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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2021-09-14 15:40:12 UTC

HMDB ID

HMDB0014439

Secondary Accession Numbers

HMDB14439

Metabolite Identification

Common Name

Etonogestrel

Description

Etonogestrel is only found in individuals that have used or taken this drug. It is a molecule used in hormonal contraceptives, most notably the subdermal implant Implanon. [Wikipedia ]Etonogestrel binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like etonogestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.

Structure

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

  Mrv0541 04191212112D          

 28 31  0  0  1  0            999 V2000
    1.8036   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    1.2211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4100    0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.9661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0189    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0189   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    1.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    2.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3044    2.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2325    2.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 19  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
  5  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 22  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 19 20  1  6  0  0  0
 22 21  2  0  0  0  0
  6 23  1  1  0  0  0
  3 24  1  6  0  0  0
  3 25  1  1  0  0  0
 18 26  1  0  0  0  0
 24 27  3  0  0  0  0
  7 28  2  0  0  0  0
M  END

HMDB0014439
     RDKit          3D
Etonogestrel
 52 55  0  0  0  0  0  0  0  0999 V2000
    2.4753   -1.8003    2.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -1.0407    1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1328   -0.0962    0.6603 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3125   -0.5062    0.1272 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928    1.2879    1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    1.9649    0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311    0.8016    0.5998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2708    0.9797   -0.0245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0584    2.1483    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    2.2639   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    0.9377   -0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2201    0.9214    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9599   -0.3441    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1937   -0.3088    0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992   -1.5517    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1110   -1.4431   -0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979   -0.2883   -0.6936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0406   -0.3425    0.2328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0877   -1.4341    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483   -2.6277    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -1.3445   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -0.0498   -0.2713 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2592    0.6026   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3493   -0.0768   -2.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -2.4666    3.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.4917    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.2169    2.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    1.8640    0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    2.7081    0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5118    2.5364    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    0.2048    1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748    1.0733   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    1.9019    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    3.0358    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.3578   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321    3.0789   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    1.8716    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924   -1.6198    1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7287   -2.4411    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264   -2.4117   -0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753   -1.2692   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806   -0.1502   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105   -0.2312    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2154   -3.4695    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -2.8378    1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1744   -1.5496   -1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -2.1457   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    1.6661   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    0.5792   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3684    0.2451   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2339   -1.1789   -2.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288    0.2701   -3.4360 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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  3
 19 21  1  0
 21 22  1  0
 22 23  1  6
 23 24  1  0
 22  3  1  0
 22  7  1  0
 18  8  1  0
 17 11  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
  8 32  1  6
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  1
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
M  END

  Mrv0541 04191212112D          

 28 31  0  0  1  0            999 V2000
    1.8036   -0.1138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    1.2211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    0.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4100    0.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390    0.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8390   -1.5089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -0.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3045   -0.2714    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3045    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4100    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4100   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.9661    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0189    1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0189    0.1411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0189   -0.6839    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2679   -1.5089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5534   -1.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    0.5536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5181    1.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    2.0461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3044    2.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2325    2.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1245    1.3786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 19 13  1  0  0  0  0
 19 17  1  0  0  0  0
 19  1  1  0  0  0  0
 13 15  1  0  0  0  0
 13  2  1  0  0  0  0
 17  3  1  0  0  0  0
 17  4  1  0  0  0  0
  5  1  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
  2  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 22  1  0  0  0  0
  3  5  1  0  0  0  0
  4  7  1  0  0  0  0
  8  9  1  0  0  0  0
 12 22  1  0  0  0  0
 13 14  1  1  0  0  0
 15 16  1  6  0  0  0
 17 18  1  1  0  0  0
 19 20  1  6  0  0  0
 22 21  2  0  0  0  0
  6 23  1  1  0  0  0
  3 24  1  6  0  0  0
  3 25  1  1  0  0  0
 18 26  1  0  0  0  0
 24 27  3  0  0  0  0
  7 28  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014439

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

> <INCHI_KEY>
GCKFUYQCUCGESZ-BPIQYHPVSA-N

> <FORMULA>
C22H28O2

> <MOLECULAR_WEIGHT>
324.4565

> <EXACT_MASS>
324.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
37.77179987549687

