SML3092

CHIR-090

≥98% (HPLC), LpxC inhibitor, powder

• Synonym(s): CHIR 090, CHIR090, N-((2S,3R)-3-Hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl)-4-((4-(morpholinomethyl)phenyl)ethynyl)benzamide, N-[(1S,2R)-2-Hydroxy-1-[(hydroxyamino)carbonyl]propyl]-4-[2-[4-(4-morpholinylmethyl)phenyl]ethynyl]benzamide
• Empirical Formula (Hill Notation): C₂₄H₂₇N₃O₅
• CAS Number: 728865-23-4
• Molecular Weight: 437.49
• NACRES: NA.77
• UNSPSC Code: 51111800
• MDL number: MFCD22665727
• Assay: ≥98% (HPLC)
• Form: powder

Properties

• Product Name: CHIR-090, ≥98% (HPLC)
• Quality Segment: 100
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: −20°C
• SMILES string: C[C@H]([C@@H](C(NO)=O)NC(C1=CC=C(C=C1)C#CC2=CC=C(C=C2)CN3CCOCC3)=O)O
• InChI: 1S/C24H27N3O5/c1-17(28)22(24(30)26-31)25-23(29)21-10-8-19(9-11-21)3-2-18-4-6-20(7-5-18)16-27-12-14-32-15-13-27/h4-11,17,22,28,31H,12-16H2,1H3,(H,25,29)(H,26,30)/t17-,22+/m1/s1
• InChI key: FQYBTYFKOHPWQT-VGSWGCGISA-N

Description

Biochem/physiol Actions

CHIR-090 is a potent, tight-binding inhibitor against LpxC, the zinc-dependent UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase essential for gram negative bacteria lipid A biosynthesis (98% inhibition of E. coli & A. aeolicus LpxC by 0.5 μg/mL (1.15 μM) CHIR-090 at pH 7.4; A. aeolicus LpxC Ki = 1.0-1.7 nM). CHIR-090 possesses remarkable antibiotic activity comparable to that of ciprofloxacin against P. aeruginosa PAO1 as well as E. coli R477 and R477 [LpxC G17S] strains by antibacterial disk tests (20 μg/2 μL per spot).

Potent, tight-binding LpxC inhibitor with remarkable antibiotic activity comparable to that of ciprofloxacin.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable