Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Ic1ccc2nc(-c3ccc(-c4cc[nH]n4)cc3)cn2c1
InChiKey
OLFQWTDIJLVADS-UHFFFAOYSA-N
Route Signature
a09e9abab4fd83a35e50b19f3def70c7518ea7cdc5af95ee650b92294b100966
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_181d60008a01c04c3bfa0ad0",
"signature": "a09e9abab4fd83a35e50b19f3def70c7518ea7cdc5af95ee650b92294b100966",
"contentHash": "f66d954831b0b31d308e770d2f5c8e18fb96f6e34d447495370eecee2023ee3c",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_a0e886708a4c24d430bac247",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00715",
"moleculeId": "sa_ec81b379e626f9c984dacb04",
"smiles": "Ic1ccc2nc(-c3ccc(-c4cc[nH]n4)cc3)cn2c1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_ec81b379e626f9c984dacb04",
"inchikey": "OLFQWTDIJLVADS-UHFFFAOYSA-N",
"smiles": "Ic1ccc2nc(-c3ccc(-c4cc[nH]n4)cc3)cn2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4726",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_ec81b379e626f9c984dacb04",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_ec81b379e626f9c984dacb04",
"inchikey": "OLFQWTDIJLVADS-UHFFFAOYSA-N",
"smiles": "Ic1ccc2nc(-c3ccc(-c4cc[nH]n4)cc3)cn2c1"
},
"smiles": "Ic1ccc2nc(-c3ccc(-c4cc[nH]n4)cc3)cn2c1",
"reactionStepId": "sa_9cbf61f067a5062d4d49ebc4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08022075B2;0134;1112316\",\"rsmi\":\"CN(C)/[CH:14]=[CH:15]/[C:11](=O)[c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][n:4]3[cH:3][c:2]([I:1])[cH:21][cH:20][c:19]3[n:18]2)[cH:17][cH:16]1.[NH2:12][NH2:13]>CCO.O>[I:1][c:2]1[cH:3][n:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][c:10](-[c:11]4[n:12][nH:13][cH:14][cH:15]4)[cH:16][cH:17]3)[n:18][c:19]2[cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"CN(C)/[CH:14]=[CH:15]/[C:11](=O)[c:10]1[cH:9][cH:8][c:7](-[c:6]2[cH:5][n:4]3[cH:3][c:2]([I:1])[cH:21][cH:20][c:19]3[n:18]2)[cH:17][cH:16]1.[NH2:12][NH2:13]>CCO.O>[I:1][c:2]1[cH:3][n:4]2[cH:5][c:6](-[c:7]3[cH:8][cH:9][c:10](-[c:11]4[n:12][nH:13][cH:14][cH:15]4)[cH:16][cH:17]3)[n:18][c:19]2[cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_9cbf61f067a5062d4d49ebc4",
"reactionHash": "9caa860c775d0ecfeeee743fd957ad4a324ee9a0228c96328265a3474a22f065"
},
"children": [
{
"id": "4727",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_5343d6a1d2fb76e42ebc4a18",
"parentId": "4726",
"isLeaf": false,
"molecule": {
"id": "sa_5343d6a1d2fb76e42ebc4a18",
"inchikey": "MTBLRWFKYSUAKO-MDZDMXLPSA-N",
"smiles": "CN(C)/C=C/C(=O)c1ccc(-c2cn3cc(I)ccc3n2)cc1"
},
"smiles": "CN(C)/C=C/C(=O)c1ccc(-c2cn3cc(I)ccc3n2)cc1",
"reactionStepId": "sa_6ef2f0acfd7cd717abb92598",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08022075B2;0132;1112315\",\"rsmi\":\"CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][n:14]3[cH:15][c:16]([I:17])[cH:18][cH:19][c:20]3[n:21]2)[cH:22][cH:23]1>CN(C)C=O>[CH3:1][N:2]([CH3:3])/[CH:4]=[CH:5]/[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][n:14]3[cH:15][c:16]([I:17])[cH:18][cH:19][c:20]3[n:21]2)[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"CO[CH:4](OC)[N:2]([CH3:1])[CH3:3].[CH3:5][C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][n:14]3[cH:15][c:16]([I:17])[cH:18][cH:19][c:20]3[n:21]2)[cH:22][cH:23]1>CN(C)C=O>[CH3:1][N:2]([CH3:3])/[CH:4]=[CH:5]/[C:6](=[O:7])[c:8]1[cH:9][cH:10][c:11](-[c:12]2[cH:13][n:14]3[cH:15][c:16]([I:17])[cH:18][cH:19][c:20]3[n:21]2)[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_6ef2f0acfd7cd717abb92598",
