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

albitiazolium   Click here for help

GtoPdb Ligand ID: 10407

Synonyms: SAR97276 | SAR97276A | T3
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Albitiazolium was the clinical lead from the bisthiazolium series, a novel class of choline analogue with potent antimalarial activity [2-3].
We display the structure of the parent compound, with PubChem and ChEMBL links provided in the table below. However, the INN-assigned compound is in complex with bromide (represented in PubChem CID 11377022) and this compound is used in the experimental data listed under the 'biological activity' tab.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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 2
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 104.7
Molecular weight 454.27
XLogP 6.8
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
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 OCCc1sc[n+](c1C)CCCCCCCCCCCC[n+]1csc(c1C)CCO
Isomeric SMILES OCCc1sc[n+](c1C)CCCCCCCCCCCC[n+]1csc(c1C)CCO
InChI InChI=1S/C24H42N2O2S2/c1-21-23(13-17-27)29-19-25(21)15-11-9-7-5-3-4-6-8-10-12-16-26-20-30-24(14-18-28)22(26)2/h19-20,27-28H,3-18H2,1-2H3/q+2
InChI Key UZPXHZIQHWKNPF-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/)
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
IUPAC Name Click here for help
2-[3-[12-[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]dodecyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethanol
International Nonproprietary Names Click here for help
INN number INN
9162 albitiazolium bromide
Synonyms Click here for help
SAR97276 | SAR97276A | T3
Database Links Click here for help
CAS Registry No. 321915-72-4 (source: Scifinder)
ChEMBL Ligand CHEMBL1183040
GtoPdb PubChem SID 385612169
PubChem CID 11377023
Search Google for chemical match using the InChIKey UZPXHZIQHWKNPF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UZPXHZIQHWKNPF
Search PubMed clinical trials albitiazolium bromide
Search PubMed titles albitiazolium bromide
Search PubMed titles/abstracts albitiazolium bromide
UniChem Compound Search for chemical match using the InChIKey UZPXHZIQHWKNPF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UZPXHZIQHWKNPF-UHFFFAOYSA-N