Arabinofuranosylcytosine triphosphate

Arabinofuranosylcytosine triphosphate is a nucleotide that inhibits the synthesis of DNA by acting as an antimetabolic agent against deoxycytidine (a component of DNA). It is the biologically active form of cytarabine.[1]

Arabinofuranosylcytosine triphosphate[1]
Names
IUPAC name
1-(4-Amino-2-oxopyrimidin-1(2H)-yl)-1-deoxy-β-D-arabinofuranose 5′-(tetrahydrogen triphosphate)
Systematic IUPAC name
O1-{[(2R,3S,4S,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxyoxolan-2-yl]methyl} tetrahydrogen triphosphate
Other names
Ara-CTP, Cytarabine triphosphate,
Cytosine arabinoside triphosphate
Identifiers
3D model (JSmol)
ChemSpider
MeSH Arabinofuranosylcytosine+triphosphate
UNII
  • InChI=1S/C10H18N3O13P3/c11-6-1-2-13(10(16)12-6)9-8(15)7(14)5(25-9)3-24-29(22,23)26-28(20,21)4-27(17,18)19/h1-2,5,7-9,14-15H,3-4H2,(H,20,21)(H,22,23)(H2,11,12,16)(H2,17,18,19)/t5-,7-,8+,9-/m1/s1 ☒N
    Key: PEZFHAVVQBLXDV-BUJSFMDZSA-N ☒N
  • InChI=1/C10H18N3O13P3/c11-6-1-2-13(10(16)12-6)9-8(15)7(14)5(25-9)3-24-29(22,23)26-28(20,21)4-27(17,18)19/h1-2,5,7-9,14-15H,3-4H2,(H,20,21)(H,22,23)(H2,11,12,16)(H2,17,18,19)/t5-,7-,8+,9-/m1/s1
    Key: PEZFHAVVQBLXDV-BUJSFMDZBE
  • c1cn(c(=O)nc1N)[C@H]2[C@H]([C@@H]([C@H](O2)COP(=O)(O)OP(=O)(CP(=O)(O)O)O)O)O
Properties
C9H16N3O14P3
Molar mass 483.156323
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Ara-CTP - Compound Summary, PubChem.
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