cytidine monophosphate

{{Chembox

| Watchedfields = changed

| verifiedrevid = 443555231

| ImageFile = CMP_chemical_structure.png

| ImageSize = 180px

| ImageAlt = Skeletal formula of cytidine monophosphate as an anion (1- charge)

| ImageFile1 = Cytidine monophosphate anion 3D spacefill.png

| ImageAlt1 = Space-filling model of the cytidine monophosphate molecule as anion (2- charge)

| IUPACName = 5′-Cytidylic acid

| SystematicName = [(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

| OtherNames = Cytidylic acid; 5'-Cytidylic acid; Cytidine 5'-monophosphate; Cytidine 5'-phosphate; Cytidylate; 5'-CMP

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 5901

| 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

| InChIKey = IERHLVCPSMICTF-XVFCMESIBY

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 307679

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = IERHLVCPSMICTF-XVFCMESISA-N

| CASNo = 63-37-6

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = F469818O25

| PubChem = 6131

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 17361

| SMILES = c1cn(c(=O)nc1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O

}}

|Section2={{Chembox Properties

| C=9 | H=14 | N=3 | O=8 | P=1

| Appearance =

| pKa = 0.8, 4.5, 6.3

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

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.{{cite journal |author=Pascal JM |title=DNA and RNA ligases: structural variations and shared mechanisms |journal=Curr. Opin. Struct. Biol. |volume=18 |issue=1 |pages=96–105 |date=February 2008 |pmid=18262407 |doi=10.1016/j.sbi.2007.12.008 }} 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-.