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

> <ALOGPS_LOGP>
3.19

> <JCHEM_LOGP>
3.6011698876666673

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.139903202038813

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.99350432223371

> <JCHEM_PKA_STRONGEST_BASIC>
-1.489207132003894

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
96.35159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
implanon

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014439
     RDKit          3D
Etonogestrel
 52 55  0  0  0  0  0  0  0  0999 V2000
    2.4753   -1.8003    2.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -1.0407    1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1328   -0.0962    0.6603 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3125   -0.5062    0.1272 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928    1.2879    1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    1.9649    0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311    0.8016    0.5998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2708    0.9797   -0.0245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0584    2.1483    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    2.2639   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    0.9377   -0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2201    0.9214    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9599   -0.3441    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1937   -0.3088    0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992   -1.5517    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1110   -1.4431   -0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979   -0.2883   -0.6936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0406   -0.3425    0.2328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0877   -1.4341    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483   -2.6277    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -1.3445   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -0.0498   -0.2713 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2592    0.6026   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3493   -0.0768   -2.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -2.4666    3.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.4917    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.2169    2.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    1.8640    0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    2.7081    0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5118    2.5364    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    0.2048    1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748    1.0733   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    1.9019    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    3.0358    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.3578   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321    3.0789   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    1.8716    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924   -1.6198    1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7287   -2.4411    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264   -2.4117   -0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753   -1.2692   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806   -0.1502   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105   -0.2312    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2154   -3.4695    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -2.8378    1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1744   -1.5496   -1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -2.1457   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    1.6661   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    0.5792   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3684    0.2451   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2339   -1.1789   -2.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288    0.2701   -3.4360 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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  3
 19 21  1  0
 21 22  1  0
 22 23  1  6
 23 24  1  0
 22  3  1  0
 22  7  1  0
 18  8  1  0
 17 11  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
  8 32  1  6
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  1
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
M  END

