Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4)transporters (4) Show 8 proteins XML

enzymes (4)transporters (4) Show 8 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 08:38:06 UTC

Update Date

2021-09-14 15:40:11 UTC

HMDB ID

HMDB0001926

Secondary Accession Numbers

HMDB01926

Metabolite Identification

Common Name

17a-Ethynylestradiol

Description

Ethinyl estradiol. A semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in oral contraceptives. -- Pubchem; estradiol (17-beta estradiol) (also oestradiol) is a sex hormone. Labelled the "female" hormone but also present in males it represents the major estrogen in humans. Critical for sexual functioning, estradiol also supports bone growth. -- Wikipedia ; One of the fascinating twists to mammalian sexual differentiation is that estradiol is one of the two active metabolites of testosterone in males (the other being dihydrotestosterone). estradiol cannot be transferred readily from the circulation into the brain. Since fetuses of both sexes are exposed to similarly high levels of maternal estradiol, it can play little role in prenatal sexual differentiation. However, testosterone enters the central nervous system more freely and significant amounts are aromatized to estradiol within the brain of most male mammals, including humans. There is now much evidence that the programming of adult male sexual behavior in "lower mammals," (such as mounting rather than lordosis behavior), is largely dependent on estradiol produced in the central nervous system during prenatal life and early infancy from testosterone. We do not yet know whether this process plays a minimal or significant part in human sexual behaviors. -- Wikipedia ; A synthetic form of estradiol, called ethinyl estradiol is a major component of hormonal contraceptive devices. Combined oral contraceptives contain ethinyl estradiol and a progestin, which both contribute to the inhibition of GnRH, LH, and FSH. The inhibition of these hormones accounts for the ability of combined oral contraceptives or birth control pills to prevent ovulation and thus prevent pregnancy. Other types of hormonal birth control contain only progestins and no ethinyl estradiol. -- Wikipedia .

Structure

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


  Mrv1652305261923532D          

 25 28  0  0  0  0            999 V2000
    7.7254    1.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3626   -1.9994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    0.5185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8116   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971   -0.7188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5921    0.7699    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971    0.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5921   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    0.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0734    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1102   -1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321   -0.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3696   -2.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -1.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2602    0.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -2.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -0.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0774    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0759    0.0864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3762   -1.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988   -1.1266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3 12  1  1  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 22  1  1  0  0  0
  6 10  1  0  0  0  0
  6 16  1  6  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  1  0  0  0  0
 16 21  3  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
  5 23  1  0  0  0  0
 23  9  1  0  0  0  0
 23 13  1  0  0  0  0
 23 24  1  6  0  0  0
  4 25  1  6  0  0  0
M  END

HMDB0001926
     RDKit          3D
17a-Ethynylestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.0504   -2.4683   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -1.3118   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    0.1001   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0141    0.9122   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    0.5680    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2760    0.7662    1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793   -0.0737    0.5217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0654    0.2035    0.6100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6428    0.0598    1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505    0.6040    1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017    0.1486    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580    0.4298    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    0.0439   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2855    0.3079   -0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3563   -0.6228   -1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009   -0.8859   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2273   -0.5072   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7786   -0.8228   -0.2742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2547   -0.8454   -1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   -0.7771   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.2424   -0.8885 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5306    1.6412   -1.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -3.4939   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9680    0.8717   -1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2257    1.5045    0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -0.2471    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214    1.8479    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    0.4814    2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -1.1329    0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    1.1937    0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893   -0.9660    2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    0.7166    2.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.2241    2.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995    1.7160    1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6313    0.9525    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8074    0.7786    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9493   -0.9274   -2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872   -1.4150   -2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6704   -1.8050    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924   -0.0603   -2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889   -1.8165   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505   -0.4367   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -1.7695   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7696    1.6227   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    2.2957   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4498    2.1525   -1.7187 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  1
  8 30  1  6
  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  1
 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


