Desogestrel

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Desogestrel are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Desogestrel?

The molecule Desogestrel presents a molecular formula of C22H30O and its IUPAC name is (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol.

Desogestrel is a synthetic progestin medication which is used in a number of hormonal contraceptive preparations. It is also used in the treatment of menopausal symptoms and endometriosis. It has a molecular weight of 288.4 g/mol and a molecular formula of C22H28O..

3D structure

Cartesian coordinates

Geometry of Desogestrel in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Desogestrel RPLCPCMSCLEKRS-BPIQYHPVSA-N chemical compound 2D structure molecule svg
Desogestrel

 

Molecule descriptors

 
IUPAC name(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
InChI codeInChI=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
SMILESC#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CCCC[C@@H]4[C@H]3C(=C)C[C@@]21CC

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (17alpha)-13-Ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17-ol
  • (8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
  • 024D225
  • 13-Ethyl-11-methylene-18,19-dinor-17alpha-pregn-4-en-20-yn-17-ol
  • 13-ethyl-11-methylene-18,19-dinor-17a-pregn-4-en-20-yn-17-ol
  • 13-ethyl-11-methylene-18,19-dinorpregn-4-en-20-yn-17alpha-ol
  • 17alpha-ethynyl-11-methylidene-18a-homo-estr-4-en-17beta-ol
  • 17alpha-ethynyl-13beta-ethyl-11-methylene-4-gonen-17-ol
  • 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17.alpha.)-
  • 18,19-Dinorpregn-4-en-20-yn-17-ol, 13-ethyl-11-methylene-, (17alpha)-
  • 54024-22-5
  • 81K9V7M3A3
  • AC-308
  • AS-13022
  • B4976
  • BCP18794
  • BDBM50423510
  • BEKYREE COMPONENT DESOGESTREL
  • C07629
  • C15951
  • CCG-267585
  • CS-3686
  • CYCLESSA COMPONENT DESOGESTREL
  • Cerazette
  • D02367
  • D4163
  • DB00304
  • DESOGEN COMPONENT DESOGESTREL
  • DESOGESTREL
  • DESOGESTREL COMPONENT OF CYCLESSA
  • DESOGESTREL COMPONENT OF DESOGEN
  • DESOGESTREL COMPONENT OF KARIVA
  • DESOGESTREL COMPONENT OF MIRCETTE
  • DESOGESTREL COMPONENT OF ORTHO-CEPT
  • DESOGESTREL COMPONENT OF VELIVET
  • DSSTox_CID_2898
  • DSSTox_GSID_22898
  • DSSTox_RID_76779
  • Desogestrel
  • Desogestrel (USAN/INN)
  • Desogestrelum
  • ENSKYCE COMPONENT DESOGESTREL
  • GTPL7065
  • HSDB 3593
  • HY-12516
  • ISIBLOOM COMPONENT DESOGESTREL
  • J-520217
  • KARIVA COMPONENT DESOGESTREL
  • LMST02030104
  • MFCD00869346
  • MIRCETTE COMPONENT DESOGESTREL
  • Mircette
  • NCGC00167449-01
  • ORG 2969
  • ORTHO-CEPT COMPONENT DESOGESTREL
  • Org-2969
  • PIMTREA COMPONENT DESOGESTREL
  • Q415304
  • SR-01000883959
  • SR-01000883959-1
  • SR-01000883959-2
  • VELIVET COMPONENT DESOGESTREL
  • VIORELE COMPONENT DESOGESTREL
  • VOLNEA COMPONENT DESOGESTREL
  • desogen
  • s4638

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4097416
  • CAS-54024-22-5
  • UNII-81K9V7M3A3
  • AKOS015963198
  • DTXSID6022898
  • CHEMBL1533
  • CHEBI:4453
  • Tox21_112453
  • EINECS 258-929-4
  • SCHEMBL41341

Physico-Chemical properties

IUPAC name(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
Molecular formulaC22H30O
Molecular weight310.473
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity97.57
LogP4.9
Topological polar surface area20.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.