Uridine monophosphate

Uridine monophosphate
Identifiers
CAS number	58-97-9 Y
PubChem	1172
MeSH	Uridine+monophosphate
SMILES	C1=CN(C(=O)NC1=O) C2C(C(C(O2)COP(=O)(O)O)O)O
Properties
Molecular formula	C9H13N2O9P
Molar mass	324.181
Melting point	202 °C (dec.) [1]
Solubility in water	good, also in methanol [1]
Acidity (pKa)	1.0, 6.4, 9.5
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Uridine monophosphate, also known as 5'-uridylic acid and abbreviated UMP, is a nucleotide that is found 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. Another common shorthand for the molecule is uridylate - the deprotonated form of the molecule, which is predominant in aqueous solution.

Biosynthesis

Uridine monophosphate is formed from orotidylic acid (orotidine 5'-monophosphate) 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. ^[2]

In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase. ^[3] Defective UMP synthase can result in orotic aciduria, a metabolic disorder.

Effects on Animal Intelligence

In a recent study, gerbils fed supplements 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.^[4]

Uridine Monophosphate in Foods

In brain research studies such as those mentioned in this article, uridine monophosphate is used as a convenient delivery compound for uridine. Uridine is the active ingredient of the compound. A common misconception is that uridine and its compounds are not available in significant quantities from foods and must be obtained from expensive supplements or prescription drugs. This is not so. Uridine monophosphate is a major component of RNA. Any food rich in RNA, such as Brewer's yeast or some organ meats, will provide significant quantities of it. For more information, consult the article on uridine.

References

See also

• Nucleoside
• Nucleotide
• DNA
• RNA
• Oligonucleotide
• Pyrimidine biosynthesis

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