Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CN1CCN(c2nccn3c(-c4cccc(NC(CN)c5ccccc5)n4)cnc23)CC1
InChiKey
SSXBTTVHJLNKBB-UHFFFAOYSA-N
Route Signature
1d7d66fa6b459660cd7573530283dca909c48a8ac6baada5f02242e856e0f779
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_efdb52341a1d2b59ed06461a",
"signature": "1d7d66fa6b459660cd7573530283dca909c48a8ac6baada5f02242e856e0f779",
"contentHash": "c494c896051dfa6fb95bf29ef574c6f6bdef3608007474ba22edc71d0b044c64",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_d3bf3fbfe84437e9daff1bce",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02737",
"moleculeId": "sa_715523859a4cb4a3d50270bc",
"smiles": "CN1CCN(c2nccn3c(-c4cccc(NC(CN)c5ccccc5)n4)cnc23)CC1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_715523859a4cb4a3d50270bc",
"inchikey": "SSXBTTVHJLNKBB-UHFFFAOYSA-N",
"smiles": "CN1CCN(c2nccn3c(-c4cccc(NC(CN)c5ccccc5)n4)cnc23)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10844",
"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_715523859a4cb4a3d50270bc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_715523859a4cb4a3d50270bc",
"inchikey": "SSXBTTVHJLNKBB-UHFFFAOYSA-N",
"smiles": "CN1CCN(c2nccn3c(-c4cccc(NC(CN)c5ccccc5)n4)cnc23)CC1"
},
"smiles": "CN1CCN(c2nccn3c(-c4cccc(NC(CN)c5ccccc5)n4)cnc23)CC1",
"reactionStepId": "sa_71a3330fb82a78cdd41270ab",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120238564A1;0374;1272665\",\"rsmi\":\"CC(C)(C)OC(=O)[NH:20][CH2:19][CH:18]([NH:17][c:16]1[cH:15][cH:14][cH:13][c:12](-[c:11]2[n:10]3[cH:9][cH:8][n:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:32][CH2:31]4)[c:30]3[n:29][cH:28]2)[n:27]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>CCO.Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10]3[c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([NH:17][CH:18]([CH2:19][NH2:20])[c:21]5[cH:22][cH:23][cH:24][cH:25][cH:26]5)[n:27]4)[cH:28][n:29][c:30]23)[CH2:31][CH2:32]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[NH:20][CH2:19][CH:18]([NH:17][c:16]1[cH:15][cH:14][cH:13][c:12](-[c:11]2[n:10]3[cH:9][cH:8][n:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:32][CH2:31]4)[c:30]3[n:29][cH:28]2)[n:27]1)[c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>CCO.Cl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10]3[c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([NH:17][CH:18]([CH2:19][NH2:20])[c:21]5[cH:22][cH:23][cH:24][cH:25][cH:26]5)[n:27]4)[cH:28][n:29][c:30]23)[CH2:31][CH2:32]1\"}",
"reactionStep": {
"id": "sa_71a3330fb82a78cdd41270ab",
"reactionHash": "0de6834374648bede145ffbcfd8341a49a1be191b40ad00fcddffbd9f59dbfaa"
},
"children": [
{
"id": "10845",
"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_60f1f2c68de92b2b302418a7",
"parentId": "10844",
"isLeaf": false,
"molecule": {
"id": "sa_60f1f2c68de92b2b302418a7",
"inchikey": "IKXBMAQKBIZXKQ-UHFFFAOYSA-N",
"smiles": "CN1CCN(c2nccn3c(-c4cccc(NC(CNC(=O)OC(C)(C)C)c5ccccc5)n4)cnc23)CC1"
},
"smiles": "CN1CCN(c2nccn3c(-c4cccc(NC(CNC(=O)OC(C)(C)C)c5ccccc5)n4)cnc23)CC1",
"reactionStepId": "sa_384cc5e9ed2ee08bab1cb1f7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120238564A1;0372;1272664\",\"rsmi\":\"Br[c:16]1[cH:15][cH:14][cH:13][c:12](-[c:11]2[n:10]3[cH:9][cH:8][n:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:39][CH2:38]4)[c:37]3[n:36][cH:35]2)[n:34]1.[NH2:17][CH:18]([CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>C1COCCO1.CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.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=C(O)O.[K+].[K+].[Pd].[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10]3[c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([NH:17][CH:18]([CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:28]5[cH:29][cH:30][cH:31][cH:32][cH:33]5)[n:34]4)[cH:35][n:36][c:37]23)[CH2:38][CH2:39]1\"},\"mapped_reaction_smiles\":\"Br[c:16]1[cH:15][cH:14][cH:13][c:12](-[c:11]2[n:10]3[cH:9][cH:8][n:7][c:6]([N:5]4[CH2:4][CH2:3][N:2]([CH3:1])[CH2:39][CH2:38]4)[c:37]3[n:36][cH:35]2)[n:34]1.