Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(CN3CC(N4CCOCC4)C3)ccc2n1
InChiKey
LVUFUVAGRNLFAL-UHFFFAOYSA-N
Route Signature
f1210f51f280a69fe3f1f1a0671a788bd1d5fdcc6b522d15a2b731127b507e6e
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_bb8a1ea0e1960225e479622a",
"signature": "f1210f51f280a69fe3f1f1a0671a788bd1d5fdcc6b522d15a2b731127b507e6e",
"contentHash": "701e7d2adab61ab08891bd6c4da352dd3ebf9b1697e5b9e8b6cb7a5e9b2599a5",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_82b5f9215b2d8f6bede3fc00",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00347",
"moleculeId": "sa_09eb5671b6cb4b179a74995b",
"smiles": "FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(CN3CC(N4CCOCC4)C3)ccc2n1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_09eb5671b6cb4b179a74995b",
"inchikey": "LVUFUVAGRNLFAL-UHFFFAOYSA-N",
"smiles": "FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(CN3CC(N4CCOCC4)C3)ccc2n1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9416",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_09eb5671b6cb4b179a74995b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_09eb5671b6cb4b179a74995b",
"inchikey": "LVUFUVAGRNLFAL-UHFFFAOYSA-N",
"smiles": "FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(CN3CC(N4CCOCC4)C3)ccc2n1"
},
"smiles": "FC(F)c1nc2ccccc2n1-c1nc(N2CCOCC2)c2nc(CN3CC(N4CCOCC4)C3)ccc2n1",
"reactionStepId": "sa_a91c127383fae358a1d5d706",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225557A1;0375;1413901\",\"rsmi\":\"Cl[c:13]1[n:14][c:15]2[c:16]([n:17][c:18]([CH2:19][N:20]3[CH2:21][CH:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH2:29]3)[cH:30][cH:31]2)[c:32]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[n:39]1.[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[nH:12]1>>[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[n:12]1-[c:13]1[n:14][c:15]2[c:16]([n:17][c:18]([CH2:19][N:20]3[CH2:21][CH:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH2:29]3)[cH:30][cH:31]2)[c:32]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[n:39]1\"},\"mapped_reaction_smiles\":\"Cl[c:13]1[n:14][c:15]2[c:16]([n:17][c:18]([CH2:19][N:20]3[CH2:21][CH:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH2:29]3)[cH:30][cH:31]2)[c:32]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[n:39]1.[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[nH:12]1>>[F:1][CH:2]([F:3])[c:4]1[n:5][c:6]2[c:7]([cH:8][cH:9][cH:10][cH:11]2)[n:12]1-[c:13]1[n:14][c:15]2[c:16]([n:17][c:18]([CH2:19][N:20]3[CH2:21][CH:22]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)[CH2:29]3)[cH:30][cH:31]2)[c:32]([N:33]2[CH2:34][CH2:35][O:36][CH2:37][CH2:38]2)[n:39]1\"}",
"reactionStep": {
"id": "sa_a91c127383fae358a1d5d706",
"reactionHash": "65b8a13146060b405dc50230e10b0c0946f26ce0f830e5eb602f09e94ce5cf83"
},
"children": [
{
"id": "9417",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_1dbf9ba847f87db622583dd6",
"parentId": "9416",
"isLeaf": true,
"molecule": {
"id": "sa_1dbf9ba847f87db622583dd6",
"inchikey": "PURNIHSRWGYONZ-UHFFFAOYSA-N",
"smiles": "FC(F)c1nc2ccccc2[nH]1"
},
"smiles": "FC(F)c1nc2ccccc2[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9418",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_8c7088f8045a687d73831ff5",
"parentId": "9416",
"isLeaf": false,
"molecule": {
"id": "sa_8c7088f8045a687d73831ff5",
"inchikey": "QWBCAQGUWOMDJO-UHFFFAOYSA-N",
"smiles": "Clc1nc(N2CCOCC2)c2nc(CN3CC(N4CCOCC4)C3)ccc2n1"
},
"smiles": "Clc1nc(N2CCOCC2)c2nc(CN3CC(N4CCOCC4)C3)ccc2n1",
