Gestodene

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

What is the Gestodene?

The molecule Gestodene presents a molecular formula of C21H26O2 and its IUPAC name is (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one.

Gestodene is a progestin, or a synthetic progestogen, which is used in hormonal birth control pills. It is a derivative of norethisterone. It was first introduced in Europe in the late 1970s..

Gestodene is a progestin that is used in hormonal birth control pills. It is a derivative of norethisterone. It was first introduced in Europe in the late 1970s..

Gestodene is a synthetic progestogen, which is used in hormonal birth control pills. It is a derivative of norethisterone, and was first introduced in Europe in the late 1970s..

Gestodene is a progestin that is used as a contraceptive. It is a synthetic progestogen, which is a derivative of norethisterone. It was first introduced in Europe in the late 1970s..

3D structure

Cartesian coordinates

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

2D drawing

 

Gestodene SIGSPDASOTUPFS-XUDSTZEESA-N chemical compound 2D structure molecule svg
Gestodene

 

Molecule descriptors

 
IUPAC name(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
InChI codeInChI=1S/C21H26O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,10,12-13,16-19,23H,3,5-9,11H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
InChI KeySIGSPDASOTUPFS-XUDSTZEESA-N
SMILESC#C[C@]1(O)C=C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[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.

  • (1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-6,12-dien-5-one
  • (8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
  • (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
  • (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
  • (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one;Gestodene
  • 13-ETHYL-17-HYDROXY-18,19-DINOR-17.ALPHA.-PREGNA-4,15-DIEN-20-YN-3-ONE
  • 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one
  • 13beta-Ethyl-17beta-hydroxy-18,19-dinorpregna-4,15-dien-20-yn-3-one
  • 1664P6E6MI
  • 17-alpha-Ethinyl-13-ethyl-17-beta-hydroxy-4,15-gonadien-3-one
  • 17alpha -Ethynyl-17beta-hydroxy-18-methyl-4,15-estradien-3-one
  • 17alpha-ethynyl-17beta-hydroxy-18-methyl-4,15-estradien-3-one
  • 17alpha-ethynyl-17beta-hydroxy-18-methyl-estra-4,15-dien-3-one
  • 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-
  • 18,19-Dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17a)-
  • 282G873
  • 60282-87-3
  • A832668
  • AB01274782-01
  • AB01274782_02
  • AC-20038
  • AC-474
  • AS-13029
  • BCP22665
  • BDBM50247973
  • BG164505
  • BRN 4237181
  • CCG-267584
  • CCRIS 9189
  • CS-1862
  • D04316
  • DB06730
  • DSSTox_CID_26478
  • DSSTox_GSID_46478
  • DSSTox_RID_81649
  • Femodene (ethinylestradiol, gestodene)
  • G0404
  • GESTODENE
  • GTPL11246
  • Gestinol
  • Gestoden
  • Gestodene
  • Gestodene (USAN/INN)
  • Gestodene- Bio-X
  • Gestodeno
  • Gestodenum
  • HSDB 3594
  • HY-B0110
  • MFCD00867858
  • Millinette (ethinylestradiol, gestodene)
  • NCGC00164611-01
  • NCGC00263565-01
  • PREGNA-4,15-DIEN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-18,19-DINOR-, (17.ALPHA.)-
  • Pregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-18,19-dinor-, (17alpha)-
  • Q-101426
  • Q408289
  • SH B 331
  • SH-546
  • SH-B-331
  • SHB 331
  • SHB-331
  • SHT-546
  • WL 70
  • s1376

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC238809420
  • CAS-60282-87-3
  • UNII-1664P6E6MI
  • AKOS024462671
  • BRD-K97197005-001-03-2
  • DTXSID6046478
  • CHEMBL1213583
  • CHEBI:135323
  • Tox21_112232
  • Tox21_112232_1
  • EINECS 262-145-8
  • SCHEMBL37271

Physico-Chemical properties

IUPAC name(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14-decahydrocyclopenta[a]phenanthren-3-one
Molecular formulaC21H26O2
Molecular weight310.43
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity92.96
LogP3.7
Topological polar surface area37.3

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.