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Cytidine monophosphate

From Wikipedia, the free encyclopedia
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 InfoCard100.000.506Edit this at Wikidata
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 mass323.198 g·mol−1
Acidity (pKa)0.8, 4.5, 6.3
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Cytidine monophosphate, also known as5'-cytidylic acid or simplycytidylate, and abbreviatedCMP, is anucleotide that is used as amonomer inRNA.[1] It is anester ofphosphoric acid with thenucleosidecytidine. CMP consists of thephosphategroup, thepentosesugarribose, and thenucleobasecytosine; hence, aribonucleoside monophosphate.As asubstituent it takes the form of the prefixcytidylyl-.

Metabolism

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CMP can be phosphorylated tocytidine diphosphate by the enzymeCMP kinase, withadenosine triphosphate orguanosine triphosphate donating the phosphate group. Sincecytidine triphosphate is generated by amination ofuridine triphosphate, the main source of CMP is from RNA being decomposed byRNAse.

See also

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References

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  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.
Nucleic acid constituents
Nucleobase
Nucleoside
Ribonucleoside
Deoxyribonucleoside
Nucleotide
(Nucleoside monophosphate)
Ribonucleotide
Deoxyribonucleotide
Cyclic nucleotide
Nucleoside diphosphate
Nucleoside triphosphate
Receptor
(ligands)
P0 (adenine)
P1
(adenosine)
P2
(nucleotide)
P2X
(ATPTooltip Adenosine triphosphate)
P2Y
Transporter
(blockers)
CNTsTooltip Concentrative nucleoside transporters
ENTsTooltip Equilibrative nucleoside transporters
PMATTooltip Plasma membrane monoamine transporter
Enzyme
(inhibitors)
XOTooltip Xanthine oxidase
Others
Others
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