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

• ChemBase ID: 133113
• Molecular Formular: C9H15N4O8P
• Molecular Mass: 338.211161
• Monoisotopic Mass: 338.06275009
• SMILES: c1nc(c(n1C1C(C(C(O1)COP(=O)(O)O)O)O)N)C(=O)N
• Canonical SMILES: OC1C(O)C(OC1n1cnc(c1N)C(=O)N)COP(=O)(O)O
• InChI: InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)
• InChIKey: NOTGFIUVDGNKRI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: aicar
• Synonyms: AICAR monophosphate; N1-(β-D-5′-Phosphoribofuranosyl)-5-aminoimidazole-4-carboxamide; NSC 283955; NSC 292227; ZMP; 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate

Database IDs

• CAS Number: 3031-94-5
• EC Number: 221-212-1
• MDL Number: MFCD00057264
• PubChem SID: 162227390; 24890538
• PubChem CID: 200

CALCULATED PROPERTIES

• Acid pKa: 1.224594
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.096153
• LogD (pH = 7.4): -6.211966
• Log P: -4.8124127
• Molar Refractivity: 69.1421 cm^3
• Polarizability: 27.062012 Å^3
• Polar Surface Area: 203.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥93%

DETAILS

Sigma Aldrich - A1393

Biochem/physiol Actions
A 5′-phosphorylated analog of cell permeable AICAR that mimics AMP. AMPK (AMP-activated protein kinase) activator.
Application
AICAR monophosphate is a 5′′-phosphorylated analog of cell permeable AICAR that mimics AMP. AICAR is an adenosine monophophate (AMP)-activated protein kinase (AMPK) activator/agonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A1393.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.