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CHIR-090

CAT: 0013-GTR19160259-01Size: 1 gDry Ice: NoHazardous: No
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CAT#:0013-GTR19160259-01Size:1 g
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Description
CHIR-090 is a very potent and selective LpxC inhibitor. CHIR-090 has excellent antibiotic activity against Pseudomonas aeruginosa and Escherichia coli. CHIR-090 is also a two-step slow, tight-binding inhibitor of E. coli LpxC with Ki = 4.0 nM, Ki* = 0.5 nM, k5 = 1.9 min-1, and k6 = 0.18 min-1. CHIR-090 at low nanomolar levels inhibits LpxC orthologues from diverse Gram-negative pathogens, including P. aeruginosa, Neisseria meningitidis, and Helicobacter pylori. In contrast, CHIR-090 is a relatively weak competitive and conventional inhibitor (lacking slow, tight-binding kinetics) of LpxC from Rhizobium leguminosarum (Ki = 340 nM), a Gram-negative plant endosymbiont that is resistant to this compound. CHIR-090 is an excellent lead for the further development of new antibiotics targeting the lipid A pathway.
CAS Number
728865-23-4
Product Name Alternative
CHIR-090 | CHIR 090 | CHIR090
Purity
>98% (HPLC)
Solubility
DMSO : ≥ 30 mg/mL; 68.57 mM
Smiles
ONC (=O) [C@@H] (NC (=O) c1ccc (cc1) C#Cc1ccc (cc1) CN1CCOCC1) [C@@H] (C) O
Molecular Formula
C24H27N3O5
Molecular Weight
437.19
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
N-[ (2S,3R) -3-hydroxy-1- (hydroxyamino) -1-oxobutan-2-yl]-4-[2-[4- (morpholin-4-ylmethyl) phenyl]ethynyl]benzamide

Chemical Information

Chir-090

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 a lipopolysaccharide biosynthesis inhibitor, an EC 3.5.1.108 (UDP-3-O-acyl-N-acetylglucosamine deacetylase) inhibitor and an antimicrobial agent. It is a member of benzamides, a hydroxamic acid, a member of morpholines, an acetylenic compound and a L-threonine derivative.

CAS Number728865-23-4
PubChem CID11546620
IUPAC NameN-[(2S,3R)-3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl]benzamide
Molecular FormulaC24H27N3O5
Molecular Weight437.5
XLogP1.3
Topological Polar Surface Area111
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Heavy Atom Count32
Formal Charge0
Complexity680
SMILES
C[C@H]([C@@H](C(=O)NO)NC(=O)C1=CC=C(C=C1)C#CC2=CC=C(C=C2)CN3CCOCC3)O
InChI
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
InChIKey
FQYBTYFKOHPWQT-VGSWGCGISA-N
Chemical Structure
2D Structure
2D structure of Chir-090
CAS: 728865-23-4
CID: 11546620
Formula: C24H27N3O5
MW: 437.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight437.5
XLogP31.3
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Exact Mass437.19507097
Monoisotopic Mass437.19507097
Topological Polar Surface Area111 Ų
Heavy Atom Count32
Formal Charge0
Complexity680
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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Alternative Products

CatalogName
MBS131423CHIR-090 (CHIR 090; CHIR090)
B1852-25CHIR-090
A12365-50CHIR-090 50mg
A12365-500CHIR-090 500mg
A12365-25CHIR-090 25mg
A12365-10CHIR-090 10mg
A12365-5CHIR-090 5mg
HY-15460R-01CHIR-090 (Standard)
A12365-100CHIR-090 100mg

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