2018-19-1

Basic information

• Product Name: 6-AZAURIDINE-5'-MONOPHOSPHATE
• Synonyms: 6-AZAURIDINE-5'-MONOPHOSPHATE;6-Aza UMP;6-Azauridine 5'-phosphoric acid;[(2R,3S,4R,5R)-5-(3,5-diketo-1,2,4-triazin-2-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate;[(2R,3S,4R,5R)-5-(3,5-dioxo-1,2,4-triazin-2-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate;[(2R,3S,4R,5R)-5-(3,5-dioxo-1,2,4-triazin-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• CAS NO: 2018-19-1
• Molecular Formula: C8H12N3O9P
• Molecular Weight: 325.17
• Mol File: 2018-19-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 2.33g/cm³
• Refractive Index: 1.809
• CAS DataBase Reference: 6-AZAURIDINE-5'-MONOPHOSPHATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-AZAURIDINE-5'-MONOPHOSPHATE(2018-19-1)
• EPA Substance Registry System: 6-AZAURIDINE-5'-MONOPHOSPHATE(2018-19-1)

Safety Data

• Hazardous Substances Data: 2018-19-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12N3O9P/c12-4-1-9-11(8(15)10-4)7-6(14)5(13)3(20-7)2-19-21(16,17)18/h1,3,5-7,13-14H,2H2,(H,10,12,15)(H2,16,17,18)/t3-,5-,6-,7-/m1/s1

Upstream product

• 56-65-5 ATP 
• 54-25-1 6-Azauridine 

Relevant articles and documents

Design of inhibitors of orotidine monophosphate decarboxylase using bioisosteric replacement and determination of inhibition kinetics

Inhibitors of orotidine monophosphate decarboxylase (ODCase) have applications in RNA viral, parasitic, and other infectious diseases. ODCase catalyzes the decarboxylation of orotidine monophosphate (OMP), producing uridine monophosphate (UMP). Novel inhibitors 6-amino-UMP and 6-cyano-UMP were designed on the basis of the substructure volumes in the substrate OMP and in an inhibitor of ODCase, barbituric acid monophosphate, BMP. A new enzyme assay method using isothermal titration calorimetry (ITC) was developed to investigate the inhibition kinetics of ODCase. The reaction rates were measured by monitoring the heat generated during the decarboxylation reaction of orotidine monophosphate. Kinetic parameters (kcat = 21 s-1 and KM = 5 μM) and the molar enthalpy (ΔHapp = 5 kcal/mol) were determined for the decarboxylation of the substrate by ODCase. Competitive inhibition of the enzyme was observed and the inhibition constants (Ki) were determined to be 12.4 μm and 29 μM for 6-aza-UMP and 6-cyano-UMP, respectively. 6-Amino-UMP was found to be among the potent inhibitors of ODCase, having an inhibition constant of 840 nM. We reveal here the first inhibitors of ODCase designed by the principles of bioisosterism and a novel method of using isothermal calorimetry for enzyme inhibition studies.