"reactionStepId": "sa_b082b85a364ea9153d5b7ed7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225557A1;0292;1413847\",\"rsmi\":\"Br[CH2:8][c:7]1[n:6][c:5]2[c:4]([n:3][c:2]([Cl:1])[n:28][c:21]2[N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[cH:20][cH:19]1.[NH:9]1[CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:18]1>>[Cl:1][c:2]1[n:3][c:4]2[c:5]([n:6][c:7]([CH2:8][N:9]3[CH2:10][CH:11]([N:12]4[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)[CH2:18]3)[cH:19][cH:20]2)[c:21]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[n:28]1\"},\"mapped_reaction_smiles\":\"Br[CH2:8][c:7]1[n:6][c:5]2[c:4]([n:3][c:2]([Cl:1])[n:28][c:21]2[N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[cH:20][cH:19]1.[NH:9]1[CH2:10][CH:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:18]1>>[Cl:1][c:2]1[n:3][c:4]2[c:5]([n:6][c:7]([CH2:8][N:9]3[CH2:10][CH:11]([N:12]4[CH2:13][CH2:14][O:15][CH2:16][CH2:17]4)[CH2:18]3)[cH:19][cH:20]2)[c:21]([N:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[n:28]1\"}",
"reactionStep": {
"id": "sa_b082b85a364ea9153d5b7ed7",
"reactionHash": "81479e4a89f2059a13c9481fb23e78312aa6d3b43129b22a9e4a0f9ff7041c4b"
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"children": [
{
"id": "9419",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_5c1d6616049a22c1a772172f",
"parentId": "9418",
"isLeaf": false,
"molecule": {
"id": "sa_5c1d6616049a22c1a772172f",
"inchikey": "AUQZPLUJXBTXDI-UHFFFAOYSA-N",
"smiles": "Clc1nc(N2CCOCC2)c2nc(CBr)ccc2n1"
},
"smiles": "Clc1nc(N2CCOCC2)c2nc(CBr)ccc2n1",
"reactionStepId": "sa_7da2963cd49b26d4b9f7307c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225557A1;0240;1413811\",\"rsmi\":\"O=C1CCC(=O)N1[Br:9].O[CH2:8][c:7]1[n:6][c:5]2[c:4]([n:3][c:2]([Cl:1])[n:19][c:12]2[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:11][cH:10]1>ClCCl.O=C1CCC(=O)N1Br.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[Cl:1][c:2]1[n:3][c:4]2[c:5]([n:6][c:7]([CH2:8][Br:9])[cH:10][cH:11]2)[c:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[n:19]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:9].O[CH2:8][c:7]1[n:6][c:5]2[c:4]([n:3][c:2]([Cl:1])[n:19][c:12]2[N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[cH:11][cH:10]1>ClCCl.O=C1CCC(=O)N1Br.O=C1CCC(=O)N1Br.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[Cl:1][c:2]1[n:3][c:4]2[c:5]([n:6][c:7]([CH2:8][Br:9])[cH:10][cH:11]2)[c:12]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[n:19]1\"}",
"reactionStep": {
"id": "sa_7da2963cd49b26d4b9f7307c",
"reactionHash": "faa4b42a8eb7a86b98fab155054ac3263aa010f3bcce9baf6976b7f106f5caa7"
},
"children": [
{
"id": "9420",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_f6ad3afea72f1613143412b4",
"parentId": "9419",
"isLeaf": false,
"molecule": {
"id": "sa_f6ad3afea72f1613143412b4",
"inchikey": "GNSPBWALOCTRIA-UHFFFAOYSA-N",
"smiles": "OCc1ccc2nc(Cl)nc(N3CCOCC3)c2n1"
},
"smiles": "OCc1ccc2nc(Cl)nc(N3CCOCC3)c2n1",
"reactionStepId": "sa_015cd32f4950c4b9b2cec033",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225557A1;0238;1413810\",\"rsmi\":\"CC(=O)[O:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9][c:10]([Cl:11])[n:12][c:13]2[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1>C1CCOC1.O.[Li+].O>[OH:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9][c:10]([Cl:11])[n:12][c:13]2[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1\"},\"mapped_reaction_smiles\":\"CC(=O)[O:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9][c:10]([Cl:11])[n:12][c:13]2[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1>C1CCOC1.O.[Li+].O>[OH:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([cH:7][cH:8]1)[n:9][c:10]([Cl:11])[n:12][c:13]2[N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1\"}",
