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Uridine monophosphate

Uridine monophosphate
Skeletal formula of UMP
Ball-and-stick model of the UMP molecule as an anion
Names
IUPAC name
[(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.000.371
MeSH Uridine+monophosphate
PubChem CID
Properties
C9H13N2O9P
Molar mass 324.18 g·mol−1
Melting point 202 °C (396 °F; 475 K) (decomposes)
good, also in methanol
Acidity (pKa) 1.0, 6.4, 9.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Uridine monophosphate (UMP), also known as 5′-uridylic acid (conjugate base uridylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleoside monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP.

Uridine monophosphate is formed from Orotidine 5'-monophosphate (orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme orotidylate decarboxylase. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 1017-fold.

In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase. Defective UMP synthase can result in orotic aciduria, a metabolic disorder.

In a study, gerbils fed a combination of uridine monophosphate, choline, and docosahexaenoic acid (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.


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