Gallery, prompt v1

Caffeine with three CF3 groups

One frozen prompt and every model that has run it, newest first.

The prompt, v1, frozen

Give the SMILES for caffeine with all three N-methyl groups replaced by trifluoromethyl groups.

Every model, its first three runs.

One square a check, in this order:

  1. Parses
  2. C8HF9N4O2
  3. Three N-CF3, no N-methyl
  4. The right molecule

passed, failed, undecided.

DeepSeek 4.1 Flash

How it is checked

Caffeine's skeleton with a CF3 on N1, N3 and N7, which is C8HF9N4O2. The prompt pack this came from gives C8H3F9N4O2, which is wrong: swapping the methyls takes all nine hydrogens with them, and only the C8 hydrogen stays. Decided with RDKit by an exact canonical match, because fluorinated isocaffeine has the same formula with a CF3 on the wrong nitrogen.

ParsesmeasuredRDKit reads the SMILES as a molecule.
C8HF9N4O2measuredMolecular formula computed from the parsed molecule.
Three N-CF3, no N-methylmeasuredEach CF3 carbon traced to a ring nitrogen, and no methyl left on any nitrogen.
The right moleculemeasuredCanonical SMILES identical to the target, so a CF3 on the wrong nitrogen fails.

When this saturates: Ask for 3D coordinates as well, so the nine fluorines have to clear each other and the carbonyls.

The rules behind all of thisThis task's prompt, checks and any checker, on GitHub