Cytidine diphosphate

{{chembox

| Verifiedfields = changed

| verifiedrevid = 443555075

|ImageFile = Cytidindiphosphat protoniert.svg

|ImageAlt = Skeletal formula of cytidine diphosphate

|ImageFile1 = Cytidine diphosphate anion 3D spacefill.png

|ImageSize1 = 210

|ImageAlt1 = Space-filling model of the Cytidine diphosphate molecule as an anion (3- anion)

|IUPACName = Cytidine 5′-(trihydrogen diphosphate)

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

|OtherNames =

|Section1={{Chembox Identifiers

| CASNo=63-38-7

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

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 54394-9-0

| CASNo2_Comment = (disodium salt)

| CASNo3_Ref = {{cascite|correct|CAS}}

| CASNo3 = 34393-59-4

| CASNo3_Comment = (trisodium salt)

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

| ChemSpiderID = 5902

| DrugBank = DB04555

| EC_number = 200-557-1

| KEGG = C00112

| InChI = 1/C9H15N3O11P2/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

| InChIKey = ZWIADYZPOWUWEW-XVFCMESIBF

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

| ChEMBL = 425252

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

| StdInChI = 1S/C9H15N3O11P2/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

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

| StdInChIKey = ZWIADYZPOWUWEW-XVFCMESISA-N

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

| UNII = 1ZH821MXU5

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = F8B9F7OXES

| UNII2_Comment = (disodium salt)

| UNII3_Ref = {{fdacite|correct|FDA}}

| UNII3 = 0TZ883O8PW

| UNII3_Comment = (trisodium salt)

| PubChem=290

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

| ChEBI = 17239

| SMILES = O=P(O)(O)OP(=O)(O)OC[C@H]2O[C@@H](N/1C(=O)/N=C(/N)\C=C\1)[C@H](O)[C@@H]2O

}}

|Section2={{Chembox Properties

| Formula=C₉H₁₅N₃O₁₁P₂

| MolarMass=403.176422

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section3={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

}}

Cytidine diphosphate, abbreviated CDP, is a nucleoside diphosphate. It is an ester of pyrophosphoric acid with the nucleoside cytidine. CDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase cytosine.

In Bacillus subtilis and Staphylococcus aureus, CDP-activated glycerol and ribitol are necessary to build wall teichoic acid.{{Citation |last1=Pereira |first1=Mark P. |title=Chapter 19 - Biosynthesis of cell wall teichoic acid polymers |date=2010-01-01 |work=Microbial Glycobiology |pages=337–350 |editor-last=Holst |editor-first=Otto |url=https://www.sciencedirect.com/science/article/pii/B9780123745460000195 |access-date=2021-12-08 |place=San Diego |publisher=Academic Press |isbn=978-0-12-374546-0 |last2=Brown |first2=Eric D. |editor2-last=Brennan |editor2-first=Patrick J. |editor3-last=Itzstein |editor3-first=Mark von |editor4-last=Moran |editor4-first=Anthony P.}}

In Rhodothermus marinus, CDP-activated inositol is necessary to form the phospholipid dialkylether glycerophosphoinositide, which contains inositol phosphate and ether-linked alkyl chains.{{Cite journal |last1=Jorge |first1=Carla D. |last2=Borges |first2=Nuno |last3=Santos |first3=Helena |date=July 2015 |title=A novel pathway for the synthesis of inositol phospholipids uses cytidine diphosphate ( CDP )-inositol as donor of the polar head group |url=https://sfamjournals.onlinelibrary.wiley.com/doi/10.1111/1462-2920.12734 |journal=Environmental Microbiology |volume=17 |issue=7 |pages=2492–2504 |doi=10.1111/1462-2920.12734 |bibcode=2015EnvMi..17.2492J |issn=1462-2912|url-access=subscription }}

CDP is commonly formed in the reaction dolichol + cytidine triphosphate (CTP) ⟶ dolichol-phosphate + CDP, which is prevalent in many biochemical pathways.{{Cite web |last=PubChem |title=Cytidine-5'-diphosphate |url=https://pubchem.ncbi.nlm.nih.gov/compound/6132 |access-date=2024-04-27 |website=pubchem.ncbi.nlm.nih.gov }}