Pregnane

Pregnane, also known as 17β-ethylandrostane or as 10β,13β-dimethyl-17β-ethylgonane, is a C21 steroid and, indirectly, a parent of progesterone. It is a parent hydrocarbon for two series of steroids stemming from 5α-pregnane (originally allopregnane) and 5β-pregnane (17β-ethyletiocholane). It has a gonane core.

Pregnane
Skeletal formula of pregnane
Ball-and-stick model of the pregnane molecule
Names
IUPAC name
5ξ-Pregnane[1]
Systematic IUPAC name
(1S,3aS,3bS,5aΞ,9aS,9bS,11aR)-1-Ethyl-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1 checkY
    Key: JWMFYGXQPXQEEM-WZBAXQLOSA-N checkY
  • InChI=1/C21H36/c1-4-15-9-11-18-17-10-8-16-7-5-6-13-20(16,2)19(17)12-14-21(15,18)3/h15-19H,4-14H2,1-3H3/t15-,16?,17-,18-,19-,20-,21+/m0/s1
    Key: JWMFYGXQPXQEEM-WZBAXQLOBZ
  • C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]2(C)CC3)CC)CC4)C
Properties
C21H36
Molar mass 288.511 g/mol
Density 0.926 g/ml
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

5β-Pregnane is the parent of pregnanediones, pregnanolones, and pregnanediols, and is found largely in urine as a metabolic product of 5β-pregnane compounds.

Pregnanes
Steroid nomenclature: Pregnanes have carbons 1 through 21.

Pregnanes are steroid derivatives with carbons present at positions 1 through 21.

Most biologically significant pregnane derivatives fall into one of two groups: pregnenes and pregnadienes. Another class is pregnatrienes.

Pregnenes
Main article: Pregnene
Cortisone

Pregnenes have a double bond. Examples include:

Pregnadienes
Main article: Pregnadiene
Cyproterone acetate

Pregnadienes have two double bonds. Examples include:

See also

References
  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 1530. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.


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