Cytidine diphosphate

Cytidine diphosphate
Names


IUPAC name Cytidine 5′-(trihydrogen diphosphate)
Systematic IUPAC name [(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl trihydrogen diphosphate
Identifiers
CAS Number	63-38-7^Y 54394-9-0 (disodium salt)^Y 34393-59-4 (trisodium salt)^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17239^Y
ChEMBL	ChEMBL425252^Y
ChemSpider	5902^Y
DrugBank	DB04555
ECHA InfoCard	100.000.507
EC Number	200-557-1
KEGG	C00112
PubChem CID	290
UNII	1ZH821MXU5^Y F8B9F7OXES (disodium salt)^Y 0TZ883O8PW (trisodium salt)^Y
CompTox Dashboard (EPA)	DTXSID501014481
InChI InChI=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^Y Key: ZWIADYZPOWUWEW-XVFCMESISA-N^Y 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 Key: ZWIADYZPOWUWEW-XVFCMESIBF
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
Properties
Chemical formula	C₉H₁₅N₃O₁₁P₂
Molar mass	403.176422
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

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 Rhodothermus marinus, CDP-activated inositol is necessary to form the phospholipid dialkylether glycerophosphoinositide, which contains inositol phosphate and ether-linked alkyl chains.^[2]

CDP is commonly formed in the reaction Dolichol + Cytidine Triphosphate (CTP) ⟶ Dolichol-phosphate + CDP, which is prevalent in many biochemical pathways.^[3]

References

^ Pereira, Mark P.; Brown, Eric D. (2010-01-01), Holst, Otto; Brennan, Patrick J.; Itzstein, Mark von; Moran, Anthony P. (eds.), "Chapter 19 - Biosynthesis of cell wall teichoic acid polymers", Microbial Glycobiology, San Diego: Academic Press, pp. 337–350, ISBN 978-0-12-374546-0, retrieved 2021-12-08
^ Jorge, Carla D.; Borges, Nuno; Santos, Helena (July 2015). "A novel pathway for the synthesis of inositol phospholipids uses cytidine diphosphate ( CDP )-inositol as donor of the polar head group". Environmental Microbiology. 17 (7): 2492–2504. Bibcode:2015EnvMi..17.2492J. doi:10.1111/1462-2920.12734. ISSN 1462-2912.
^ PubChem. "Cytidine-5'-diphosphate". pubchem.ncbi.nlm.nih.gov. Retrieved 2024-04-27.

Nucleic acid constituents

Ribonucleoside	Adenosine Guanosine 5-Methyluridine Uridine 5-Methylcytidine Cytidine Pseudouridine Inosine N⁶-Methyladenosine Xanthosine Wybutosine
Deoxyribonucleoside	Deoxyadenosine Deoxyguanosine Thymidine Deoxyuridine Deoxycytidine Deoxyinosine Deoxyxanthosine

Nucleotide
(Nucleoside monophosphate)

Ribonucleotide	AMP GMP m⁵UMP UMP CMP IMP XMP
Deoxyribonucleotide	dAMP dGMP dTMP dUMP dCMP dIMP dXMP
Cyclic nucleotide	cAMP cGMP c-di-GMP c-di-AMP cADPR cGAMP

Nucleoside diphosphate

ADP GDP m⁵UDP UDP CDP Xanthosine diphosphate
dADP dGDP dTDP dUDP dCDP

ATP GTP m⁵UTP UTP CTP ITP XTP
dATP dGTP dTTP dUTP dCTP dITP dXTP

Receptor
(ligands)

P2X
(ATPTooltip Adenosine triphosphate)

CNTsTooltip Concentrative nucleoside transporters	6-Hydroxy-7-methoxyflavone Adenosine dMeThPmR Estradiol KGO-2142 KGO-2173 MeThPmR Phloridzin Progesterone
ENTsTooltip Equilibrative nucleoside transporters	Barbiturates Benzodiazepines Cilostazol Dilazep Dipyridamole Estradiol Ethanol Hexobendine NBMPR Pentoxifylline Progesterone Propentofylline
PMATTooltip Plasma membrane monoamine transporter	Decynium-22

XOTooltip Xanthine oxidase	Allopurinol Amflutizole Benzbromarone Caffeic acid Cinnamaldehyde Cinnamomum osmophloeum Febuxostat Myo-inositol Kaempferol Myricetin Niraxostat Oxipurinol Phytic acid Pistacia integerrima Propolis Quercetin Tisopurine Topiroxostat
Others	Aminopterin Azathioprine Methotrexate Mycophenolic acid Pemetrexed Pralatrexate Many others