Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCN(CC)CCNC(=O)c1cc(C)c(C=C2C(=O)Nc3cccc(-c4ccc(Cl)cc4)c32)[nH]1
InChiKey
GLOSOHQUVRBAKU-UHFFFAOYSA-N
Route Signature
184563e25f17f7ccad8fedfcd1743cd1e63073c26774081f4a7360fc8bd51535
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_eeb6e0d360bd1417140c3323",
"signature": "184563e25f17f7ccad8fedfcd1743cd1e63073c26774081f4a7360fc8bd51535",
"contentHash": "a0e04ddf9ca8816a5dcf2189c51ed5a272daa69dc7f4a7ffeb52b75741dbe7ab",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_99243359d180f3d44c6dbee5",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-00343",
"moleculeId": "sa_36d9adb6496b9248ec29097a",
"smiles": "CCN(CC)CCNC(=O)c1cc(C)c(C=C2C(=O)Nc3cccc(-c4ccc(Cl)cc4)c32)[nH]1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_36d9adb6496b9248ec29097a",
"inchikey": "GLOSOHQUVRBAKU-UHFFFAOYSA-N",
"smiles": "CCN(CC)CCNC(=O)c1cc(C)c(C=C2C(=O)Nc3cccc(-c4ccc(Cl)cc4)c32)[nH]1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "627",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_36d9adb6496b9248ec29097a",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_36d9adb6496b9248ec29097a",
"inchikey": "GLOSOHQUVRBAKU-UHFFFAOYSA-N",
"smiles": "CCN(CC)CCNC(=O)c1cc(C)c(C=C2C(=O)Nc3cccc(-c4ccc(Cl)cc4)c32)[nH]1"
},
"smiles": "CCN(CC)CCNC(=O)c1cc(C)c(C=C2C(=O)Nc3cccc(-c4ccc(Cl)cc4)c32)[nH]1",
"reactionStepId": "sa_329fe21c52422da3ee179431",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040157909A1;0928;181193\",\"rsmi\":\"O=[CH:16][c:15]1[c:13]([CH3:14])[cH:12][c:11]([C:9]([NH:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:10])[nH:34]1.[CH2:17]1[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][c:25](-[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[c:33]21>C1CCNCC1.CCO>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([CH3:14])[c:15]([CH:16]=[C:17]2[C:18](=[O:19])[NH:20][c:21]3[cH:22][cH:23][cH:24][c:25](-[c:26]4[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]4)[c:33]32)[nH:34]1\"},\"mapped_reaction_smiles\":\"O=[CH:16][c:15]1[c:13]([CH3:14])[cH:12][c:11]([C:9]([NH:8][CH2:7][CH2:6][N:3]([CH2:2][CH3:1])[CH2:4][CH3:5])=[O:10])[nH:34]1.[CH2:17]1[C:18](=[O:19])[NH:20][c:21]2[cH:22][cH:23][cH:24][c:25](-[c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[c:33]21>C1CCNCC1.CCO>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([CH3:14])[c:15]([CH:16]=[C:17]2[C:18](=[O:19])[NH:20][c:21]3[cH:22][cH:23][cH:24][c:25](-[c:26]4[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]4)[c:33]32)[nH:34]1\"}",
"reactionStep": {
"id": "sa_329fe21c52422da3ee179431",
"reactionHash": "0190618410aad26de4eb24945f93665334083d43de97c6905373a93df53fd78d"
},
"children": [
{
"id": "628",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_a64c80d63938d61b86d7b46d",
"parentId": "627",
"isLeaf": false,
"molecule": {
"id": "sa_a64c80d63938d61b86d7b46d",
"inchikey": "LVSISMOXMMDULK-UHFFFAOYSA-N",
"smiles": "O=C1Cc2c(cccc2-c2ccc(Cl)cc2)N1"
},
"smiles": "O=C1Cc2c(cccc2-c2ccc(Cl)cc2)N1",
"reactionStepId": "sa_1b070beabf526d245be1d997",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040157909A1;0359;181058\",\"rsmi\":\"CC[OH:1].[cH:2]1[cH:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[cH:13][cH:14][cH:15][c:16]2[nH:17]1>CC(=O)O.CC(=O)O.CC(C)(C)O.Br.Br.Br.[Zn].c1ccncc1.c1ccncc1.c1ccncc1>[O:1]=[C:2]1[CH2:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[cH:13][cH:14][cH:15][c:16]2[NH:17]1\"},\"mapped_reaction_smiles\":\"CC[OH:1].[cH:2]1[cH:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[cH:13][cH:14][cH:15][c:16]2[nH:17]1>CC(=O)O.CC(=O)O.CC(C)(C)O.Br.Br.Br.[Zn].c1ccncc1.c1ccncc1.c1ccncc1>[O:1]=[C:2]1[CH2:3][c:4]2[c:5](-[c:6]3[cH:7][cH:8][c:9]([Cl:10])[cH:11][cH:12]3)[cH:13][cH:14][cH:15][c:16]2[NH:17]1\"}",
