diff --git a/.gitignore b/.gitignore
index 9ede6f6c..4264994a 100644
--- a/.gitignore
+++ b/.gitignore
@@ -16,3 +16,4 @@ node_modules/
 static/css/output.css
 
 *.code-workspace
+/pnpm-workspace.yaml
diff --git a/epdb/models.py b/epdb/models.py
index 7fefa928..67a34829 100644
--- a/epdb/models.py
+++ b/epdb/models.py
@@ -1241,7 +1241,12 @@ class SimpleAmbitRule(SimpleRule):
         return "simple-rule"
 
     def apply(self, smiles):
-        return FormatConverter.apply(smiles, self.smirks)
+        return FormatConverter.apply(
+            smiles,
+            self.smirks,
+            reactant_filter_smarts=self.reactant_filter_smarts,
+            product_filter_smarts=self.product_filter_smarts,
+        )
 
     @property
     def reactants_smarts(self):
diff --git a/tests/test_simpleambitrule.py b/tests/test_simpleambitrule.py
index 7647da27..851c0757 100644
--- a/tests/test_simpleambitrule.py
+++ b/tests/test_simpleambitrule.py
@@ -5,6 +5,7 @@ from django.test import TestCase
 
 from epdb.logic import PackageManager
 from epdb.models import SimpleAmbitRule, User
+from utilities.chem import FormatConverter
 
 
 class SimpleAmbitRuleTest(TestCase):
@@ -189,7 +190,9 @@ class SimpleAmbitRuleTest(TestCase):
         test_smiles = "CCO"
         result = rule.apply(test_smiles)
 
-        mock_apply.assert_called_once_with(test_smiles, rule.smirks)
+        mock_apply.assert_called_once_with(
+            test_smiles, rule.smirks, reactant_filter_smarts=None, product_filter_smarts=None
+        )
         self.assertEqual(result, ["product1", "product2"])
 
     def test_reactants_smarts_property(self):
@@ -338,3 +341,41 @@ class SimpleAmbitRuleTest(TestCase):
         self.assertEqual(
             rule._meta.get_field("product_filter_smarts").verbose_name, "Product Filter SMARTS"
         )
+
+    def test_reactant_filter_smarts(self):
+        rule = SimpleAmbitRule.create(
+            package=self.package,
+            smirks="[#6,#8,#16:6]-[#6:4](=[O:5])[#6:2]=[#6;!$(CO)!$(C=CN[H])!$(C(=C)N[H]):1]>>[#8]([H])-[#6:1]-[#6:2]-[#6:4](-[#6,#8,#16:6])=[O:5]",
+            reactant_filter_smarts="[$(OC(=O)C=CC=CC(O)=O),$(OC1C=CC=CC1O)]",
+            product_filter_smarts=None,
+        )
+
+        SMILES = "OC(=O)C=CC=CC(O)=O"
+        res = FormatConverter.apply(SMILES, rule.smirks)
+
+        # Assert Rule triggers, if we use FormatConverter without reactant_filter_smarts passed along
+        self.assertTrue(len(res) > 0)
+
+        res = rule.apply(SMILES)
+
+        # Check if reactant_filter_smarts prevents rule from application
+        self.assertTrue(len(res) == 0)
+
+    def test_product_filter_smarts(self):
+        rule = SimpleAmbitRule.create(
+            package=self.package,
+            smirks="[#6,#8,#16:6]-[#6:4](=[O:5])[#6:2]=[#6;!$(CO)!$(C=CN[H])!$(C(=C)N[H]):1]>>[#8]([H])-[#6:1]-[#6:2]-[#6:4](-[#6,#8,#16:6])=[O:5]",
+            reactant_filter_smarts=None,
+            product_filter_smarts="[$(O=C(O)C=CC=CC(O)CC(=O)O)]",
+        )
+
+        SMILES = "OC(=O)C=CC=CC=CC(O)=O"
+        res = FormatConverter.apply(SMILES, rule.smirks)
+
+        # Assert Rule triggers, if we use FormatConverter without product_filter_smarts passed along
+        self.assertTrue(len(res) > 0)
+
+        res = rule.apply(SMILES)
+
+        # Check if reactant_filter_smarts prevents rule from application
+        self.assertTrue(len(res) == 0)
diff --git a/utilities/chem.py b/utilities/chem.py
index cec5e7d8..2d0fd99c 100644
--- a/utilities/chem.py
+++ b/utilities/chem.py
@@ -279,6 +279,24 @@ class FormatConverter(object):
         except Exception:
             return False
 
+    @staticmethod
+    def smarts_matches(mol: str | Chem.Mol, smarts: str) -> bool:
+        """
+        Returns True if the SMARTS pattern matches the given SMILES / Molecule.
+        """
+        _mol = mol
+        if isinstance(mol, str):
+            _mol = Chem.MolFromSmiles(mol)
+
+        if _mol is None:
+            raise ValueError(f"Invalid Molecule: {mol}")
+
+        pattern = Chem.MolFromSmarts(smarts)
+        if pattern is None:
+            raise ValueError(f"Invalid SMARTS: {smarts}")
+
+        return _mol.HasSubstructMatch(pattern)
+
     @staticmethod
     def apply(
         smiles: str,
@@ -288,6 +306,8 @@ class FormatConverter(object):
         standardize: bool = True,
         kekulize: bool = True,
         remove_stereo: bool = True,
+        reactant_filter_smarts: str | None = None,
+        product_filter_smarts: str | None = None,
     ) -> List["ProductSet"]:
         logger.debug(f"Applying {smirks} on {smiles}")
 
@@ -306,6 +326,15 @@ class FormatConverter(object):
                 Chem.SanitizeMol(mol)
                 mol = Chem.AddHs(mol)
 
+            # Check if reactant_filter_smarts matches and we shouldn't apply the rule
+            if reactant_filter_smarts and FormatConverter.smarts_matches(
+                mol, reactant_filter_smarts
+            ):
+                logger.debug(
+                    f"Reactant {FormatConverter.to_smiles(mol)} matches {reactant_filter_smarts}, skipping"
+                )
+                return list(pss)
+
             # apply!
             sites = rxn.RunReactants((mol,))
             logger.debug(f"{len(sites)} products sets generated")
@@ -321,6 +350,17 @@ class FormatConverter(object):
                                 p = FormatConverter.standardize(
                                     Chem.MolToSmiles(p), remove_stereo=remove_stereo
                                 )
+
+                                if product_filter_smarts and FormatConverter.smarts_matches(
+                                    p, product_filter_smarts
+                                ):
+                                    logger.debug(
+                                        f"Product {FormatConverter.to_smiles(mol)} matches {product_filter_smarts}, skipping"
+                                    )
+                                    # clear products we might have already collected
+                                    prods.clear()
+                                    break
+
                                 prods.append(p)
 
                             # if kekulize:
@@ -357,7 +397,7 @@ class FormatConverter(object):
         except Exception as e:
             logger.error(f"Applying {smirks} on {smiles} failed:\n{e}")
 
-        return pss
+        return list(pss)
 
     @staticmethod
     def MACCS(smiles):