Desogestrel (CHEM016659)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:39:39 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016659
Identification
Common NameDesogestrel
ClassSmall Molecule
Description
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 olHMDB
13-Ethyl-11-methylene-18,19-dinor-17 alpha-pregn-4-en-20-yn-17-olHMDB
MarvelonHMDB
Organon brand OF desogestrelHMDB
alpha-Pregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-18,19-dinor-17HMDB
Chemical FormulaC22H30O
Average Molecular Mass310.473 g/mol
Monoisotopic Mass310.230 g/mol
CAS Registry Number54024-22-5
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
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 IdentifierInChI=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
Description 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 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1290000000-9475ca0bf2f8bacf92e6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0uxr-2259000000-f9baa1c23b9a2a4c85d3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0059000000-aa79c27f1567e9a1bbb8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-1191000000-6107987c3071dc2f2bceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-6490000000-517254a3119708155490Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-a4421231af9da549d34eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0049000000-5671ecc974cfc97a058dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-055f-0090000000-f5a84a6463500aef18beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-bd627e7955e8c8fb1ae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0009000000-bd627e7955e8c8fb1ae0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-0091000000-dde68f19d9643d308450Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0239000000-4888d713f81fa1d000c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0951000000-5d7499db9a7f85012ce3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003r-1930000000-2bccd3c0a6581ed2a815Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB00304
HMDB IDHMDB0014449
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDesogestrel
Chemspider ID37400
ChEBI ID4453
PubChem Compound ID40973
Kegg Compound IDC07629
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
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.
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.
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.
7. The lipid handbook with CD-ROM