smiles-js 2.0.3 → 2.1.0

package/test-integration/__snapshots__/cholesterol-drugs.test.js.snap

@@ -2190,3 +2190,179 @@ export const v21 = v19.attach(2, v20);
 export const v22 = Ring({ atoms: 'C', size: 3, ringNumber: 3 });
 export const v23 = Molecule([v3, v18, v21, v22]);"
 `;
+
+exports[`Cholesterol Integration Test parses cholesterol 1`] = `
+{
+  "components": [
+    {
+      "atoms": [
+        "C",
+        "[C@H]",
+      ],
+      "attachments": {
+        "2": [
+          {
+            "atoms": [
+              "C",
+              "C",
+              "C",
+              "C",
+              "C",
+            ],
+            "attachments": {
+              "4": [
+                {
+                  "atoms": [
+                    "C",
+                  ],
+                  "attachments": {},
+                  "bonds": [
+                    null,
+                  ],
+                  "type": "linear",
+                },
+              ],
+            },
+            "bonds": [
+              null,
+              null,
+              null,
+              null,
+              null,
+            ],
+            "type": "linear",
+          },
+        ],
+      },
+      "bonds": [
+        null,
+      ],
+      "type": "linear",
+    },
+    {
+      "rings": [
+        {
+          "atoms": "C",
+          "attachments": {},
+          "bonds": [
+            null,
+            null,
+            null,
+            null,
+            null,
+          ],
+          "offset": 0,
+          "ringNumber": 1,
+          "size": 5,
+          "substitutions": {
+            "1": "[C@H]",
+            "4": "[C@@H]",
+            "5": "[C@@]",
+          },
+          "type": "ring",
+        },
+        {
+          "atoms": "[C@H]",
+          "attachments": {},
+          "bonds": [
+            null,
+            null,
+            null,
+            null,
+            null,
+            null,
+          ],
+          "offset": 3,
+          "ringNumber": 2,
+          "size": 6,
+          "substitutions": {
+            "1": "[C@@H]",
+            "2": "[C@@]",
+            "3": "C",
+            "4": "C",
+          },
+          "type": "ring",
+        },
+        {
+          "atoms": "C",
+          "attachments": {},
+          "bonds": [
+            null,
+            null,
+            null,
+            "=",
+            null,
+            null,
+          ],
+          "offset": 0,
+          "ringNumber": 3,
+          "size": 6,
+          "substitutions": {
+            "1": "[C@H]",
+            "2": "[C@H]",
+            "6": "[C@@]",
+          },
+          "type": "ring",
+        },
+        {
+          "atoms": "C",
+          "attachments": {},
+          "bonds": [
+            null,
+            null,
+            null,
+            null,
+            null,
+            null,
+          ],
+          "offset": 0,
+          "ringNumber": 4,
+          "size": 6,
+          "substitutions": {
+            "2": "[C@@]",
+            "5": "[C@@H]",
+          },
+          "type": "ring",
+        },
+      ],
+      "type": "fused_ring",
+    },
+    {
+      "atoms": [
+        "C",
+      ],
+      "attachments": {},
+      "bonds": [],
+      "type": "linear",
+    },
+  ],
+  "type": "molecule",
+}
+`;
+
+exports[`Cholesterol Integration Test generates valid code via toCode() 1`] = `
+"export const v1 = Linear(['C', '[C@H]']);
+export const v2 = Linear(['C', 'C', 'C', 'C', 'C']);
+export const v3 = Linear(['C']);
+export const v4 = v2.attach(4, v3);
+export const v5 = v1.attach(2, v4);
+export const v6 = Ring({ atoms: 'C', size: 5 });
+export const v7 = v6.substitute(1, '[C@H]');
+export const v8 = v7.substitute(4, '[C@@H]');
+export const v9 = v8.substitute(5, '[C@@]');
+export const v10 = Ring({ atoms: '[C@H]', size: 6, ringNumber: 2, offset: 3, branchDepths: [0, 0, 1, 1, 1, 1] });
+export const v11 = v10.substitute(1, '[C@@H]');
+export const v12 = v11.substitute(2, '[C@@]');
+export const v13 = v12.substitute(3, 'C');
+export const v14 = v13.substitute(4, 'C');
+export const v15 = Ring({ atoms: 'C', size: 6, ringNumber: 3, bonds: [null, null, null, '=', null, null] });
+export const v16 = v15.substitute(1, '[C@H]');
+export const v17 = v16.substitute(2, '[C@H]');
+export const v18 = v17.substitute(6, '[C@@]');
+export const v19 = Ring({ atoms: 'C', size: 6, ringNumber: 4, branchDepths: [1, 1, 2, 2, 2, 3], leadingBond: '=' });
+export const v20 = v19.substitute(2, '[C@@]');
+export const v21 = v20.substitute(5, '[C@@H]');
+export const v22 = FusedRing({ metadata: { rings: [{ ring: v9, start: 8, end: 12, atoms: [{ position: 8, depth: 0, value: '[C@H]', rings: [1, 1] }, { position: 9, depth: 0, value: 'C', rings: [1] }, { position: 10, depth: 0, value: 'C', rings: [1] }, { position: 11, depth: 0, value: '[C@@H]', rings: [2, 1, 2] }, { position: 12, depth: 0, value: '[C@@]', rings: [1, 2] }] }, { ring: v14, start: 11, end: 16, atoms: [{ position: 11, depth: 0, value: '[C@@H]', rings: [2, 1, 2] }, { position: 12, depth: 0, value: '[C@@]', rings: [1, 2] }, { position: 13, depth: 1, value: 'C', rings: [2], branchId: 20 }, { position: 14, depth: 1, value: 'C', rings: [2], branchId: 20 }, { position: 15, depth: 1, value: '[C@H]', rings: [3, 2, 3], branchId: 20 }, { position: 16, depth: 1, value: '[C@H]', rings: [2, 3], branchId: 20 }] }, { ring: v18, start: 15, end: 20, atoms: [{ position: 15, depth: 1, value: '[C@H]', rings: [3, 2, 3], branchId: 20 }, { position: 16, depth: 1, value: '[C@H]', rings: [2, 3], branchId: 20 }, { position: 17, depth: 1, value: 'C', rings: [3], branchId: 20 }, { position: 18, depth: 1, value: 'C', rings: [3], branchId: 20 }, { position: 19, depth: 1, value: 'C', bond: '=', rings: [4, 3, 4], branchId: 20 }, { position: 20, depth: 1, value: '[C@@]', rings: [3, 4], branchId: 20 }] }, { ring: v21, start: 19, end: 24, atoms: [{ position: 19, depth: 1, value: 'C', bond: '=', rings: [4, 3, 4], branchId: 20 }, { position: 20, depth: 1, value: '[C@@]', rings: [3, 4], branchId: 20 }, { position: 21, depth: 2, value: 'C', rings: [4], branchId: 34 }, { position: 22, depth: 2, value: 'C', rings: [4], branchId: 34 }, { position: 23, depth: 2, value: '[C@@H]', rings: [4], branchId: 34 }, { position: 24, depth: 3, value: 'C', rings: [4], branchId: 38 }] }], atoms: [{ position: 25, depth: 2, value: 'O', branchId: 34 }, { position: 26, depth: 1, value: 'C', branchId: 20 }] } });
+export const v23 = Linear(['C']);
+export const v24 = Molecule([v5, v22, v23]);"
+`;

