Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014449

Secondary Accession Numbers

HMDB14449

Metabolite Identification

Common Name

Desogestrel

Description

Desogestrel is only found in individuals that have used or taken this drug. It is a synthetic progestational hormone used often as the progestogenic component of combined oral contraceptive agents. [PubChem]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 desogestrel 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

304
  Mrv0541 02231214352D          

 27 30  0  0  1  0            999 V2000
    5.9104    1.5551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    0.5186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3833   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689   -0.7189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9544   -0.3064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1640    0.7700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1640   -0.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6689    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6455    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6821   -1.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9544    0.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -1.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6689    1.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323    1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5006    1.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -0.9628    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -1.0446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    0.0236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163   -0.0647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2  8  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3 24  1  6  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 25  1  1  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  5 26  1  6  0  0  0
  6  9  1  0  0  0  0
  6 18  1  0  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 10 27  1  1  0  0  0
 11 14  1  0  0  0  0
 12 21  2  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 20  2  0  0  0  0
 16 19  1  0  0  0  0
 18 23  3  0  0  0  0
 19 22  1  0  0  0  0
 20 22  1  0  0  0  0
M  END

HMDB0014449
     RDKit          3D
Desogestrel
 53 56  0  0  0  0  0  0  0  0999 V2000
    3.5903    0.9686    2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    0.4558    1.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.1738    0.2802 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3132   -1.2290    0.2220 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    0.8790   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3313    1.3418   -1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848    0.7254   -0.3411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0539    0.6616   -0.7487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5100    2.0952   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871    2.2516   -1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    1.0348   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9621    0.8731   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6013   -0.4235   -0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869   -0.6630    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -0.1577    1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -0.0606    0.0925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8112    0.1517    0.4932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1411   -1.0668    1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7077   -2.2505    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024   -0.8975    1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9985   -0.5692    0.0745 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7684   -1.7341   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504   -1.6721   -2.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579    1.4138    3.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773   -1.1478    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    1.7607   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3774    0.5796   -1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2611    2.4645   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878    1.1497   -2.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932    1.3731    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809    0.0397   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    2.6445    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    2.6252   -1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523    2.5818   -2.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3761    3.1403   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4269    1.6197   -1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212   -1.2144   -1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6742   -0.3768   -1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5761   -1.7718    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3803   -0.1837    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    0.8885    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.7823    2.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -1.0000   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    0.9171    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -2.4567    0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029   -3.0801    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837   -0.0509    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -1.8332    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2315   -2.6231   -0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763   -1.9469   -0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.4333   -2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837   -2.7353   -2.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.1027   -2.8889 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
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 18 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 17  8  1  0
 16 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  6
 17 44  1  1
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  END

304
  Mrv0541 02231214352D          

 27 30  0  0  1  0            999 V2000
    5.9104    1.5551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    0.5186    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3833   -0.3064    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6689   -0.7189    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9544   -0.3064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1640    0.7700    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1640   -0.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6689    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6455    0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2036   -0.7246    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6821   -1.5783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9544    0.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3833    1.3436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9412   -2.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1970   -1.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389   -0.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6689    1.7561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8323    1.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6570   -0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    0.9311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5006    1.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4532   -0.9628    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2430   -1.0446    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5260    0.0236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2163   -0.0647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  2  8  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  3 24  1  6  0  0  0
  4  5  1  0  0  0  0
  4 11  1  0  0  0  0
  4 25  1  1  0  0  0
  5 10  1  0  0  0  0
  5 12  1  0  0  0  0
  5 26  1  6  0  0  0
  6  9  1  0  0  0  0
  6 18  1  0  0  0  0
  7  9  1  0  0  0  0
  8 12  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 10 27  1  1  0  0  0
 11 14  1  0  0  0  0
 12 21  2  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 20  2  0  0  0  0
 16 19  1  0  0  0  0
 18 23  3  0  0  0  0
 19 22  1  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014449

