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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2019-07-23 05:59:52 UTC
HMDB IDHMDB0014449
Secondary Accession Numbers
  • HMDB14449
Metabolite Identification
Common NameDesogestrel
DescriptionDesogestrel 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
Data?1563861592
Synonyms
ValueSource
13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-olChEBI
CerazetteChEBI
DesogestrelumChEBI
13-Ethyl-11-methylene-18,19-dinor-17a-pregn-4-en-20-yn-17-olGenerator
13-Ethyl-11-methylene-18,19-dinor-17α-pregn-4-en-20-yn-17-olGenerator
13 Ethyl 11 methylene 18,19 dinor 17 alpha pregn 4 en 20 yn 17 olMeSH
13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-olMeSH
MarvelonMeSH
Organon brand OF desogestrelMeSH
alpha-Pregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-18,19-dinor-17MeSH
Chemical FormulaC22H30O
Average Molecular Weight310.473
Monoisotopic Molecular Weight310.229665582
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 Namemircette
CAS Registry Number54024-22-5
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 KeyRPLCPCMSCLEKRS-BPIQYHPVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrane steroids. These are steroids with a structure based on the estrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrane 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 FrameworkAliphatic 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
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point109.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.003 g/LNot Available
LogP4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.003 g/LALOGPS
logP4.3ALOGPS
logP4.42ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)17.99ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity95.73 m³·mol⁻¹ChemAxon
Polarizability37.54 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1290000000-9475ca0bf2f8bacf92e6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uxr-2259000000-f9baa1c23b9a2a4c85d3JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0059000000-aa79c27f1567e9a1bbb8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1191000000-6107987c3071dc2f2bceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-6490000000-517254a3119708155490JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-a4421231af9da549d34eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0049000000-5671ecc974cfc97a058dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-055f-0090000000-f5a84a6463500aef18beJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00304 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00304 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00304
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID37400
KEGG Compound IDC07629
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDesogestrel
METLIN IDNot Available
PubChem Compound40973
PDB IDNot Available
ChEBI ID4453
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

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
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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
  1. 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 ]
  2. 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 ]
  3. 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 ]