package/test-integration/__snapshots__/endocannabinoids.test.js.snap

@@ -308,7 +308,7 @@ export const v7 = v6.substitute(5, 'O');
 export const v8 = Linear(['C']);
 export const v9 = v7.attach(4, v8, { sibling: true });
 export const v10 = Ring({ atoms: 'C', size: 6, ringNumber: 3, offset: 4, bonds: [null, '=', null, null, null, null], branchDepths: [1, 1, 1, 2, 2, 2] });
-export const v11 = FusedRing({ metadata: { rings: [{ ring: v5, start: 5, end: 18, atoms: [{ position: 5, depth: 0, value: 'C', rings: [1, 1] }, { position: 6, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 7, depth: 0, value: 'C', rings: [1] }, { position: 8, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1] }, { position: 9, depth: 1, value: 'C', rings: [3, 3, 2, 1] }, { position: 10, depth: 1, value: 'C', rings: [3, 1] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [3, 1] }, { position: 12, depth: 2, value: 'C', rings: [3, 1] }, { position: 13, depth: 2, value: 'C', rings: [3, 1] }, { position: 14, depth: 2, value: 'C', rings: [3, 2, 1] }, { position: 15, depth: 2, value: 'C', rings: [2, 1] }, { position: 16, depth: 3, value: 'O', rings: [2, 1] }, { position: 17, depth: 3, value: 'C', rings: [2, 1] }, { position: 18, depth: 3, value: 'C', bond: '=', rings: [1] }] }, { ring: v9, start: 8, end: 17, atoms: [{ position: 8, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1] }, { position: 9, depth: 1, value: 'C', rings: [3, 3, 2, 1] }, { position: 14, depth: 2, value: 'C', rings: [3, 2, 1] }, { position: 15, depth: 2, value: 'C', rings: [2, 1] }, { position: 16, depth: 3, value: 'O', rings: [2, 1] }, { position: 17, depth: 3, value: 'C', rings: [2, 1] }] }, { ring: v10, start: 9, end: 14, atoms: [{ position: 9, depth: 1, value: 'C', rings: [3, 3, 2, 1] }, { position: 10, depth: 1, value: 'C', rings: [3, 1] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [3, 1] }, { position: 12, depth: 2, value: 'C', rings: [3, 1] }, { position: 13, depth: 2, value: 'C', rings: [3, 1] }, { position: 14, depth: 2, value: 'C', rings: [3, 2, 1] }] }], atoms: [{ position: 20, depth: 2, value: 'C' }, { position: 21, depth: 1, value: 'C' }] } });
+export const v11 = FusedRing({ metadata: { rings: [{ ring: v5, start: 5, end: 18, atoms: [{ position: 5, depth: 0, value: 'C', rings: [1, 1] }, { position: 6, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 7, depth: 0, value: 'C', rings: [1] }, { position: 8, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1], branchId: 10 }, { position: 9, depth: 1, value: 'C', rings: [3, 3, 2, 1], branchId: 10 }, { position: 10, depth: 1, value: 'C', rings: [3, 1], branchId: 10 }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [3, 1], branchId: 10 }, { position: 12, depth: 2, value: 'C', rings: [3, 1], branchId: 19 }, { position: 13, depth: 2, value: 'C', rings: [3, 1], branchId: 19 }, { position: 14, depth: 2, value: 'C', rings: [3, 2, 1], branchId: 19 }, { position: 15, depth: 2, value: 'C', rings: [2, 1], branchId: 19 }, { position: 16, depth: 3, value: 'O', rings: [2, 1], branchId: 25 }, { position: 17, depth: 3, value: 'C', rings: [2, 1], branchId: 25 }, { position: 18, depth: 3, value: 'C', bond: '=', rings: [1], branchId: 25 }] }, { ring: v9, start: 8, end: 17, atoms: [{ position: 8, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1], branchId: 10 }, { position: 9, depth: 1, value: 'C', rings: [3, 3, 2, 1], branchId: 10 }, { position: 14, depth: 2, value: 'C', rings: [3, 2, 1], branchId: 19 }, { position: 15, depth: 2, value: 'C', rings: [2, 1], branchId: 19 }, { position: 16, depth: 3, value: 'O', rings: [2, 1], branchId: 25 }, { position: 17, depth: 3, value: 'C', rings: [2, 1], branchId: 25 }] }, { ring: v10, start: 9, end: 14, atoms: [{ position: 9, depth: 1, value: 'C', rings: [3, 3, 2, 1], branchId: 10 }, { position: 10, depth: 1, value: 'C', rings: [3, 1], branchId: 10 }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [3, 1], branchId: 10 }, { position: 12, depth: 2, value: 'C', rings: [3, 1], branchId: 19 }, { position: 13, depth: 2, value: 'C', rings: [3, 1], branchId: 19 }, { position: 14, depth: 2, value: 'C', rings: [3, 2, 1], branchId: 19 }] }], atoms: [{ position: 20, depth: 2, value: 'C', branchId: 19 }, { position: 21, depth: 1, value: 'C', branchId: 10 }] } });
 export const v12 = Linear(['O']);
 export const v13 = Molecule([v1, v11, v12]);"
 `;
@@ -651,7 +651,7 @@ export const v15 = v13.attach(4, v14, { sibling: true });
 export const v16 = Ring({ atoms: 'C', size: 6, ringNumber: 3, offset: 4 });
 export const v17 = Linear(['O'], ['=']);
 export const v18 = v16.attach(3, v17);
-export const v19 = FusedRing({ metadata: { rings: [{ ring: v11, start: 9, end: 23, atoms: [{ position: 9, depth: 0, value: 'C', rings: [1, 1] }, { position: 10, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 11, depth: 0, value: 'C', rings: [1] }, { position: 12, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1] }, { position: 13, depth: 1, value: 'C', rings: [3, 3, 2, 1] }, { position: 14, depth: 1, value: 'C', rings: [3, 1] }, { position: 15, depth: 1, value: 'C', rings: [3, 1] }, { position: 17, depth: 1, value: 'C', rings: [3, 1] }, { position: 18, depth: 1, value: 'C', rings: [3, 1] }, { position: 19, depth: 1, value: 'C', rings: [3, 2, 1] }, { position: 20, depth: 1, value: 'C', rings: [2, 1] }, { position: 21, depth: 2, value: 'O', rings: [2, 1] }, { position: 22, depth: 2, value: 'C', rings: [2, 1] }, { position: 23, depth: 2, value: 'C', bond: '=', rings: [1] }] }, { ring: v15, start: 12, end: 22, atoms: [{ position: 12, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1] }, { position: 13, depth: 1, value: 'C', rings: [3, 3, 2, 1] }, { position: 19, depth: 1, value: 'C', rings: [3, 2, 1] }, { position: 20, depth: 1, value: 'C', rings: [2, 1] }, { position: 21, depth: 2, value: 'O', rings: [2, 1] }, { position: 22, depth: 2, value: 'C', rings: [2, 1] }] }, { ring: v18, start: 13, end: 19, atoms: [{ position: 13, depth: 1, value: 'C', rings: [3, 3, 2, 1] }, { position: 14, depth: 1, value: 'C', rings: [3, 1] }, { position: 15, depth: 1, value: 'C', rings: [3, 1] }, { position: 17, depth: 1, value: 'C', rings: [3, 1] }, { position: 18, depth: 1, value: 'C', rings: [3, 1] }, { position: 19, depth: 1, value: 'C', rings: [3, 2, 1] }] }], atoms: [{ position: 25, depth: 1, value: 'C' }] } });
+export const v19 = FusedRing({ metadata: { rings: [{ ring: v11, start: 9, end: 23, atoms: [{ position: 9, depth: 0, value: 'C', rings: [1, 1] }, { position: 10, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 11, depth: 0, value: 'C', rings: [1] }, { position: 12, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1], branchId: 18 }, { position: 13, depth: 1, value: 'C', rings: [3, 3, 2, 1], branchId: 18 }, { position: 14, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 15, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 17, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 18, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 19, depth: 1, value: 'C', rings: [3, 2, 1], branchId: 18 }, { position: 20, depth: 1, value: 'C', rings: [2, 1], branchId: 18 }, { position: 21, depth: 2, value: 'O', rings: [2, 1], branchId: 35 }, { position: 22, depth: 2, value: 'C', rings: [2, 1], branchId: 35 }, { position: 23, depth: 2, value: 'C', bond: '=', rings: [1], branchId: 35 }] }, { ring: v15, start: 12, end: 22, atoms: [{ position: 12, depth: 1, value: 'C', bond: '=', rings: [2, 2, 1], branchId: 18 }, { position: 13, depth: 1, value: 'C', rings: [3, 3, 2, 1], branchId: 18 }, { position: 19, depth: 1, value: 'C', rings: [3, 2, 1], branchId: 18 }, { position: 20, depth: 1, value: 'C', rings: [2, 1], branchId: 18 }, { position: 21, depth: 2, value: 'O', rings: [2, 1], branchId: 35 }, { position: 22, depth: 2, value: 'C', rings: [2, 1], branchId: 35 }] }, { ring: v18, start: 13, end: 19, atoms: [{ position: 13, depth: 1, value: 'C', rings: [3, 3, 2, 1], branchId: 18 }, { position: 14, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 15, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 17, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 18, depth: 1, value: 'C', rings: [3, 1], branchId: 18 }, { position: 19, depth: 1, value: 'C', rings: [3, 2, 1], branchId: 18 }] }], atoms: [{ position: 25, depth: 1, value: 'C', branchId: 18 }] } });
 export const v20 = Linear(['O']);
 export const v21 = Molecule([v5, v19, v20]);"
 `;

