CCR2-RA-[R]   Click here for help

GtoPdb Ligand ID: 9431

Synonyms: analog 49 (Dasse et al., 2007) [1]
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: CCR2-RA-[R] is an allosteric antagonist of the CC chemokine receptor 2 (CCR2) [1]. Allosteric modulation by CCR2-RA-[R] prevents formation of the G-protein-binding interface and hence G-protein coupling by blocking the required activation-associated changes in receptor conformation [3]. The chemical structure presented here is that held with the PDB X-ray structure reported in [3].
CCR2-RA-[R] is claimed as chiral example 125 in patent US6936633 [4].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 57.61
Molecular weight 351.1
XLogP 5.09
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES Clc1ccc(c(c1)F)N1C(C2CCCCC2)C(=C(C1=O)O)C(=O)C
Isomeric SMILES Clc1ccc(c(c1)F)N1[C@H](C2CCCCC2)C(=C(C1=O)O)C(=O)C
InChI InChI=1S/C18H19ClFNO3/c1-10(22)15-16(11-5-3-2-4-6-11)21(18(24)17(15)23)14-8-7-12(19)9-13(14)20/h7-9,11,16,23H,2-6H2,1H3/t16-/m1/s1
InChI Key VQNLJXWZGVRLBA-MRXNPFEDSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-3-acetyl-1-(4-chloro-2-fluorophenyl)-2-cyclohexyl-4-hydroxy-2H-pyrrol-5-one
Synonyms Click here for help
analog 49 (Dasse et al., 2007) [1]
Database Links Click here for help
GtoPdb PubChem SID 328083531
PubChem CID 12093170
RCSB PDB Ligand VT5
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SynPHARM 84096 (in complex with CCR2)