Cytidine triphosphate

{{short description|Chemical compound}}

{{Chembox

| verifiedrevid = 446646289

| ImageFile=Cytidintriphosphat_protoniert.svg

| ImageSize=240px

| ImageAlt = Skeletal formula of cytidine triphosphate as an anion (3- charge)

| ImageFile1 = Cytidine triphosphate anion 3D spacefill.png

| ImageSize1 = 220

| ImageAlt1 = Space-filling model of the cytidine triphosphate molecule as an anion (4- charge)

| IUPACName=Cytidine 5′-(tetrahydrogen triphosphate)

| SystematicName=O¹-{[(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} tetrahydrogen triphosphate

| OtherNames=CTP; Cytidine-5'-triphosphate

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 19952488

| InChI = 1/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

| InChIKey = PCDQPRRSZKQHHS-XVFCMESIBL

| InChI1 = 1/C9H13N3O5.3H3O4P/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;3*1-5(2,3)4/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);3*(H3,1,2,3,4)/t4-,6-,7-,8-;;;/m1.../s1

| InChIKey1 = NPIWPFUCEAMYFN-LLWADOMFBY

| SMILES1 = OP(O)(=O)O.OP(O)(=O)O.OP(O)(=O)O.N/C1=N/C(=O)N(/C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O

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

| StdInChI = 1S/C9H13N3O5.3H3O4P/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8;3*1-5(2,3)4/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16);3*(H3,1,2,3,4)/t4-,6-,7-,8-;;;/m1.../s1

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

| StdInChIKey = NPIWPFUCEAMYFN-LLWADOMFSA-N

| CASNo=65-47-4

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

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

| UNII = K0118UX80T

| PubChem=6176

| IUPHAR_ligand = 1741

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

| MeSHName = Cytidine+triphosphate

}}

|Section2={{Chembox Properties

| Formula=C₉H₁₆N₃O₁₄P₃

| MolarMass=483.156

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Cytidine triphosphate (CTP) is a pyrimidine nucleoside triphosphate. CTP, much like ATP, consists of a ribose sugar, and three phosphate groups. The major difference between the two molecules is the base used, which in CTP is cytosine.

CTP is a substrate in the synthesis of RNA.

CTP is a high-energy molecule similar to ATP, but its role as an energy coupler is limited to a much smaller subset of metabolic reactions.

CTP is a coenzyme in metabolic reactions like the synthesis of glycerophospholipids, where it is used for activation and transfer of diacylglycerol and lipid head groups,{{Cite book|last1=Buchanan|first1=Bob B.|url=https://archive.org/details/biochemistrymole00buch|title=Biochemistry & molecular biology of plants|last2=Gruissem|first2=Wilhelm|last3=Jones|first3=Russell L.|publisher=American society of plant physiology|year=2000|isbn=978-0-943088-39-6|edition=1st|url-access=registration|name-list-style=vanc}} and glycosylation of proteins.

CTP acts as an inhibitor of the enzyme aspartate carbamoyltransferase, which is used in pyrimidine biosynthesis.Blackburn, G. Michael. Nucleic Acids in Chemistry and Biology. The Royal Society of Chemistry, 2006, p. 119-120.