Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cn1cc(-c2cc3nccn3c(-c3cnn(C4(CC#N)CC5(COC5)C4)c3)n2)cn1
InChiKey
CWZMCYRDDXLYLG-UHFFFAOYSA-N
Route Signature
b606b2de527414c38b613527b0084c1eb02a2c4207999f64878752e4c8d1b38b
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_123c91076e77192b8cc5bc0b",
"signature": "b606b2de527414c38b613527b0084c1eb02a2c4207999f64878752e4c8d1b38b",
"contentHash": "b547264dcff07f2d45771e26e91367cb24b6a67f0649afc132e9fec9c7d44ebb",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_2270f1d3e4ce50d3af742c93",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02652",
"moleculeId": "sa_63647b90bb71aea1abdd62f1",
"smiles": "Cn1cc(-c2cc3nccn3c(-c3cnn(C4(CC#N)CC5(COC5)C4)c3)n2)cn1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_63647b90bb71aea1abdd62f1",
"inchikey": "CWZMCYRDDXLYLG-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc3nccn3c(-c3cnn(C4(CC#N)CC5(COC5)C4)c3)n2)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10816",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_63647b90bb71aea1abdd62f1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_63647b90bb71aea1abdd62f1",
"inchikey": "CWZMCYRDDXLYLG-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc3nccn3c(-c3cnn(C4(CC#N)CC5(COC5)C4)c3)n2)cn1"
},
"smiles": "Cn1cc(-c2cc3nccn3c(-c3cnn(C4(CC#N)CC5(COC5)C4)c3)n2)cn1",
"reactionStepId": "sa_e450165e64e234759a2e5d3f",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08962596B2;0999;1583409\",\"rsmi\":\"[C:16]1(=[CH:17][C:18]#[N:19])[CH2:20][C:21]2([CH2:22][O:23][CH2:24]2)[CH2:25]1.[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](-[c:13]3[cH:14][nH:15][n:26][cH:27]3)[n:28]2)[cH:29][n:30]1>C1CCC2=NCCCN2CC1.CC#N>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](-[c:13]3[cH:14][n:15]([C:16]4([CH2:17][C:18]#[N:19])[CH2:20][C:21]5([CH2:22][O:23][CH2:24]5)[CH2:25]4)[n:26][cH:27]3)[n:28]2)[cH:29][n:30]1\"},\"mapped_reaction_smiles\":\"[C:16]1(=[CH:17][C:18]#[N:19])[CH2:20][C:21]2([CH2:22][O:23][CH2:24]2)[CH2:25]1.[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](-[c:13]3[cH:14][nH:15][n:26][cH:27]3)[n:28]2)[cH:29][n:30]1>C1CCC2=NCCCN2CC1.CC#N>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](-[c:13]3[cH:14][n:15]([C:16]4([CH2:17][C:18]#[N:19])[CH2:20][C:21]5([CH2:22][O:23][CH2:24]5)[CH2:25]4)[n:26][cH:27]3)[n:28]2)[cH:29][n:30]1\"}",
"reactionStep": {
"id": "sa_e450165e64e234759a2e5d3f",
"reactionHash": "34f003e70b286b52c461679b7c1d3101acccdc4416fa7e84895392bd98f8876c"
},
"children": [
{
"id": "10817",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_6dd0ac14ea0899bde4f66438",
"parentId": "10816",
"isLeaf": false,
"molecule": {
"id": "sa_6dd0ac14ea0899bde4f66438",
"inchikey": "JAZNQCLYKJCNEB-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc3nccn3c(-c3cn[nH]c3)n2)cn1"
},
"smiles": "Cn1cc(-c2cc3nccn3c(-c3cn[nH]c3)n2)cn1",