"reactionHash": "e28d9337945910fdd95a0f0c3d0ab686a3a3f9b01e87a379d153af0636743738"
},
"children": [
{
"id": "4728",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_dc1cd257f1d213d8147a7153",
"parentId": "4727",
"isLeaf": false,
"molecule": {
"id": "sa_dc1cd257f1d213d8147a7153",
"inchikey": "QTXWFLGYBJJQCK-UHFFFAOYSA-N",
"smiles": "CC(=O)c1ccc(-c2cn3cc(I)ccc3n2)cc1"
},
"smiles": "CC(=O)c1ccc(-c2cn3cc(I)ccc3n2)cc1",
"reactionStepId": "sa_4fa88786470e2a0f8c91331d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08022075B2;0129;1112314\",\"rsmi\":\"[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1>ClC(Cl)Cl.[Mn+4].[O-2].[O-2]>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1>ClC(Cl)Cl.[Mn+4].[O-2].[O-2]>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_4fa88786470e2a0f8c91331d",
"reactionHash": "89315ad8aea75307a367063bcdc91ed2d6a39ea4ad5cdf476db399c631d17f68"
},
"children": [
{
"id": "4729",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_043d4ec44a151c5f04c73837",
"parentId": "4728",
"isLeaf": false,
"molecule": {
"id": "sa_043d4ec44a151c5f04c73837",
"inchikey": "ZRNKSCJSNDRJMW-UHFFFAOYSA-N",
"smiles": "CC(O)c1ccc(-c2cn3cc(I)ccc3n2)cc1"
},
"smiles": "CC(O)c1ccc(-c2cn3cc(I)ccc3n2)cc1",
"reactionStepId": "sa_a8b58ee247231747e7e5fa5c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08022075B2;0127;1112313\",\"rsmi\":\"Br[Mg][CH3:1].[CH:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1>C1CCOC1.O.Cl.N>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1\"},\"mapped_reaction_smiles\":\"Br[Mg][CH3:1].[CH:2](=[O:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1>C1CCOC1.O.Cl.N>[CH3:1][CH:2]([OH:3])[c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][c:12]([I:13])[cH:14][cH:15][c:16]3[n:17]2)[cH:18][cH:19]1\"}",
"reactionStep": {
"id": "sa_a8b58ee247231747e7e5fa5c",
"reactionHash": "16f4d68140ec2420b719745ec04963e0c57fa9ce9bc8004bae74736d3b1d17c4"
},
"children": [
{
"id": "4730",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_1f49d1fc04ca53874d94e458",
"parentId": "4729",
"isLeaf": true,
"molecule": {
"id": "sa_1f49d1fc04ca53874d94e458",
"inchikey": "AVFUHBJCUUTGCD-UHFFFAOYSA-M",
"smiles": "[CH3][Mg][Br]"
},
"smiles": "[CH3][Mg][Br]",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4731",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_25e0a2fe30dbbd8965493587",
"parentId": "4729",
"isLeaf": false,
"molecule": {
"id": "sa_25e0a2fe30dbbd8965493587",
"inchikey": "CENKWUBPECITGQ-UHFFFAOYSA-N",
"smiles": "O=Cc1ccc(-c2cn3cc(I)ccc3n2)cc1"
},
"smiles": "O=Cc1ccc(-c2cn3cc(I)ccc3n2)cc1",
"reactionStepId": "sa_13f0e9ea03bf1e57d8571bc2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08022075B2;0116;1112309\",\"rsmi\":\"N#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]3[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1.O=S(O)(O)=[O:1]>C1CCOC1.CC(C)C[Al+]CC(C)C.CCOCC.ClCCl.Cl.[HH].[Mg+2].N>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]3[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"N#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]3[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1.O=S(O)(O)=[O:1]>C1CCOC1.CC(C)C[Al+]CC(C)C.CCOCC.ClCCl.Cl.[HH].[Mg+2].N>[O:1]=[CH:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]3[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_13f0e9ea03bf1e57d8571bc2",