  Mrv1652305261923532D          

 25 28  0  0  0  0            999 V2000
    7.7254    1.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3626   -1.9994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    0.5185    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8116   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971   -0.7188    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5921    0.7699    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0971    0.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5921   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827    0.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0734    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1102   -1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8116    1.3434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6321   -0.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3696   -2.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6255   -1.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2602    0.9263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8538   -2.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0855   -0.6947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0774    1.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0759    0.0864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3827   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3762   -1.1312    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988   -1.1266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  2 20  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3 12  1  1  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  5 11  1  0  0  0  0
  5 22  1  1  0  0  0
  6 10  1  0  0  0  0
  6 16  1  6  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
 11 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 18  1  0  0  0  0
 16 21  3  0  0  0  0
 17 19  2  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
  5 23  1  0  0  0  0
 23  9  1  0  0  0  0
 23 13  1  0  0  0  0
 23 24  1  6  0  0  0
  4 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001926

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

> <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-SLHNCBLASA-N

> <FORMULA>
C20H24O2

> <MOLECULAR_WEIGHT>
296.4034

> <EXACT_MASS>
296.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.53354161278887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-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>
(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001926
     RDKit          3D
17a-Ethynylestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.0504   -2.4683   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -1.3118   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    0.1001   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0141    0.9122   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    0.5680    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2760    0.7662    1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793   -0.0737    0.5217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0654    0.2035    0.6100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6428    0.0598    1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505    0.6040    1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017    0.1486    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580    0.4298    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    0.0439   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2855    0.3079   -0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3563   -0.6228   -1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009   -0.8859   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2273   -0.5072   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7786   -0.8228   -0.2742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2547   -0.8454   -1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   -0.7771   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.2424   -0.8885 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5306    1.6412   -1.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -3.4939   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9680    0.8717   -1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2257    1.5045    0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -0.2471    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214    1.8479    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    0.4814    2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -1.1329    0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    1.1937    0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893   -0.9660    2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    0.7166    2.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.2241    2.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995    1.7160    1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6313    0.9525    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8074    0.7786    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9493   -0.9274   -2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872   -1.4150   -2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6704   -1.8050    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924   -0.0603   -2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889   -1.8165   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505   -0.4367   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -1.7695   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7696    1.6227   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    2.2957   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4498    2.1525   -1.7187 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  1
  8 30  1  6
  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  1
 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                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  O   UNK     0      14.421   2.902   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       4.410  -3.732   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.715   0.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.715  -0.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.381  -1.342   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.172   1.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.381   1.738   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.172  -1.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.048   0.968   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      15.070   0.198   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.406  -2.946   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.715   2.508   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.647  -1.352   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.023  -3.758   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.634  -2.956   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.419   1.729   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.219  -0.484   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.194  -3.803   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.760  -1.297   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.747  -2.968   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.944   1.965   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0      11.342   0.161   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0      10.048  -0.572   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      10.036  -2.112   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      12.878  -2.103   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   20                                                            
CONECT    3    4    6    7   12                                             
CONECT    4    3    5    8   25                                             
CONECT    5    4   11   22   23                                             
CONECT    6    1    3   10   16                                             
CONECT    7    3    9                                                       
CONECT    8    4   10                                                       
CONECT    9    7   23                                                       
CONECT   10    6    8                                                       
CONECT   11    5   14                                                       
CONECT   12    3                                                            
CONECT   13   15   17   23                                                  
CONECT   14   11   15                                                       
CONECT   15   13   14   18                                                  
CONECT   16    6   21                                                       
CONECT   17   13   19                                                       
CONECT   18   15   20                                                       
CONECT   19   17   20                                                       
CONECT   20    2   18   19                                                  
CONECT   21   16                                                            
CONECT   22    5                                                            
CONECT   23    5    9   13   24                                             
CONECT   24   23                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0001926
HETATM    1  C1  UNL     1       4.050  -2.468  -1.042  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.735  -1.312  -0.909  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.325   0.100  -0.741  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.014   0.912  -1.632  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.624   0.568   0.679  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.276   0.766   1.348  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.379  -0.074   0.522  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.065   0.204   0.610  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.643   0.060   1.991  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.051   0.604   1.979  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.802   0.149   0.766  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.158   0.430   0.738  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.920   0.044  -0.344  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.285   0.308  -0.409  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.356  -0.623  -1.409  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.001  -0.886  -1.346  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.227  -0.507  -0.274  1.00  0.00           C  
HETATM   18  C16 UNL     1      -0.779  -0.823  -0.274  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.255  -0.845  -1.666  1.00  0.00           C  
HETATM   20  C18 UNL     1       1.222  -0.777  -1.799  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.848   0.242  -0.888  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.531   1.641  -1.309  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.317  -3.494  -1.148  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.968   0.872  -1.404  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.226   1.504   0.664  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.190  -0.247   1.189  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.021   1.848   1.318  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.318   0.481   2.418  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.572  -1.133   0.711  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.378   1.194   0.225  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.589  -0.966   2.378  1.00  0.00           H  
HETATM   32  H10 UNL     1      -0.052   0.717   2.667  1.00  0.00           H  
HETATM   33  H11 UNL     1      -2.589   0.224   2.865  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.999   1.716   1.949  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.631   0.953   1.560  1.00  0.00           H  
HETATM   36  H14 UNL     1      -6.807   0.779   0.290  1.00  0.00           H  
HETATM   37  H15 UNL     1      -4.949  -0.927  -2.259  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.587  -1.415  -2.206  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.670  -1.805   0.238  1.00  0.00           H  
HETATM   40  H18 UNL     1      -0.792  -0.060  -2.247  1.00  0.00           H  
HETATM   41  H19 UNL     1      -0.589  -1.817  -2.128  1.00  0.00           H  
HETATM   42  H20 UNL     1       1.451  -0.437  -2.852  1.00  0.00           H  
HETATM   43  H21 UNL     1       1.708  -1.770  -1.712  1.00  0.00           H  
HETATM   44  H22 UNL     1       0.770   1.623  -2.104  1.00  0.00           H  
HETATM   45  H23 UNL     1       1.183   2.296  -0.488  1.00  0.00           H  
HETATM   46  H24 UNL     1       2.450   2.153  -1.719  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

