({[({[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

• ChemBase ID: 160203
• Molecular Formular: C9H17N4O14P3
• Molecular Mass: 498.170963
• Monoisotopic Mass: 497.99541113
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1cnc(c1N)C(=O)N)COP(=O)(OP(=O)(O)OP(=O)(O)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1cnc(c1N)C(=O)N
• InChI: InChI=1S/C9H17N4O14P3/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(25-9)1-24-29(20,21)27-30(22,23)26-28(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H,20,21)(H,22,23)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
• InChIKey: OCDLJXCWVQPFCK-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: 5-Amino-1-[5-O-[hydroxy[[hydroxy(phosphonooxy)phosphinyl]oxy]phosphinyl]-β-D-ribofuranosyl]-1H-Imidazole-4-carboxamide; 5-Amino-4-imidazolecarboxamide riboside 5'-triphosphate; ZTP; AICAR Triphosphate; 5-Aminoimidazole-4-carboxamide-1-β-D-Ribofuranosyl 5'-Triphosphate; AICAR Monophosphate; 5-Aminoimidazole-4-carboxamide-1-β-D-Ribofuranosyl 5'-Monophosphate

Database IDs

• CAS Number: 3031-94-5; 82989-82-0
• PubChem SID: 162254338
• PubChem CID: 128476

CALCULATED PROPERTIES

• Acid pKa: 0.8952274
• H Acceptors: 13
• H Donor: 8
• LogD (pH = 5.5): -10.173806
• LogD (pH = 7.4): -10.935304
• Log P: -5.558034
• Molar Refractivity: 90.8879 cm^3
• Polarizability: 36.673523 Å^3
• Polar Surface Area: 296.44 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White to Light Pink Solid
• Melting Point: >160°C dec.

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A611765

A phosphorylated derivative of AICAR monophosphate (A611705) or ZMP. Accumulates in microorganisms when there is a depletion of folate intermediates needed to metabolize ZMP to inosine monophosphate (IMP).

REFERENCES

• Sidi, Y. et al.: J. Clinic. Inv., 76, 2416 (1985)
• Mullane, K., et al.: Trends Cardiovasc Med., 3, 227 (1985)
• Browne, G.J., et al.: J. Biol. Chem., 279, 13, 12220 (2004)