quabodepistat   Click here for help

GtoPdb Ligand ID: 13059

Synonyms: OPC-167832
Compound class: Synthetic organic
Comment: Quabodepistat is a 3,4-dihydrocarbostyril derivative. It is an inhibitor of decaprenylphosphoryl-beta-D-ribose oxidase (DprE1), an essential mycobacterial cell wall biosynthesis enzyme, and has potent antimycobacterial activity [3]. Quabodepistat is under clinical development by Otsuka Pharmaceutical (Tokyo, Japan) as a treatment for tuberculosis (TB).

quabodepistat is commercially available from our sponsors

2D Structure
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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.

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Physico-chemical Properties
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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.

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Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 4
Topological polar surface area 82.03
Molecular weight 456.84
XLogP 1.68
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
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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/)

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Canonical SMILES C1CC(=O)NC2=C1C(=CC=C2F)OC[C@@]3(CCN(C[C@H]3O)C4=C(C=C(C=C4F)Cl)F)O
Isomeric SMILES C1CC(=O)NC2=C(C=CC(=C21)OC[C@@]3(CCN(C[C@H]3O)C4=C(C=C(C=C4F)Cl)F)O)F
InChI InChI=1S/C21H20ClF3N2O4/c22-11-7-14(24)20(15(25)8-11)27-6-5-21(30,17(28)9-27)10-31-16-3-2-13(23)19-12(16)1-4-18(29)26-19/h2-3,7-8,17,28,30H,1,4-6,9-10H2,(H,26,29)/t17-,21-/m1/s1
InChI Key XZISSTDXPBUCJA-DYESRHJHSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
5-[[(3R,4R)-1-(4-chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy]-8-fluoro-3,4-dihydro-1H-quinolin-2-one
International Nonproprietary Names Click here for help
INN number INN
11737 quabodepistat
Synonyms Click here for help
OPC-167832
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Quabodepistat
Other databases
CAS Registry No. 1883747-71-4 (source: Scifinder)
ChEMBL Ligand CHEMBL5095080
DrugBank Ligand DB17770
GtoPdb PubChem SID 491299841
PubChem CID 118904282
Search Google for chemical match using the InChIKey XZISSTDXPBUCJA-DYESRHJHSA-N
Search Google for chemicals with the same backbone XZISSTDXPBUCJA
Search PubMed clinical trials quabodepistat
Search PubMed titles quabodepistat
Search PubMed titles/abstracts quabodepistat
UniChem Compound Search for chemical match using the InChIKey XZISSTDXPBUCJA-DYESRHJHSA-N
UniChem Connectivity Search for chemical match using the InChIKey XZISSTDXPBUCJA-DYESRHJHSA-N

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

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MedChemExpress
Quabodepistat (links to external site)
Cat. No. HY-134940