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

> <INCHI_KEY>
RPLCPCMSCLEKRS-BPIQYHPVSA-N

> <FORMULA>
C22H30O

> <MOLECULAR_WEIGHT>
310.473

> <EXACT_MASS>
310.229665582

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
37.541347454533124

> <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-17-methylidenetetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-ol

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
4.420642466666667

> <ALOGPS_LOGS>
-5.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.993504322234944

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4894412094544354

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
95.73349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mircette

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014449
     RDKit          3D
Desogestrel
 53 56  0  0  0  0  0  0  0  0999 V2000
    3.5903    0.9686    2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    0.4558    1.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.1738    0.2802 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3132   -1.2290    0.2220 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    0.8790   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3313    1.3418   -1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848    0.7254   -0.3411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0539    0.6616   -0.7487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5100    2.0952   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871    2.2516   -1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    1.0348   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9621    0.8731   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6013   -0.4235   -0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869   -0.6630    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -0.1577    1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -0.0606    0.0925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8112    0.1517    0.4932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1411   -1.0668    1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7077   -2.2505    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024   -0.8975    1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9985   -0.5692    0.0745 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7684   -1.7341   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504   -1.6721   -2.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579    1.4138    3.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773   -1.1478    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    1.7607   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3774    0.5796   -1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2611    2.4645   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878    1.1497   -2.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932    1.3731    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809    0.0397   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    2.6445    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    2.6252   -1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523    2.5818   -2.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3761    3.1403   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4269    1.6197   -1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212   -1.2144   -1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6742   -0.3768   -1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5761   -1.7718    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3803   -0.1837    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    0.8885    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.7823    2.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -1.0000   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    0.9171    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -2.4567    0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029   -3.0801    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837   -0.0509    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -1.8332    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2315   -2.6231   -0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763   -1.9469   -0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.4333   -2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837   -2.7353   -2.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.1027   -2.8889 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
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 18 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 17  8  1  0
 16 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  6
 17 44  1  1
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 304                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.033   2.903   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      10.049   0.968   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.049  -0.572   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.715  -1.342   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.382  -0.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.506   1.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.506  -1.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.715   1.738   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.405   0.198   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.980  -1.353   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.740  -2.946   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.382   0.968   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.049   2.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.357  -3.759   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.968  -2.957   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.553  -0.484   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.715   3.278   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.754   2.340   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.093  -1.297   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.527  -3.803   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.048   1.738   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080  -2.968   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.001   3.244   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      10.179  -1.797   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       9.787  -1.950   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       8.449   0.044   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.004  -0.121   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    3    6    8   13                                             
CONECT    3    2    4    7   24                                             
CONECT    4    3    5   11   25                                             
CONECT    5    4   10   12   26                                             
CONECT    6    1    2    9   18                                             
CONECT    7    3    9                                                       
CONECT    8    2   12                                                       
CONECT    9    6    7                                                       
CONECT   10    5   15   16   27                                             
CONECT   11    4   14                                                       
CONECT   12    5    8   21                                                  
CONECT   13    2   17                                                       
CONECT   14   11   15                                                       
CONECT   15   10   14   20                                                  
CONECT   16   10   19                                                       
CONECT   17   13                                                            
CONECT   18    6   23                                                       
CONECT   19   16   22                                                       
CONECT   20   15   22                                                       
CONECT   21   12                                                            
CONECT   22   19   20                                                       
CONECT   23   18                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    5                                                            
CONECT   27   10                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