HMDB0001926
     RDKit          3D
17a-Ethynylestradiol
 46 49  0  0  0  0  0  0  0  0999 V2000
    4.0504   -2.4683   -1.0422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7351   -1.3118   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3253    0.1001   -0.7409 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0141    0.9122   -1.6318 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6243    0.5680    0.6792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2760    0.7662    1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3793   -0.0737    0.5217 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0654    0.2035    0.6100 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6428    0.0598    1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505    0.6040    1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8017    0.1486    0.7657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1580    0.4298    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9204    0.0439   -0.3439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2855    0.3079   -0.4092 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3563   -0.6228   -1.4094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0009   -0.8859   -1.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2273   -0.5072   -0.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7786   -0.8228   -0.2742 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2547   -0.8454   -1.6659 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2221   -0.7771   -1.7995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8478    0.2424   -0.8885 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5306    1.6412   -1.3087 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3168   -3.4939   -1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9680    0.8717   -1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2257    1.5045    0.6645 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -0.2471    1.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0214    1.8479    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178    0.4814    2.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -1.1329    0.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3785    1.1937    0.2252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893   -0.9660    2.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0523    0.7166    2.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5886    0.2241    2.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9995    1.7160    1.9486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6313    0.9525    1.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8074    0.7786    0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9493   -0.9274   -2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5872   -1.4150   -2.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6704   -1.8050    0.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924   -0.0603   -2.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5889   -1.8165   -2.1280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4505   -0.4367   -2.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7076   -1.7695   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7696    1.6227   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1829    2.2957   -0.4882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4498    2.1525   -1.7187 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  1
  8 30  1  6
  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  1
 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-Ethinyl-3,17-estradiol	ChEBI
17-Ethinyl-3,17-oestradiol	ChEBI
17-Ethinylestradiol	ChEBI
17alpha-Ethinyl estradiol	ChEBI
Ethinyl estradiol	ChEBI
Ethinylestradiol	ChEBI
Ethinyloestradiol	ChEBI
Ethynyl estradiol	ChEBI
Estinyl	Kegg
17a-Ethinyl estradiol	Generator
17Α-ethinyl estradiol	Generator
17-Ethynylestradiol	HMDB
17-Ethynylestradiol ram	HMDB
17-Ethynyloestradiol	HMDB
17a-Ethinyl-17b-estradiol	HMDB
17a-Ethinylestradiol	HMDB
17a-Ethynyl-17b-oestradiol	HMDB
17a-Ethynylestradiol-L7b	HMDB
17a-Ethynyloestradiol	HMDB
17a-Ethynyloestradiol-17b	HMDB
Alora	HMDB
Amenoron	HMDB
Anovlar	HMDB
Chee-O-gen	HMDB
Chee-O-genf	HMDB
Diognat-e	HMDB
Diogyn e	HMDB
Diogyn-e	HMDB
Dyloform	HMDB
Ertonyl	HMDB
Esclim	HMDB
Esteed	HMDB
Estigyn	HMDB
Eston-e	HMDB
Estoral	HMDB
Estoral {[orion]}	HMDB
Estorals	HMDB
Estring	HMDB
Estrogen	HMDB
Ethidol	HMDB
Ethinoral	HMDB
Ethinylestriol	HMDB
Ethynylestradiol	HMDB
Eticyclin	HMDB
Eticyclol	HMDB
Eticylol	HMDB
Etinestrol	HMDB
Etinestryl	HMDB
Etinoestryl	HMDB
Etistradiol	HMDB
Etivex	HMDB
Feminone	HMDB
Fempatch	HMDB
Follicoral	HMDB
Ginestrene	HMDB
Gynodiol	HMDB
Gynolett	HMDB
Inestra	HMDB
Innofem	HMDB
Kolpolyn	HMDB
Linoral	HMDB
Lynoral	HMDB
Menolyn	HMDB
Menostar	HMDB
Neo-estrone	HMDB
Nogest-S	HMDB
Novestrol	HMDB
Oradiol	HMDB
Orestralyn	HMDB
Orestrayln	HMDB
Ovex	HMDB
Palonyl	HMDB
Perovex	HMDB
Primogyn	HMDB
Primogyn C	HMDB
Primogyn m	HMDB
Progynon C	HMDB
Progynon m	HMDB
Spanestrin	HMDB
Thiuram e	HMDB
Thiuranide	HMDB
Vagifem	HMDB
Ylestrol	HMDB
Ethinyl estradiol, (8 alpha)-isomer	HMDB
Ethinyl estradiol, (8 alpha,17 alpha)-isomer	HMDB
Jenapharm, ethinylestradiol	HMDB
Effik brand OF ethinyl estradiol	HMDB
Estradiol, ethynyl	HMDB
Ethinyl estradiol hemihydrate	HMDB
Ethinyl estradiol, (9 beta,17 alpha)-isomer	HMDB
Ethinylestradiol jenapharm	HMDB
Microfollin	HMDB
Microfollin forte	HMDB
Estradiol, ethinyl	HMDB
Ethinyl estradiol, (8 alpha,9 beta,13 alpha,14 beta)-isomer	HMDB
Ethinyl oestradiol effik	HMDB
Schering brand OF ethinyl estradiol	HMDB
Schering-plough brand OF ethinyl estradiol	HMDB
Ethinyl-oestradiol effik	HMDB
Hemihydrate, ethinyl estradiol	HMDB
Jenapharm brand OF ethinyl estradiol	HMDB
Organon brand OF ethinyl estradiol	HMDB

