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bulaquine   Click here for help

GtoPdb Ligand ID: 10414

Synonyms: CDRI-80/53 | elubaquine
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Bulaquine is an 8-aminoquinoline derivative that has antimalarial activity and is a synthetic analogue of primaquine.
The INN record for bulaquine indicates that it is a racemic mixture.

The Malaria tab on this ligand page provides additional curator comments of relevance to the Guide to MALARIA PHARMACOLOGY.
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 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 72.48
Molecular weight 369.21
XLogP 3.37
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 COc1cc(NC(CCCNC(=C2CCOC2=O)C)C)c2c(c1)cccn2
Isomeric SMILES COc1cc(NC(CCCN/C(=C/2\CCOC2=O)/C)C)c2c(c1)cccn2
InChI InChI=1S/C21H27N3O3/c1-14(6-4-9-22-15(2)18-8-11-27-21(18)25)24-19-13-17(26-3)12-16-7-5-10-23-20(16)19/h5,7,10,12-14,22,24H,4,6,8-9,11H2,1-3H3/b18-15+
InChI Key ADCOUXIGWFEYJP-OBGWFSINSA-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
(3E)-3-[1-[4-[(6-methoxyquinolin-8-yl)amino]pentylamino]ethylidene]oxolan-2-one
International Nonproprietary Names Click here for help
INN number INN
7927 bulaquine
Synonyms Click here for help
CDRI-80/53 | elubaquine
Database Links Click here for help
CAS Registry No. 79781-00-3 (source: Scifinder)
ChEMBL Ligand CHEMBL2106578
GtoPdb PubChem SID 385612174
PubChem CID 3036820
Search Google for chemical match using the InChIKey ADCOUXIGWFEYJP-OBGWFSINSA-N
Search Google for chemicals with the same backbone ADCOUXIGWFEYJP
Search PubMed clinical trials bulaquine
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Search PubMed titles/abstracts bulaquine
UniChem Compound Search for chemical match using the InChIKey ADCOUXIGWFEYJP-OBGWFSINSA-N
UniChem Connectivity Search for chemical match using the InChIKey ADCOUXIGWFEYJP-OBGWFSINSA-N