COMPND    HMDB0014449
HETATM    1  C1  UNL     1       3.590   0.969   2.701  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.516   0.456   1.603  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.424  -0.174   0.280  1.00  0.00           C  
HETATM    4  O1  UNL     1       4.313  -1.229   0.222  1.00  0.00           O  
HETATM    5  C4  UNL     1       3.685   0.879  -0.764  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.331   1.342  -1.290  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.385   0.725  -0.341  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.054   0.662  -0.749  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.510   2.095  -0.901  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.987   2.252  -1.061  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.714   1.035  -0.742  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.962   0.873  -1.230  1.00  0.00           C  
HETATM   13  C12 UNL     1      -4.601  -0.424  -0.827  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.487  -0.663   0.661  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.195  -0.158   1.256  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.214  -0.061   0.093  1.00  0.00           C  
HETATM   17  C16 UNL     1      -0.811   0.152   0.493  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.141  -1.067   1.024  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.708  -2.250   1.156  1.00  0.00           C  
HETATM   20  C19 UNL     1       1.302  -0.898   1.415  1.00  0.00           C  
HETATM   21  C20 UNL     1       1.999  -0.569   0.074  1.00  0.00           C  
HETATM   22  C21 UNL     1       1.768  -1.734  -0.791  1.00  0.00           C  
HETATM   23  C22 UNL     1       2.250  -1.672  -2.202  1.00  0.00           C  
HETATM   24  H1  UNL     1       3.658   1.414   3.664  1.00  0.00           H  
HETATM   25  H2  UNL     1       4.977  -1.148   0.955  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.194   1.761  -0.270  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.377   0.580  -1.558  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.261   2.465  -1.177  1.00  0.00           H  
HETATM   29  H6  UNL     1       2.188   1.150  -2.351  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.393   1.373   0.590  1.00  0.00           H  
HETATM   31  H8  UNL     1      -0.281   0.040  -1.612  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.235   2.644   0.048  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.066   2.625  -1.693  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.152   2.582  -2.127  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.376   3.140  -0.476  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.427   1.620  -1.845  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.121  -1.214  -1.437  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.674  -0.377  -1.148  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.576  -1.772   0.816  1.00  0.00           H  
HETATM   40  H17 UNL     1      -5.380  -0.184   1.131  1.00  0.00           H  
HETATM   41  H18 UNL     1      -3.404   0.889   1.600  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.876  -0.782   2.076  1.00  0.00           H  
HETATM   43  H20 UNL     1      -2.315  -1.000  -0.525  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.770   0.917   1.290  1.00  0.00           H  
HETATM   45  H22 UNL     1      -1.735  -2.457   0.886  1.00  0.00           H  
HETATM   46  H23 UNL     1      -0.103  -3.080   1.565  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.384  -0.051   2.111  1.00  0.00           H  
HETATM   48  H25 UNL     1       1.728  -1.833   1.824  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.232  -2.623  -0.314  1.00  0.00           H  
HETATM   50  H27 UNL     1       0.676  -1.947  -0.823  1.00  0.00           H  
HETATM   51  H28 UNL     1       3.329  -1.433  -2.294  1.00  0.00           H  
HETATM   52  H29 UNL     1       2.184  -2.735  -2.592  1.00  0.00           H  
HETATM   53  H30 UNL     1       1.599  -1.103  -2.889  1.00  0.00           H  
CONECT    1    2    2    2   24
CONECT    2    3
CONECT    3    4    5   21
CONECT    4   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8   21   30
CONECT    8    9   17   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   12   16
CONECT   12   13   36
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   17   43
CONECT   17   18   44
CONECT   18   19   19   20
CONECT   19   45   46
CONECT   20   21   47   48
CONECT   21   22
CONECT   22   23   49   50
CONECT   23   51   52   53
END

