workbench 0.8.202__py3-none-any.whl → 0.8.220__py3-none-any.whl

workbench/algorithms/dataframe/compound_dataset_overlap.py

@@ -0,0 +1,321 @@
+"""Compound Dataset Overlap Analysis
+
+This module provides utilities for comparing two molecular datasets based on
+Tanimoto similarity in fingerprint space. It helps quantify the "overlap"
+between datasets in chemical space.
+
+Use cases:
+    - Train/test split validation: Ensure test set isn't too similar to training
+    - Dataset comparison: Compare proprietary vs public datasets
+    - Novelty assessment: Find compounds in query dataset that are novel vs reference
+"""
+
+import logging
+from typing import Optional, Tuple
+
+import pandas as pd
+
+from workbench.algorithms.dataframe.fingerprint_proximity import FingerprintProximity
+
+# Set up logging
+log = logging.getLogger("workbench")
+
+
+class CompoundDatasetOverlap:
+    """Compare two molecular datasets using Tanimoto similarity.
+
+    Builds a FingerprintProximity model on the reference dataset, then queries
+    with SMILES from the query dataset to find the nearest neighbor in the
+    reference for each query compound. This guarantees cross-dataset matches.
+
+    Attributes:
+        prox: FingerprintProximity instance on reference dataset
+        overlap_df: Results DataFrame with similarity scores for each query compound
+    """
+
+    def __init__(
+        self,
+        df_reference: pd.DataFrame,
+        df_query: pd.DataFrame,
+        id_column_reference: str = "id",
+        id_column_query: str = "id",
+        radius: int = 2,
+        n_bits: int = 2048,
+    ) -> None:
+        """
+        Initialize the CompoundDatasetOverlap analysis.
+
+        Args:
+            df_reference: Reference dataset (DataFrame with SMILES)
+            df_query: Query dataset (DataFrame with SMILES)
+            id_column_reference: ID column name in df_reference
+            id_column_query: ID column name in df_query
+            radius: Morgan fingerprint radius (default: 2 = ECFP4)
+            n_bits: Number of fingerprint bits (default: 2048)
+        """
+        self.id_column_reference = id_column_reference
+        self.id_column_query = id_column_query
+        self._radius = radius
+        self._n_bits = n_bits
+
+        # Store copies of the dataframes
+        self.df_reference = df_reference.copy()
+        self.df_query = df_query.copy()
+
+        # Find SMILES columns
+        self._smiles_col_reference = self._find_smiles_column(self.df_reference)
+        self._smiles_col_query = self._find_smiles_column(self.df_query)
+
+        if self._smiles_col_reference is None:
+            raise ValueError("Reference dataset must have a SMILES column")
+        if self._smiles_col_query is None:
+            raise ValueError("Query dataset must have a SMILES column")
+
+        log.info(f"Reference dataset: {len(self.df_reference)} compounds")
+        log.info(f"Query dataset: {len(self.df_query)} compounds")
+
+        # Build FingerprintProximity on reference dataset only
+        self.prox = FingerprintProximity(
+            self.df_reference,
+            id_column=id_column_reference,
+            radius=radius,
+            n_bits=n_bits,
+        )
+
+        # Compute cross-dataset overlap
+        self.overlap_df = self._compute_cross_dataset_overlap()
+
+    @staticmethod
+    def _find_smiles_column(df: pd.DataFrame) -> Optional[str]:
+        """Find the SMILES column in a DataFrame (case-insensitive)."""
+        for col in df.columns:
+            if col.lower() == "smiles":
+                return col
+        return None
+
+    def _compute_cross_dataset_overlap(self) -> pd.DataFrame:
+        """For each query compound, find nearest neighbor in reference using neighbors_from_smiles."""
+        log.info(f"Computing nearest neighbors in reference for {len(self.df_query)} query compounds")
+
+        # Get SMILES list from query dataset
+        query_smiles = self.df_query[self._smiles_col_query].tolist()
+        query_ids = self.df_query[self.id_column_query].tolist()
+
+        # Query all compounds against reference (get only nearest neighbor)
+        neighbors_df = self.prox.neighbors_from_smiles(query_smiles, n_neighbors=1)
+
+        # Build results with query IDs
+        results = []
+        for i, (q_id, q_smi) in enumerate(zip(query_ids, query_smiles)):
+            # Find the row for this query SMILES
+            match = neighbors_df[neighbors_df["query_id"] == q_smi]
+            if len(match) > 0:
+                row = match.iloc[0]
+                results.append(
+                    {
+                        "id": q_id,
+                        "smiles": q_smi,
+                        "nearest_neighbor_id": row["neighbor_id"],
+                        "tanimoto_similarity": row["similarity"],
+                    }
+                )
+            else:
+                # Should not happen, but handle gracefully
+                results.append(
+                    {
+                        "id": q_id,
+                        "smiles": q_smi,
+                        "nearest_neighbor_id": None,
+                        "tanimoto_similarity": 0.0,
+                    }
+                )
+
+        result_df = pd.DataFrame(results)
+
+        # Add nearest neighbor SMILES from reference
+        ref_smiles_map = self.df_reference.set_index(self.id_column_reference)[self._smiles_col_reference]
+        result_df["nearest_neighbor_smiles"] = result_df["nearest_neighbor_id"].map(ref_smiles_map)
+
+        return result_df.sort_values("tanimoto_similarity", ascending=False).reset_index(drop=True)
+
+    def summary_stats(self) -> pd.DataFrame:
+        """Return distribution statistics for nearest-neighbor Tanimoto similarities."""
+        return (
+            self.overlap_df["tanimoto_similarity"]
+            .describe(percentiles=[0.01, 0.05, 0.1, 0.25, 0.5, 0.75, 0.9, 0.95, 0.99])
+            .to_frame()
+        )
+
+    def novel_compounds(self, threshold: float = 0.4) -> pd.DataFrame:
+        """Return query compounds that are novel (low similarity to reference).
+
+        Args:
+            threshold: Maximum Tanimoto similarity to consider "novel" (default: 0.4)
+
+        Returns:
+            DataFrame of query compounds with similarity below threshold
+        """
+        novel = self.overlap_df[self.overlap_df["tanimoto_similarity"] < threshold].copy()
+        return novel.sort_values("tanimoto_similarity", ascending=True).reset_index(drop=True)
+
+    def similar_compounds(self, threshold: float = 0.7) -> pd.DataFrame:
+        """Return query compounds that are similar to reference (high overlap).
+
+        Args:
+            threshold: Minimum Tanimoto similarity to consider "similar" (default: 0.7)
+
+        Returns:
+            DataFrame of query compounds with similarity above threshold
+        """
+        similar = self.overlap_df[self.overlap_df["tanimoto_similarity"] >= threshold].copy()
+        return similar.sort_values("tanimoto_similarity", ascending=False).reset_index(drop=True)
+
+    def overlap_fraction(self, threshold: float = 0.7) -> float:
+        """Return fraction of query compounds that overlap with reference above similarity threshold.
+
+        Args:
+            threshold: Minimum Tanimoto similarity to consider "overlapping"
+
+        Returns:
+            Fraction of query compounds with nearest neighbor similarity >= threshold
+        """
+        n_overlapping = (self.overlap_df["tanimoto_similarity"] >= threshold).sum()
+        return n_overlapping / len(self.overlap_df)
+
+    def plot_histogram(self, bins: int = 50, figsize: Tuple[int, int] = (10, 6)) -> None:
+        """Plot histogram of nearest-neighbor Tanimoto similarities.