HEADER    PROTEIN                                 19-APR-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-12         0                                  
HETATM    1  C   UNK     0       3.367  -0.212   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.568  -2.047   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.367   2.279   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.568   2.573   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.272   1.033   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.099  -0.507   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.765   1.803   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.765  -2.817   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.099  -2.047   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.433   0.263   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.433  -2.817   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.766  -0.507   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.568  -0.507   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       0.568   1.033   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0      -0.765   0.263   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -0.765  -1.277   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       1.902   1.803   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.902   3.343   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.902   0.263   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       1.902  -1.277   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0      -6.100  -2.817   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.766  -2.047   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      -2.099   1.033   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0       4.700   3.049   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.367   3.819   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.568   4.113   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.034   3.819   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.099   2.573   0.000  0.00  0.00           C+0
CONECT    1   19    5                                                       
CONECT    2   13    8                                                       
CONECT    3   17    5   24   25                                             
CONECT    4   17    7                                                       
CONECT    5    1    3                                                       
CONECT    6   15    9   10   23                                             
CONECT    7   15    4   28                                                  
CONECT    8    2    9                                                       
CONECT    9    6   11    8                                                  
CONECT   10    6   12                                                       
CONECT   11    9   22                                                       
CONECT   12   10   22                                                       
CONECT   13   19   15    2   14                                             
CONECT   14   13                                                            
CONECT   15   13    6    7   16                                             
CONECT   16   15                                                            
CONECT   17   19    3    4   18                                             
CONECT   18   17   26                                                       
CONECT   19   13   17    1   20                                             
CONECT   20   19                                                            
CONECT   21   22                                                            
CONECT   22   11   12   21                                                  
CONECT   23    6                                                            
CONECT   24    3   27                                                       
CONECT   25    3                                                            
CONECT   26   18                                                            
CONECT   27   24                                                            
CONECT   28    7                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014439
HETATM    1  C1  UNL     1       2.475  -1.800   2.634  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.781  -1.041   1.748  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.133  -0.096   0.660  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.313  -0.506   0.127  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.193   1.288   1.299  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.872   1.965   0.932  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.031   0.802   0.600  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.271   0.980  -0.025  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.058   2.148   0.484  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.278   2.264  -0.454  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.984   0.938  -0.312  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.220   0.921   0.134  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.960  -0.344   0.295  1.00  0.00           C  
HETATM   14  O2  UNL     1      -6.194  -0.309   0.333  1.00  0.00           O  
HETATM   15  C13 UNL     1      -4.099  -1.552   0.395  1.00  0.00           C  
HETATM   16  C14 UNL     1      -3.111  -1.443  -0.749  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.198  -0.288  -0.694  1.00  0.00           C  
HETATM   18  C16 UNL     1      -1.041  -0.342   0.233  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.088  -1.434   0.088  1.00  0.00           C  
HETATM   20  C18 UNL     1      -0.448  -2.628   0.534  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.268  -1.345  -0.501  1.00  0.00           C  
HETATM   22  C20 UNL     1       1.970  -0.050  -0.271  1.00  0.00           C  
HETATM   23  C21 UNL     1       2.259   0.603  -1.590  1.00  0.00           C  
HETATM   24  C22 UNL     1       3.349  -0.077  -2.379  1.00  0.00           C  
HETATM   25  H1  UNL     1       2.189  -2.467   3.408  1.00  0.00           H  
HETATM   26  H2  UNL     1       4.304  -1.492   0.052  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.242   1.217   2.404  1.00  0.00           H  
HETATM   28  H4  UNL     1       4.059   1.864   0.967  1.00  0.00           H  
HETATM   29  H5  UNL     1       2.031   2.708   0.146  1.00  0.00           H  
HETATM   30  H6  UNL     1       1.512   2.536   1.834  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.904   0.205   1.542  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.275   1.073  -1.133  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.447   1.902   1.492  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.429   3.036   0.443  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.891   2.358  -1.488  1.00  0.00           H  
HETATM   36  H12 UNL     1      -2.932   3.079  -0.153  1.00  0.00           H  
HETATM   37  H13 UNL     1      -4.697   1.872   0.386  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.592  -1.620   1.378  1.00  0.00           H  
HETATM   39  H15 UNL     1      -4.729  -2.441   0.185  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.626  -2.412  -0.987  1.00  0.00           H  
HETATM   41  H17 UNL     1      -3.775  -1.269  -1.658  1.00  0.00           H  
HETATM   42  H18 UNL     1      -1.781  -0.150  -1.727  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.410  -0.231   1.294  1.00  0.00           H  
HETATM   44  H20 UNL     1       0.215  -3.470   0.453  1.00  0.00           H  
HETATM   45  H21 UNL     1      -1.412  -2.838   1.007  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.174  -1.550  -1.587  1.00  0.00           H  
HETATM   47  H23 UNL     1       1.923  -2.146  -0.100  1.00  0.00           H  
HETATM   48  H24 UNL     1       2.561   1.666  -1.504  1.00  0.00           H  
HETATM   49  H25 UNL     1       1.355   0.579  -2.232  1.00  0.00           H  
HETATM   50  H26 UNL     1       4.368   0.245  -2.083  1.00  0.00           H  
HETATM   51  H27 UNL     1       3.234  -1.179  -2.424  1.00  0.00           H  
HETATM   52  H28 UNL     1       3.229   0.270  -3.436  1.00  0.00           H  
CONECT    1    2    2    2   25
CONECT    2    3
CONECT    3    4    5   22
CONECT    4   26
CONECT    5    6   27   28
CONECT    6    7   29   30
CONECT    7    8   22   31
CONECT    8    9   18   32
CONECT    9   10   33   34
CONECT   10   11   35   36
CONECT   11   12   12   17
CONECT   12   13   37
CONECT   13   14   14   15
CONECT   15   16   38   39
CONECT   16   17   40   41
CONECT   17   18   42
CONECT   18   19   43
CONECT   19   20   20   21
CONECT   20   44   45
CONECT   21   22   46   47
CONECT   22   23
CONECT   23   24   48   49
CONECT   24   50   51   52
END

