Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:49 UTC |
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Update Date | 2022-03-07 02:51:37 UTC |
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HMDB ID | HMDB0014449 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Desogestrel |
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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. |
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Structure | [H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H] 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 |
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Synonyms | Value | Source |
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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 |
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Chemical Formula | C22H30O |
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Average Molecular Weight | 310.473 |
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Monoisotopic Molecular Weight | 310.229665582 |
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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 |
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Traditional Name | mircette |
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CAS Registry Number | 54024-22-5 |
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SMILES | [H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC(=C)[C@]1([H])[C@@]3([H])CCCC=C3CC[C@@]21[H] |
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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 |
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InChI Key | RPLCPCMSCLEKRS-BPIQYHPVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Estrane steroids |
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Direct Parent | Estrane steroids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic homopolycyclic compounds |
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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 )
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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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 |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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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 |
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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.
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