Cytidine monophosphate

Cytidine monophosphate
Names
	IUPAC name [(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1-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
CAS Number	63-37-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17361 ;
ChEMBL	ChEMBL307679 ;
ChemSpider	5901 ;
ECHA InfoCard	100.000.506
PubChem CID	6131;
UNII	F469818O25 ;
CompTox Dashboard (EPA)	DTXSID50889322 ;
	InChI 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 Key: IERHLVCPSMICTF-XVFCMESISA-N ; 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;
	SMILES c1cn(c(=O)nc1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O;
Properties
Chemical formula	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).

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-.

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.

^ 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.

Names


IUPAC name [(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1-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
CAS Number	63-37-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17361
ChEMBL	ChEMBL307679
ChemSpider	5901
ECHA InfoCard	100.000.506
PubChem CID	6131
UNII	F469818O25
CompTox Dashboard (EPA)	DTXSID50889322
InChI 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 Key: IERHLVCPSMICTF-XVFCMESISA-N 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
SMILES c1cn(c(=O)nc1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
Properties
Chemical formula	C₉H₁₄N₃O₈P
Molar mass	323.198 g·mol⁻¹
Acidity (pK_a)	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).