SMILES History

• The motivation for SMILES is the desire to come up with a compact machine and human-readable chemical nomenclature.
• Also important features: canonicalizable and comprehensive.
• Typical connection table representations take up more bytes. e.g. MDL mol file reprsentation for methane -

  	
    -CPSS-  0606911105
  
    1  0  0  0  0  0  0  0  0  0  0
     -4.5200    2.8100    0.0000 C   0  0     0  0  0  0  0  0
  

• Three publications exist on SMILES
  1. Encoding rules (1988): abstract.
  2. Canonicalization (aka, "uniquification") (1989): abstract.
  3. Depictions (1990): abstract.