Many metabolites are chemically reactive and unstable, and thus prone to chemical damage. In general, any reaction that occurs in vitro under physiological conditions can also occur in vivo. Some metabolites are so reactive that their half-life in a cell is measured in minutes. For example, the glycolytic intermediate 1,3-bisphosphoglyceric acid has a half-life of 27 minutes in vivo. Typical types of chemical damage reactions that can occur to metabolites are racemization, rearrangement, elimination, photodissociation, addition, and condensation.