bindarit   

GtoPdb Ligand ID: 11124

Synonyms: AF-2838 | AF2838
Compound class: Synthetic organic
Comment: Bindarit is a compound with anti-inflammatory activity. In vitro, that is primarily associated with an inhibition of MCP-1 (CCL2) production and subsequent reduction in monocyte recruitment and differentiation. It has been shown to directly interact with fatty acid binding protein 4 (FABP4) and this is proposed to underlie its mechanism of action [1]. In this mechanism bindarit modulates the phosphorylation state of p38α and AKT2 and selectively increases FABP4 expression, all in a PPARγ-dependent manner, and these effects are associated with a decrease in MCP-1 production.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 64.35
Molecular weight 324.15
XLogP 3.34
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OC(=O)C(OCc1nn(c2c1cccc2)Cc1ccccc1)(C)C
Isomeric SMILES OC(=O)C(OCc1nn(c2c1cccc2)Cc1ccccc1)(C)C
InChI InChI=1S/C19H20N2O3/c1-19(2,18(22)23)24-13-16-15-10-6-7-11-17(15)21(20-16)12-14-8-4-3-5-9-14/h3-11H,12-13H2,1-2H3,(H,22,23)
InChI Key MTHORRSSURHQPZ-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
IUPAC Name
2-[(1-benzylindazol-3-yl)methoxy]-2-methylpropanoic acid
International Nonproprietary Names
INN number INN
6689 bindarit
Synonyms
AF-2838 | AF2838
Database Links
CAS Registry No. 130641-38-2 (source: WHO INN record)
ChEMBL Ligand CHEMBL2107549
DrugBank Ligand DB12739
GtoPdb PubChem SID 434122184
PubChem CID 71354
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