HMDB0014449
     RDKit          3D
Desogestrel
 53 56  0  0  0  0  0  0  0  0999 V2000
    3.5903    0.9686    2.7008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5159    0.4558    1.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4244   -0.1738    0.2802 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3132   -1.2290    0.2220 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6853    0.8790   -0.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3313    1.3418   -1.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3848    0.7254   -0.3411 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0539    0.6616   -0.7487 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5100    2.0952   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871    2.2516   -1.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7141    1.0348   -0.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9621    0.8731   -1.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6013   -0.4235   -0.8267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4869   -0.6630    0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1948   -0.1577    1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136   -0.0606    0.0925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8112    0.1517    0.4932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1411   -1.0668    1.0235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7077   -2.2505    1.1560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024   -0.8975    1.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9985   -0.5692    0.0745 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7684   -1.7341   -0.7910 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2504   -1.6721   -2.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6579    1.4138    3.6643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9773   -1.1478    0.9554 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1940    1.7607   -0.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3774    0.5796   -1.5576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2611    2.4645   -1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1878    1.1497   -2.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3932    1.3731    0.5903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2809    0.0397   -1.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350    2.6445    0.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0657    2.6252   -1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523    2.5818   -2.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3761    3.1403   -0.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4269    1.6197   -1.8451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1212   -1.2144   -1.4371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6742   -0.3768   -1.1476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5761   -1.7718    0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3803   -0.1837    1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    0.8885    1.5996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8763   -0.7823    2.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3155   -1.0000   -0.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    0.9171    1.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -2.4567    0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1029   -3.0801    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3837   -0.0509    2.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7280   -1.8332    1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2315   -2.6231   -0.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6763   -1.9469   -0.8233 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290   -1.4333   -2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1837   -2.7353   -2.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5990   -1.1027   -2.8889 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
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  3
 18 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21  3  1  0
 21  7  1  0
 17  8  1  0
 16 11  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
  7 30  1  1
  8 31  1  6
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  6
 17 44  1  1
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
 23 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol	ChEBI
Cerazette	ChEBI
Desogestrelum	ChEBI
13-Ethyl-11-methylene-18,19-dinor-17a-pregn-4-en-20-yn-17-ol	Generator
13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-ol	Generator
13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 ol	HMDB
13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-ol	HMDB
Marvelon	HMDB
Organon brand OF desogestrel	HMDB
alpha-Pregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-18,19-dinor-17	HMDB

Chemical Formula

C₂₂H₃₀O

Average Molecular Weight

310.473

Monoisotopic Molecular Weight

310.229665582

IUPAC Name

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

Traditional Name

mircette

CAS Registry Number

54024-22-5

SMILES

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

InChI Identifier

InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1

InChI Key

RPLCPCMSCLEKRS-BPIQYHPVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrane steroids

Alternative Parents

Substituents

17-hydroxysteroid
Hydroxysteroid
Estrane-skeleton
Delta-4-steroid
Ynone
Tertiary alcohol
Cyclic alcohol
Acetylide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:4453 )
17beta-hydroxy steroid (CHEBI:4453 )
C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C07629 )
C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030104 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014449)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	109.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.003 g/L	Not Available
LogP	4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	4.3	ALOGPS
logP	4.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	17.99	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.73 m³·mol⁻¹	ChemAxon
Polarizability	37.54 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]+	175.048	31661259
DarkChem	[M-H]-	169.48	31661259
DeepCCS	[M-2H]-	212.681	30932474
DeepCCS	[M+Na]+	187.653	30932474
AllCCS	[M+H]+	180.6	32859911
AllCCS	[M+H-H2O]+	177.5	32859911
AllCCS	[M+NH4]+	183.4	32859911
AllCCS	[M+Na]+	184.2	32859911
AllCCS	[M-H]-	186.7	32859911
AllCCS	[M+Na-2H]-	186.8	32859911
AllCCS	[M+HCOO]-	187.1	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.	8.57 minutes	32390414
Predicted by Siyang on May 30, 2022	20.1184 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2846.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	584.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	241.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	269.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	485.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	926.7 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	913.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1745.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	518.8 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	1637.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	633.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	476.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	392.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	660.6 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Desogestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]	3262.0	Standard polar	33892256
Desogestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]	2568.7	Standard non polar	33892256
Desogestrel	[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H]	2418.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Desogestrel,1TMS,isomer #1	C#C[C@]1(O[Si](C)(C)C)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3C(=C)C[C@@]21CC	2551.8	Semi standard non polar	33892256
Desogestrel,1TBDMS,isomer #1	C#C[C@]1(O[Si](C)(C)C(C)(C)C)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3C(=C)C[C@@]21CC	2824.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Desogestrel GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1290000000-9475ca0bf2f8bacf92e6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desogestrel GC-MS (1 TMS) - 70eV, Positive	splash10-0uxr-2259000000-f9baa1c23b9a2a4c85d3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Desogestrel 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 - Desogestrel 10V, Positive-QTOF	splash10-03di-0059000000-aa79c27f1567e9a1bbb8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 20V, Positive-QTOF	splash10-01q9-1191000000-6107987c3071dc2f2bce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 40V, Positive-QTOF	splash10-0f6x-6490000000-517254a3119708155490	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 10V, Negative-QTOF	splash10-0a4i-0009000000-a4421231af9da549d34e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 20V, Negative-QTOF	splash10-0a4i-0049000000-5671ecc974cfc97a058d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 40V, Negative-QTOF	splash10-055f-0090000000-f5a84a6463500aef18be	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 10V, Negative-QTOF	splash10-0a4i-0009000000-bd627e7955e8c8fb1ae0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 20V, Negative-QTOF	splash10-0a4i-0009000000-bd627e7955e8c8fb1ae0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 40V, Negative-QTOF	splash10-0bt9-0091000000-dde68f19d9643d308450	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 10V, Positive-QTOF	splash10-03di-0239000000-4888d713f81fa1d000c4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 20V, Positive-QTOF	splash10-0159-0951000000-5d7499db9a7f85012ce3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Desogestrel 40V, Positive-QTOF	splash10-003r-1930000000-2bccd3c0a6581ed2a815	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00304	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00304	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00304

