CCR5 antagonist 34   

GtoPdb Ligand ID: 10106

Compound class: Synthetic organic
Comment: This CCR5 antagonist was designed to overcome some of the detrimental issues associated with the approved CCR5 antagonist maraviroc (an HIV entry inhibitor drug;) such as CYP450 inhibition, hERG inhibition and viral resistance [2]. It is one of the chemical structures claimed in patent WO2015101265A1 belonging to the Shanghai Institute of Materia Medica [1].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 9
Topological polar surface area 91.29
Molecular weight 519.28
XLogP 6.21
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES O=C(C1CCC(CC1)(F)F)NC(c1ccsc1)CCN1C2CCC1CC(C2)n1c(C)nnc1C(C)C
Isomeric SMILES O=C(C1CCC(CC1)(F)F)N[C@H](c1ccsc1)CCN1[C@@H]2CC[C@H]1C[C@@H](C2)n1c(C)nnc1C(C)C
InChI InChI=1S/C27H39F2N5OS/c1-17(2)25-32-31-18(3)34(25)23-14-21-4-5-22(15-23)33(21)12-8-24(20-9-13-36-16-20)30-26(35)19-6-10-27(28,29)11-7-19/h9,13,16-17,19,21-24H,4-8,10-12,14-15H2,1-3H3,(H,30,35)/t21-,22+,23-,24-/m0/s1
InChI Key KESMRFWRGXZDEF-KIHHCIJBSA-N
Classification
Compound class Synthetic organic
IUPAC Name
4,4-difluoro-N-[(1S)-3-[(1S,5R)-3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-3-ylpropyl]cyclohexane-1-carboxamide
Database Links
GtoPdb PubChem SID 381118816
PubChem CID 91820689
RCSB PDB Ligand A4X
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