Cytidine monophosphate

Cytidine monophosphate, also known as 5'-cytidylic acid or simply cytidylate, and abbreviated CMP, is a nucleotide that is used as a monomer in RNA.[1] It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine; hence, a ribonucleoside monophosphate. As a substituent it takes the form of the prefix cytidylyl-.

Cytidine monophosphate
Skeletal formula of cytidine monophosphate as an anion (1- charge)
Space-filling model of the cytidine monophosphate molecule as anion (2- charge)
Names
IUPAC name
5′-Cytidylic acid
Systematic IUPAC name
[(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
Cytidylic acid; 5'-Cytidylic acid; Cytidine 5'-monophosphate; Cytidine 5'-phosphate; Cytidylate; 5'-CMP
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.506
UNII
  • InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 checkY
    Key: IERHLVCPSMICTF-XVFCMESISA-N checkY
  • InChI=1/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
    Key: IERHLVCPSMICTF-XVFCMESIBY
  • c1cn(c(=O)nc1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
Properties
C9H14N3O8P
Molar mass 323.198 g·mol−1
Acidity (pKa) 0.8, 4.5, 6.3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Metabolism

CMP can be phosphorylated to cytidine diphosphate by the enzyme CMP kinase, with adenosine triphosphate or guanosine triphosphate donating the phosphate group. Since cytidine triphosphate is generated by amination of uridine triphosphate, the main source of CMP is from RNA being decomposed by RNAse.

See also

References
  1. Pascal JM (February 2008). "DNA and RNA ligases: structural variations and shared mechanisms". Curr. Opin. Struct. Biol. 18 (1): 96–105. doi:10.1016/j.sbi.2007.12.008. PMID 18262407.
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