"reactionStepId": "sa_88fa49ae10581f83f6d54d28",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08962596B2;0714;1583293\",\"rsmi\":\"CC1(C)OB([c:13]2[cH:14][nH:15][n:16][cH:17]2)OC1(C)C.Cl[c:12]1[n:11]2[c:7]([cH:6][c:5](-[c:4]3[cH:3][n:2]([CH3:1])[n:20][cH:19]3)[n:18]1)[n:8][cH:9][cH:10]2>COCCOC.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](-[c:13]3[cH:14][nH:15][n:16][cH:17]3)[n:18]2)[cH:19][n:20]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:13]2[cH:14][nH:15][n:16][cH:17]2)OC1(C)C.Cl[c:12]1[n:11]2[c:7]([cH:6][c:5](-[c:4]3[cH:3][n:2]([CH3:1])[n:20][cH:19]3)[n:18]1)[n:8][cH:9][cH:10]2>COCCOC.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](-[c:13]3[cH:14][nH:15][n:16][cH:17]3)[n:18]2)[cH:19][n:20]1\"}",
"reactionStep": {
"id": "sa_88fa49ae10581f83f6d54d28",
"reactionHash": "d8df192a3f244001a14ee0be19c2fb8b54f2e4392d0fb16798945717ee6eb56b"
},
"children": [
{
"id": "10818",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_35bd649b9280fc9f125f1c92",
"parentId": "10817",
"isLeaf": false,
"molecule": {
"id": "sa_35bd649b9280fc9f125f1c92",
"inchikey": "CBUBGDTWTQZLKI-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc3nccn3c(Cl)n2)cn1"
},
"smiles": "Cn1cc(-c2cc3nccn3c(Cl)n2)cn1",
"reactionStepId": "sa_0dc616e5e127d65b0fc33d63",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08962596B2;0712;1583292\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:13].O=[c:12]1[n:11]2[c:7]([cH:6][c:5](-[c:4]3[cH:3][n:2]([CH3:1])[n:16][cH:15]3)[nH:14]1)[n:8][cH:9][cH:10]2>CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C.CCOC(C)=O.CO.ClCCl>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12]([Cl:13])[n:14]2)[cH:15][n:16]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:13].O=[c:12]1[n:11]2[c:7]([cH:6][c:5](-[c:4]3[cH:3][n:2]([CH3:1])[n:16][cH:15]3)[nH:14]1)[n:8][cH:9][cH:10]2>CCN(C(C)C)C(C)C.CCN(C(C)C)C(C)C.CCOC(C)=O.CO.ClCCl>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12]([Cl:13])[n:14]2)[cH:15][n:16]1\"}",
"reactionStep": {
"id": "sa_0dc616e5e127d65b0fc33d63",
"reactionHash": "3e673079e63b50964a849231ef8e16114875bc925e4d4b10acc7554b6e6b40d9"
},
"children": [
{
"id": "10819",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_8c004c05334b55b34372a1f5",
"parentId": "10818",
"isLeaf": false,
"molecule": {
"id": "sa_8c004c05334b55b34372a1f5",
"inchikey": "FMKMDJDCGLADOP-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc3nccn3c(=O)[nH]2)cn1"
},
"smiles": "Cn1cc(-c2cc3nccn3c(=O)[nH]2)cn1",
"reactionStepId": "sa_d825fb66c7eb2713c13ad5ff",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08962596B2;0710;1583291\",\"rsmi\":\"CC1(C)OB([c:4]2[cH:3][n:2]([CH3:1])[n:16][cH:15]2)OC1(C)C.Cl[c:5]1[cH:6][c:7]2[n:8][cH:9][cH:10][n:11]2[c:12](=[O:13])[nH:14]1>CC(C)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=P(O)(O)O.[K+].[K+].[K+].[Pd].[Pd]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](=[O:13])[nH:14]2)[cH:15][n:16]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:4]2[cH:3][n:2]([CH3:1])[n:16][cH:15]2)OC1(C)C.Cl[c:5]1[cH:6][c:7]2[n:8][cH:9][cH:10][n:11]2[c:12](=[O:13])[nH:14]1>CC(C)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=P(O)(O)O.[K+].[K+].[K+].[Pd].[Pd]>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]3[n:8][cH:9][cH:10][n:11]3[c:12](=[O:13])[nH:14]2)[cH:15][n:16]1\"}",