"reactionHash": "92d35ea768002d01c0e4d56d732efb5fb87bbfc7896552e0007e4a46bda80575"
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"children": [
{
"id": "4732",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_a538ca410f1833f7a9788be8",
"parentId": "4731",
"isLeaf": true,
"molecule": {
"id": "sa_a538ca410f1833f7a9788be8",
"inchikey": "QAOWNCQODCNURD-UHFFFAOYSA-N",
"smiles": "O=S(=O)(O)O"
},
"smiles": "O=S(=O)(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4733",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_534b7b699350cecb467f9670",
"parentId": "4731",
"isLeaf": false,
"molecule": {
"id": "sa_534b7b699350cecb467f9670",
"inchikey": "QLKFVZYGKIIIPF-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(-c2cn3cc(I)ccc3n2)cc1"
},
"smiles": "N#Cc1ccc(-c2cn3cc(I)ccc3n2)cc1",
"reactionStepId": "sa_8b0e6fd28f9fb17290e6ba9b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08022075B2;0113;1112308\",\"rsmi\":\"O=[C:7]([c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]1)[CH2:8]Br.[n:9]1[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]1[NH2:16]>CCO.O.O=C(O)O.[Na+]>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]3[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[C:7]([c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:18][cH:17]1)[CH2:8]Br.[n:9]1[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]1[NH2:16]>CCO.O.O=C(O)O.[Na+]>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[cH:8][n:9]3[cH:10][c:11]([I:12])[cH:13][cH:14][c:15]3[n:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
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"reactionHash": "aa4a8d277ef989c9e86ee0b9a06e165c0838f27780c73050dfc7c70feebd5fee"
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"children": [
{
"id": "4734",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_8547d2c0b742ebb4dc52b7fd",
"parentId": "4733",
"isLeaf": true,
"molecule": {
"id": "sa_8547d2c0b742ebb4dc52b7fd",
"inchikey": "IVILGUFRMDBUEQ-UHFFFAOYSA-N",
"smiles": "N=c1ccc(I)c[nH]1"
},
"smiles": "Nc1ccc(I)cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "4735",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_97e1bbbf8f38c68735aa0eb3",
"parentId": "4733",
"isLeaf": true,
"molecule": {
"id": "sa_97e1bbbf8f38c68735aa0eb3",
"inchikey": "LJANCPRIUMHGJE-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(C(=O)CBr)cc1"
},
"smiles": "N#Cc1ccc(C(=O)CBr)cc1",
"reactionStepId": null,
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}
]
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]
}
]
}
]
},
{
"id": "4736",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_d78fcb876b2dc2bc451d189d",
"parentId": "4727",
"isLeaf": true,
"molecule": {
"id": "sa_d78fcb876b2dc2bc451d189d",
"inchikey": "ZSXGLVDWWRXATF-UHFFFAOYSA-N",
"smiles": "COC(OC)N(C)C"
},
"smiles": "COC(OC)N(C)C",
"reactionStepId": null,
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}
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},
{
"id": "4737",
"routeId": "sa_181d60008a01c04c3bfa0ad0",
"moleculeId": "sa_681b90bfe3789a310096845b",
"parentId": "4726",
"isLeaf": true,
"molecule": {
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"inchikey": "OAKJQQAXSVQMHS-UHFFFAOYSA-N",
"smiles": "NN"
},
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}
]
}
}