5'-Phosphoribosyl-4-carboxy-5-aminoimidazole

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5'-Phosphoribosyl-4-carboxy-5-aminoimidazole

IUPAC name 5-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(phosphonooxymethyl)oxolan-2-yl]imidazole-4-carboxylic acid
Other names Carboxyaminoimidazole ribotide, Carboxyaminoimidazole ribonucleotide, CAIR, 5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid
Identifiers
CAS number	6001-14-5
PubChem	165388
ChemSpider	144983^Y
ChEBI	CHEBI:28413
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)N)C(=O)O O=P(O)(O)OC[C@H]2O[C@@H](n1cnc(C(=O)O)c1N)[C@H](O)[C@@H]2O
InChI InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1^Y Key: XFVULMDJZXYMSG-ZIYNGMLESA-N^Y InChI=1/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1 Key: XFVULMDJZXYMSG-ZIYNGMLEBD
Properties
Molecular formula	C₉H₁₄N₃O₉P
Molar mass	339.196 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'-Phosphoribosyl-4-carboxy-5-aminoimidazole (or CAIR) is an intermediate in the formation of purines.

It is formed by phosphoribosylaminoimidazole carboxylase.

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: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

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