Chemical Formula

C₂₀H₂₄O₂

Average Molecular Weight

296.4034

Monoisotopic Molecular Weight

296.177630012

IUPAC Name

(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

Traditional Name

(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,14-diol

CAS Registry Number

57-63-6

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3

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-SLHNCBLASA-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

terminal acetylenic compound (CHEBI:4903 )
17-hydroxy steroid (CHEBI:4903 )
3-hydroxy steroid (CHEBI:4903 )
C18 steroids (estrogens) and derivatives (C07534 )
C18 steroids (estrogens) and derivatives (LMST02010036 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.011 mg/mL at 27 °C	Not Available
LogP	3.67	HANSCH,C ET AL. (1995)

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	34.53 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]+	171.882	31661259
DarkChem	[M-H]-	167.936	31661259
AllCCS	[M+H]+	174.783	32859911
AllCCS	[M-H]-	181.44	32859911
DeepCCS	[M-2H]-	213.883	30932474
DeepCCS	[M+Na]+	188.632	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]-	181.4	32859911
AllCCS	[M+Na-2H]-	181.2	32859911
AllCCS	[M+HCOO]-	181.1	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.	7.28 minutes	32390414
Predicted by Siyang on May 30, 2022	15.1167 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2264.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	376.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	835.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	740.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1373.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	492.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1505.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	463.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	425.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	338.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	26.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
17a-Ethynylestradiol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	4116.9	Standard polar	33892256
17a-Ethynylestradiol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2723.8	Standard non polar	33892256
17a-Ethynylestradiol	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3	2802.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
17a-Ethynylestradiol,1TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C	2763.4	Semi standard non polar	33892256
17a-Ethynylestradiol,1TMS,isomer #2	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC=C4[C@H]3CC[C@@]21C	2733.1	Semi standard non polar	33892256
17a-Ethynylestradiol,2TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC=C4[C@H]3CC[C@@]21C	2844.6	Semi standard non polar	33892256
17a-Ethynylestradiol,1TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O)=CC=C4[C@H]3CC[C@@]21C	3032.8	Semi standard non polar	33892256
17a-Ethynylestradiol,1TBDMS,isomer #2	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@@]21C	3023.6	Semi standard non polar	33892256
17a-Ethynylestradiol,2TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C(C)(C)C)=CC=C4[C@H]3CC[C@@]21C	3360.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Bladder
Brain
Epidermis
Fibroblasts
Intestine
Kidney
Liver
Neuron
Ovary
Pancreas
Placenta
Platelet
Prostate
Skeletal Muscle
Spleen
Testis
Thyroid Gland

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00016 (0.000084-0.00027) uM	Adult (>18 years old)	Both	Normal	10342082	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Prostate cancer	20975847	details

Associated Disorders and Diseases

Disease References

Prostate cancer
Madu CO, Lu Y: Novel diagnostic biomarkers for prostate cancer. J Cancer. 2010 Oct 6;1:150-77. [PubMed:20975847 ]

Associated OMIM IDs

176807 (Prostate cancer)

