5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid

• ChemBase ID: 125463
• Molecular Formular: C9H14N3O9P
• Molecular Mass: 339.195921
• Monoisotopic Mass: 339.04676567
• SMILES: O=P(O)(O)OC[C@H]1O[C@@H](n2cnc(C(=O)O)c2N)[C@H](O)[C@@H]1O
• Canonical SMILES: O[C@@H]1[C@H](O)[C@H](O[C@H]1n1cnc(c1N)C(=O)O)COP(=O)(O)O
• 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
• InChIKey: XFVULMDJZXYMSG-ZIYNGMLESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid
• IUPAC Traditional name: 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid
• Synonyms: Carboxyaminoimidazole ribotide; Carboxyaminoimidazole ribonucleotide; CAIR; 5-amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid; 5'-Phosphoribosyl-4-carboxy-5-aminoimidazole

Database IDs

• CAS Number: 6001-14-5
• PubChem SID: 162219813
• PubChem CID: 165388
• CHEBI ID: 28413
• Chemspider ID: 144983
• Wikipedia Title: 5'-Phosphoribosyl-4-carboxy-5-aminoimidazole

CALCULATED PROPERTIES

• Acid pKa: 1.1680692
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -5.604776
• LogD (pH = 7.4): -7.1916585
• Log P: -3.7563503
• Molar Refractivity: 67.3199 cm^3
• Polarizability: 26.627869 Å^3
• Polar Surface Area: 197.59 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false