Uridine monophosphate

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 ribonucleotide monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP. Covalent attachment of UMP (e.g., to a protein such as adenylyltransferase) is called uridylylation (or sometimes uridylation).^[2]

Uridine monophosphate

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
CAS Number	58-97-9 Y
3D model (JSmol)	Interactive image
ChemSpider	5808 N
ECHA InfoCard	100.000.371
IUPHAR/BPS	5125
MeSH	Uridine+monophosphate
PubChem CID	6030
UNII	E2OU15WN0N Y
CompTox Dashboard (EPA)	DTXSID40861596 DTXSID20883211, DTXSID40861596
InChI InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 N Key: DJJCXFVJDGTHFX-XVFCMESISA-N N InChI=1/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 Key: DJJCXFVJDGTHFX-XVFCMESIBD
SMILES c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
Properties
Chemical formula	C9H13N2O9P
Molar mass	324.182 g·mol−1
Melting point	202 °C (396 °F; 475 K) (decomposes)[1]
Solubility in water	good, also in methanol [1]
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 verify (what is YN ?) Infobox references

Biosynthesis

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.^[3]

In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase.^[4] Defective UMP synthase can result in orotic aciduria, a metabolic disorder.

Effects on animal intelligence

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.^[5]

In foods

In brain research studies, uridine monophosphate is used as a convenient delivery compound for uridine.^[6] Uridine is the active component of this compound. Uridine is present in many foods, mainly in the form of RNA. Non-phosphorylated uridine is not bioavailable beyond first-pass metabolism, as it is almost entirely catabolised in the liver and gastrointestinal tract.^[7]

See also

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

References

1. Lide M, Lide DR (1998). CRC Handbook of Chemistry and Physics (87 ed.). CRC Press. pp. 3–56. ISBN 978-0-8493-0594-8.
2. Voet D, Voet JG, Pratt CW (2008). Fundamentals of Biochemistry (3rd ed.). John Wiley & Sons.
3. Berg J, Tymoczko JL, Stryer L (2006). Biochemistry (6th ed.). San Francisco: W. H. Freeman. ISBN 0-7167-8724-5.
4. Winkler JK, Suttle DP (July 1988). "Analysis of UMP synthase gene and mRNA structure in hereditary orotic aciduria fibroblasts". American Journal of Human Genetics. 43 (1): 86–94. PMC 1715274. PMID 2837086.
5. Holguin S, Martinez J, Chow C, Wurtman R (November 2008). "Dietary uridine enhances the improvement in learning and memory produced by administering DHA to gerbils". FASEB Journal. 22 (11): 3938–46. doi:10.1096/fj.08-112425. PMC 2574024. PMID 18606862.

   • "Get Smart About What You Eat And You Might Actually Improve Your Intelligence". ScienceDaily (Press release). July 3, 2008.
6. Wurtman RJ, Cansev M, Sakamoto T, Ulus IH (2009). "Use of phosphatide precursors to promote synaptogenesis". Annual Review of Nutrition. 29: 59–87. doi:10.1146/annurev-nutr-080508-141059. PMID 19400698.
7. Gasser T, Moyer JD, Handschumacher RE (August 1981). "Novel single-pass exchange of circulating uridine in rat liver". Science. 213 (4509): 777–8. Bibcode:1981Sci...213..777G. doi:10.1126/science.7256279. PMID 7256279.