Uridine monophosphate

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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 (
JSmol
)
ChemSpider
ECHA InfoCard
 100.000.371 Edit this at Wikidata
IUPHAR/BPS
MeSH Uridine+monophosphate
UNII
  • 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
C9H13N2O9P
Molar mass 324.182 g·mol−1
Melting point 202 °C (396 °F; 475 K) (decomposes)[1]
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).
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Uridine monophosphate (UMP), also known as 5′-uridylic acid (

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]

Biosynthesis

Uridine monophosphate is formed from

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

References

  1. ^
    ISBN 978-0-8493-0594-8
    .
  2. ^ Voet D, Voet JG, Pratt CW (2008). Fundamentals of Biochemistry (3rd ed.). John Wiley & Sons.
  3. ISBN 0-7167-8724-5
    .
  4. PMID 2837086
    .
  5. PMID 18606862
    .
  6. PMID 19400698
    .
  7. PMID 7256279
    .
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