External Links

DrugBank ID

DB00977

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003598

KNApSAcK ID

Not Available

Chemspider ID

5770

KEGG Compound ID

C07534

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ethinyl estradiol

METLIN ID

6392

PubChem Compound

5991

PDB ID

Not Available

ChEBI ID

4903

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

Kaufer D, Ogle WO, Pincus ZS, Clark KL, Nicholas AC, Dinkel KM, Dumas TC, Ferguson D, Lee AL, Winters MA, Sapolsky RM: Restructuring the neuronal stress response with anti-glucocorticoid gene delivery. Nat Neurosci. 2004 Sep;7(9):947-53. Epub 2004 Aug 8. [PubMed:15300253 ]
Czernik PJ, Little JM, Barone GW, Raufman JP, Radominska-Pandya A: Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa. Drug Metab Dispos. 2000 Oct;28(10):1210-6. [PubMed:10997942 ]
Stabile LP, Davis AL, Gubish CT, Hopkins TM, Luketich JD, Christie N, Finkelstein S, Siegfried JM: Human non-small cell lung tumors and cells derived from normal lung express both estrogen receptor alpha and beta and show biological responses to estrogen. Cancer Res. 2002 Apr 1;62(7):2141-50. [PubMed:11929836 ]
Li X, Strauss L, Kaatrasalo A, Mayerhofer A, Huhtaniemi I, Santti R, Makela S, Poutanen M: Transgenic mice expressing p450 aromatase as a model for male infertility associated with chronic inflammation in the testis. Endocrinology. 2006 Mar;147(3):1271-7. Epub 2005 Nov 23. [PubMed:16306085 ]
Wernert N: [Immunohistochemistry of the prostate and prostate carcinomas]. Veroff Pathol. 1991;135:1-163. [PubMed:2038892 ]
Zhang L, Sukhareva M, Barker JL, Maric D, Hao Y, Chang YH, Ma W, O'Shaughnessy T, Rubinow DR: Direct binding of estradiol enhances Slack (sequence like a calcium-activated potassium channel) channels' activity. Neuroscience. 2005;131(2):275-82. [PubMed:15708472 ]
Herrero P, Soto PF, Dence CS, Kisrieva-Ware Z, Delano DA, Peterson LR, Gropler RJ: Impact of hormone replacement on myocardial fatty acid metabolism: potential role of estrogen. J Nucl Cardiol. 2005 Sep-Oct;12(5):574-81. [PubMed:16171718 ]
Shah MG, Maibach HI: Estrogen and skin. An overview. Am J Clin Dermatol. 2001;2(3):143-50. [PubMed:11705091 ]
Safi R, Kovacic A, Gaillard S, Murata Y, Simpson ER, McDonnell DP, Clyne CD: Coactivation of liver receptor homologue-1 by peroxisome proliferator-activated receptor gamma coactivator-1alpha on aromatase promoter II and its inhibition by activated retinoid X receptor suggest a novel target for breast-specific antiestrogen therapy. Cancer Res. 2005 Dec 15;65(24):11762-70. [PubMed:16357189 ]
vom Saal FS, Grant WM, McMullen CW, Laves KS: High fetal estrogen concentrations: correlation with increased adult sexual activity and decreased aggression in male mice. Science. 1983 Jun 17;220(4603):1306-9. [PubMed:6857252 ]
Schmitt PM, Gohil K, Kaufman MP: Spinal estrogen attenuates the exercise pressor reflex but has little effect on the expression of genes regulating neurotransmitters in the dorsal root ganglia. J Appl Physiol (1985). 2006 Mar;100(3):958-64. Epub 2005 Nov 23. [PubMed:16306253 ]
