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Pregnane

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Pregnane
Skeletal formula of pregnane
Ball-and-stick model of the pregnane molecule
Names
IUPAC name 5ξ-Pregnane
Systematic IUPAC name (1S,3aS,3bS,5aΞ,9aS,9bS,11aR)-1-Ethyl-9a,11a-dimethylhexadecahydro-1H-cyclopentaphenanthrene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: JWMFYGXQPXQEEM-WZBAXQLOSA-N
  • 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/s1Key: JWMFYGXQPXQEEM-WZBAXQLOBZ
SMILES
  • C41CCCC1(3(2CC(2(C)CC3)CC)CC4)C
Properties
Chemical formula 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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.

External links

Steroid classification
C17
C18
C19
C20
C21
C23
C24
C27
Functional group
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