What's wrong with this molecule?

This should be cAMP but please don't take the pictures serious. I don't know what I was thinking when I made them. It looks aweful. I am sorry. There are three bad mistakes in there.

Do you find what's wrong with the molecule? There are two mistakes with the constitution and a geometrical one.

The nice thing about it is that it shows again that you do need some chemical understanding even if you become a theorist. So my life won't consist only of typing in numbers if I will go into that direction.



If you want to know something about cAMP, here you go:

This molecule is derived from the last one if you let the 3'-OH group of ribose attack the first phosphorous atom. This is done inside cells by an enzyme appropriately called adenylate cyclase. Adenylate cyclase is activated by the α-subunit of a G protein that received a GTP group after the initial messenger bonded to an adrenergic receptor.

That sounds like a pretty complex mechanism but it gets longer. Cyclic AMP does not work by itself. In a next step it activates an enzyme called protein kinase A. This enzyme will phosphorylate other enzymes thereby activating them. That will finally have an effect on the metabolism.

Since cAMP is a second messenger of adrenaline it activates enzymes associated with it. They involve glycogen breakdown and fatty acid mobilisation. In general it will activate the organism.

Caffeine which has a similar structure works by inhibiting the phosphodiesterase that breaks down cAMP to AMP. After taking in caffeine, cAMP will stay in the cells longer and its stimulating effect is amplified.

These images were again calculated with UFF in ArgusLab. UFF is a simple fast force field method that normally produces good results (unless the person using it messes it up).