Kalaitzidis D, Ok J, Sulak L 2nd, Starczynowski DT, Gilmore TD: Characterization of a human REL-estrogen receptor fusion protein with a reverse conditional transforming activity in chicken spleen cells. Oncogene. 2004 Sep 30;23(45):7580-7. [PubMed:15326488 ]
Pierard-Franchimont C, Letawe C, Goffin V, Pierard GE: Skin water-holding capacity and transdermal estrogen therapy for menopause: a pilot study. Maturitas. 1995 Sep;22(2):151-4. [PubMed:8538484 ]
de la Monte SM, Moore GW, Hutchins GM: Metastatic behavior of prostate cancer. Cluster analysis of patterns with respect to estrogen treatment. Cancer. 1986 Aug 15;58(4):985-93. [PubMed:3719562 ]
Harris H, Henderson R, Bhat R, Komm B: Regulation of metallothionein II messenger ribonucleic acid measures exogenous estrogen receptor-beta activity in SAOS-2 and LNCaPLN3 cells. Endocrinology. 2001 Feb;142(2):645-52. [PubMed:11159835 ]
Frolich A, Christensen L, Andersen J: Estrogen receptors appear undetectable in the C-cells of the human thyroid gland. Bone. 1990;11(6):393-6. [PubMed:1706609 ]
Siiteri PK: Review of studies on estrogen biosynthesis in the human. Cancer Res. 1982 Aug;42(8 Suppl):3269s-3273s. [PubMed:7083184 ]
Koehler KF, Helguero LA, Haldosen LA, Warner M, Gustafsson JA: Reflections on the discovery and significance of estrogen receptor beta. Endocr Rev. 2005 May;26(3):465-78. Epub 2005 Apr 27. [PubMed:15857973 ]
Moro L, Reineri S, Piranda D, Pietrapiana D, Lova P, Bertoni A, Graziani A, Defilippi P, Canobbio I, Torti M, Sinigaglia F: Nongenomic effects of 17beta-estradiol in human platelets: potentiation of thrombin-induced aggregation through estrogen receptor beta and Src kinase. Blood. 2005 Jan 1;105(1):115-21. Epub 2004 Jun 15. [PubMed:15198955 ]
Nakano Y, Oshima T, Ozono R, Ueda A, Oue Y, Matsuura H, Sanada M, Ohama K, Chayama K, Kambe M: Estrogen replacement suppresses function of thrombin stimulated platelets by inhibiting Ca(2+) influx and raising cyclic adenosine monophosphate. Cardiovasc Res. 2002 Feb 15;53(3):634-41. [PubMed:11861034 ]
(). FDA label.. .

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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

References

Wang B, Sanchez RI, Franklin RB, Evans DC, Huskey SE: The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol. Drug Metab Dispos. 2004 Nov;32(11):1209-12. Epub 2004 Aug 10. [PubMed:15304426 ]

Enzyme Details

2. Cytochrome P450 2C8

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

References

Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]

Enzyme Details

3. Nuclear receptor subfamily 1 group I member 2

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
Gene Name:: NR1I2
Uniprot ID:: O75469
Molecular weight:: 49761.2

References

Xue Y, Moore LB, Orans J, Peng L, Bencharit S, Kliewer SA, Redinbo MR: Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. Mol Endocrinol. 2007 May;21(5):1028-38. Epub 2007 Feb 27. [PubMed:17327420 ]

