Gonane

Gonane

Names
IUPAC name 2(8S,9R,10S,13S,14R)-2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydro-1H-cyclopenta[a]phenanthrene
Identifiers
CAS Number	4732-76-7 (1R,2S,10S,11R,15S)- heptadecane N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:35528 Y
ChemSpider	5256859 (1R,2S,10S,11R,15S)- heptadecane Y 5256861 (1R,2S,7R,10S,11R,15S)- heptadecane Y 5256860 (1R,2S,7S,10S,11R,15S)- heptadecane Y 1077 Y
KEGG	C19639 N
PubChem CID	1108 6857523 (1R,2S,10S,11R,15S)- heptadecane 6857525 (1R,2S,7R,10S,11R,15S)- heptadecane 6857524 (1R,2S,7S,10S,11R,15S)- heptadecane
InChI InChI=1S/C17H28/c1-2-6-14-12(4-1)8-10-17-15-7-3-5-13(15)9-11-16(14)17/h12-17H,1-11H2/t12?,13-,14-,15+,16+,17-/m0/s1 Y Key: UACIBCPNAKBWHX-CTBOZYAPSA-N Y
SMILES C2C1[C@H](CCCC1)[C@H]3CC[C@H]4[C@H]([C@@H]3C2)CCC4
Properties
Chemical formula	C17H28
Molar mass	232.41 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Gonane (C17), also known as perhydrocyclopenta[a]phenanthrene, is a tetracyclic hydrocarbon ring structure and the fundamental steroid nucleus. It consists of a phenanthrene ring fused with a cyclopentane ring. Unlike steroid hormones, gonane has no methyl groups at the C10 and C13 positions and no side chain at the C17 position. Because gonane has six centers of chirality, it has 64 (2⁶) theoretically possible stereoisomers. However, only a few of these stereoisomers are actually encountered with steroids. The most common stereoisomers of gonane are 5α-gonane and 5β-gonane.

5α-Gonane

5β-Gonane

5α-Gonane, side-perspective view

5β-Gonane, side-perspective view

Estrane (C18) is the 13β-methyl variant of gonane, androstane (C19) is the 10β,13β-dimethyl variant of gonane, and pregnane (C21) is the 10β,13β-dimethyl, 17β-ethyl variant of gonane.