Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCNc1n[nH]c2c(Br)c(NC(=O)N[C@H](C)c3ccccc3)ncc12
InChiKey
JDDBADLJKVGIJW-SNVBAGLBSA-N
Route Signature
a0e2a9cde5edb8f57dbff3d5b003d044211436a630d597f603f9ddab9a85458f
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_0482f73f5d21ec2573ab0b10",
"signature": "a0e2a9cde5edb8f57dbff3d5b003d044211436a630d597f603f9ddab9a85458f",
"contentHash": "4e9799cd88e6e3d50aeb5dae84db373f6362b2040ad74c0d4f94632c17e8c3a9",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_abde95b0b9a4e8534f69e2f5",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00753",
"moleculeId": "sa_0990c3c116df80d233dde3b5",
"smiles": "CCNc1n[nH]c2c(Br)c(NC(=O)N[C@H](C)c3ccccc3)ncc12",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_0990c3c116df80d233dde3b5",
"inchikey": "JDDBADLJKVGIJW-SNVBAGLBSA-N",
"smiles": "CCNc1n[nH]c2c(Br)c(NC(=O)N[C@H](C)c3ccccc3)ncc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "4816",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_0990c3c116df80d233dde3b5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0990c3c116df80d233dde3b5",
"inchikey": "JDDBADLJKVGIJW-SNVBAGLBSA-N",
"smiles": "CCNc1n[nH]c2c(Br)c(NC(=O)N[C@H](C)c3ccccc3)ncc12"
},
"smiles": "CCNc1n[nH]c2c(Br)c(NC(=O)N[C@H](C)c3ccccc3)ncc12",
"reactionStepId": "sa_8caaaf3a97f46e7f3a52da48",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266895A1;0512;1758143\",\"rsmi\":\"O=C1CCC(=O)N1[Br:25].[CH3:1][CH2:2][NH:3][c:4]1[n:5][nH:6][c:7]2[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[cH:24]2>CC#N.CN(C)C=O>[CH3:1][CH2:2][NH:3][c:4]1[n:5][nH:6][c:7]2[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[c:24]2[Br:25]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:25].[CH3:1][CH2:2][NH:3][c:4]1[n:5][nH:6][c:7]2[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[cH:24]2>CC#N.CN(C)C=O>[CH3:1][CH2:2][NH:3][c:4]1[n:5][nH:6][c:7]2[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[c:24]2[Br:25]\"}",
"reactionStep": {
"id": "sa_8caaaf3a97f46e7f3a52da48",
"reactionHash": "6923e5d56de72092ef758c82ac72e639da3e22616e9b382194474a133aa60a8b"
},
"children": [
{
"id": "4817",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "4816",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4818",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_f51f220b7ec4f925c7a79b14",
"parentId": "4816",
"isLeaf": false,
"molecule": {
"id": "sa_f51f220b7ec4f925c7a79b14",
"inchikey": "XMPPRDZNRYRKEN-LLVKDONJSA-N",
"smiles": "CCNc1n[nH]c2cc(NC(=O)N[C@H](C)c3ccccc3)ncc12"
},
"smiles": "CCNc1n[nH]c2cc(NC(=O)N[C@H](C)c3ccccc3)ncc12",
"reactionStepId": "sa_8ffb76f98025c37923fdbca5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266895A1;0458;1758128\",\"rsmi\":\"c1ccc(C(c2ccccc2)(c2ccccc2)[n:6]2[n:5][c:4]([NH:3][CH2:2][CH3:1])[c:8]3[c:7]2[cH:24][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:10][cH:9]3)cc1>CC[SiH](CC)CC.O=C(O)C(F)(F)F>[CH3:1][CH2:2][NH:3][c:4]1[n:5][nH:6][c:7]2[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[cH:24]2\"},\"mapped_reaction_smiles\":\"c1ccc(C(c2ccccc2)(c2ccccc2)[n:6]2[n:5][c:4]([NH:3][CH2:2][CH3:1])[c:8]3[c:7]2[cH:24][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[n:10][cH:9]3)cc1>CC[SiH](CC)CC.O=C(O)C(F)(F)F>[CH3:1][CH2:2][NH:3][c:4]1[n:5][nH:6][c:7]2[c:8]1[cH:9][n:10][c:11]([NH:12][C:13](=[O:14])[NH:15][C@H:16]([CH3:17])[c:18]1[cH:19][cH:20][cH:21][cH:22][cH:23]1)[cH:24]2\"}",
"reactionStep": {
"id": "sa_8ffb76f98025c37923fdbca5",
"reactionHash": "2d65626d0c725f98ab98e601a27bf47deb3ff2d2f3913d3d017e7eff6b4612f0"
},
"children": [
{
"id": "4819",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_9082cbcc777e0a51c6c3540c",