Enzyme Details

4. 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

Micevych PE, Chaban V, Ogi J, Dewing P, Lu JK, Sinchak K: Estradiol stimulates progesterone synthesis in hypothalamic astrocyte cultures. Endocrinology. 2007 Feb;148(2):782-9. Epub 2006 Nov 9. [PubMed:17095591 ]
Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. [PubMed:17124377 ]
Brama M, Gnessi L, Basciani S, Cerulli N, Politi L, Spera G, Mariani S, Cherubini S, Scotto d'Abusco A, Scandurra R, Migliaccio S: Cadmium induces mitogenic signaling in breast cancer cell by an ERalpha-dependent mechanism. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):102-8. Epub 2006 Nov 27. [PubMed:17125913 ]
Lehnes K, Winder AD, Alfonso C, Kasid N, Simoneaux M, Summe H, Morgan E, Iann MC, Duncan J, Eagan M, Tavaluc R, Evans CH Jr, Russell R, Wang A, Hu F, Stoica A: The effect of estradiol on in vivo tumorigenesis is modulated by the human epidermal growth factor receptor 2/phosphatidylinositol 3-kinase/Akt1 pathway. Endocrinology. 2007 Mar;148(3):1171-80. Epub 2006 Nov 30. [PubMed:17138652 ]
Mukai H, Tsurugizawa T, Ogiue-Ikeda M, Murakami G, Hojo Y, Ishii H, Kimoto T, Kawato S: Local neurosteroid production in the hippocampus: influence on synaptic plasticity of memory. Neuroendocrinology. 2006;84(4):255-63. Epub 2006 Dec 1. [PubMed:17142999 ]
Notch EG, Mayer GD: 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8. doi: 10.1016/j.aquatox.2009.01.001. Epub 2009 Jan 23. [PubMed:19237207 ]
Bennink HJ: Reprint of Are all estrogens the same? Maturitas. 2008 Sep-Oct;61(1-2):195-201. [PubMed:19434891 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Kauffmann HM, Schrenk D: Sequence analysis and functional characterization of the 5'-flanking region of the rat multidrug resistance protein 2 (mrp2) gene. Biochem Biophys Res Commun. 1998 Apr 17;245(2):325-31. [PubMed:9571149 ]
Trauner M, Arrese M, Soroka CJ, Ananthanarayanan M, Koeppel TA, Schlosser SF, Suchy FJ, Keppler D, Boyer JL: The rat canalicular conjugate export pump (Mrp2) is down-regulated in intrahepatic and obstructive cholestasis. Gastroenterology. 1997 Jul;113(1):255-64. [PubMed:9207286 ]

Enzyme Details

2. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Lee JM, Trauner M, Soroka CJ, Stieger B, Meier PJ, Boyer JL: Expression of the bile salt export pump is maintained after chronic cholestasis in the rat. Gastroenterology. 2000 Jan;118(1):163-72. [PubMed:10611165 ]
Huang L, Smit JW, Meijer DK, Vore M: Mrp2 is essential for estradiol-17beta(beta-D-glucuronide)-induced cholestasis in rats. Hepatology. 2000 Jul;32(1):66-72. [PubMed:10869290 ]

Enzyme Details

3. Multidrug resistance protein 1

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

References

Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871 ]

Enzyme Details

4. Sodium/bile acid cotransporter

General function:: Involved in bile acid:sodium symporter activity
Specific function:: The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:: SLC10A1
Uniprot ID:: Q14973
Molecular weight:: 38118.64

References

Lee JM, Trauner M, Soroka CJ, Stieger B, Meier PJ, Boyer JL: Expression of the bile salt export pump is maintained after chronic cholestasis in the rat. Gastroenterology. 2000 Jan;118(1):163-72. [PubMed:10611165 ]

Showing metabocard for 17a-Ethynylestradiol (HMDB0001926)

MOL for HMDB0001926 (17a-Ethynylestradiol)

3D MOL for HMDB0001926 (17a-Ethynylestradiol)

3D SDF for HMDB0001926 (17a-Ethynylestradiol)

3D-SDF for HMDB0001926 (17a-Ethynylestradiol)

PDB for HMDB0001926 (17a-Ethynylestradiol)

3D PDB for HMDB0001926 (17a-Ethynylestradiol)

SMILES for HMDB0001926 (17a-Ethynylestradiol)

INCHI for HMDB0001926 (17a-Ethynylestradiol)

Structure for HMDB0001926 (17a-Ethynylestradiol)

3D Structure for HMDB0001926 (17a-Ethynylestradiol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

Transporters

References

References

References

References