timcodar   Click here for help

GtoPdb Ligand ID: 10868

Synonyms: VX-853 | VX853
Compound class: Synthetic organic
Comment: Timcodar (VX-853) is a pyridine compound that was developed by Vertex Pharmaceuticals. It acts as a mammalian and bacterial efflux pump inhibitor. It was proposed to enhance activity of antibacterials such as rifampin, by inhibiting their efflux via bacterial efflux pumps [1,3]. It was also investigated for potential to prevent efflux of chemotherapy drugs, to enhance cancer treatment, and has been proposed as a possible antiobesity therapy [2].
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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Click here for structure editor
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 7
Hydrogen bond donors 0
Rotatable bonds 20
Topological polar surface area 111.16
Molecular weight 748.3
XLogP 6.26
No. Lipinski's rules broken 2

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 COc1cc(cc(c1OC)OC)C(=O)C(=O)N([C@H](C(=O)N(C(CCc1ccncc1)CCc1ccncc1)Cc1ccccc1)Cc1ccc(cc1)Cl)C
Isomeric SMILES COc1cc(cc(c1OC)OC)C(=O)C(=O)N([C@H](C(=O)N(C(CCc1ccncc1)CCc1ccncc1)Cc1ccccc1)Cc1ccc(cc1)Cl)C
InChI InChI=1S/C43H45ClN4O6/c1-47(43(51)40(49)34-27-38(52-2)41(54-4)39(28-34)53-3)37(26-32-10-14-35(44)15-11-32)42(50)48(29-33-8-6-5-7-9-33)36(16-12-30-18-22-45-23-19-30)17-13-31-20-24-46-25-21-31/h5-11,14-15,18-25,27-28,36-37H,12-13,16-17,26,29H2,1-4H3/t37-/m0/s1
InChI Key MQSMWZHHUGSULF-QNGWXLTQSA-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
(2S)-N-benzyl-3-(4-chlorophenyl)-N-(1,5-dipyridin-4-ylpentan-3-yl)-2-[methyl-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]amino]propanamide
International Nonproprietary Names Click here for help
INN number INN
7807 timcodar
Synonyms Click here for help
VX-853 | VX853
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Timcodar
Other databases
BindingDB Ligand 50388313
CAS Registry No. 179033-51-3 (source: WHO INN record)
ChEMBL Ligand CHEMBL2059028
DrugBank Ligand DB12761
GtoPdb PubChem SID 405560309
PubChem CID 9811664
Search Google for chemical match using the InChIKey MQSMWZHHUGSULF-QNGWXLTQSA-N
Search Google for chemicals with the same backbone MQSMWZHHUGSULF
Search PubMed clinical trials timcodar
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Search PubMed titles/abstracts timcodar
UniChem Compound Search for chemical match using the InChIKey MQSMWZHHUGSULF-QNGWXLTQSA-N
UniChem Connectivity Search for chemical match using the InChIKey MQSMWZHHUGSULF-QNGWXLTQSA-N