"parentId": "4818",
"isLeaf": false,
"molecule": {
"id": "sa_9082cbcc777e0a51c6c3540c",
"inchikey": "GROOKFQPFMXSQL-AREMUKBSSA-N",
"smiles": "CCNc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2cc(NC(=O)N[C@H](C)c3ccccc3)ncc12"
},
"smiles": "CCNc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2cc(NC(=O)N[C@H](C)c3ccccc3)ncc12",
"reactionStepId": "sa_3cc8f11099588d626433de72",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266895A1;0457;1758127\",\"rsmi\":\"Cl[c:30]1[n:29][cH:28][c:27]2[c:4]([NH:3][CH2:2][CH3:1])[n:5][n:6]([C:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:26]2[cH:43]1.[NH2:31][C:32](=[O:33])[NH:34][C@H:35]([CH3:36])[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1>C1CCOC1.CC(C)(C)O.COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.[Na+]>[CH3:1][CH2:2][NH:3][c:4]1[n:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[c:27]1[cH:28][n:29][c:30]([NH:31][C:32](=[O:33])[NH:34][C@H:35]([CH3:36])[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1)[cH:43]2\"},\"mapped_reaction_smiles\":\"Cl[c:30]1[n:29][cH:28][c:27]2[c:4]([NH:3][CH2:2][CH3:1])[n:5][n:6]([C:7]([c:8]3[cH:9][cH:10][cH:11][cH:12][cH:13]3)([c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[c:20]3[cH:21][cH:22][cH:23][cH:24][cH:25]3)[c:26]2[cH:43]1.[NH2:31][C:32](=[O:33])[NH:34][C@H:35]([CH3:36])[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1>C1CCOC1.CC(C)(C)O.COc1ccc(OC)c(P(C2CCCCC2)C2CCCCC2)c1-c1c(C(C)C)cc(C(C)C)cc1C(C)C.[Na+]>[CH3:1][CH2:2][NH:3][c:4]1[n:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[c:27]1[cH:28][n:29][c:30]([NH:31][C:32](=[O:33])[NH:34][C@H:35]([CH3:36])[c:37]1[cH:38][cH:39][cH:40][cH:41][cH:42]1)[cH:43]2\"}",
"reactionStep": {
"id": "sa_3cc8f11099588d626433de72",
"reactionHash": "24e9a0accb5d057063a082a4c91d95f7c1aeafb16d6829193097e479123eb277"
},
"children": [
{
"id": "4820",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_52de66e98384852b10a07e7c",
"parentId": "4819",
"isLeaf": true,
"molecule": {
"id": "sa_52de66e98384852b10a07e7c",
"inchikey": "ALVBVEKNACPPAB-SSDOTTSWSA-N",
"smiles": "C[C@@H](NC(N)=O)c1ccccc1"
},
"smiles": "C[C@@H](NC(N)=O)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "4821",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_2deb30dd1a469748aec0b240",
"parentId": "4819",
"isLeaf": false,
"molecule": {
"id": "sa_2deb30dd1a469748aec0b240",
"inchikey": "FPIGTQQFSWOBAK-UHFFFAOYSA-N",
"smiles": "CCNc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2cc(Cl)ncc12"
},
"smiles": "CCNc1nn(C(c2ccccc2)(c2ccccc2)c2ccccc2)c2cc(Cl)ncc12",
"reactionStepId": "sa_1a4a4a2c4a6a6cdabe69d967",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266895A1;0456;1758126\",\"rsmi\":\"I[c:4]1[n:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[c:27]1[cH:28][n:29][c:30]([Cl:31])[cH:32]2.[CH3:1][CH2:2][NH2:3]>CS(C)=O.Cl.O=C(O)[C@@H]1CCCN1.O=C(O)O.[Cu]I.[K+].[K+].N.O>[CH3:1][CH2:2][NH:3][c:4]1[n:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[c:27]1[cH:28][n:29][c:30]([Cl:31])[cH:32]2\"},\"mapped_reaction_smiles\":\"I[c:4]1[n:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[c:27]1[cH:28][n:29][c:30]([Cl:31])[cH:32]2.[CH3:1][CH2:2][NH2:3]>CS(C)=O.Cl.O=C(O)[C@@H]1CCCN1.O=C(O)O.[Cu]I.[K+].[K+].N.O>[CH3:1][CH2:2][NH:3][c:4]1[n:5][n:6]([C:7]([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)([c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[c:20]2[cH:21][cH:22][cH:23][cH:24][cH:25]2)[c:26]2[c:27]1[cH:28][n:29][c:30]([Cl:31])[cH:32]2\"}",
"reactionStep": {
"id": "sa_1a4a4a2c4a6a6cdabe69d967",