package/test-integration/__snapshots__/hypertension-medication.test.js.snap

@@ -535,7 +535,7 @@ export const v4 = v3.substitute(5, 'N');
 export const v5 = Linear(['O'], ['=']);
 export const v6 = v4.attach(4, v5);
 export const v7 = Ring({ atoms: 'C', size: 5, ringNumber: 2, offset: 2, branchDepths: [0, 1, 1, 1, 1] });
-export const v8 = FusedRing({ metadata: { rings: [{ ring: v6, start: 4, end: 13, atoms: [{ position: 4, depth: 0, value: 'C', rings: [1, 1] }, { position: 5, depth: 0, value: 'N', bond: '=', rings: [1] }, { position: 6, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 11, depth: 0, value: 'C', rings: [1] }, { position: 13, depth: 0, value: 'N', rings: [1] }] }, { ring: v7, start: 6, end: 10, atoms: [{ position: 6, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 7, depth: 1, value: 'C', rings: [2] }, { position: 8, depth: 1, value: 'C', rings: [2] }, { position: 9, depth: 1, value: 'C', rings: [2] }, { position: 10, depth: 1, value: 'C', rings: [2] }] }] } });
+export const v8 = FusedRing({ metadata: { rings: [{ ring: v6, start: 4, end: 13, atoms: [{ position: 4, depth: 0, value: 'C', rings: [1, 1] }, { position: 5, depth: 0, value: 'N', bond: '=', rings: [1] }, { position: 6, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 11, depth: 0, value: 'C', rings: [1] }, { position: 13, depth: 0, value: 'N', rings: [1] }] }, { ring: v7, start: 6, end: 10, atoms: [{ position: 6, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 7, depth: 1, value: 'C', rings: [2], branchId: 10 }, { position: 8, depth: 1, value: 'C', rings: [2], branchId: 10 }, { position: 9, depth: 1, value: 'C', rings: [2], branchId: 10 }, { position: 10, depth: 1, value: 'C', rings: [2], branchId: 10 }] }] } });
 export const v9 = Linear(['C']);
 export const v10 = Ring({ atoms: 'C', size: 6, ringNumber: 3, bonds: ['=', null, '=', null, '=', null], branchDepths: [0, 0, 0, 0, 1, 1] });
 export const v11 = Ring({ atoms: 'C', size: 6, ringNumber: 4, bonds: ['=', null, '=', null, '=', null] });

package/test-integration/__snapshots__/nsaids-otc.test.js.snap

@@ -288,7 +288,7 @@ exports[`Naproxen Integration Test generates valid code via toCode() 1`] = `
 "export const v1 = Linear(['C', 'O']);
 export const v2 = Ring({ atoms: 'c', size: 6, branchDepths: [0, 0, 0, 0, 1, 1] });
 export const v3 = Ring({ atoms: 'c', size: 6, ringNumber: 2, offset: 3, branchDepths: [0, 0, 0, 1, 1, 1] });
-export const v4 = FusedRing({ metadata: { rings: [{ ring: v2, start: 2, end: 11, atoms: [{ position: 2, depth: 0, value: 'c', rings: [1, 1] }, { position: 3, depth: 0, value: 'c', rings: [1] }, { position: 4, depth: 0, value: 'c', rings: [1] }, { position: 5, depth: 0, value: 'c', rings: [2, 2, 1] }, { position: 10, depth: 1, value: 'c', rings: [2, 1] }, { position: 11, depth: 1, value: 'c', rings: [1] }] }, { ring: v3, start: 5, end: 10, atoms: [{ position: 5, depth: 0, value: 'c', rings: [2, 2, 1] }, { position: 6, depth: 0, value: 'c', rings: [2] }, { position: 7, depth: 0, value: 'c', rings: [2] }, { position: 8, depth: 1, value: 'c', rings: [2] }, { position: 9, depth: 1, value: 'c', rings: [2] }, { position: 10, depth: 1, value: 'c', rings: [2, 1] }] }] } });
+export const v4 = FusedRing({ metadata: { rings: [{ ring: v2, start: 2, end: 11, atoms: [{ position: 2, depth: 0, value: 'c', rings: [1, 1] }, { position: 3, depth: 0, value: 'c', rings: [1] }, { position: 4, depth: 0, value: 'c', rings: [1] }, { position: 5, depth: 0, value: 'c', rings: [2, 2, 1] }, { position: 10, depth: 1, value: 'c', rings: [2, 1], branchId: 10 }, { position: 11, depth: 1, value: 'c', rings: [1], branchId: 10 }] }, { ring: v3, start: 5, end: 10, atoms: [{ position: 5, depth: 0, value: 'c', rings: [2, 2, 1] }, { position: 6, depth: 0, value: 'c', rings: [2] }, { position: 7, depth: 0, value: 'c', rings: [2] }, { position: 8, depth: 1, value: 'c', rings: [2], branchId: 10 }, { position: 9, depth: 1, value: 'c', rings: [2], branchId: 10 }, { position: 10, depth: 1, value: 'c', rings: [2, 1], branchId: 10 }] }] } });
 export const v5 = Linear(['C', 'C', 'O']);
 export const v6 = Linear(['C']);
 export const v7 = v5.attach(1, v6);