"reactionStep": {
"id": "sa_d825fb66c7eb2713c13ad5ff",
"reactionHash": "f4dcdad4eead5d584c67d0b7602309f0e035c28ff4c84fc159c94e6475bdac5f"
},
"children": [
{
"id": "10820",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_e6114abb2d7683d6ba0e8d0b",
"parentId": "10819",
"isLeaf": true,
"molecule": {
"id": "sa_e6114abb2d7683d6ba0e8d0b",
"inchikey": "MORDDYJPVSRHAG-UHFFFAOYSA-N",
"smiles": "O=c1[nH]c(Cl)cc2nccn12"
},
"smiles": "O=c1[nH]c(Cl)cc2nccn12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10821",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_8ccec6fc9194e5fbc0d06993",
"parentId": "10819",
"isLeaf": true,
"molecule": {
"id": "sa_8ccec6fc9194e5fbc0d06993",
"inchikey": "UCNGGGYMLHAMJG-UHFFFAOYSA-N",
"smiles": "Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1"
},
"smiles": "Cn1cc(B2OC(C)(C)C(C)(C)O2)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10822",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "10818",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10823",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_228b9e0da2a721dc2ba56581",
"parentId": "10817",
"isLeaf": true,
"molecule": {
"id": "sa_228b9e0da2a721dc2ba56581",
"inchikey": "TVOJIBGZFYMWDT-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cn[nH]c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cn[nH]c2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10824",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_de3b816fa29b2961ff0923aa",
"parentId": "10816",
"isLeaf": false,
"molecule": {
"id": "sa_de3b816fa29b2961ff0923aa",
"inchikey": "XYCFQQUAIAXFMX-UHFFFAOYSA-N",
"smiles": "N#CC=C1CC2(COC2)C1"
},
"smiles": "N#CC=C1CC2(COC2)C1",
"reactionStepId": "sa_dc5374f1b572bd7fc88db2ca",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08962596B2;0998;1583408\",\"rsmi\":\"CCOP(=O)(OCC)[CH2:3][C:2]#[N:1].O=[C:4]1[CH2:5][C:6]2([CH2:7][O:8][CH2:9]2)[CH2:10]1>C1CCOC1.CC(C)(C)O.[K+]>[N:1]#[C:2][CH:3]=[C:4]1[CH2:5][C:6]2([CH2:7][O:8][CH2:9]2)[CH2:10]1\"},\"mapped_reaction_smiles\":\"CCOP(=O)(OCC)[CH2:3][C:2]#[N:1].O=[C:4]1[CH2:5][C:6]2([CH2:7][O:8][CH2:9]2)[CH2:10]1>C1CCOC1.CC(C)(C)O.[K+]>[N:1]#[C:2][CH:3]=[C:4]1[CH2:5][C:6]2([CH2:7][O:8][CH2:9]2)[CH2:10]1\"}",
"reactionStep": {
"id": "sa_dc5374f1b572bd7fc88db2ca",
"reactionHash": "2d70b8d14035186c4959f83bf191b5645f5a7e0e5af2805fc168e4b17f3053f2"
},
"children": [
{
"id": "10825",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_2431ee2278086969b3061a62",
"parentId": "10824",
"isLeaf": true,
"molecule": {
"id": "sa_2431ee2278086969b3061a62",
"inchikey": "JWNCVDJOXJTJPB-UHFFFAOYSA-N",
"smiles": "O=C1CC2(COC2)C1"
},
"smiles": "O=C1CC2(COC2)C1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10826",
"routeId": "sa_123c91076e77192b8cc5bc0b",
"moleculeId": "sa_a122c0e2133d59dd0be2bf68",
"parentId": "10824",
"isLeaf": true,
"molecule": {
"id": "sa_a122c0e2133d59dd0be2bf68",
"inchikey": "KWMBADTWRIGGGG-UHFFFAOYSA-N",
"smiles": "CCOP(=O)(CC#N)OCC"
},
"smiles": "CCOP(=O)(CC#N)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}