 Adenosine 3',5'-bisphosphate

Adenosine 3′,5′-bisphosphate, often abbreviated PAP, is a nucleotide with separate phosphate groups attached at the 3′ and 5′ positions of the ribose in adenosine. The positions are part of its identity: two phosphate groups on different sugar positions do not make the same structure as the linked phosphate chain of adenosine diphosphate.^[ref]

An important reaction example is sulfation using PAPS. In the reaction catalyzed by heparan sulfate glucosamine N-sulfotransferase, PAPS transfers a sulfur-containing group to a glucosamine unit in heparan sulfate, leaving adenosine 3',5'-bisphosphate. The product retains the two phosphate groups but lacks the transferred sulfo group. Counting phosphorus atoms alone would therefore fail to distinguish donor from product.^[ref]

This is a useful example of why a molecular formula or a count of functional groups is less informative than a chemical structure: attachment positions and connectivity determine which molecule is present.