+
+        Args:
+            bins: Number of histogram bins
+            figsize: Figure size (width, height)
+        """
+        import matplotlib.pyplot as plt
+
+        fig, ax = plt.subplots(figsize=figsize)
+        ax.hist(self.overlap_df["tanimoto_similarity"], bins=bins, edgecolor="black", alpha=0.7)
+        ax.set_xlabel("Tanimoto Similarity (query → nearest in reference)")
+        ax.set_ylabel("Count")
+        ax.set_title(f"Dataset Overlap: {len(self.overlap_df)} query compounds")
+        ax.axvline(x=0.4, color="red", linestyle="--", label="Novel threshold (0.4)")
+        ax.axvline(x=0.7, color="green", linestyle="--", label="Similar threshold (0.7)")
+        ax.legend()
+
+        # Add summary stats as text
+        stats = self.overlap_df["tanimoto_similarity"]
+        textstr = f"Mean: {stats.mean():.3f}\nMedian: {stats.median():.3f}\nStd: {stats.std():.3f}"
+        ax.text(
+            0.02,
+            0.98,
+            textstr,
+            transform=ax.transAxes,
+            verticalalignment="top",
+            bbox=dict(boxstyle="round", facecolor="wheat", alpha=0.5),
+        )
+
+        plt.tight_layout()
+        plt.show()
+
+
+# =============================================================================
+# Testing
+# =============================================================================
+if __name__ == "__main__":
+    print("=" * 80)
+    print("Testing CompoundDatasetOverlap")
+    print("=" * 80)
+
+    # Test 1: Basic functionality with SMILES data
+    print("\n1. Testing with SMILES data...")
+
+    # Reference dataset: Known drug-like compounds
+    reference_data = {
+        "id": ["aspirin", "caffeine", "glucose", "ibuprofen", "naproxen", "ethanol", "methanol", "propanol"],
+        "smiles": [
+            "CC(=O)OC1=CC=CC=C1C(=O)O",  # aspirin
+            "CN1C=NC2=C1C(=O)N(C(=O)N2C)C",  # caffeine
+            "C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)O)O)O",  # glucose
+            "CC(C)CC1=CC=C(C=C1)C(C)C(=O)O",  # ibuprofen
+            "COC1=CC2=CC(C(C)C(O)=O)=CC=C2C=C1",  # naproxen
+            "CCO",  # ethanol
+            "CO",  # methanol
+            "CCCO",  # propanol
+        ],
+    }
+
+    # Query dataset: Compounds to compare against reference
+    query_data = {
+        "id": ["acetaminophen", "theophylline", "benzene", "toluene", "phenol", "aniline"],
+        "smiles": [
+            "CC(=O)NC1=CC=C(C=C1)O",  # acetaminophen - similar to aspirin
+            "CN1C=NC2=C1C(=O)NC(=O)N2",  # theophylline - similar to caffeine
+            "c1ccccc1",  # benzene - simple aromatic
+            "Cc1ccccc1",  # toluene - similar to benzene
+            "Oc1ccccc1",  # phenol - hydroxyl benzene
+            "Nc1ccccc1",  # aniline - amino benzene
+        ],
+    }
+
+    df_reference = pd.DataFrame(reference_data)
+    df_query = pd.DataFrame(query_data)
+
+    print(f"   Reference: {len(df_reference)} compounds, Query: {len(df_query)} compounds")
+
+    overlap = CompoundDatasetOverlap(
+        df_reference, df_query, id_column_reference="id", id_column_query="id", radius=2, n_bits=1024
+    )
+
+    print("\n   Overlap results:")
+    print(overlap.overlap_df[["id", "nearest_neighbor_id", "tanimoto_similarity"]].to_string(index=False))
+
+    print("\n   Summary statistics:")
+    print(overlap.summary_stats())
+
+    # Test 2: Novel and similar compound identification
+    print("\n2. Testing novel/similar compound identification...")
+
+    similar = overlap.similar_compounds(threshold=0.3)
+    print(f"   Similar compounds (sim >= 0.3): {len(similar)}")
+    if len(similar) > 0:
+        print(similar[["id", "nearest_neighbor_id", "tanimoto_similarity"]].to_string(index=False))
+
+    novel = overlap.novel_compounds(threshold=0.3)
+    print(f"\n   Novel compounds (sim < 0.3): {len(novel)}")
+    if len(novel) > 0:
+        print(novel[["id", "nearest_neighbor_id", "tanimoto_similarity"]].to_string(index=False))
+
+    # Test 3: With Workbench data (if available)
+    print("\n3. Testing with Workbench FeatureSet (if available)...")
