estradiol,1TMS,isomer #1	C#C[C@@]1(O)CCC2C3CCC4=CC(O[Si](C)(C)C)=CC=C4C3CC[C@]21C	2793.8	Semi standard non polar	33892256
17-alpha-ethinyl estradiol,1TMS,isomer #2	C#C[C@@]1(O[Si](C)(C)C)CCC2C3CCC4=CC(O)=CC=C4C3CC[C@]21C	2802.0	Semi standard non polar	33892256
17-alpha-ethinyl estradiol,2TMS,isomer #1	C#C[C@@]1(O[Si](C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C)=CC=C4C3CC[C@]21C	2818.3	Semi standard non polar	33892256
17-alpha-ethinyl estradiol,1TBDMS,isomer #1	C#C[C@@]1(O)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]21C	3053.9	Semi standard non polar	33892256
17-alpha-ethinyl estradiol,1TBDMS,isomer #2	C#C[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O)=CC=C4C3CC[C@]21C	3059.2	Semi standard non polar	33892256
17-alpha-ethinyl estradiol,2TBDMS,isomer #1	C#C[C@@]1(O[Si](C)(C)C(C)(C)C)CCC2C3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4C3CC[C@]21C	3291.5	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 - 17-alpha-ethinyl estradiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-06e9-1790000000-97e42defde6a5591ff4b	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-alpha-ethinyl estradiol GC-MS (2 TMS) - 70eV, Positive	splash10-01t9-3264900000-27be1780fbc6934a75b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 17-alpha-ethinyl estradiol 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 - 17-alpha-ethinyl estradiol 10V, Positive-QTOF	splash10-0002-0090000000-89a5dd187a0734435168	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Positive-QTOF	splash10-0002-0490000000-8b572ab8ad360f61dfa1	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Positive-QTOF	splash10-00ou-6970000000-9f88e843a581bd8c854c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 10V, Negative-QTOF	splash10-0002-0090000000-a8d4f94acb064b2180bf	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Negative-QTOF	splash10-0002-0090000000-aca0d5b383c05de9d27e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Negative-QTOF	splash10-00or-0090000000-b88c1863016a38d10d2d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 10V, Positive-QTOF	splash10-0fb9-0090000000-140df4b7237411cfd0ce	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Positive-QTOF	splash10-0ufs-0980000000-79591004571f5f0fec86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Positive-QTOF	splash10-0aor-2970000000-3e2f3da85a85341ca1b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 10V, Negative-QTOF	splash10-0002-0090000000-ebc6f53e480399549577	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 20V, Negative-QTOF	splash10-0002-0090000000-d430c31e0747b683c198	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 17-alpha-ethinyl estradiol 40V, Negative-QTOF	splash10-014l-2690000000-6e5b4a34072199f058cb	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131770026

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 17-alpha-ethinyl estradiol (HMDB0061097)

MOL for HMDB0061097 (17-alpha-ethinyl estradiol)

3D MOL for HMDB0061097 (17-alpha-ethinyl estradiol)

3D SDF for HMDB0061097 (17-alpha-ethinyl estradiol)

3D-SDF for HMDB0061097 (17-alpha-ethinyl estradiol)

PDB for HMDB0061097 (17-alpha-ethinyl estradiol)

3D PDB for HMDB0061097 (17-alpha-ethinyl estradiol)

SMILES for HMDB0061097 (17-alpha-ethinyl estradiol)

INCHI for HMDB0061097 (17-alpha-ethinyl estradiol)

Structure for HMDB0061097 (17-alpha-ethinyl estradiol)

3D Structure for HMDB0061097 (17-alpha-ethinyl estradiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra