Testosterone (and steroids) naming

Hi all,

I tried to use the naming function for steroids compounds and I obtain non-common IUPAC name. So I try to name Testosterone and I obtain this (with the new analysis box) :

You can remark that even the traditional name is not "Testosterone".

If I look at Chemspider (http://www.chemspider.com/Chemical-Structure.5791.html), or Pubchem (for example), or if I use the naming function of ISIS; I obtain this more typical IUPAC name:

(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

 

Can you explain me the rules you are using for the naming of such compounds?

Thanks in advance,

Lionel

 

Bonjour Lionel,

Thank you for your question. The name generated is indeed not the preferred name for such compound. It uses an alternative nomenclature (Von Bayer bridged cycles), which does represent the structure, but in a more complicated way. We plan to improve this in the future. This limitation is listed in the current limitations in the Structure to Name User Guide:

• Some aspects of nomenclature are only partially implemented, in particular complex cases of fused systems, ring assemblies of size 3+ and multiplicative nomenclature. In those cases, a non-preferred but chemically correct name will be generated.

In any case, the traditional name should be testosterone, we are investigating why this is not the case here.

Best regards,

Daniel

Bonjour Daniel,

Sorry I did not look at the guide before...

Thanks for your feedback and for investigating the "traditional name".

Lionel