"reactionStep": {
"id": "sa_1b070beabf526d245be1d997",
"reactionHash": "a0a2135d00ab845f4070c1a3ed704d20e7a3b3be1e6ab50c68f83800c0d0b98a"
},
"children": [
{
"id": "629",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_33e13ec2728228f913970fcd",
"parentId": "628",
"isLeaf": false,
"molecule": {
"id": "sa_33e13ec2728228f913970fcd",
"inchikey": "FPFWVEZFKHSRIJ-UHFFFAOYSA-N",
"smiles": "Clc1ccc(-c2cccc3[nH]ccc23)cc1"
},
"smiles": "Clc1ccc(-c2cccc3[nH]ccc23)cc1",
"reactionStepId": "sa_55d2fe73daae4aabdd0e3ff1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040157909A1;0271;181030\",\"rsmi\":\"Br[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:16][cH:15]1.CC1(C)OB([c:6]2[c:7]3[cH:8][cH:9][nH:10][c:11]3[cH:12][cH:13][cH:14]2)OC1(C)C>C1CCOC1.CCOC(C)=O.[Na+].O.[Pd]>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]3[cH:8][cH:9][nH:10][c:11]3[cH:12][cH:13][cH:14]2)[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"Br[c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:16][cH:15]1.CC1(C)OB([c:6]2[c:7]3[cH:8][cH:9][nH:10][c:11]3[cH:12][cH:13][cH:14]2)OC1(C)C>C1CCOC1.CCOC(C)=O.[Na+].O.[Pd]>[Cl:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[c:7]3[cH:8][cH:9][nH:10][c:11]3[cH:12][cH:13][cH:14]2)[cH:15][cH:16]1\"}",
"reactionStep": {
"id": "sa_55d2fe73daae4aabdd0e3ff1",
"reactionHash": "2530c7fb961c75b3b4cf20a72ba32404850b91d71494ffe5ff58b0c5bfd8dd8e"
},
"children": [
{
"id": "630",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_c2acd7cb6cef4ac70850f3e7",
"parentId": "629",
"isLeaf": true,
"molecule": {
"id": "sa_c2acd7cb6cef4ac70850f3e7",
"inchikey": "NHDODQWIKUYWMW-UHFFFAOYSA-N",
"smiles": "Clc1ccc(Br)cc1"
},
"smiles": "Clc1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "631",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_8da454c67215591176323435",
"parentId": "629",
"isLeaf": true,
"molecule": {
"id": "sa_8da454c67215591176323435",
"inchikey": "QDCIXBBEUHMLDN-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C"
},
"smiles": "CC1(C)OB(c2cccc3[nH]ccc23)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "632",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "628",
"isLeaf": true,
"molecule": {
"id": "sa_afaca116b303dc7d01346819",
"inchikey": "LFQSCWFLJHTTHZ-UHFFFAOYSA-N",
"smiles": "CCO"
},
"smiles": "CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "633",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_d3e008db9258d9574d2fae56",
"parentId": "627",
"isLeaf": false,
"molecule": {
"id": "sa_d3e008db9258d9574d2fae56",
"inchikey": "TYWPZTNLGFVYBD-UHFFFAOYSA-N",
"smiles": "CCN(CC)CCNC(=O)c1cc(C)c(C=O)[nH]1"
},
"smiles": "CCN(CC)CCNC(=O)c1cc(C)c(C=O)[nH]1",
"reactionStepId": "sa_f20c462037e8f1429b25d132",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040157909A1;0529;181098\",\"rsmi\":\"O[C:9](=[O:10])[c:11]1[cH:12][c:13]([CH3:14])[c:15]([CH:16]=[O:17])[nH:18]1.[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8]>CN(C)C=O.CN(C)CCCN=C=N.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([CH3:14])[c:15]([CH:16]=[O:17])[nH:18]1\"},\"mapped_reaction_smiles\":\"O[C:9](=[O:10])[c:11]1[cH:12][c:13]([CH3:14])[c:15]([CH:16]=[O:17])[nH:18]1.[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH2:8]>CN(C)C=O.CN(C)CCCN=C=N.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][N:3]([CH2:4][CH3:5])[CH2:6][CH2:7][NH:8][C:9](=[O:10])[c:11]1[cH:12][c:13]([CH3:14])[c:15]([CH:16]=[O:17])[nH:18]1\"}",
