ACHN-975   Click here for help

GtoPdb Ligand ID: 13333

PDB Ligand
Compound class: Synthetic organic
Comment: ACHN-975 is a hydroxamate-based inhibitor of bacterial UDP-3-O-acyl-N-acetylglucosamine deacetylase (LpxC) and first-in-class to advance to clinical evaluation [2].
2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 5
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 124.68
Molecular weight 369.42
XLogP 0.54
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
Canonical SMILES CC(C)([C@@H](C(=O)NO)NC(=O)C1=CC=C(C#CC#C[C@@H]2C[C@H]2CO)C=C1)N
Isomeric SMILES CC(C)([C@@H](C(=O)NO)NC(=O)C1=CC=C(C=C1)C#CC#C[C@@H]2C[C@H]2CO)N
InChI InChI=1S/C20H23N3O4/c1-20(2,21)17(19(26)23-27)22-18(25)14-9-7-13(8-10-14)5-3-4-6-15-11-16(15)12-24/h7-10,15-17,24,27H,11-12,21H2,1-2H3,(H,22,25)(H,23,26)/t15-,16+,17-/m1/s1
InChI Key GOCUUDXEOKIQRU-IXDOHACOSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Erwin AL. (2016)
Antibacterial Drug Discovery Targeting the Lipopolysaccharide Biosynthetic Enzyme LpxC.
Cold Spring Harb Perspect Med, 6 (7). [PMID:27235477]
2. Krause KM, Haglund CM, Hebner C, Serio AW, Lee G, Nieto V, Cohen F, Kane TR, Machajewski TD, Hildebrandt D et al.. (2019)
Potent LpxC Inhibitors with In Vitro Activity against Multidrug-Resistant Pseudomonas aeruginosa.
Antimicrob Agents Chemother, 63 (11). [PMID:31451507]
3. Niu Z, Lei P, Wang Y, Wang J, Yang J, Zhang J. (2023)
Small molecule LpxC inhibitors against gram-negative bacteria: Advances and future perspectives.
Eur J Med Chem, 253: 115326. [PMID:37023679]
4. Raetz CR. (1993)
Bacterial endotoxins: extraordinary lipids that activate eucaryotic signal transduction.
J Bacteriol, 175 (18): 5745-53. [PMID:8376321]
5. Raetz CR, Guan Z, Ingram BO, Six DA, Song F, Wang X, Zhao J. (2009)
Discovery of new biosynthetic pathways: the lipid A story.
J Lipid Res, 50 Suppl (Suppl): S103-8. [PMID:18974037]