example 373 [WO2012093101]   Click here for help

GtoPdb Ligand ID: 8296

Compound class: Synthetic organic
Comment: Example 373 from patent WO2012093101 [2], is an exemplar small molecule complement factor D inhibitor, with potential to treat age-related macular degneration (AMD). Other preferred examples are highlighted in [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 10
Topological polar surface area 142.48
Molecular weight 524.14
XLogP 1.77
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES N#CCOc1ccc2c(c1)c(NC(=O)N1C3CC3CC1C(=O)NCc1cccc(c1F)Cl)cn2C(=O)N
Isomeric SMILES N#CCOc1ccc2c(c1)c(NC(=O)N1[C@@H]3C[C@@H]3C[C@H]1C(=O)NCc1cccc(c1F)Cl)cn2C(=O)N
InChI InChI=1S/C25H22ClFN6O4/c26-17-3-1-2-13(22(17)27)11-30-23(34)21-9-14-8-20(14)33(21)25(36)31-18-12-32(24(29)35)19-5-4-15(10-16(18)19)37-7-6-28/h1-5,10,12,14,20-21H,7-9,11H2,(H2,29,35)(H,30,34)(H,31,36)/t14-,20-,21+/m1/s1
InChI Key SOCAXRLFGRNEPK-IFZYUDKTSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(1R,3S,5R)-2-N-[1-carbamoyl-5-(cyanomethoxy)indol-3-yl]-3-N-[(3-chloro-2-fluorophenyl)methyl]-2-azabicyclo[3.1.0]hexane-2,3-dicarboxamide
Database Links Click here for help
BindingDB Ligand 50400274
ChEMBL Ligand CHEMBL2180765
GtoPdb PubChem SID 252166508
PubChem CID 57412074
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