5-Formamidoimidazole-4-carboxamide ribotide

Summary

5-Formamidoimidazole-4-carboxamide ribotide (or FAICAR) is an intermediate in the formation of purines. It is formed by the enzyme AICAR transformylase from AICAR and 10-formyltetrahydrofolate.[1]

5-Formamidoimidazole-4-carboxamide ribotide
Names
IUPAC name
(1R)-1,4-Anhydro-1-(4-carbamoyl-5-formamido-1H-imidazol-1-yl)-D-ribitol 5-(dihydrogen phosphate)
Systematic IUPAC name
[(2R,3S,4R,5R)-5-(4-Carbamoyl-5-formamido-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
5-Formamidoimidazole-4-carboxamide ribonucleotide,
FAICAR
Identifiers
  • 13018-54-7 ☒N
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEBI
  • CHEBI:18381 checkY
ChEMBL
  • ChEMBL521310 checkY
ChemSpider
  • 145893 checkY
MeSH 5-formamidoimidazole-4-carboxamide+ribotide
  • 166760
  • DTXSID50156384 Edit this at Wikidata
  • InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1 checkY
    Key: ABCOOORLYAOBOZ-KQYNXXCUSA-N checkY
  • InChI=1/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1
    Key: ABCOOORLYAOBOZ-KQYNXXCUBS
  • C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)NC=O)C(=O)N
  • O=P(O)(O)OC[C@H]2O[C@@H](n1cnc(C(=O)N)c1NC=O)[C@H](O)[C@@H]2O
Properties
C10H15N4O9P
Molar mass 366.223 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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Infobox references

References edit

  1. ^ USA.gov (2005-06-24). "FAICAR C10H15N4O9P". PubChem. National Center for Biotechnology Information. Retrieved 2022-07-09.