5-amino-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide

• ChemBase ID: 75709
• Molecular Formular: C9H14N4O5
• Molecular Mass: 258.23126
• Monoisotopic Mass: 258.09641957
• SMILES: n1([C@H]2O[C@@H](CO)[C@@H]([C@@H]2O)O)c(c(C(=O)N)nc1)N
• Canonical SMILES: OC[C@@H]1O[C@@H]([C@H]([C@H]1O)O)n1cnc(c1N)C(=O)N
• InChI: InChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m0/s1
• InChIKey: RTRQQBHATOEIAF-GIMIYPNGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide
• IUPAC Traditional name: 5-amino-1-[(2S,3S,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
• Synonyms: AICAR; 5-Amino-1H-imidazole-4-carboxamide-1-beta-D-ribofuranoside

Database IDs

• CAS Number: 2627-69-2
• MDL Number: MFCD00869751
• PubChem SID: 162040627
• PubChem CID: 54285342

CALCULATED PROPERTIES

• Acid pKa: 12.449647
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -2.6328213
• LogD (pH = 7.4): -2.5593672
• Log P: -2.5583196
• Molar Refractivity: 58.2692 cm^3
• Polarizability: 22.46471 Å^3
• Polar Surface Area: 156.85 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 214-215°C

Safety Information

• Storage Warning: Irritant/Hygroscopic/Store under Argon/Store at -20°C