Pregnane

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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

CAS Number

* 481-26-5 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:8386 Y

ChemSpider |

* 5256760 Y

PubChem CID

* 6857422

UNII |

* 10Z78HHV4C Y

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/s1 Y

Key: JWMFYGXQPXQEEM-WZBAXQLOSA-N Y

* 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

SMILES

* C41CCCC[C@@]1([C@@H]3[C@H]([C@@H]2CC[C@@H]([C@@]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 [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

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.

## Contents

* 1 Pregnanes
* 2 Pregnenes
* 3 Pregnadienes
* 4 See also
* 5 References
* 6 External links

## 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: Biology:Pregnene

Cortisone

Pregnenes have a double bond. Examples include:

* Cortisone
* Hydrocortisone
* Progesterone

## Pregnadienes

Main article: Biology:Pregnadiene

Cyproterone acetate

Pregnadienes have two double bonds. Examples include:

* Cyproterone acetate
* Danazol
* Fluocinonide

## See also

* 5β-Pregnane
* Pregnanedione
* Pregnanediol
* 19-Norpregnane
* Androstane
* Estrane

## 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. pp. 1530. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.

## External links

* Pregnanes at the US National Library of Medicine Medical Subject Headings (MeSH)
* PubChem
* Diagram at qmul.ac.uk
* Definition of Pregnane
* Progesterone Chemistry
* Progesterone record in European Bioinformatics database

* v
* t
* e

Steroid classification

C17|

* Gonane

C18|

* Estrane: Dehydrogenated: Estrene
* Estradiene
* Estratriene; Substituted: Estratrienolone
* Estratrienediol
* Estratrienetriol

C19|

* Androstane: Dehydrogenated: Androstene
* Androstadiene
* Androstatriene; Substituted: Androstanol
* Androstenol
* Androstanone
* Androstenone
* Androstanediol
* Androstenediol
* Androstanedione
* Androstenedione
* Androstenetrione
* Androstanolone
* Androstenolone
* Androstadienol
* Androstadienone; Etiocholane

C20|

* 19-Norpregnane

C21|

* Pregnane: Dehydrogenated: Pregnene
* Pregnadiene
* Pregnatriene; Substituted: Pregnanediol
* Pregnanetriol
* Pregnenediol
* Pregnanedione
* Pregnenedione
* 5α-Pregnane
* 5β-Pregnane

C23|

* Cardanolide

C24|

* Cholane
* Bile acid

C27|

* Cholestane

Functional group|

* 17-Ketosteroid
* Hydroxysteroid
* Halogenated steroid

Elements removed|

* Norsteroid
* Secosteroid

Elements replaced|

* Azasteroid

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