+
+    try:
+        from workbench.api import FeatureSet
+
+        fs = FeatureSet("aqsol_features")
+        full_df = fs.pull_dataframe()[:1000]  # Limit to first 1000 for testing
+
+        # Split into reference and query sets
+        df_reference = full_df.sample(frac=0.8, random_state=42)
+        df_query = full_df.drop(df_reference.index)
+
+        print(f"   Reference set: {len(df_reference)} compounds")
+        print(f"   Query set: {len(df_query)} compounds")
+
+        overlap = CompoundDatasetOverlap(
+            df_reference, df_query, id_column_reference=fs.id_column, id_column_query=fs.id_column
+        )
+
+        print("\n   Summary statistics:")
+        print(overlap.summary_stats())
+
+        print(f"\n   Overlap fraction (sim >= 0.7): {overlap.overlap_fraction(0.7):.2%}")
+        print(f"   Overlap fraction (sim >= 0.5): {overlap.overlap_fraction(0.5):.2%}")
+        print(f"   Novel compounds (sim < 0.4): {len(overlap.novel_compounds(0.4))}")
+
+        # Uncomment to show histogram
+        overlap.plot_histogram()
+
+    except Exception as e:
+        print(f"   Skipping Workbench test: {e}")
+
+    print("\n" + "=" * 80)
+    print("✅ All CompoundDatasetOverlap tests completed!")
+    print("=" * 80)

workbench/algorithms/dataframe/feature_space_proximity.py

@@ -1,101 +1,194 @@
 import pandas as pd
+import numpy as np
+from sklearn.preprocessing import StandardScaler
+from sklearn.neighbors import NearestNeighbors
+from typing import List, Optional
 import logging
 
 # Workbench Imports
 from workbench.algorithms.dataframe.proximity import Proximity
 from workbench.algorithms.dataframe.projection_2d import Projection2D
-from workbench.core.views.inference_view import InferenceView
-from workbench.api import FeatureSet, Model
 
 # Set up logging
 log = logging.getLogger("workbench")
 
 
 class FeatureSpaceProximity(Proximity):
-    def __init__(self, model: Model, n_neighbors: int = 10) -> None:
+    """Proximity computations for numeric feature spaces using Euclidean distance."""
+
+    def __init__(
+        self,
+        df: pd.DataFrame,
+        id_column: str,
+        features: List[str],
+        target: Optional[str] = None,
+        include_all_columns: bool = False,
+    ):
         """
         Initialize the FeatureSpaceProximity class.
 
         Args:
-            model (Model): A Workbench model object.
-            n_neighbors (int): Number of neighbors to compute. Defaults to 10.
+            df: DataFrame containing data for neighbor computations.
+            id_column: Name of the column used as the identifier.
+            features: List of feature column names to be used for neighbor computations.
+            target: Name of the target column. Defaults to None.
+            include_all_columns: Include all DataFrame columns in neighbor results. Defaults to False.
         """
-
-        # Grab the features and target from the model
-        features = model.features()
-        target = model.target()
-
-        # Grab the feature set for the model
-        fs = FeatureSet(model.get_input())
-
-        # If we have a "inference" view, pull the data from that view
-        view_name = f"inf_{model.name.replace('-', '_')}"
-        if view_name in fs.views():
-            self.df = fs.view(view_name).pull_dataframe()
-
-        # Otherwise, pull the data from the feature set and run inference
-        else:
-            inf_view = InferenceView.create(model)
-            self.df = inf_view.pull_dataframe()
-
-        # Call the parent class constructor
-        super().__init__(self.df, id_column=fs.id_column, features=features, target=target, n_neighbors=n_neighbors)
-
-        # Project the data to 2D
-        self.df = Projection2D().fit_transform(self.df, features=features)
-
-
+        # Validate and filter features before calling parent init
+        self._raw_features = features
+        super().__init__(
+            df, id_column=id_column, features=features, target=target, include_all_columns=include_all_columns
+        )
+
+    def _prepare_data(self) -> None:
+        """Filter out non-numeric features and drop NaN rows."""