HMDB0014439
     RDKit          3D
Etonogestrel
 52 55  0  0  0  0  0  0  0  0999 V2000
    2.4753   -1.8003    2.6336 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7808   -1.0407    1.7479 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1328   -0.0962    0.6603 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3125   -0.5062    0.1272 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1928    1.2879    1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8721    1.9649    0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311    0.8016    0.5998 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2708    0.9797   -0.0245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0584    2.1483    0.4839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775    2.2639   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9835    0.9377   -0.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2201    0.9214    0.1337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9599   -0.3441    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1937   -0.3088    0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0992   -1.5517    0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1110   -1.4431   -0.7489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1979   -0.2883   -0.6936 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0406   -0.3425    0.2328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0877   -1.4341    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4483   -2.6277    0.5345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676   -1.3445   -0.5015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9699   -0.0498   -0.2713 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2592    0.6026   -1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3493   -0.0768   -2.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1887   -2.4666    3.4080 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -1.4917    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2415    1.2169    2.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0594    1.8640    0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0313    2.7081    0.1461 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5118    2.5364    1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9045    0.2048    1.5422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2748    1.0733   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4470    1.9019    1.4922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4292    3.0358    0.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905    2.3578   -1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321    3.0789   -0.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6967    1.8716    0.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5924   -1.6198    1.3775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7287   -2.4411    0.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264   -2.4117   -0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7753   -1.2692   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7806   -0.1502   -1.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4105   -0.2312    1.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2154   -3.4695    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4122   -2.8378    1.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1744   -1.5496   -1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232   -2.1457   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5614    1.6661   -1.5043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3546    0.5792   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3684    0.2451   -2.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2339   -1.1789   -2.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288    0.2701   -3.4360 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  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  3
 19 21  1  0
 21 22  1  0
 22 23  1  6
 23 24  1  0
 22  3  1  0
 22  7  1  0
 18  8  1  0
 17 11  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  1
  8 32  1  6
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  1
 20 44  1  0
 20 45  1  0
 21 46  1  0
 21 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 24 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Ketodesogestrel	ChEBI
3-Oxodesogestrel	ChEBI
Etonogestrelum	ChEBI
Implanon	ChEBI
3-Keto-desogestrel	HMDB
3-oxo Desogestrel	HMDB
Nourypharma brand OF 3-keto-desogestrel	HMDB
Organon brand OF 3-keto-desogestrel	HMDB
Nexplanon	HMDB
13-Ethyl-17-hydroxy-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one	HMDB

Chemical Formula

C₂₂H₂₈O₂

Average Molecular Weight

324.4565

Monoisotopic Molecular Weight

324.20893014

IUPAC Name

(1S,2R,10S,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxy-17-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one

Traditional Name

implanon

CAS Registry Number

54048-10-1

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

InChI Key

GCKFUYQCUCGESZ-BPIQYHPVSA-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-oxo-delta-4-steroid
3-oxosteroid
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
Delta-4-steroid
Cyclohexenone
Ynone
Cyclic alcohol
Tertiary alcohol
Cyclic ketone
Ketone
Acetylide
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:50777 )
3-oxo steroid (CHEBI:50777 )
3-oxo Delta(4)-steroid (CHEBI:50777 )
17beta-hydroxy steroid (CHEBI:50777 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Organ

Liver (HMDB: HMDB0014439)
Kidney (HMDB: HMDB0014439)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014439)