package/test-integration/__snapshots__/nsaids-prescription.test.js.snap

@@ -365,7 +365,7 @@ export const v6 = v5.substitute(5, 'O');
 export const v7 = Linear(['C', 'C']);
 export const v8 = v6.attach(6, v7);
 export const v9 = Linear(['O'], ['=']);
-export const v10 = FusedRing({ metadata: { rings: [{ ring: v2, start: 2, end: 7, atoms: [{ position: 2, depth: 0, value: 'C', rings: [1, 1] }, { position: 3, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 1, 2] }, { position: 5, depth: 0, value: 'C', bond: '=', rings: [1, 2] }, { position: 6, depth: 1, value: 'C', rings: [1] }, { position: 7, depth: 1, value: 'C', bond: '=', rings: [1] }] }, { ring: v4, start: 4, end: 14, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 1, 2] }, { position: 5, depth: 0, value: 'C', bond: '=', rings: [1, 2] }, { position: 12, depth: 0, value: 'N', rings: [2] }, { position: 13, depth: 0, value: 'C', rings: [3, 2, 3] }, { position: 14, depth: 0, value: 'C', bond: '=', rings: [2, 3] }] }, { ring: v8, start: 13, end: 18, atoms: [{ position: 13, depth: 0, value: 'C', rings: [3, 2, 3] }, { position: 14, depth: 0, value: 'C', bond: '=', rings: [2, 3] }, { position: 15, depth: 0, value: 'C', rings: [3] }, { position: 16, depth: 0, value: 'C', rings: [3] }, { position: 17, depth: 0, value: 'O', rings: [3] }, { position: 18, depth: 0, value: 'C', rings: [3] }] }], atoms: [{ position: 8, depth: 1, value: 'C' }, { position: 9, depth: 1, value: 'C', attachments: [v9] }, { position: 11, depth: 1, value: 'O' }] } });
+export const v10 = FusedRing({ metadata: { rings: [{ ring: v2, start: 2, end: 7, atoms: [{ position: 2, depth: 0, value: 'C', rings: [1, 1] }, { position: 3, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 1, 2] }, { position: 5, depth: 0, value: 'C', bond: '=', rings: [1, 2] }, { position: 6, depth: 1, value: 'C', rings: [1], branchId: 10 }, { position: 7, depth: 1, value: 'C', bond: '=', rings: [1], branchId: 10 }] }, { ring: v4, start: 4, end: 14, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 1, 2] }, { position: 5, depth: 0, value: 'C', bond: '=', rings: [1, 2] }, { position: 12, depth: 0, value: 'N', rings: [2] }, { position: 13, depth: 0, value: 'C', rings: [3, 2, 3] }, { position: 14, depth: 0, value: 'C', bond: '=', rings: [2, 3] }] }, { ring: v8, start: 13, end: 18, atoms: [{ position: 13, depth: 0, value: 'C', rings: [3, 2, 3] }, { position: 14, depth: 0, value: 'C', bond: '=', rings: [2, 3] }, { position: 15, depth: 0, value: 'C', rings: [3] }, { position: 16, depth: 0, value: 'C', rings: [3] }, { position: 17, depth: 0, value: 'O', rings: [3] }, { position: 18, depth: 0, value: 'C', rings: [3] }] }], atoms: [{ position: 8, depth: 1, value: 'C', branchId: 10 }, { position: 9, depth: 1, value: 'C', branchId: 10, attachments: [v9] }, { position: 11, depth: 1, value: 'O', branchId: 10 }] } });
 export const v11 = Linear(['C', 'C']);
 export const v12 = Molecule([v1, v10, v11]);"
 `;
@@ -822,7 +822,7 @@ exports[`Nabumetone Integration Test generates valid code via toCode() 1`] = `
 "export const v1 = Linear(['C', 'O']);
 export const v2 = Ring({ atoms: 'C', size: 6, bonds: ['=', null, '=', null, '=', null], branchDepths: [0, 0, 0, 1, 1, 1] });
 export const v3 = Ring({ atoms: 'C', size: 6, ringNumber: 2, offset: 2, bonds: ['=', null, null, null, '=', null], branchDepths: [0, 0, 0, 1, 1, 1] });
-export const v4 = FusedRing({ metadata: { rings: [{ ring: v2, start: 2, end: 11, atoms: [{ position: 2, depth: 0, value: 'C', rings: [1, 1] }, { position: 3, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 9, depth: 1, value: 'C', bond: '=', rings: [2, 1] }, { position: 10, depth: 1, value: 'C', rings: [1] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [1] }] }, { ring: v3, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 5, depth: 0, value: 'C', bond: '=', rings: [2] }, { position: 6, depth: 0, value: 'C', rings: [2] }, { position: 7, depth: 1, value: 'C', rings: [2] }, { position: 8, depth: 1, value: 'C', rings: [2] }, { position: 9, depth: 1, value: 'C', bond: '=', rings: [2, 1] }] }] } });
+export const v4 = FusedRing({ metadata: { rings: [{ ring: v2, start: 2, end: 11, atoms: [{ position: 2, depth: 0, value: 'C', rings: [1, 1] }, { position: 3, depth: 0, value: 'C', bond: '=', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 9, depth: 1, value: 'C', bond: '=', rings: [2, 1], branchId: 11 }, { position: 10, depth: 1, value: 'C', rings: [1], branchId: 11 }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [1], branchId: 11 }] }, { ring: v3, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 5, depth: 0, value: 'C', bond: '=', rings: [2] }, { position: 6, depth: 0, value: 'C', rings: [2] }, { position: 7, depth: 1, value: 'C', rings: [2], branchId: 11 }, { position: 8, depth: 1, value: 'C', rings: [2], branchId: 11 }, { position: 9, depth: 1, value: 'C', bond: '=', rings: [2, 1], branchId: 11 }] }] } });
 export const v5 = Linear(['C', 'C', 'C', 'C']);
 export const v6 = Linear(['O'], ['=']);
 export const v7 = v5.attach(3, v6);