"reactionStep": {
"id": "sa_f20c462037e8f1429b25d132",
"reactionHash": "69a96eaafd766d3e2fe6feb0e16bb370454ef201957fac32fc1620d995070917"
},
"children": [
{
"id": "634",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_433aecc2a1cffb124dde820c",
"parentId": "633",
"isLeaf": false,
"molecule": {
"id": "sa_433aecc2a1cffb124dde820c",
"inchikey": "KSDGAOCOGSTQKI-UHFFFAOYSA-N",
"smiles": "Cc1cc(C(=O)O)[nH]c1C=O"
},
"smiles": "Cc1cc(C(=O)O)[nH]c1C=O",
"reactionStepId": "sa_6bd55c3f2179d7d006a79234",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040157909A1;0525;181097\",\"rsmi\":\"CC[O:10][C:8]([c:7]1[nH:6][c:3]([CH:4]=[O:5])[c:2]([CH3:1])[cH:11]1)=[O:9]>CCO.O.[K+].O>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[nH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11]1\"},\"mapped_reaction_smiles\":\"CC[O:10][C:8]([c:7]1[nH:6][c:3]([CH:4]=[O:5])[c:2]([CH3:1])[cH:11]1)=[O:9]>CCO.O.[K+].O>[CH3:1][c:2]1[c:3]([CH:4]=[O:5])[nH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11]1\"}",
"reactionStep": {
"id": "sa_6bd55c3f2179d7d006a79234",
"reactionHash": "8d0554d7c8dd6cbb64779ed575c0ac514952353ba764c98838c7984a1cae99ca"
},
"children": [
{
"id": "635",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_57135d4e2ab558be591f26b7",
"parentId": "634",
"isLeaf": false,
"molecule": {
"id": "sa_57135d4e2ab558be591f26b7",
"inchikey": "JGRYFRGKFUAPLI-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(C)c(C=O)[nH]1"
},
"smiles": "CCOC(=O)c1cc(C)c(C=O)[nH]1",
"reactionStepId": "sa_71a21ccfc9e3910f851b340d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20040157909A1;0521;181096\",\"rsmi\":\"CN(C)[CH:11]=[O:12].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[cH:10][nH:13]1>O.O=P(Cl)(Cl)Cl.[Na+].O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[c:10]([CH:11]=[O:12])[nH:13]1\"},\"mapped_reaction_smiles\":\"CN(C)[CH:11]=[O:12].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[cH:10][nH:13]1>O.O=P(Cl)(Cl)Cl.[Na+].O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([CH3:9])[c:10]([CH:11]=[O:12])[nH:13]1\"}",
"reactionStep": {
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"reactionHash": "691879eb53cefe99b4a92597b4949af4863e0841a7a4e5de9dd559406f4651ec"
},
"children": [
{
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"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_3154179643d757cab7d8f8a2",
"parentId": "635",
"isLeaf": true,
"molecule": {
"id": "sa_3154179643d757cab7d8f8a2",
"inchikey": "RWFKYBVNHRKZSN-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1cc(C)c[nH]1"
},
"smiles": "CCOC(=O)c1cc(C)c[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "637",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_e0b5e93d36242e79e81ef68c",
"parentId": "635",
"isLeaf": true,
"molecule": {
"id": "sa_e0b5e93d36242e79e81ef68c",
"inchikey": "ZMXDDKWLCZADIW-UHFFFAOYSA-N",
"smiles": "CN(C)C=O"
},
"smiles": "CN(C)C=O",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "638",
"routeId": "sa_eeb6e0d360bd1417140c3323",
"moleculeId": "sa_c3a84f1b1eab42bc499f0e6f",
"parentId": "633",
"isLeaf": true,
"molecule": {
"id": "sa_c3a84f1b1eab42bc499f0e6f",
"inchikey": "UDGSVBYJWHOHNN-UHFFFAOYSA-N",
"smiles": "CCN(CC)CCN"
},
"smiles": "CCN(CC)CCN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
}