Endogenous

Endogenous (HMDB: HMDB0014439)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0074 g/L	Not Available
LogP	3.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0074 g/L	ALOGPS
logP	3.19	ALOGPS
logP	3.6	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	17.99	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.35 m³·mol⁻¹	ChemAxon
Polarizability	37.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.052	31661259
DarkChem	[M-H]-	178.737	31661259
DeepCCS	[M-2H]-	212.077	30932474
DeepCCS	[M+Na]+	186.833	30932474
AllCCS	[M+H]+	182.8	32859911
AllCCS	[M+H-H2O]+	179.9	32859911
AllCCS	[M+NH4]+	185.5	32859911
AllCCS	[M+Na]+	186.3	32859911
AllCCS	[M-H]-	187.8	32859911
AllCCS	[M+Na-2H]-	188.0	32859911
AllCCS	[M+HCOO]-	188.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Etonogestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	3928.6	Standard polar	33892256
Etonogestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2803.0	Standard non polar	33892256
Etonogestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]	2804.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Etonogestrel,1TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3C(=C)C[C@@]21CC	2870.7	Semi standard non polar	33892256
Etonogestrel,1TMS,isomer #2	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(O[Si](C)(C)C)=CC[C@@H]4[C@H]3C(=C)C[C@@]21CC	2785.8	Semi standard non polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	2860.8	Semi standard non polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	2834.8	Standard non polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	3243.6	Standard polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	3122.8	Semi standard non polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	3043.2	Semi standard non polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	3355.5	Semi standard non polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	3264.6	Standard non polar	33892256
Etonogestrel,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[C@@H]4[C@H]3C(=C)C[C@@]21CC	3412.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Etonogestrel GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0490000000-f19630a72a1129f10bf7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etonogestrel GC-MS (1 TMS) - 70eV, Positive	splash10-0159-1229000000-b23d32067ab6b2d731e5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Etonogestrel 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 - Etonogestrel 10V, Positive-QTOF	splash10-004i-0029000000-79342e3a25ab8393fcf3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 20V, Positive-QTOF	splash10-0a6r-0293000000-7fba9509e41963586a90	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 40V, Positive-QTOF	splash10-0kto-4490000000-f371adb91716a8b2a97c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 10V, Negative-QTOF	splash10-00di-0009000000-c3db9c113e21a37a1583	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 20V, Negative-QTOF	splash10-00di-0039000000-ec939c554edfb95cfa48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 40V, Negative-QTOF	splash10-05mp-0091000000-4d1d86fd76db62f4f394	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 10V, Positive-QTOF	splash10-0a4i-0019000000-1228eaafd8c11f200430	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 20V, Positive-QTOF	splash10-002b-0911000000-325050413fe1b814de62	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 40V, Positive-QTOF	splash10-0002-0910000000-a6075096a7ada684910b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 10V, Negative-QTOF	splash10-00di-0009000000-60a003deddef6c16e354	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 20V, Negative-QTOF	splash10-00di-0009000000-ef1eddb9bebeae35c843	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Etonogestrel 40V, Negative-QTOF	splash10-00vj-0093000000-272f3ab06ca7eae7c3ac	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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	Taking drug identified by DrugBank entry DB00294	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00294	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00294

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5292944

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etonogestrel

METLIN ID

Not Available

PubChem Compound

6917715

PDB ID

Not Available

ChEBI ID

50777

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.

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

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Progesterone receptor

General function:: Involved in sequence-specific DNA binding transcription factor activity
Specific function:: Isoform A is inactive in stimulating c-Src/MAPK signaling on hormone stimulation
Gene Name:: PGR
Uniprot ID:: P06401
Molecular weight:: 98980.0

References

Macpherson AM, Archer DF, Leslie S, Charnock-Jones DS, Makkink WK, Smith SK: The effect of etonogestrel on VEGF, oestrogen and progesterone receptor immunoreactivity and endothelial cell number in human endometrium. Hum Reprod. 1999 Dec;14(12):3080-7. [PubMed:10601100 ]
Charnock-Jones DS, Macpherson AM, Archer DF, Leslie S, Makkink WK, Sharkey AM, Smith SK: The effect of progestins on vascular endothelial growth factor, oestrogen receptor and progesterone receptor immunoreactivity and endothelial cell density in human endometrium. Hum Reprod. 2000 Aug;15 Suppl 3:85-95. [PubMed:11041225 ]
Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [PubMed:15063480 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

3. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Showing metabocard for Etonogestrel (HMDB0014439)

MOL for HMDB0014439 (Etonogestrel)

3D MOL for HMDB0014439 (Etonogestrel)

3D SDF for HMDB0014439 (Etonogestrel)

3D-SDF for HMDB0014439 (Etonogestrel)

PDB for HMDB0014439 (Etonogestrel)

3D PDB for HMDB0014439 (Etonogestrel)

SMILES for HMDB0014439 (Etonogestrel)

INCHI for HMDB0014439 (Etonogestrel)

Structure for HMDB0014439 (Etonogestrel)

3D Structure for HMDB0014439 (Etonogestrel)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References