package/test-integration/__snapshots__/opioids.test.js.snap

@@ -134,7 +134,7 @@ export const v6 = v5.substitute(6, 'O');
 export const v7 = Ring({ atoms: 'C', size: 9, ringNumber: 4, offset: 4, bonds: [null, null, null, null, null, null, null, '=', null], branchDepths: [0, 0, 0, 0, 0, 0, 0, 1, 1] });
 export const v8 = v7.substitute(5, 'O');
 export const v9 = Ring({ atoms: 'C', size: 6, ringNumber: 5, bonds: ['=', null, '=', null, '=', null], branchDepths: [0, 0, 0, 1, 2, 2] });
-export const v10 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 6, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }] }, { ring: v4, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }] }, { ring: v6, start: 4, end: 16, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 15, depth: 0, value: 'O', rings: [3, 4] }, { position: 16, depth: 0, value: 'C', rings: [3, 4] }] }, { ring: v8, start: 5, end: 19, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 15, depth: 0, value: 'O', rings: [3, 4] }, { position: 16, depth: 0, value: 'C', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [4] }, { position: 18, depth: 1, value: 'C', rings: [4] }, { position: 19, depth: 1, value: 'C', bond: '=', rings: [4] }] }, { ring: v9, start: 8, end: 13, atoms: [{ position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }, { position: 10, depth: 0, value: 'C', rings: [5] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [5] }, { position: 12, depth: 2, value: 'C', rings: [5] }, { position: 13, depth: 2, value: 'C', bond: '=', rings: [5] }] }], atoms: [{ position: 14, depth: 1, value: 'O' }] } });
+export const v10 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 6, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }] }, { ring: v4, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }] }, { ring: v6, start: 4, end: 16, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 15, depth: 0, value: 'O', rings: [3, 4] }, { position: 16, depth: 0, value: 'C', rings: [3, 4] }] }, { ring: v8, start: 5, end: 19, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 15, depth: 0, value: 'O', rings: [3, 4] }, { position: 16, depth: 0, value: 'C', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [4] }, { position: 18, depth: 1, value: 'C', rings: [4], branchId: 34 }, { position: 19, depth: 1, value: 'C', bond: '=', rings: [4], branchId: 34 }] }, { ring: v9, start: 8, end: 13, atoms: [{ position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }, { position: 10, depth: 0, value: 'C', rings: [5] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [5], branchId: 19 }, { position: 12, depth: 2, value: 'C', rings: [5], branchId: 22 }, { position: 13, depth: 2, value: 'C', bond: '=', rings: [5], branchId: 22 }] }], atoms: [{ position: 14, depth: 1, value: 'O', branchId: 19 }] } });
 export const v11 = Linear(['O']);
 export const v12 = Molecule([v1, v10, v11]);"
 `;
@@ -273,7 +273,7 @@ export const v6 = v5.substitute(6, 'O');
 export const v7 = Ring({ atoms: 'C', size: 9, ringNumber: 4, offset: 4, bonds: [null, null, null, null, null, null, null, '=', null], branchDepths: [0, 0, 0, 0, 0, 0, 0, 1, 1] });
 export const v8 = v7.substitute(5, 'O');
 export const v9 = Ring({ atoms: 'C', size: 6, ringNumber: 5, bonds: ['=', null, '=', null, '=', null], branchDepths: [0, 0, 0, 1, 2, 2] });
-export const v10 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 6, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }] }, { ring: v4, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }] }, { ring: v6, start: 4, end: 17, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }] }, { ring: v8, start: 5, end: 20, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }, { position: 18, depth: 0, value: 'C', rings: [4] }, { position: 19, depth: 1, value: 'C', rings: [4] }, { position: 20, depth: 1, value: 'C', bond: '=', rings: [4] }] }, { ring: v9, start: 8, end: 13, atoms: [{ position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }, { position: 10, depth: 0, value: 'C', rings: [5] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [5] }, { position: 12, depth: 2, value: 'C', rings: [5] }, { position: 13, depth: 2, value: 'C', bond: '=', rings: [5] }] }], atoms: [{ position: 14, depth: 1, value: 'O' }, { position: 15, depth: 1, value: 'C' }] } });
+export const v10 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 6, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }] }, { ring: v4, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }] }, { ring: v6, start: 4, end: 17, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }] }, { ring: v8, start: 5, end: 20, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }, { position: 18, depth: 0, value: 'C', rings: [4] }, { position: 19, depth: 1, value: 'C', rings: [4], branchId: 35 }, { position: 20, depth: 1, value: 'C', bond: '=', rings: [4], branchId: 35 }] }, { ring: v9, start: 8, end: 13, atoms: [{ position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }, { position: 10, depth: 0, value: 'C', rings: [5] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [5], branchId: 19 }, { position: 12, depth: 2, value: 'C', rings: [5], branchId: 22 }, { position: 13, depth: 2, value: 'C', bond: '=', rings: [5], branchId: 22 }] }], atoms: [{ position: 14, depth: 1, value: 'O', branchId: 19 }, { position: 15, depth: 1, value: 'C', branchId: 19 }] } });
 export const v11 = Linear(['O']);
 export const v12 = Molecule([v1, v10, v11]);"
 `;
@@ -459,7 +459,7 @@ export const v11 = v10.substitute(11, 'O');
 export const v12 = Linear(['O'], ['=']);
 export const v13 = v11.attach(2, v12, { sibling: true });
 export const v14 = Ring({ atoms: 'C', size: 6, ringNumber: 5, bonds: ['=', null, '=', null, '=', null], branchDepths: [1, 1, 1, 2, 3, 3] });