[NH2:17][CH:18]([CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1>C1COCCO1.CN(C)c1ccccc1-c1ccccc1P(C1CCCCC1)C1CCCCC1.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=C(O)O.[K+].[K+].[Pd].[Pd]>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10]3[c:11](-[c:12]4[cH:13][cH:14][cH:15][c:16]([NH:17][CH:18]([CH2:19][NH:20][C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[c:28]5[cH:29][cH:30][cH:31][cH:32][cH:33]5)[n:34]4)[cH:35][n:36][c:37]23)[CH2:38][CH2:39]1\"}",
"reactionStep": {
"id": "sa_384cc5e9ed2ee08bab1cb1f7",
"reactionHash": "e5f4690d4a1404ec4f818cecec37af03db399dcc9c163e806d0b5d7faea45f2c"
},
"children": [
{
"id": "10846",
"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_eee2b8fb732b2c3f99c58d4f",
"parentId": "10845",
"isLeaf": false,
"molecule": {
"id": "sa_eee2b8fb732b2c3f99c58d4f",
"inchikey": "CLUUDOMFHPDBIR-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCC(N)c1ccccc1"
},
"smiles": "CC(C)(C)OC(=O)NCC(N)c1ccccc1",
"reactionStepId": "sa_5154f4a263bd531e042fc375",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120238564A1;0344;1272656\",\"rsmi\":\"O=C1c2ccccc2C(=O)[N:11]1[CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>C1CCOC1.CO.NN.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([NH2:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O=C1c2ccccc2C(=O)[N:11]1[CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>C1CCOC1.CO.NN.O>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([NH2:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_5154f4a263bd531e042fc375",
"reactionHash": "9b441f29045390a9968c1f11f53090c137aa30f093ef9353e5899ff9d775510a"
},
"children": [
{
"id": "10847",
"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_ade3287ed271a4a762c25200",
"parentId": "10846",
"isLeaf": false,
"molecule": {
"id": "sa_ade3287ed271a4a762c25200",
"inchikey": "PCAGGDPDFPRJCB-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NCC(c1ccccc1)N1C(=O)c2ccccc2C1=O"
},
"smiles": "CC(C)(C)OC(=O)NCC(c1ccccc1)N1C(=O)c2ccccc2C1=O",
"reactionStepId": "sa_4ee487abb33fb4f209800cb2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120238564A1;0342;1272655\",\"rsmi\":\"O[CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[NH:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27]>CCOC(=O)/N=N/C(=O)OCC.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[N:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27]\"},\"mapped_reaction_smiles\":\"O[CH:10]([CH2:9][NH:8][C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[NH:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27]>CCOC(=O)/N=N/C(=O)OCC.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1)[N:17]1[C:18](=[O:19])[c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[C:26]1=[O:27]\"}",
"reactionStep": {
"id": "sa_4ee487abb33fb4f209800cb2",
"reactionHash": "af6818375c53427e2c287f27ef660ce88a98c0cf46b9eecf38ff952e5ce20c4b"
},
"children": [
{
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"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_891010af53df947a922bc269",
"parentId": "10847",
"isLeaf": false,
"molecule": {
"id": "sa_891010af53df947a922bc269",
"inchikey": "FSRZPRRAZVZKFE-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(O)=NCC(O)c1ccccc1"
},
"smiles": "CC(C)(C)OC(=O)NCC(O)c1ccccc1",
"reactionStepId": "sa_5d8885ab96cc62aae216d98c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120238564A1;0340;1272654\",\"rsmi\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][CH2:9][CH:10]([OH:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>C1CCOC1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([OH:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].[NH2:8][CH2:9][CH:10]([OH:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>C1CCOC1>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([OH:11])[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"}",
