Showing Metabocard for 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate (BASm0006225)
| Common Name | 5-amino-1-(5-phospho-d-ribosyl)imidazole-4-carboxylate |
|---|---|
| Description | N5-carboxyaminoimidazole ribonucleotide is a member of the chemical class known as 1-Phosphoribosyl-imidazoles. These are organic compounds containing the imidazole ring linked to a ribose phosphate through a 1-2 bond. The carbamic acid, N5-carboxyaminoimidazole ribonucleotide (N5-CAIR) is an intermediate in purine biosynthesis in E. coli. (PMID 7918411 ) Formation of 4-carboxy-5-aminoimidazole ribonucleotide (CAIR) in the purine pathway in most prokaryotes requires ATP, HCO3-, aminoimidazole ribonucleotide (AIR), and the gene products PurK and PurE. PurK catalyzes the conversion of AIR to N5-carboxyaminoimidazole ribonucleotide (N5-CAIR) in a reaction that requires both ATP and HCO3-. PurE catalyzes the unusual rearrangement of N5-CAIR to CAIR. |
| Structure | |
| Molecular Formula | C9H14N3O9P |
| Average Mass | 339.19590 |
| Monoisotopic Mass | 339.04677 |
| IUPAC Name | 5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-1H-imidazole-4-carboxylate |
| Traditional Name | 5-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}imidazole-4-carboxylate |
| CAS Registry Number | Not Available |
| SMILES | Nc1c(C(=O)[O-])[nH+]cn1[C@@H]1O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]1O |
| InChI Identifier | InChI=1S/C9H14N3O9P/c13-6-4(2-20-22(17,18)19)21-8(7(6)14)12-3-10-1-5(12)11-9(15)16/h1,3-4,6-8,11,13-14H,2H2,(H,15,16)(H2,17,18,19) |
| InChI Key | JHLXDWGVSYMXPL-UHFFFAOYSA-N |
| CHEBI ID | CHEBI:77657 |
| HMDB ID | HMDB12268 |
| State | Not Available |
| Water Solubility | 3.70e+00 g/l |
| logP | -1.96 |
| logS | -1.98 |
| pKa (Strongest Acidic) | Not Available |
| pKa (Strongest Basic) | Not Available |
| Hydrogen Acceptor Count | 10 |
| Hydrogen Donor Count | 5 |
| Polar Surface Area | 200.42 Ų |
| Rotatable Bond Count | 5 |
| Physiological Charge | Not Available |
| Formal Charge | -1 |
| Refractivity | 78.16 m³·mol⁻¹ |
| Polarizability | 27.83 |