Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)[C@@H](Cn1cc(CO)nn1)Nc1nc(-c2c[nH]c3ncc(F)cc23)ncc1F
InChiKey
NPPXREMMNBSCRB-MRXNPFEDSA-N
Route Signature
555f14448e4e1c6467de0cdab2f382cfc4349005990f39b30eecac9e7f5c4370
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_bd62b610d7844f55249a95e8",
"signature": "555f14448e4e1c6467de0cdab2f382cfc4349005990f39b30eecac9e7f5c4370",
"contentHash": "12e006d21d79559b939b5c65e245e67fde89a90e9274cc32e1444ceafad21379",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_db1addeb3ab37a908eabb893",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00227",
"moleculeId": "sa_af4989324c7b16ad0a924626",
"smiles": "CC(C)(C)[C@@H](Cn1cc(CO)nn1)Nc1nc(-c2c[nH]c3ncc(F)cc23)ncc1F",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_af4989324c7b16ad0a924626",
"inchikey": "NPPXREMMNBSCRB-MRXNPFEDSA-N",
"smiles": "CC(C)(C)[C@@H](Cn1cc(CO)nn1)Nc1nc(-c2c[nH]c3ncc(F)cc23)ncc1F"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "3699",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_af4989324c7b16ad0a924626",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_af4989324c7b16ad0a924626",
"inchikey": "NPPXREMMNBSCRB-MRXNPFEDSA-N",
"smiles": "CC(C)(C)[C@@H](Cn1cc(CO)nn1)Nc1nc(-c2c[nH]c3ncc(F)cc23)ncc1F"
},
"smiles": "CC(C)(C)[C@@H](Cn1cc(CO)nn1)Nc1nc(-c2c[nH]c3ncc(F)cc23)ncc1F",
"reactionStepId": "sa_b57a19a843940f2615ab4cc1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150191468A1;0574;1720401\",\"rsmi\":\"Cc1ccc(S(=O)(=O)[n:20]2[cH:19][c:18](-[c:17]3[n:16][c:15]([NH:14][C@@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6][n:7]4[cH:8][c:9]([CH2:10][OH:11])[n:12][n:13]4)[c:30]([F:31])[cH:29][n:28]3)[c:27]3[c:21]2[n:22][cH:23][c:24]([F:25])[cH:26]3)cc1>C1CCOC1.CCOC(C)=O.CO.Cl.N.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][n:7]1[cH:8][c:9]([CH2:10][OH:11])[n:12][n:13]1)[NH:14][c:15]1[n:16][c:17](-[c:18]2[cH:19][nH:20][c:21]3[n:22][cH:23][c:24]([F:25])[cH:26][c:27]23)[n:28][cH:29][c:30]1[F:31]\"},\"mapped_reaction_smiles\":\"Cc1ccc(S(=O)(=O)[n:20]2[cH:19][c:18](-[c:17]3[n:16][c:15]([NH:14][C@@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:6][n:7]4[cH:8][c:9]([CH2:10][OH:11])[n:12][n:13]4)[c:30]([F:31])[cH:29][n:28]3)[c:27]3[c:21]2[n:22][cH:23][c:24]([F:25])[cH:26]3)cc1>C1CCOC1.CCOC(C)=O.CO.Cl.N.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][n:7]1[cH:8][c:9]([CH2:10][OH:11])[n:12][n:13]1)[NH:14][c:15]1[n:16][c:17](-[c:18]2[cH:19][nH:20][c:21]3[n:22][cH:23][c:24]([F:25])[cH:26][c:27]23)[n:28][cH:29][c:30]1[F:31]\"}",
"reactionStep": {
"id": "sa_b57a19a843940f2615ab4cc1",
"reactionHash": "363033961da00baea37b259013d6d54e2793988b75f31ddc1a675f3afd4f43f4"
},
"children": [
{
"id": "3700",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_478a83c1543b850d197d27e5",
"parentId": "3699",
"isLeaf": false,
"molecule": {
"id": "sa_478a83c1543b850d197d27e5",
"inchikey": "WFMDZUJKUIVLSC-HSZRJFAPSA-N",
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(N[C@H](Cn4cc(CO)nn4)C(C)(C)C)n3)c3cc(F)cnc32)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)n2cc(-c3ncc(F)c(N[C@H](Cn4cc(CO)nn4)C(C)(C)C)n3)c3cc(F)cnc32)cc1",
"reactionStepId": "sa_2efa6b666688d2e226e61272",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150191468A1;0573;1720400\",\"rsmi\":\"CC1(C)OB([c:11]2[cH:10][n:9]([S:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:41][cH:40]3)(=[O:7])=[O:8])[c:39]3[c:33]2[cH:34][c:35]([F:36])[cH:37][n:38]3)OC1(C)C.Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]([CH2:20][n:21]2[cH:22][c:23]([CH2:24][OH:25])[n:26][n:27]2)[C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O.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.OCc1c[nH]nn1.[K+].[K+].[K+].[Pd].[Pd]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11](-[c:12]3[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]([CH2:20][n:21]4[cH:22][c:23]([CH2:24][OH:25])[n:26][n:27]4)[C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]3)[c:33]3[cH:34][c:35]([F:36])[cH:37][n:38][c:39]23)[cH:40][cH:41]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:11]2[cH:10][n:9]([S:6]([c:5]3[cH:4][cH:3][c:2]([CH3:1])[cH:41][cH:40]3)(=[O:7])=[O:8])[c:39]3[c:33]2[cH:34][c:35]([F:36])[cH:37][n:38]3)OC1(C)C.Cl[c:12]1[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]([CH2:20][n:21]2[cH:22][c:23]([CH2:24][OH:25])[n:26][n:27]2)[C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]1>CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O.