diff --git a/splits/chirality_finetune/README.md b/splits/chirality_finetune/README.md new file mode 100644 index 0000000..3ab9e2a --- /dev/null +++ b/splits/chirality_finetune/README.md @@ -0,0 +1,105 @@ +# Chirality fine-tuning split + +The train / validation / test split used for the chirality fine-tuning experiments. It is an +8:1:1 split of the chirality set by **Bemis–Murcko scaffold of the parent molecule**: every parent +molecule, together with all of its enumerated stereoisomers and all of their conformers, falls +entirely inside one of the three splits, and no scaffold is shared between splits. + +The files index the published dataset `EscheWang/3dcs`, config `chirality` (fields +`key` / `mol_id` / `en_id` / `n_conformers` / `offset` / `mol_blocks`). + +| File | Data rows | Content | +|---|---|---| +| `train.csv` | 11,927 | one row per stereoisomer entry | +| `valid.csv` | 1,496 | one row per stereoisomer entry | +| `test.csv` | 1,480 | one row per stereoisomer entry | + +Each file has the header `key,mol_id,en_id`, and the three columns are copied verbatim from the +corresponding row of the `chirality` config, so `key` can be used as a join key directly. Rows are +sorted by `mol_id`, then by `en_id`. A `key` looks like + +``` +CHEMBL1255901::en1_A3:S;A8:S +``` + +i.e. `::en_:;...`, where the suffix lists the CIP label assigned to +each stereocentre of that stereoisomer. + +## Counts + +| | train | valid | test | total | +|---|---|---|---|---| +| Entries (`key`) | 11,927 | 1,496 | 1,480 | 14,903 | +| Parent molecules (`mol_id`) | 3,072 | 431 | 400 | 3,903 | +| … of which have ≥ 2 stereoisomers | 3,024 | 421 | 397 | 3,842 | +| Conformers (sum of `n_conformers`) | 42,389 | 5,071 | 4,931 | 52,391 | +| Distinct Murcko scaffolds | 1,995 | 195 | 271 | 2,461 | + +Ratios: 80.0 / 10.0 / 9.9 % by entry, 78.7 / 11.0 / 10.2 % by parent molecule, +80.9 / 9.7 / 9.4 % by conformer. + +Both molecule counts are given because they are used in different places. 3,072 / 431 / 400 is the +number of distinct `mol_id` values in each file. 3,024 / 421 / 397 is the number of parent molecules +that contribute at least two stereoisomers, which is the subset that supports a within-molecule +stereoisomer comparison; the remaining 48 / 10 / 3 molecules contribute a single stereoisomer entry +each. + +The union of the three files is the whole `chirality` config: all 14,903 rows and all 52,391 +conformers are assigned to exactly one split, with no row left over and no row in two splits. + +## Verification + +All numbers below were recomputed from `EscheWang/3dcs` (config `chirality`) with RDKit 2026.03.6 +rather than carried over from the original run. + +| Check | Result | +|---|---| +| Every row of the three files resolves to a row of the `chirality` config | 14,903 / 14,903 matched, 0 unmatched | +| `mol_id` and `en_id` agree with the values stored in the dataset | 0 mismatches over 14,903 rows | +| Union of the three splits vs. the full `chirality` config | set-equal; 0 rows in only one of the two | +| A `key` appears in two splits | 0 for all three pairs | +| A `mol_id` appears in two splits | 0 for all three pairs | +| A Murcko scaffold appears in two splits | 0 for all three pairs | +| Conformer counts (`n_conformers`) sum to the per-split totals above | agrees | + +Scaffolds were computed from the `mol_blocks` field: for each `mol_id`, the first conformer of its +first stereoisomer was parsed with `Chem.MolFromMolBlock(..., removeHs=True)` and reduced with +`MurckoScaffold.MurckoScaffoldSmiles(mol=mol, includeChirality=False)`. All 3,903 molecules parsed +and produced a scaffold. Ignoring chirality is the stricter test here, since it merges scaffolds +that differ only in stereochemistry and can therefore only create collisions, not hide them. + +125 of the molecules are acyclic and so reduce to the empty Murcko scaffold. All 125 are in +`valid.csv`, which is why `valid` has 431 molecules but only 195 distinct scaffolds. The empty +scaffold is confined to a single split, so it does not cause any train/valid/test scaffold sharing; +the scaffold-overlap counts above are 0 whether or not the empty scaffold is included. + +## Use + +```python +import pandas as pd +from datasets import load_dataset + +ds = load_dataset("EscheWang/3dcs", "chirality", split="train") + +keys = set(pd.read_csv("splits/chirality_finetune/test.csv")["key"]) +test = ds.filter(lambda batch: [k in keys for k in batch["key"]], batched=True) + +print(test.num_rows, sum(test["n_conformers"])) # 1480 4931 +``` + +`mol_id` and `en_id` are included as separate columns so that the same files can be used to group +by parent molecule (for example, to build stereoisomer pairs within a molecule) without having to +parse `key`. + +## Scope + +These files are the data split only. The fine-tuning code and the fine-tuned checkpoints are not +part of this repository. + +## SHA-256 + +``` +160658b1e57f5797a0102f6cde3668111261775dee94f1984f72f8e2207ce5cf train.csv +6928e3bbf3b15358e5e347791a42c1d67ad0de07c0bfa0416e3c792505b0a15c valid.csv +fe36850cf81bf67ae4d9eba2c9ed3365d5ca4ae464651295c459cba3b976867f test.csv +``` diff --git a/splits/chirality_finetune/test.csv b/splits/chirality_finetune/test.csv new file mode 100644 index 0000000..7e9818d --- /dev/null +++ b/splits/chirality_finetune/test.csv @@ -0,0 +1,1481 @@ +key,mol_id,en_id +CHEMBL1040::en0_A4:S;A14:R;A16:S;A17:R;A28:R,CHEMBL1040,0 +CHEMBL1040::en1_A4:R;A14:R;A16:S;A17:R;A28:R,CHEMBL1040,1 +CHEMBL1040::en2_A4:S;A14:S;A16:S;A17:R;A28:R,CHEMBL1040,2 +CHEMBL1040::en3_A4:R;A14:S;A16:S;A17:R;A28:R,CHEMBL1040,3 +CHEMBL1040::en4_A4:S;A14:R;A16:R;A17:R;A28:R,CHEMBL1040,4 +CHEMBL1042::en0_A4:S;A14:R;A16:S;A17:R;A27:R,CHEMBL1042,0 +CHEMBL1042::en1_A4:R;A14:R;A16:S;A17:R;A27:R,CHEMBL1042,1 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