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).
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 CDK toolkit. 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
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.

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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
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 OPC-167832
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
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UniChem Compound Search for chemical match using the InChIKey XZISSTDXPBUCJA-DYESRHJHSA-N
UniChem Connectivity Search for chemical match using the InChIKey XZISSTDXPBUCJA-DYESRHJHSA-N