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Deoxycytidine monophosphate

Chemical compound From Wikipedia, the free encyclopedia

Deoxycytidine monophosphate (dCMP), also known as deoxycytidylic acid or deoxycytidylate in its conjugate acid and conjugate base forms, respectively, is a deoxynucleotide and one of the four monomers that make up DNA. In a DNA double helix, it will base pair with deoxyguanosine monophosphate.[1]

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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 InfoCard 100.012.591 Edit this at Wikidata
MeSH Deoxycytidine+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 mass 307.199 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Medical use

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

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