-export const v15 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 11, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 2, 1, 3] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }, { position: 11, depth: 1, value: 'C', rings: [1, 3, 4] }] }, { ring: v6, start: 4, end: 10, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 2, 1, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 9, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }] }, { ring: v9, start: 4, end: 14, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 2, 1, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 9, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }, { position: 11, depth: 1, value: 'C', rings: [1, 3, 4] }, { position: 12, depth: 1, value: 'C', rings: [3, 4] }, { position: 13, depth: 1, value: 'C', rings: [5, 3, 5, 4] }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 5, 4] }] }, { ring: v13, start: 5, end: 21, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 9, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }, { position: 11, depth: 1, value: 'C', rings: [1, 3, 4] }, { position: 12, depth: 1, value: 'C', rings: [3, 4] }, { position: 13, depth: 1, value: 'C', rings: [5, 3, 5, 4] }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 5, 4] }, { position: 15, depth: 1, value: 'C', rings: [5, 4] }, { position: 21, depth: 1, value: 'O', rings: [4] }] }, { ring: v14, start: 13, end: 18, atoms: [{ position: 13, depth: 1, value: 'C', rings: [5, 3, 5, 4] }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 5, 4] }, { position: 15, depth: 1, value: 'C', rings: [5, 4] }, { position: 16, depth: 2, value: 'C', bond: '=', rings: [5] }, { position: 17, depth: 3, value: 'C', rings: [5] }, { position: 18, depth: 3, value: 'C', bond: '=', rings: [5] }] }], atoms: [{ position: 19, depth: 2, value: 'O' }, { position: 20, depth: 2, value: 'C' }] } });
+export const v15 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 11, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 2, 1, 3] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }, { position: 11, depth: 1, value: 'C', rings: [1, 3, 4], branchId: 19 }] }, { ring: v6, start: 4, end: 10, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 2, 1, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 9, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }] }, { ring: v9, start: 4, end: 14, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 2, 1, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 9, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }, { position: 11, depth: 1, value: 'C', rings: [1, 3, 4], branchId: 19 }, { position: 12, depth: 1, value: 'C', rings: [3, 4], branchId: 19 }, { position: 13, depth: 1, value: 'C', rings: [5, 3, 5, 4], branchId: 19 }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 5, 4], branchId: 19 }] }, { ring: v13, start: 5, end: 21, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 9, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 10, depth: 0, value: 'C', rings: [2, 1, 3, 4] }, { position: 11, depth: 1, value: 'C', rings: [1, 3, 4], branchId: 19 }, { position: 12, depth: 1, value: 'C', rings: [3, 4], branchId: 19 }, { position: 13, depth: 1, value: 'C', rings: [5, 3, 5, 4], branchId: 19 }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 5, 4], branchId: 19 }, { position: 15, depth: 1, value: 'C', rings: [5, 4], branchId: 19 }, { position: 21, depth: 1, value: 'O', rings: [4], branchId: 19 }] }, { ring: v14, start: 13, end: 18, atoms: [{ position: 13, depth: 1, value: 'C', rings: [5, 3, 5, 4], branchId: 19 }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 5, 4], branchId: 19 }, { position: 15, depth: 1, value: 'C', rings: [5, 4], branchId: 19 }, { position: 16, depth: 2, value: 'C', bond: '=', rings: [5], branchId: 29 }, { position: 17, depth: 3, value: 'C', rings: [5], branchId: 32 }, { position: 18, depth: 3, value: 'C', bond: '=', rings: [5], branchId: 32 }] }], atoms: [{ position: 19, depth: 2, value: 'O', branchId: 29 }, { position: 20, depth: 2, value: 'C', branchId: 29 }] } });
 export const v16 = Linear(['O']);
 export const v17 = Molecule([v1, v15, v16]);"
 `;
@@ -605,7 +605,7 @@ export const v8 = v7.substitute(5, 'O');
 export const v9 = Linear(['O'], ['=']);
 export const v10 = v8.attach(7, v9);
 export const v11 = Ring({ atoms: 'C', size: 6, ringNumber: 5, bonds: ['=', null, '=', null, '=', null], branchDepths: [0, 0, 0, 1, 2, 2] });
-export const v12 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 6, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }] }, { ring: v4, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }] }, { ring: v6, start: 4, end: 17, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }] }, { ring: v10, start: 5, end: 21, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }, { position: 18, depth: 0, value: 'C', rings: [4] }, { position: 20, depth: 0, value: 'C', rings: [4] }, { position: 21, depth: 0, value: 'C', rings: [4] }] }, { ring: v11, start: 8, end: 13, atoms: [{ position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }, { position: 10, depth: 0, value: 'C', rings: [5] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [5] }, { position: 12, depth: 2, value: 'C', rings: [5] }, { position: 13, depth: 2, value: 'C', bond: '=', rings: [5] }] }], atoms: [{ position: 14, depth: 1, value: 'O' }, { position: 15, depth: 1, value: 'C' }] } });
+export const v12 = FusedRing({ metadata: { rings: [{ ring: v3, start: 1, end: 6, atoms: [{ position: 1, depth: 0, value: 'N', rings: [1, 1] }, { position: 2, depth: 0, value: 'C', rings: [1] }, { position: 3, depth: 0, value: 'C', rings: [1] }, { position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }] }, { ring: v4, start: 4, end: 9, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }] }, { ring: v6, start: 4, end: 17, atoms: [{ position: 4, depth: 0, value: 'C', rings: [2, 3, 1, 2, 3] }, { position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }] }, { ring: v10, start: 5, end: 21, atoms: [{ position: 5, depth: 0, value: 'C', rings: [4, 1, 2, 3, 4] }, { position: 6, depth: 0, value: 'C', rings: [1, 2, 3, 4] }, { position: 7, depth: 0, value: 'C', rings: [2, 3, 4] }, { position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 16, depth: 0, value: 'O', rings: [3, 4] }, { position: 17, depth: 0, value: 'C', rings: [3, 4] }, { position: 18, depth: 0, value: 'C', rings: [4] }, { position: 20, depth: 0, value: 'C', rings: [4] }, { position: 21, depth: 0, value: 'C', rings: [4] }] }, { ring: v11, start: 8, end: 13, atoms: [{ position: 8, depth: 0, value: 'C', rings: [5, 2, 5, 3, 4] }, { position: 9, depth: 0, value: 'C', bond: '=', rings: [2, 5] }, { position: 10, depth: 0, value: 'C', rings: [5] }, { position: 11, depth: 1, value: 'C', bond: '=', rings: [5], branchId: 19 }, { position: 12, depth: 2, value: 'C', rings: [5], branchId: 22 }, { position: 13, depth: 2, value: 'C', bond: '=', rings: [5], branchId: 22 }] }], atoms: [{ position: 14, depth: 1, value: 'O', branchId: 19 }, { position: 15, depth: 1, value: 'C', branchId: 19 }] } });
 export const v13 = Molecule([v1, v12]);"
 `;
 

