GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

WQ-3810   Click here for help

GtoPdb Ligand ID: 14374

Compound class: Synthetic organic
Comment: WQ-3810 is a fluoroquinolone antibacterial compound, with broad-spectrum activity against Gram-negative and Gram-positive bacteria and against mycobacteria [1-4].
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 8
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 111.26
Molecular weight 461.44
XLogP 2.09
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)NC1CN(C1)C2=C(C)C3=C(C=C2F)C(=O)C(=CN3C4=NC(=C(C=C4F)F)N)C(=O)O
Isomeric SMILES CC1=C2C(=CC(=C1N3CC(C3)NC(C)C)F)C(=O)C(=CN2C4=C(C=C(C(=N4)N)F)F)C(=O)O
InChI InChI=1S/C22H22F3N5O3/c1-9(2)27-11-6-29(7-11)18-10(3)17-12(4-14(18)23)19(31)13(22(32)33)8-30(17)21-16(25)5-15(24)20(26)28-21/h4-5,8-9,11,27H,6-7H2,1-3H3,(H2,26,28)(H,32,33)
InChI Key MJMVUQNNSOBCGF-UHFFFAOYSA-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. Itoh K, Kuramoto Y, Amano H, Kazamori D, Yazaki A. (2015)
Discovery of WQ-3810: Design, synthesis, and evaluation of 7-(3-alkylaminoazetidin-1-yl)fluoro-quinolones as orally active antibacterial agents.
Eur J Med Chem, 103: 354-60. [PMID:26363871]
2. Kazamori D, Aoi H, Sugimoto K, Ueshima T, Amano H, Itoh K, Kuramoto Y, Yazaki A. (2014)
In vitro activity of WQ-3810, a novel fluoroquinolone, against multidrug-resistant and fluoroquinolone-resistant pathogens.
Int J Antimicrob Agents, 44 (5): 443-9. [PMID:25239276]
3. Ouchi Y, Mukai T, Koide K, Yamaguchi T, Park JH, Kim H, Yokoyama K, Tamaru A, Gordon SV, Nakajima C et al.. (2020)
WQ-3810: A new fluoroquinolone with a high potential against fluoroquinolone-resistant Mycobacterium tuberculosis.
Tuberculosis (Edinb), 120: 101891. [PMID:31778929]
4. Park JH, Yamaguchi T, Ouchi Y, Koide K, Mori S, Kim H, Mukai T, Nakajima C, Suzuki Y. (2020)
WQ-3810 inhibits DNA gyrase activity in ofloxacin-resistant Mycobacterium leprae.
J Infect Chemother, 26 (4): 335-342. [PMID:31839561]
5. Prasad NK, Seiple IB, Cirz RT, Rosenberg OS. (2022)
Leaks in the Pipeline: a Failure Analysis of Gram-Negative Antibiotic Development from 2010 to 2020.
Antimicrob Agents Chemother, 66 (5): e0005422. [PMID:35471042]