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Deoxycytidine monophosphate

From Wikipedia, the free encyclopedia
Deoxycytidine monophosphate
Skeletal formula of deoxycytidine monophosphate as an anion (1- charge)
Space-filling model of the deoxycytidine monophosphate molecule as an anion (2- charge)
Names
IUPAC name
2′-Deoxycytidylic acid
Systematic IUPAC name
[(2R,3S,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.012.591Edit this at Wikidata
MeSHDeoxycytidine+monophosphate
UNII
  • InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1 checkY
    Key: NCMVOABPESMRCP-SHYZEUOFSA-N checkY
  • InChI=1/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
    Key: NCMVOABPESMRCP-SHYZEUOFBL
  • c1cn(c(=O)nc1N)[C@H]2C[C@@H]([C@H](O2)COP(=O)(O)O)O
Properties
C9H14N3O7P
Molar mass307.199 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Deoxycytidine monophosphate (dCMP), also known asdeoxycytidylic acid ordeoxycytidylate in itsconjugate acid and conjugate base forms, respectively, is adeoxynucleotide and one of the fourmonomers that make upDNA. In aDNA double helix, it will base pair withdeoxyguanosine monophosphate.[1]

Medical use

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Deoxycytidine monophosphate is a molecule of interest in treating genetic disorders such as thymidine kinase 2 (TK2) deficiency. In the case ofTK2 deficiency, dCMP in conjunction withdeoxythymidine monophosphate (dTMP) to bypass the deficiency in theTK2 enzyme.[2] Additionally dCMP is an indicator of several metabolite deficiency pathways such as UMP synthase deficiency ororotic aciduria.[3]

See also

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References

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  1. ^"Human Metabolome Database: Showing metabocard for dCMP (HMDB0001202)".hmdb.ca. Retrieved2024-12-10.
  2. ^Garone, Caterina; Garcia‐Diaz, Beatriz; Emmanuele, Valentina; Lopez, Luis C; Tadesse, Saba; Akman, Hasan O; Tanji, Kurenai; Quinzii, Catarina M; Hirano, Michio (August 2014)."Deoxypyrimidine monophosphate bypass therapy for thymidine kinase 2 deficiency".EMBO Molecular Medicine.6 (8):1016–1027.doi:10.15252/emmm.201404092.ISSN 1757-4676.PMC 4154130.
  3. ^PubChem."Deoxycytidine 5'-monophosphate".pubchem.ncbi.nlm.nih.gov. Retrieved2024-12-10.
Nucleic acid constituents
Nucleobase
Nucleoside
Ribonucleoside
Deoxyribonucleoside
Nucleotide
(Nucleoside monophosphate)
Ribonucleotide
Deoxyribonucleotide
Cyclic nucleotide
Nucleoside diphosphate
Nucleoside triphosphate
Retrieved from "https://en.wikipedia.org/w/index.php?title=Deoxycytidine_monophosphate&oldid=1311313810"
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