5-Formamidoimidazole-4-carboxamide ribotide

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5-Formamidoimidazole-4-carboxamide ribotide

IUPAC name [(2R,3S,4R,5R)-5-(4-Carbamoyl-5-formamidoimidazol-1-yl)- 3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names 5-Formamidoimidazole-4-carboxamide ribonucleotide, FAICAR
Identifiers
CAS number	13018-54-7
PubChem	166760
ChemSpider	145893^Y
MeSH	5-formamidoimidazole-4-carboxamide+ribotide
ChEBI	CHEBI:18381^Y
ChEMBL	CHEMBL521310^Y
Jmol-3D images	Image 1 Image 2
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)N O=P(O)(O)OC[C@H]2O[C@@H](n1cnc(C(=O)N)c1NC=O)[C@H](O)[C@@H]2O
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/s1^Y Key: ABCOOORLYAOBOZ-KQYNXXCUSA-N^Y 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
Properties
Molecular formula	C₁₀H₁₅N₄O₉P
Molar mass	366.22 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

Nucleotide metabolic intermediates

Purine metabolism

Anabolism	R5P→IMP: R5P · PRPP · PRA · GAR · FGAR · FGAM · AIR · CAIR · SAICAR · AICAR · FAICAR IMP→AMP: Adenylosuccinate IMP→GMP: Xanthosine monophosphate

Catabolism	Hypoxanthine · Xanthine · Uric acid · 5-Hydroxyisourate

Pyrimidine metabolism

Anabolism	Carbamoyl phosphate · Carbamoyl aspartic acid · 4,5-Dihydroorotic acid · Orotic acid · Orotidine 5'-monophosphate · Uridine monophosphate

Catabolism	uracil: Dihydrouracil · 3-Ureidopropionic acid · β-Alanine thymine: Dihydrothymine · β-Ureidoisobutyric acid · 3-Aminoisobutyric acid

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

biochemical families: proteins (amino acids/intermediates) · nucleic acids (constituents/intermediates) · carbohydrates (glycoproteins, alcohols, glycosides)
lipids (fatty acids/intermediates, phospholipids, steroids, sphingolipids, eicosanoids) · tetrapyrroles/intermediates

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5-Formamidoimidazole-4-carboxamide ribotide