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Comment by _Microft | Hacker News Reader

I knew that cyclobutane existed (a ring of four carbon atoms with attached hydrogen atoms which is 'weird' in the sense that the angles between the bonds are not what would be expected for a carbon atom with four bonds [0]) but learned about the existence of ladderanes today. Their structure looks just soo unusual.

https://en.wikipedia.org/wiki/Ladderane

Speaking of unusual structures, here is something like a 2D version of a ladderane:

https://en.wikipedia.org/wiki/Fenestrane

[0] https://en.wikipedia.org/wiki/Orbital_hybridisation#sp3

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It's interesting that one group of compounds is named using the Latin, in this case for "window" (fenestrane), but "ladderane" makes use of an ordinary English word (by way of Old English and Germanic).

I guess I would have expected a Latin-derived name like "escalane" instead.

Follow the first link/s in these articles and somewhere you will find „jawsamycin“. A part of this molecule looks a lot like a row of teeth…

Shark teeth (https://mobile.twitter.com/germhuntermd/status/1285971314134...)

Oh and it contains luciferase?

The common names for compounds/compound classes like this are usually just left to the person that discovers them. The standardized naming scheme is set by the IUPAC and the name that you get for any reasonably complicated molecule will be a mouthful.

A mouthful? You're not wrong ...

https://www.ebi.ac.uk/chebi/searchId.do?chebiId=132927

"8-[(1S,2R,3R,4S,6S,7S,8S,9S,12R)-pentacyclo[6.4.0.0^2,7.0^3,6.0^9,12]dodecan-4-yl]octanoic acid"

Not sure how I would format the ring closure notation (like 0^2,7 is meant to be superscript)

I glanced at the structures first before reading the text and assumed they were oddballs synthesized in the lab. It’s incredible that these are all natural products. Leptocillin also looks astonishingly weird.

> here is something like a 2D version of a ladderane

Don't know about that analogy. To me, the 3D version of a fenestrane wouldn't be a ladderane, but rather an https://en.wikipedia.org/wiki/Adamantane

And the last example from the article, a tetrasubstituted cyclobutane, probably tells you that the functional groups connected to the cyclobutane could alleviate some of the ring strain in plain cyclobutane.

Similarly, cyclopropane also has incredible ring strain and likely won't be found in nature, but plenty of derivatives can.

Interestingly, cyclobutane and cyclopropane do not have a large difference in ring strain (within about 4% of each other). Cyclopropanes are well known in natural product structures. One of the weirdest is this natural product, U-106305, which has 6 cyclopropanes. Made by a strain of Streptomyces! https://pubs.acs.org/doi/pdf/10.1021/ja9619420

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