ferroquine   Click here for help

GtoPdb Ligand ID: 9972

Synonyms: SSR97193
Antimalarial Ligand
Compound class: Synthetic organic
Comment: Ferroquine is a 4-aminoquinoline antimalarial compound with a novel ferrocenic group in its side chain.
The ferrocenic group causes rendering problems, with different images of the chemical structure found across web resources. We show the structure provided by NIH US National Library of Medicine (InChIKey IRJOHJGUSPNBRI-UHFFFAOYSA-N). PubChem provide a different InChIKey DLYPREQTTOHKSM-UHFFFAOYSA-N with two structural representations PubChem CID 56841801 (link in table below) and PubChem CID 76419023.

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 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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 28.16
Molecular weight 433.1
XLogP 2.62
No. Lipinski's rules broken 0
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.

✖
Canonical SMILES CN(CC1=C(CNc2ccnc3c2ccc(c3)Cl)C=C(C1)[Fe]C1=CC=CC1)C
Isomeric SMILES CN(CC1=C(CNc2ccnc3c2ccc(c3)Cl)C=C(C1)[Fe]C1=CC=CC1)C
InChI InChI=1S/C18H19ClN3.C5H5.Fe/c1-22(2)12-14-5-3-4-13(14)11-21-17-8-9-20-18-10-15(19)6-7-16(17)18;1-2-4-5-3-1;/h4,6-10H,5,11-12H2,1-2H3,(H,20,21);1-3H,4H2;
InChI Key IRJOHJGUSPNBRI-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Ligand families/groups Antimalarial ligands
International Nonproprietary Names Click here for help
INN number INN
8774 ferroquine
Synonyms Click here for help
SSR97193
Database Links Click here for help
CAS Registry No. 185055-67-8 (source: Scifinder)
GtoPdb PubChem SID 374883859
PubChem CID 56841801
Search Google for chemical match using the InChIKey IRJOHJGUSPNBRI-UHFFFAOYSA-N
Search Google for chemicals with the same backbone IRJOHJGUSPNBRI
Search PubMed clinical trials ferroquine
Search PubMed titles ferroquine
Search PubMed titles/abstracts ferroquine
UniChem Compound Search for chemical match using the InChIKey IRJOHJGUSPNBRI-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey IRJOHJGUSPNBRI-UHFFFAOYSA-N