Allopregnane

Allopregnane, also known as 5α-pregnane or as 10β,13β-dimethyl-17β-ethyl-5α-gonane, is a steroid and a parent compound of a variety of steroid derivatives.[1][2] It is one of the epimers of pregnane, the other being 5β-pregnane. Derivatives of allopregnane include the naturally occurring steroids allopregnanolone, allopregnanediol, isopregnanolone, and 5α-dihydroprogesterone.

Allopregnane
Names
IUPAC name
5α-Pregnane
Systematic IUPAC name
(1S,3aS,3bS,5aR,9aS,9bS,11aR)-1-Ethyl-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene
Other names
Allopregnane; 17β-Ethyl-5α-androstane; 10β,13β-Dimethyl-17β-ethyl-5α-gonane
Identifiers
3D model (JSmol)
2502007
ChEBI
ChemSpider
ECHA InfoCard 100.010.345
EC Number
  • 211-378-3
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
    Key: JWMFYGXQPXQEEM-GCOKGBOCSA-N
  • CC[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCCC4)C)C
Properties
C21H36
Molar mass 288.519 g/mol
Hazards
GHS labelling:
H413
P273, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. Schneider, J. J. (November 1952). "Conversion of desoxycorticosterone to four allopregnane metabolites by rat liver in vitro". J Biol Chem. 199 (1): 235–244. doi:10.1016/S0021-9258(18)44830-2. PMID 12999835.
  2. William M. Haynes (22 June 2016). CRC Handbook of Chemistry and Physics, 97th Edition. CRC Press. pp. 3–. ISBN 978-1-4987-5429-3.


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