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

37400

KEGG Compound ID

C07629

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Desogestrel

METLIN ID

Not Available

PubChem Compound

40973

PDB ID

Not Available

ChEBI ID

4453

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

Gentile DM, Verhoeven CH, Shimada T, Back DJ: The role of CYP2C in the in vitro bioactivation of the contraceptive steroid desogestrel. J Pharmacol Exp Ther. 1998 Dec;287(3):975-82. [PubMed:9864282 ]
Korhonen T, Tolonen A, Uusitalo J, Lundgren S, Jalonen J, Laine K: The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. Br J Clin Pharmacol. 2005 Jul;60(1):69-75. [PubMed:15963096 ]
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. 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

Bergink EW, van Meel F, Turpijn EW, van der Vies J: Binding of progestagens to receptor proteins in MCF-7 cells. J Steroid Biochem. 1983 Nov;19(5):1563-70. [PubMed:6645495 ]
Fuhrmann U, Slater EP, Fritzemeier KH: Characterization of the novel progestin gestodene by receptor binding studies and transactivation assays. Contraception. 1995 Jan;51(1):45-52. [PubMed:7750284 ]
Kloosterboer HJ, Vonk-Noordegraaf CA, Turpijn EW: Selectivity in progesterone and androgen receptor binding of progestagens used in oral contraceptives. Contraception. 1988 Sep;38(3):325-32. [PubMed:3139361 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. 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

Fuhrmann U, Slater EP, Fritzemeier KH: Characterization of the novel progestin gestodene by receptor binding studies and transactivation assays. Contraception. 1995 Jan;51(1):45-52. [PubMed:7750284 ]
Rabe T, Bohlmann MK, Rehberger-Schneider S, Prifti S: Induction of estrogen receptor-alpha and -beta activities by synthetic progestins. Gynecol Endocrinol. 2000 Apr;14(2):118-26. [PubMed:10836199 ]
Juchem M, Pollow K: Binding of oral contraceptive progestogens to serum proteins and cytoplasmic receptor. Am J Obstet Gynecol. 1990 Dec;163(6 Pt 2):2171-83. [PubMed:2175153 ]

Showing metabocard for Desogestrel (HMDB0014449)

MOL for HMDB0014449 (Desogestrel)

3D MOL for HMDB0014449 (Desogestrel)

3D SDF for HMDB0014449 (Desogestrel)

3D-SDF for HMDB0014449 (Desogestrel)

PDB for HMDB0014449 (Desogestrel)

3D PDB for HMDB0014449 (Desogestrel)

SMILES for HMDB0014449 (Desogestrel)

INCHI for HMDB0014449 (Desogestrel)

Structure for HMDB0014449 (Desogestrel)

3D Structure for HMDB0014449 (Desogestrel)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References