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.OCc1c[nH]nn1.[K+].[K+].[K+].[Pd].[Pd]>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][c:11](-[c:12]3[n:13][cH:14][c:15]([F:16])[c:17]([NH:18][C@H:19]([CH2:20][n:21]4[cH:22][c:23]([CH2:24][OH:25])[n:26][n:27]4)[C:28]([CH3:29])([CH3:30])[CH3:31])[n:32]3)[c:33]3[cH:34][c:35]([F:36])[cH:37][n:38][c:39]23)[cH:40][cH:41]1\"}",
"reactionStep": {
"id": "sa_2efa6b666688d2e226e61272",
"reactionHash": "5326f14f0767dfb16b9cb8fec03a4de0b9cff3d450754f59d35acbce7ecbff2b"
},
"children": [
{
"id": "3701",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_fb590130b1f9acad1138b0b1",
"parentId": "3700",
"isLeaf": true,
"molecule": {
"id": "sa_fb590130b1f9acad1138b0b1",
"inchikey": "NBTQILYOTKPKRZ-UHFFFAOYSA-N",
"smiles": "Cc1ccc(S(=O)(=O)n2cc(B3OC(C)(C)C(C)(C)O3)c3cc(F)cnc32)cc1"
},
"smiles": "Cc1ccc(S(=O)(=O)n2cc(B3OC(C)(C)C(C)(C)O3)c3cc(F)cnc32)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3702",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_6d8dc769e26ef4725df52ebb",
"parentId": "3700",
"isLeaf": false,
"molecule": {
"id": "sa_6d8dc769e26ef4725df52ebb",
"inchikey": "VPKDTUDXPIBTEJ-SNVBAGLBSA-N",
"smiles": "CC(C)(C)[C@@H](Cn1cc(CO)nn1)Nc1nc(Cl)ncc1F"
},
"smiles": "CC(C)(C)[C@@H](Cn1cc(CO)nn1)Nc1nc(Cl)ncc1F",
"reactionStepId": "sa_3253ea9298262b9b3c4f8bb2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150191468A1;0571;1720399\",\"rsmi\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][N:7]=[N+:13]=[N-:12])[NH:14][c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]1[F:22].[CH:8]#[C:9][CH2:10][OH:11]>C1CCOC1.Cc1ccccc1>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][n:7]1[cH:8][c:9]([CH2:10][OH:11])[n:12][n:13]1)[NH:14][c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]1[F:22]\"},\"mapped_reaction_smiles\":\"[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][N:7]=[N+:13]=[N-:12])[NH:14][c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]1[F:22].[CH:8]#[C:9][CH2:10][OH:11]>C1CCOC1.Cc1ccccc1>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][n:7]1[cH:8][c:9]([CH2:10][OH:11])[n:12][n:13]1)[NH:14][c:15]1[n:16][c:17]([Cl:18])[n:19][cH:20][c:21]1[F:22]\"}",
"reactionStep": {
"id": "sa_3253ea9298262b9b3c4f8bb2",
"reactionHash": "efbb509f2159a177b39ca101fbaf52b4127b5000b414382c25542da4ce58b875"
},
"children": [
{
"id": "3703",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_c58a4b616256a73ac49fb169",
"parentId": "3702",
"isLeaf": true,
"molecule": {
"id": "sa_c58a4b616256a73ac49fb169",
"inchikey": "TVDSBUOJIPERQY-UHFFFAOYSA-N",
"smiles": "C#CCO"
},
"smiles": "C#CCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3704",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_e02eb78531dbbf09dbdb444d",
"parentId": "3702",
"isLeaf": false,
"molecule": {
"id": "sa_e02eb78531dbbf09dbdb444d",
"inchikey": "USVZJRWCICBJSK-SSDOTTSWSA-N",
"smiles": "CC(C)(C)[C@@H](CN=[N+]=[N-])Nc1nc(Cl)ncc1F"
},
"smiles": "CC(C)(C)[C@@H](CN=[N+]=[N-])Nc1nc(Cl)ncc1F",
"reactionStepId": "sa_a263b9393c42d6c520fbcd00",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150191468A1;0570;1720398\",\"rsmi\":\"CS(=O)(=O)O[CH2:6][C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[NH:10][c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[F:18].[N-:7]=[N+:8]=[N-:9]>CN(C)C=O.O.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][N:7]=[N+:8]=[N-:9])[NH:10][c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[F:18]\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:6][C@H:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[NH:10][c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[F:18].[N-:7]=[N+:8]=[N-:9]>CN(C)C=O.O.[Na+]>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][N:7]=[N+:8]=[N-:9])[NH:10][c:11]1[n:12][c:13]([Cl:14])[n:15][cH:16][c:17]1[F:18]\"}",
