| Identification | Back Directory | [Name]
CHIR-090 | [CAS]
728865-23-4 | [Synonyms]
CS-2285
CHIR-090
CHIR-090 (CHIR 090
N-[(1S,2R)-2-Hydroxy-1-[(hydroxyamino)carbonyl]propyl]-4-[[4-(4-morpholinylmethyl)phenyl]ethynyl]benzamide
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide
Benzamide, N-[(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl]-4-[2-[4-(4-morpholinylmethyl)phenyl]ethynyl]-
N-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morphChemicalbookolin-4-ylmethyl)phenyl]ethynyl]benzamide | [Molecular Formula]
C24H27N3O5 | [MDL Number]
MFCD22665727 | [MOL File]
728865-23-4.mol | [Molecular Weight]
437.488 |
| Chemical Properties | Back Directory | [Description]
CHIR-090 is the first reported compound that in fact kills both E. coli and Pseudomonas aeruginosa in bacterial disk diffusion assays (Liang et al. 2011). Nonetheless, CHIR-090 was about 600-fold less effective against LpxC orthologs from the Rhizobiaceae family than against E. coli LpxC. In this way, studies have shown that the removal of morpholine ring, based on a chemical scaffold of reduced radius, was able to increase affinity by 20-fold for LpxC enzymes from the Rhizobiaceae family of bacteria and enhance the antibiotic activity against E. coli and P. aeruginosa by 2–4 fold over CHIR-090. | [density ]
1.33±0.1 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
≥21.85 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O | [form ]
solid | [pka]
9.11±0.40(Predicted) | [color ]
White to off-white |
| Hazard Information | Back Directory | [Definition]
ChEBI: CHIR-090 is an L-threonine derivative obtained by formal condensation of the carboxy group of 4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzoic acid with the amino group of N-hydroxy-L-threoninamide. It has a role as an antimicrobial agent, a lipopolysaccharide biosynthesis inhibitor and an EC 3.5.1.108 (UDP-3-O-acyl-N-acetylglucosamine deacetylase) inhibitor. It is an acetylenic compound, a member of morpholines, a member of benzamides, a L-threonine derivative and a hydroxamic acid. | [target]
LpxC |
|
|