"reactionStep": {
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"reactionHash": "eb62850e086467f5ffcd1509a2a6e97b7d7176b32d1bcf7c948650c6f4ec9c86"
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"children": [
{
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"smiles": "CC(=O)OCc1ccc2nc(Cl)nc(N3CCOCC3)c2n1"
},
"smiles": "CC(=O)OCc1ccc2nc(Cl)nc(N3CCOCC3)c2n1",
"reactionStepId": "sa_24521a3acda60b5207ffa371",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225557A1;0236;1413809\",\"rsmi\":\"Cl[c:16]1[c:8]2[n:7][c:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[cH:11][cH:10][c:9]2[n:12][c:13]([Cl:14])[n:15]1.[NH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1>CCO>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][c:8]2[c:9]([cH:10][cH:11]1)[n:12][c:13]([Cl:14])[n:15][c:16]2[N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1\"},\"mapped_reaction_smiles\":\"Cl[c:16]1[c:8]2[n:7][c:6]([CH2:5][O:4][C:2]([CH3:1])=[O:3])[cH:11][cH:10][c:9]2[n:12][c:13]([Cl:14])[n:15]1.[NH:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1>CCO>[CH3:1][C:2](=[O:3])[O:4][CH2:5][c:6]1[n:7][c:8]2[c:9]([cH:10][cH:11]1)[n:12][c:13]([Cl:14])[n:15][c:16]2[N:17]1[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1\"}",
"reactionStep": {
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"children": [
{
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"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_a066b710772bffb69a70d89c",
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"isLeaf": true,
"molecule": {
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"inchikey": "UKFAIQLEAXKYBV-UHFFFAOYSA-N",
"smiles": "CC(=O)OCc1ccc2nc(Cl)nc(Cl)c2n1"
},
"smiles": "CC(=O)OCc1ccc2nc(Cl)nc(Cl)c2n1",
"reactionStepId": null,
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"metadata": null,
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{
"id": "9423",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_39d71c291f7fdf13918cc969",
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"molecule": {
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"inchikey": "YNAVUWVOSKDBBP-UHFFFAOYSA-N",
"smiles": "C1COCCN1"
},
"smiles": "C1COCCN1",
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}
]
}
]
},
{
"id": "9424",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "9419",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
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}
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},
{
"id": "9425",
"routeId": "sa_bb8a1ea0e1960225e479622a",
"moleculeId": "sa_4b0f1dec9f090d898f97d842",
"parentId": "9418",
"isLeaf": false,
"molecule": {
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"inchikey": "GLHXYSFEVOAOSL-UHFFFAOYSA-N",
"smiles": "C1CN(C2CNC2)CCO1"
},
"smiles": "C1CN(C2CNC2)CCO1",
"reactionStepId": "sa_a03e8f1854630e1de5406b25",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130225557A1;0292;1413846\",\"rsmi\":\"CC(C)(C)OC(=O)[N:6]1[CH2:5][CH:4]([N:3]2[CH2:2][CH2:1][O:10][CH2:9][CH2:8]2)[CH2:7]1>C1COCCO1.Cl.ClCCl>[CH2:1]1[CH2:2][N:3]([CH:4]2[CH2:5][NH:6][CH2:7]2)[CH2:8][CH2:9][O:10]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:6]1[CH2:5][CH:4]([N:3]2[CH2:2][CH2:1][O:10][CH2:9][CH2:8]2)[CH2:7]1>C1COCCO1.Cl.ClCCl>[CH2:1]1[CH2:2][N:3]([CH:4]2[CH2:5][NH:6][CH2:7]2)[CH2:8][CH2:9][O:10]1\"}",
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"children": [
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},
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}
]
}
}