package/test-integration/__snapshots__/steroids.test.js.snap

@@ -1757,7 +1757,7 @@ export const v18 = v16.attach(7, v17, { sibling: true });
 export const v19 = Ring({ atoms: 'C', size: 6, ringNumber: 4, bonds: ['=', null, null, '=', null, null] });
 export const v20 = Linear(['O'], ['=']);
 export const v21 = v19.attach(3, v20);
-export const v22 = FusedRing({ metadata: { rings: [{ ring: v6, start: 1, end: 17, atoms: [{ position: 1, depth: 0, value: 'C', rings: [1, 2, 1, 2] }, { position: 2, depth: 0, value: 'C', rings: [1, 2] }, { position: 3, depth: 0, value: 'C', rings: [1, 2] }, { position: 5, depth: 0, value: 'C', rings: [3, 3, 1, 2] }, { position: 17, depth: 0, value: 'C', rings: [1, 2] }] }, { ring: v15, start: 1, end: 22, atoms: [{ position: 1, depth: 0, value: 'C', rings: [1, 2, 1, 2] }, { position: 2, depth: 0, value: 'C', rings: [1, 2] }, { position: 3, depth: 0, value: 'C', rings: [1, 2] }, { position: 5, depth: 0, value: 'C', rings: [3, 3, 1, 2] }, { position: 17, depth: 0, value: 'C', rings: [1, 2] }, { position: 19, depth: 0, value: 'C', rings: [2] }, { position: 21, depth: 0, value: 'C', rings: [2] }, { position: 22, depth: 0, value: 'C', rings: [2] }] }, { ring: v18, start: 5, end: 15, atoms: [{ position: 5, depth: 0, value: 'C', rings: [3, 3, 1, 2] }, { position: 6, depth: 0, value: 'C', rings: [3] }, { position: 7, depth: 1, value: 'C', rings: [3] }, { position: 8, depth: 1, value: 'C', rings: [3] }, { position: 9, depth: 1, value: 'C', rings: [4, 3, 4] }, { position: 10, depth: 1, value: 'C', bond: '=', rings: [3, 4] }, { position: 11, depth: 1, value: 'C', rings: [3, 4] }, { position: 13, depth: 1, value: 'C', rings: [3, 4] }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 4] }, { position: 15, depth: 1, value: 'C', rings: [3, 4] }] }, { ring: v21, start: 9, end: 15, atoms: [{ position: 9, depth: 1, value: 'C', rings: [4, 3, 4] }, { position: 10, depth: 1, value: 'C', bond: '=', rings: [3, 4] }, { position: 11, depth: 1, value: 'C', rings: [3, 4] }, { position: 13, depth: 1, value: 'C', rings: [3, 4] }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 4] }, { position: 15, depth: 1, value: 'C', rings: [3, 4] }] }], atoms: [{ position: 16, depth: 1, value: 'C' }] } });
+export const v22 = FusedRing({ metadata: { rings: [{ ring: v6, start: 1, end: 17, atoms: [{ position: 1, depth: 0, value: 'C', rings: [1, 2, 1, 2] }, { position: 2, depth: 0, value: 'C', rings: [1, 2] }, { position: 3, depth: 0, value: 'C', rings: [1, 2] }, { position: 5, depth: 0, value: 'C', rings: [3, 3, 1, 2] }, { position: 17, depth: 0, value: 'C', rings: [1, 2] }] }, { ring: v15, start: 1, end: 22, atoms: [{ position: 1, depth: 0, value: 'C', rings: [1, 2, 1, 2] }, { position: 2, depth: 0, value: 'C', rings: [1, 2] }, { position: 3, depth: 0, value: 'C', rings: [1, 2] }, { position: 5, depth: 0, value: 'C', rings: [3, 3, 1, 2] }, { position: 17, depth: 0, value: 'C', rings: [1, 2] }, { position: 19, depth: 0, value: 'C', rings: [2] }, { position: 21, depth: 0, value: 'C', rings: [2] }, { position: 22, depth: 0, value: 'C', rings: [2] }] }, { ring: v18, start: 5, end: 15, atoms: [{ position: 5, depth: 0, value: 'C', rings: [3, 3, 1, 2] }, { position: 6, depth: 0, value: 'C', rings: [3] }, { position: 7, depth: 1, value: 'C', rings: [3], branchId: 12 }, { position: 8, depth: 1, value: 'C', rings: [3], branchId: 12 }, { position: 9, depth: 1, value: 'C', rings: [4, 3, 4], branchId: 12 }, { position: 10, depth: 1, value: 'C', bond: '=', rings: [3, 4], branchId: 12 }, { position: 11, depth: 1, value: 'C', rings: [3, 4], branchId: 12 }, { position: 13, depth: 1, value: 'C', rings: [3, 4], branchId: 12 }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 4], branchId: 12 }, { position: 15, depth: 1, value: 'C', rings: [3, 4], branchId: 12 }] }, { ring: v21, start: 9, end: 15, atoms: [{ position: 9, depth: 1, value: 'C', rings: [4, 3, 4], branchId: 12 }, { position: 10, depth: 1, value: 'C', bond: '=', rings: [3, 4], branchId: 12 }, { position: 11, depth: 1, value: 'C', rings: [3, 4], branchId: 12 }, { position: 13, depth: 1, value: 'C', rings: [3, 4], branchId: 12 }, { position: 14, depth: 1, value: 'C', bond: '=', rings: [3, 4], branchId: 12 }, { position: 15, depth: 1, value: 'C', rings: [3, 4], branchId: 12 }] }], atoms: [{ position: 16, depth: 1, value: 'C', branchId: 12 }] } });
 export const v23 = Linear(['C', 'C', 'O']);
 export const v24 = Linear(['O'], ['=']);
 export const v25 = v23.attach(1, v24);
@@ -2027,7 +2027,7 @@ export const v21 = Linear(['O'], ['=']);
 export const v22 = v20.attach(3, v21);
 export const v23 = Linear(['C']);
 export const v24 = v22.attach(6, v23);
-export const v25 = FusedRing({ metadata: { rings: [{ ring: v4, start: 3, end: 27, atoms: [{ position: 3, depth: 0, value: 'C', rings: [1, 1] }, { position: 4, depth: 0, value: 'O', rings: [1] }, { position: 5, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 26, depth: 0, value: 'C', rings: [2, 1] }, { position: 27, depth: 1, value: 'O', rings: [1] }] }, { ring: v7, start: 5, end: 26, atoms: [{ position: 5, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 6, depth: 0, value: 'C', rings: [2] }, { position: 7, depth: 0, value: 'C', rings: [3, 3, 2] }, { position: 24, depth: 0, value: 'C', rings: [3, 2] }, { position: 26, depth: 0, value: 'C', rings: [2, 1] }] }, { ring: v14, start: 7, end: 24, atoms: [{ position: 7, depth: 0, value: 'C', rings: [3, 3, 2] }, { position: 8, depth: 0, value: 'C', rings: [4, 4, 3] }, { position: 19, depth: 0, value: 'C', rings: [4, 3] }, { position: 21, depth: 0, value: 'C', rings: [3] }, { position: 23, depth: 0, value: 'C', rings: [3] }, { position: 24, depth: 0, value: 'C', rings: [3, 2] }] }, { ring: v19, start: 8, end: 19, atoms: [{ position: 8, depth: 0, value: 'C', rings: [4, 4, 3] }, { position: 9, depth: 0, value: 'C', rings: [4] }, { position: 10, depth: 0, value: 'C', rings: [4] }, { position: 11, depth: 0, value: 'C', rings: [5, 5, 4] }, { position: 17, depth: 0, value: 'C', rings: [5, 4] }, { position: 19, depth: 0, value: 'C', rings: [4, 3] }] }, { ring: v24, start: 11, end: 17, atoms: [{ position: 11, depth: 0, value: 'C', rings: [5, 5, 4] }, { position: 12, depth: 0, value: 'C', bond: '=', rings: [5] }, { position: 13, depth: 0, value: 'C', rings: [5] }, { position: 15, depth: 0, value: 'C', rings: [5] }, { position: 16, depth: 0, value: 'C', bond: '=', rings: [5] }, { position: 17, depth: 0, value: 'C', rings: [5, 4] }] }] } });
+export const v25 = FusedRing({ metadata: { rings: [{ ring: v4, start: 3, end: 27, atoms: [{ position: 3, depth: 0, value: 'C', rings: [1, 1] }, { position: 4, depth: 0, value: 'O', rings: [1] }, { position: 5, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 26, depth: 0, value: 'C', rings: [2, 1] }, { position: 27, depth: 1, value: 'O', rings: [1], branchId: 49 }] }, { ring: v7, start: 5, end: 26, atoms: [{ position: 5, depth: 0, value: 'C', rings: [2, 2, 1] }, { position: 6, depth: 0, value: 'C', rings: [2] }, { position: 7, depth: 0, value: 'C', rings: [3, 3, 2] }, { position: 24, depth: 0, value: 'C', rings: [3, 2] }, { position: 26, depth: 0, value: 'C', rings: [2, 1] }] }, { ring: v14, start: 7, end: 24, atoms: [{ position: 7, depth: 0, value: 'C', rings: [3, 3, 2] }, { position: 8, depth: 0, value: 'C', rings: [4, 4, 3] }, { position: 19, depth: 0, value: 'C', rings: [4, 3] }, { position: 21, depth: 0, value: 'C', rings: [3] }, { position: 23, depth: 0, value: 'C', rings: [3] }, { position: 24, depth: 0, value: 'C', rings: [3, 2] }] }, { ring: v19, start: 8, end: 19, atoms: [{ position: 8, depth: 0, value: 'C', rings: [4, 4, 3] }, { position: 9, depth: 0, value: 'C', rings: [4] }, { position: 10, depth: 0, value: 'C', rings: [4] }, { position: 11, depth: 0, value: 'C', rings: [5, 5, 4] }, { position: 17, depth: 0, value: 'C', rings: [5, 4] }, { position: 19, depth: 0, value: 'C', rings: [4, 3] }] }, { ring: v24, start: 11, end: 17, atoms: [{ position: 11, depth: 0, value: 'C', rings: [5, 5, 4] }, { position: 12, depth: 0, value: 'C', bond: '=', rings: [5] }, { position: 13, depth: 0, value: 'C', rings: [5] }, { position: 15, depth: 0, value: 'C', rings: [5] }, { position: 16, depth: 0, value: 'C', bond: '=', rings: [5] }, { position: 17, depth: 0, value: 'C', rings: [5, 4] }] }] } });
 export const v26 = Linear(['C', 'C', 'O']);
 export const v27 = Linear(['O'], ['=']);
 export const v28 = v26.attach(1, v27);