+        # Validate features
+        self.features = self._validate_features(self.df, self._raw_features)
+
+        # Drop NaN rows for the features we're using
+        self.df = self.df.dropna(subset=self.features).copy()
+
+    def _validate_features(self, df: pd.DataFrame, features: List[str]) -> List[str]:
+        """Remove non-numeric features and log warnings."""
+        non_numeric = [f for f in features if f not in df.select_dtypes(include=["number"]).columns]
+        if non_numeric:
+            log.warning(f"Non-numeric features {non_numeric} aren't currently supported, excluding them")
+        return [f for f in features if f not in non_numeric]
+
+    def _build_model(self) -> None:
+        """Standardize features and fit Nearest Neighbors model."""
+        self.scaler = StandardScaler()
+        X = self.scaler.fit_transform(self.df[self.features])
+        self.nn = NearestNeighbors().fit(X)
+
+    def _transform_features(self, df: pd.DataFrame) -> np.ndarray:
+        """Transform features using the fitted scaler."""
+        return self.scaler.transform(df[self.features])
+
+    def _project_2d(self) -> None:
+        """Project the numeric features to 2D for visualization."""
+        if len(self.features) >= 2:
+            self.df = Projection2D().fit_transform(self.df, features=self.features)
+
+
+# Testing the FeatureSpaceProximity class
 if __name__ == "__main__":
+
     pd.set_option("display.max_columns", None)
     pd.set_option("display.width", 1000)
 
-    # Test a Workbench classification Model
-    m = Model("wine-classification")
-    fsp = FeatureSpaceProximity(m)
-
-    # Neighbors Test using a single row from FeatureSet
-    fs = FeatureSet(m.get_input())
+    # Create a sample DataFrame
+    data = {
+        "ID": [1, 2, 3, 4, 5],
+        "Feature1": [0.1, 0.2, 0.3, 0.4, 0.5],
+        "Feature2": [0.5, 0.4, 0.3, 0.2, 0.1],
+        "Feature3": [2.5, 2.4, 2.3, 2.3, np.nan],
+    }
+    df = pd.DataFrame(data)
+
+    # Test the FeatureSpaceProximity class
+    features = ["Feature1", "Feature2", "Feature3"]
+    prox = FeatureSpaceProximity(df, id_column="ID", features=features)
+    print(prox.neighbors(1, n_neighbors=2))
+
+    # Test the neighbors method with radius
+    print(prox.neighbors(1, radius=2.0))
+
+    # Test with Features list
+    prox = FeatureSpaceProximity(df, id_column="ID", features=["Feature1"])
+    print(prox.neighbors(1))
+
+    # Create a sample DataFrame
+    data = {
+        "id": ["a", "b", "c", "d", "e"],  # Testing string IDs
+        "Feature1": [0.1, 0.2, 0.3, 0.4, 0.5],
+        "Feature2": [0.5, 0.4, 0.3, 0.2, 0.1],
+        "target": [1, 0, 1, 0, 5],
+    }
+    df = pd.DataFrame(data)
+
+    # Test with String Ids
+    prox = FeatureSpaceProximity(
+        df,
+        id_column="id",
+        features=["Feature1", "Feature2"],
+        target="target",
+        include_all_columns=True,
+    )
+    print(prox.neighbors(["a", "b"]))
+
+    # Test duplicate IDs
+    data = {
+        "id": ["a", "b", "c", "d", "d"],  # Duplicate ID (d)
+        "Feature1": [0.1, 0.2, 0.3, 0.4, 0.5],
+        "Feature2": [0.5, 0.4, 0.3, 0.2, 0.1],
+        "target": [1, 0, 1, 0, 5],
+    }
+    df = pd.DataFrame(data)
+    prox = FeatureSpaceProximity(df, id_column="id", features=["Feature1", "Feature2"], target="target")
+    print(df.equals(prox.df))
+
+    # Test on real data from Workbench
+    from workbench.api import FeatureSet, Model
+
+    fs = FeatureSet("aqsol_features")
+    model = Model("aqsol-regression")
+    features = model.features()