"reactionHash": "246dd984390464d4ce577f67d2a78ad55a91232bc8362b5ce0a112b38d67790e"
},
"children": [
{
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"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_20ef4dc4d3b922eda27d0fa9",
"parentId": "4821",
"isLeaf": false,
"molecule": {
"id": "sa_20ef4dc4d3b922eda27d0fa9",
"inchikey": "FCONEXKZUYAZQG-UHFFFAOYSA-N",
"smiles": "Clc1cc2c(cn1)c(I)nn2C(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"smiles": "Clc1cc2c(cn1)c(I)nn2C(c1ccccc1)(c1ccccc1)c1ccccc1",
"reactionStepId": "sa_fce27a333c19010699cffa8d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266895A1;0391;1758097\",\"rsmi\":\"Cl[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[c:8]([I:9])[n:10][nH:11]2>C1CCOC1.[HH].[Na+]>[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[c:8]([I:9])[n:10][n:11]2[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Cl[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1.[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[c:8]([I:9])[n:10][nH:11]2>C1CCOC1.[HH].[Na+]>[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[c:8]([I:9])[n:10][n:11]2[C:12]([c:13]1[cH:14][cH:15][cH:16][cH:17][cH:18]1)([c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
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"reactionHash": "19491ba2a95908213827d17618ea769039c43e686569e6e24b743d7439721538"
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"children": [
{
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"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_966de284747392e3a06c0765",
"parentId": "4822",
"isLeaf": true,
"molecule": {
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"inchikey": "JBWKIWSBJXDJDT-UHFFFAOYSA-N",
"smiles": "ClC(c1ccccc1)(c1ccccc1)c1ccccc1"
},
"smiles": "ClC(c1ccccc1)(c1ccccc1)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "4824",
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"molecule": {
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"inchikey": "METUREDHGCAEJK-UHFFFAOYSA-N",
"smiles": "Clc1cc2[nH]nc(I)c2cn1"
},
"smiles": "Clc1cc2[nH]nc(I)c2cn1",
"reactionStepId": "sa_ea8ec0dc0854749e10b8dfdb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266895A1;0390;1758096\",\"rsmi\":\"I[I:9].[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[cH:8][n:10][nH:11]2>CN(C)C=O.[K+].O>[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[c:8]([I:9])[n:10][nH:11]2\"},\"mapped_reaction_smiles\":\"I[I:9].[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[cH:8][n:10][nH:11]2>CN(C)C=O.[K+].O>[Cl:1][c:2]1[cH:3][c:4]2[c:5]([cH:6][n:7]1)[c:8]([I:9])[n:10][nH:11]2\"}",
"reactionStep": {
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"reactionHash": "18398922502ce64669ba8594236fe37a028e3b1413aa10f6106931f5418f0e6f"
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"children": [
{
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"parentId": "4824",
"isLeaf": true,
"molecule": {
"id": "sa_46956982a42f266fa0e955ce",
"inchikey": "AAJIQIWPVIWCGA-UHFFFAOYSA-N",
"smiles": "Clc1cc2n[nH]cc2cn1"
},
"smiles": "Clc1cc2[nH]ncc2cn1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "4826",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
"moleculeId": "sa_bc6c113460696c6012e3bdf5",
"parentId": "4824",
"isLeaf": true,
"molecule": {
"id": "sa_bc6c113460696c6012e3bdf5",
"inchikey": "PNDPGZBMCMUPRI-UHFFFAOYSA-N",
"smiles": "II"
},
"smiles": "II",
"reactionStepId": null,
"template": null,
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}
]
}
]
},
{
"id": "4827",
"routeId": "sa_0482f73f5d21ec2573ab0b10",
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