"reactionStep": {
"id": "sa_a263b9393c42d6c520fbcd00",
"reactionHash": "c86af7125fd8a8f3006efb939593447b92fae29c1457a97b0d1a2e76f61d1582"
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"children": [
{
"id": "3705",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_3430ff5dce31d75a2981c51e",
"parentId": "3704",
"isLeaf": false,
"molecule": {
"id": "sa_3430ff5dce31d75a2981c51e",
"inchikey": "BGUYNPATMDNWCR-MRVPVSSYSA-N",
"smiles": "CC(C)(C)[C@@H](COS(C)(=O)=O)Nc1nc(Cl)ncc1F"
},
"smiles": "CC(C)(C)[C@@H](COS(C)(=O)=O)Nc1nc(Cl)ncc1F",
"reactionStepId": "sa_c61553d0e9667bbbc647b79d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150191468A1;0408;1720315\",\"rsmi\":\"Cl[S:8]([CH3:9])(=[O:10])=[O:11].[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][OH:7])[NH:12][c:13]1[n:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[F:20]>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][O:7][S:8]([CH3:9])(=[O:10])=[O:11])[NH:12][c:13]1[n:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[F:20]\"},\"mapped_reaction_smiles\":\"Cl[S:8]([CH3:9])(=[O:10])=[O:11].[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][OH:7])[NH:12][c:13]1[n:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[F:20]>CCN(CC)CC.ClCCl>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][O:7][S:8]([CH3:9])(=[O:10])=[O:11])[NH:12][c:13]1[n:14][c:15]([Cl:16])[n:17][cH:18][c:19]1[F:20]\"}",
"reactionStep": {
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"reactionHash": "9d35b7bb6beb3426f0ca086ced34555c813e3d6b4f7f06e14a879502b841b1a3"
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"children": [
{
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"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "3705",
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"molecule": {
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"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "3707",
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"moleculeId": "sa_1d9fb9a07d5bebdfd217583f",
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"molecule": {
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"inchikey": "YUFRLVWCUYFCMH-SSDOTTSWSA-N",
"smiles": "CC(C)(C)[C@@H](CO)Nc1nc(Cl)ncc1F"
},
"smiles": "CC(C)(C)[C@@H](CO)Nc1nc(Cl)ncc1F",
"reactionStepId": "sa_13231f271cb95ad6345d5584",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150191468A1;0337;1720288\",\"rsmi\":\"Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16].[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][OH:7])[NH2:8]>CCN(CC)CC.CN(C)C=O.Cl.N>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][OH:7])[NH:8][c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16]\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16].[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][OH:7])[NH2:8]>CCN(CC)CC.CN(C)C=O.Cl.N>[CH3:1][C:2]([CH3:3])([CH3:4])[C@@H:5]([CH2:6][OH:7])[NH:8][c:9]1[n:10][c:11]([Cl:12])[n:13][cH:14][c:15]1[F:16]\"}",
"reactionStep": {
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"children": [
{
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"parentId": "3707",
"isLeaf": true,
"molecule": {
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"inchikey": "JBULSURVMXPBNA-RXMQYKEDSA-N",
"smiles": "CC(C)(C)[C@H](N)CO"
},
"smiles": "CC(C)(C)[C@H](N)CO",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "3709",
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"parentId": "3707",
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"molecule": {
"id": "sa_8af2da9c6a57b37ead795aa6",
"inchikey": "WHPFEQUEHBULBW-UHFFFAOYSA-N",
"smiles": "Fc1cnc(Cl)nc1Cl"
},
"smiles": "Fc1cnc(Cl)nc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
},
{
"id": "3710",
"routeId": "sa_bd62b610d7844f55249a95e8",
"moleculeId": "sa_50a8f83dd89c267fbada1205",
"parentId": "3704",
"isLeaf": true,
"molecule": {
"id": "sa_50a8f83dd89c267fbada1205",
"inchikey": "IVRMZWNICZWHMI-UHFFFAOYSA-N",
"smiles": "[N]N=[N-]"
},
"smiles": "[N-]=[N+]=[N-]",
"reactionStepId": null,
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}
]
}
]
}
]
}
]
}
}