     df = fs.pull_dataframe()
-    single_query_neighbors = fsp.neighbors(df.iloc[[0]])
-    print("\nNeighbors for Query ID:", df.iloc[0][fs.id_column])
-    print(single_query_neighbors)
-
-    # Test a Workbench regression model
-    m = Model("abalone-regression")
-    fsp = FeatureSpaceProximity(m)
-
-    # Neighbors Test using a multiple rows from FeatureSet
-    fs = FeatureSet(m.get_input())
-    df = fs.pull_dataframe()
-    query_neighbors = fsp.neighbors(df.iloc[0:2])
-    print("\nNeighbors for Query ID:", df.iloc[0][fs.id_column])
-    print(query_neighbors)
-
-    # Test a Workbench regression model
-    m = Model("aqsol-regression")
-    fsp = FeatureSpaceProximity(m)
-
-    # Neighbors Test using a multiple rows from FeatureSet
-    fs = FeatureSet(m.get_input())
-    df = fs.pull_dataframe()
-    query_neighbors = fsp.neighbors(df.iloc[5:7])
-    print("\nNeighbors for Query ID:", df.iloc[5][fs.id_column])
-    print(query_neighbors)
-
-    # Time the all_neighbors method
-    import time
-
-    start_time = time.time()
-    all_neighbors_df = fsp.all_neighbors()
-    end_time = time.time()
-    print("\nTime taken for all_neighbors:", end_time - start_time)
-    print("\nAll Neighbors DataFrame:")
-    print(all_neighbors_df)
-
-    # Show a scatter plot of the data
+    prox = FeatureSpaceProximity(df, id_column=fs.id_column, features=model.features(), target=model.target())
+    print("\n" + "=" * 80)
+    print("Testing Neighbors...")
+    print("=" * 80)
+    test_id = df[fs.id_column].tolist()[0]
+    print(f"\nNeighbors for ID {test_id}:")
+    print(prox.neighbors(test_id))
+
+    print("\n" + "=" * 80)
+    print("Testing isolated_compounds...")
+    print("=" * 80)
+
+    # Test isolated data in the top 1%
+    isolated_1pct = prox.isolated(top_percent=1.0)
+    print(f"\nTop 1% most isolated compounds (n={len(isolated_1pct)}):")
+    print(isolated_1pct)
+
+    # Test isolated data in the top 5%
+    isolated_5pct = prox.isolated(top_percent=5.0)
+    print(f"\nTop 5% most isolated compounds (n={len(isolated_5pct)}):")
+    print(isolated_5pct)
+
+    print("\n" + "=" * 80)
+    print("Testing target_gradients...")
+    print("=" * 80)
+
+    # Test with different parameters
+    gradients_1pct = prox.target_gradients(top_percent=1.0, min_delta=1.0)
+    print(f"\nTop 1% target gradients (min_delta=5.0) (n={len(gradients_1pct)}):")
+    print(gradients_1pct)
+
+    gradients_5pct = prox.target_gradients(top_percent=5.0, min_delta=5.0)
+    print(f"\nTop 5% target gradients (min_delta=5.0) (n={len(gradients_5pct)}):")
+    print(gradients_5pct)
+
+    # Test proximity_stats
+    print("\n" + "=" * 80)
+    print("Testing proximity_stats...")
+    print("=" * 80)
+    stats = prox.proximity_stats()
+    print(stats)
+
+    # Plot the distance distribution using pandas
+    print("\n" + "=" * 80)
+    print("Plotting distance distribution...")
+    print("=" * 80)
+    prox.df["nn_distance"].hist(bins=50, figsize=(10, 6), edgecolor="black")
+
+    # Visualize the 2D projection
+    print("\n" + "=" * 80)
+    print("Visualizing 2D Projection...")
+    print("=" * 80)
     from workbench.web_interface.components.plugin_unit_test import PluginUnitTest
     from workbench.web_interface.components.plugins.scatter_plot import ScatterPlot
 
-    # Run the Unit Test on the Plugin using the new DataFrame with 'x' and 'y'
-    unit_test = PluginUnitTest(ScatterPlot, input_data=fsp.df, x="x", y="y")
+    unit_test = PluginUnitTest(ScatterPlot, input_data=prox.df[:1000], x="x", y="y", color=model.target())
     unit_test.run()