"reactionStep": {
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"reactionHash": "2e2fe115df6cc7abafadf5f1ef509a4044d3b661af5107898feb9c33804373f6"
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"children": [
{
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"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_b273d4d4546165bca2b249b5",
"parentId": "10848",
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"molecule": {
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"inchikey": "DYHSDKLCOJIUFX-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C"
},
"smiles": "CC(C)(C)OC(=O)OC(=O)OC(C)(C)C",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "10850",
"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_efe0eb09531dc41c5235630d",
"parentId": "10848",
"isLeaf": true,
"molecule": {
"id": "sa_efe0eb09531dc41c5235630d",
"inchikey": "ULSIYEODSMZIPX-UHFFFAOYSA-N",
"smiles": "NCC(O)c1ccccc1"
},
"smiles": "NCC(O)c1ccccc1",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "10851",
"routeId": "sa_efdb52341a1d2b59ed06461a",
"moleculeId": "sa_55c000779ce0b3d5072b008b",
"parentId": "10847",
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"molecule": {
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"inchikey": "XKJCHHZQLQNZHY-UHFFFAOYSA-N",
"smiles": "O=C1N=C(O)c2ccccc21"
},
"smiles": "O=C1NC(=O)c2ccccc21",
"reactionStepId": null,
"template": null,
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}
]
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]
},
{
"id": "10852",
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"moleculeId": "sa_3ede2e2d925d0f17a2790d2f",
"parentId": "10845",
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"molecule": {
"id": "sa_3ede2e2d925d0f17a2790d2f",
"inchikey": "MPVGYBXKOXQIMS-UHFFFAOYSA-N",
"smiles": "CN1CCN(c2nccn3c(-c4cccc(Br)n4)cnc23)CC1"
},
"smiles": "CN1CCN(c2nccn3c(-c4cccc(Br)n4)cnc23)CC1",
"reactionStepId": "sa_24c3760b0cdf69be287aca56",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120238564A1;0311;1272646\",\"rsmi\":\"Cl[c:6]1[n:7][cH:8][cH:9][n:10]2[c:11](-[c:12]3[n:13][c:14]([Br:15])[cH:16][cH:17][cH:18]3)[cH:19][n:20][c:21]12.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:22][CH2:23]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10]3[c:11](-[c:12]4[n:13][c:14]([Br:15])[cH:16][cH:17][cH:18]4)[cH:19][n:20][c:21]23)[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[n:7][cH:8][cH:9][n:10]2[c:11](-[c:12]3[n:13][c:14]([Br:15])[cH:16][cH:17][cH:18]3)[cH:19][n:20][c:21]12.[CH3:1][N:2]1[CH2:3][CH2:4][NH:5][CH2:22][CH2:23]1>CC(C)O.CCN(C(C)C)C(C)C>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[n:7][cH:8][cH:9][n:10]3[c:11](-[c:12]4[n:13][c:14]([Br:15])[cH:16][cH:17][cH:18]4)[cH:19][n:20][c:21]23)[CH2:22][CH2:23]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_513cbf1b8d13aff0b62eb838",
"parentId": "10852",
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"molecule": {
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"inchikey": "PVOAHINGSUIXLS-UHFFFAOYSA-N",
"smiles": "CN1CCNCC1"
},
"smiles": "CN1CCNCC1",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "10854",
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"moleculeId": "sa_cb09a1a44efb58cb233477d7",
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"molecule": {
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"inchikey": "UZEFZKDDIXXZRU-UHFFFAOYSA-N",
"smiles": "Clc1nccn2c(-c3cccc(Br)n3)cnc12"
},
"smiles": "Clc1nccn2c(-c3cccc(Br)n3)cnc12",
"reactionStepId": null,
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}
]
}
]
}
]
}
}