package/test-integration/cholesterol-drugs.test.js

@@ -12,6 +12,7 @@ const EZETIMIBE_SMILES = 'C[C@H]1[C@@H](O)[C@H](O[C@H]1c2ccc(F)cc2)c3ccc(O)cc3C(
 const FENOFIBRATE_SMILES = 'CC(C)OC(=O)C(C)(C)Oc1ccc(cc1)C(=O)c2ccc(Cl)cc2';
 const GEMFIBROZIL_SMILES = 'CC1=CC(C)=CC=C1CCCC(C)(C)C(=O)O';
 const PITAVASTATIN_SMILES = 'CC(C)c1nc(nc(c1/C=C/[C@@H](O)C[C@@H](O)CC(=O)O)c2ccc(F)cc2)NC(=O)C3CC3';
+const CHOLESTEROL_SMILES = 'C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C';
 
 describe('Atorvastatin Integration Test', () => {
   test('parses atorvastatin', () => {
@@ -412,3 +413,43 @@ describe('Pitavastatin Integration Test', () => {
     expect(reconstructed.smiles).toBe(PITAVASTATIN_SMILES);
   });
 });
+
+describe('Cholesterol Integration Test', () => {
+  test('parses cholesterol', () => {
+    const ast = parse(CHOLESTEROL_SMILES);
+    const obj = ast.toObject();
+    expect(obj).toMatchSnapshot();
+    expect(ast.smiles).toBe(CHOLESTEROL_SMILES);
+  });
+
+  test('generates valid code via toCode()', () => {
+    const ast = parse(CHOLESTEROL_SMILES);
+    const code = ast.toCode('v');
+    expect(code).toMatchSnapshot();
+  });
+
+  test('generated code is valid JavaScript', () => {
+    const ast = parse(CHOLESTEROL_SMILES);
+    const code = ast.toCode('v');
+    const executableCode = stripExports(code);
+
+    let factory;
+    expect(() => {
+      factory = createFunction('Ring', 'Linear', 'FusedRing', 'Molecule', executableCode);
+    }).not.toThrow();
+    expect(typeof factory).toBe('function');
+  });
+
+  test('codegen round-trip: generated code produces valid SMILES', () => {
+    const ast = parse(CHOLESTEROL_SMILES);
+    const code = ast.toCode('v');
+    const executableCode = stripExports(code);
+
+    const varMatch = code.match(/export const (v\d+) = /g);
+    const lastVar = varMatch ? varMatch[varMatch.length - 1].match(/export const (v\d+)/)[1] : 'v1';
+
+    const reconstructed = executeCode(executableCode, lastVar);
+
+    expect(reconstructed.smiles).toBe(CHOLESTEROL_SMILES);
+  });
+});

package/test-integration/cholesterol.test.js

@@ -0,0 +1,112 @@
+import { describe, test, expect } from 'bun:test';
+import { parse } from '../src/parser/index.js';
+import { codegenRoundTrip } from './utils.js';
+
+const CHOLESTEROL_SMILES = 'C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C';
+
+describe('Cholesterol - Divide and Conquer', () => {
+  // Cholesterol SMILES:
+  // C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
+  //
+  // The failure: ring 4 is being dropped
+  // Expected: ...CC=C4[C@@]3(CC[C@@H](C4)O)C)C
+  // Received: ...CC=C[C@@]3(CC[C@@H](C)O)C)C
+
+  // Level 1: Simple ring closures
+  test('simple ring', () => {
+    const s = 'C1CCCCC1';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 2: Two fused rings (decalin-like)
+  test('two fused rings', () => {
+    const s = 'C1CCC2CCCCC2C1';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 3: Ring closure inside a branch - the core pattern
+  test('ring closure in branch: C1CCC(C1)C', () => {
+    const s = 'C1CCC(C1)C';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 4: Two ring numbers, one closing in a branch
+  test('two rings, one closing in branch: C1CC2CCC(C2)C1', () => {
+    const s = 'C1CC2CCC(C2)C1';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 5: Ring opening and closing with different numbers in nested context
+  test('ring 4 opens and closes in branch: C4CCC(C4)', () => {
+    const s = 'C4CCC(C4)';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 6: The specific pattern from cholesterol - ring opens, then closes inside a parenthesized branch
+  test('ring open at atom, close inside branch argument: CC=C4C(CC(C4)O)', () => {
+    const s = 'CC=C4C(CC(C4)O)';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 7: Closer to cholesterol D-ring pattern
+  test('cholesterol D-ring pattern: CC=C4C(CCC(C4)O)C', () => {
+    const s = 'CC=C4C(CCC(C4)O)C';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 8: Add ring 3 fused with ring 4
+  test('fused rings 3+4: C3CC=C4C3(CCC(C4)O)C', () => {
+    const s = 'C3CC=C4C3(CCC(C4)O)C';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 9: The C/D ring system from cholesterol (without stereo)
+  test('C/D ring system: C2CC=C4C(CC2)(CCC(C4)O)C', () => {
+    const s = 'C2CC=C4C(CC2)(CCC(C4)O)C';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 10: Three fused rings (A/B/C ring without stereo)
+  test('three fused rings: C1CCC2C1CCC3CC=C4C3(CCC(C4)O)C', () => {
+    const s = 'C1CCC2C1CCC3C2CC=C4C3(CCC(C4)O)C';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 11: Isolate multiple branches on same atom with ring closures
+  test('two branches with ring closures: C1C(C1)(C2)CC2', () => {
+    const s = 'C1C(C1)(C2)CC2';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 12: Minimal failing pattern - ring closure in second branch
+  test('ring close in second branch: C4CC(C)(C4)', () => {
+    const s = 'C4CC(C)(C4)';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 13: Full cholesterol (no stereo) to isolate stereo vs ring issue
+  test('cholesterol without stereochemistry', () => {
+    const s = 'CC(CCCC(C)C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C';
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+
+  // Level 14: Full cholesterol with stereochemistry
+  test('full cholesterol', () => {
+    const s = CHOLESTEROL_SMILES;
+    expect(parse(s).smiles).toBe(s);
+    expect(codegenRoundTrip(s).smiles).toBe(s);
+  });
+});