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

CAS NumberN

3D model (JSmol)

ChEBIY

ChEMBLY

ChemSpiderY

MeSH

PubChem CID

CompTox Dashboard (EPA)

InChI 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/s1YKey: ABCOOORLYAOBOZ-KQYNXXCUSA-NYInChI=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/s1Key: ABCOOORLYAOBOZ-KQYNXXCUBS

SMILES C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)NC=O)C(=O)NO=P(O)(O)OC[C@H]2O[C@@H](n1cnc(C(=O)N)c1NC=O)[C@H](O)[C@@H]2O

Properties

Chemical formulaC10H15N4O9P

Molar mass366.223 g·mol−1

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

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.