Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C(=O)Nc1ccc2c(=O)n(C)[nH]c2c1)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O
InChiKey
YGCUMUHGVWVKJG-UHFFFAOYSA-N
Route Signature
d3faa0dd85bb053afb58c9ca74024c6dda4319e04906362e241f5bf75d4f521e
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_732d1803fcb43491d70b9da5",
"signature": "d3faa0dd85bb053afb58c9ca74024c6dda4319e04906362e241f5bf75d4f521e",
"contentHash": "0922648f3e85097c5f960e11f1a6c964327613a2c8398e1be726a6fb736db2c6",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_7e4c2407535072daf6f303a0",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01584",
"moleculeId": "sa_10418dd52a026ce400daa94c",
"smiles": "CC(C(=O)Nc1ccc2c(=O)n(C)[nH]c2c1)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_10418dd52a026ce400daa94c",
"inchikey": "YGCUMUHGVWVKJG-UHFFFAOYSA-N",
"smiles": "CC(C(=O)Nc1ccc2c(=O)n(C)[nH]c2c1)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10309",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_10418dd52a026ce400daa94c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_10418dd52a026ce400daa94c",
"inchikey": "YGCUMUHGVWVKJG-UHFFFAOYSA-N",
"smiles": "CC(C(=O)Nc1ccc2c(=O)n(C)[nH]c2c1)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O"
},
"smiles": "CC(C(=O)Nc1ccc2c(=O)n(C)[nH]c2c1)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O",
"reactionStepId": "sa_e614903053b377ba17852c13",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;2074;1843033\",\"rsmi\":\"CC(C)(C)OC(=O)[n:14]1[n:12]([CH3:13])[c:10](=[O:11])[c:9]2[cH:8][cH:7][c:6]([NH:5][C:3]([CH:2]([CH3:1])[n:17]3[cH:18][cH:19][c:20](-[c:21]4[c:22]([C:23]#[N:24])[cH:25][cH:26][c:27]([Cl:28])[cH:29]4)[cH:30][c:31]3=[O:32])=[O:4])[cH:16][c:15]21>O=C(O)C(F)(F)F>[CH3:1][CH:2]([C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]([CH3:13])[nH:14][c:15]2[cH:16]1)[n:17]1[cH:18][cH:19][c:20](-[c:21]2[c:22]([C:23]#[N:24])[cH:25][cH:26][c:27]([Cl:28])[cH:29]2)[cH:30][c:31]1=[O:32]\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[n:14]1[n:12]([CH3:13])[c:10](=[O:11])[c:9]2[cH:8][cH:7][c:6]([NH:5][C:3]([CH:2]([CH3:1])[n:17]3[cH:18][cH:19][c:20](-[c:21]4[c:22]([C:23]#[N:24])[cH:25][cH:26][c:27]([Cl:28])[cH:29]4)[cH:30][c:31]3=[O:32])=[O:4])[cH:16][c:15]21>O=C(O)C(F)(F)F>[CH3:1][CH:2]([C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]([CH3:13])[nH:14][c:15]2[cH:16]1)[n:17]1[cH:18][cH:19][c:20](-[c:21]2[c:22]([C:23]#[N:24])[cH:25][cH:26][c:27]([Cl:28])[cH:29]2)[cH:30][c:31]1=[O:32]\"}",
"reactionStep": {
"id": "sa_e614903053b377ba17852c13",
"reactionHash": "0b44ea379a56f413679a5451ea9475b7b99503646d4abf09a8fa595c258499e4"
},
"children": [
{
"id": "10310",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_dcfe432f0d966c6d3ecac04c",
"parentId": "10309",
"isLeaf": false,
"molecule": {
"id": "sa_dcfe432f0d966c6d3ecac04c",
"inchikey": "BJKOFFBRPKGSAA-UHFFFAOYSA-N",
"smiles": "CC(C(=O)Nc1ccc2c(=O)n(C)n(C(=O)OC(C)(C)C)c2c1)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O"
},
"smiles": "CC(C(=O)Nc1ccc2c(=O)n(C)n(C(=O)OC(C)(C)C)c2c1)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O",
"reactionStepId": "sa_e9b4daad84f5ce31aa498108",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;0739;1842677\",\"rsmi\":\"O[C:3]([CH:2]([CH3:1])[n:24]1[cH:25][cH:26][c:27](-[c:28]2[c:29]([C:30]#[N:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]2)[cH:37][c:38]1=[O:39])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]([CH3:13])[n:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]2[cH:23]1>>[CH3:1][CH:2]([C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]([CH3:13])[n:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]2[cH:23]1)[n:24]1[cH:25][cH:26][c:27](-[c:28]2[c:29]([C:30]#[N:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]2)[cH:37][c:38]1=[O:39]\"},\"mapped_reaction_smiles\":\"O[C:3]([CH:2]([CH3:1])[n:24]1[cH:25][cH:26][c:27](-[c:28]2[c:29]([C:30]#[N:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]2)[cH:37][c:38]1=[O:39])=[O:4].[NH2:5][c:6]1[cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]([CH3:13])[n:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]2[cH:23]1>>[CH3:1][CH:2]([C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]2[c:10](=[O:11])[n:12]([CH3:13])[n:14]([C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[c:22]2[cH:23]1)[n:24]1[cH:25][cH:26][c:27](-[c:28]2[c:29]([C:30]#[N:31])[cH:32][cH:33][c:34]([Cl:35])[cH:36]2)[cH:37][c:38]1=[O:39]\"}",
"reactionStep": {
"id": "sa_e9b4daad84f5ce31aa498108",
"reactionHash": "9f63f638b89c756391ea1d1affa8e36d695e8937d56b4e8b6c84a8504fae3b72"
},
"children": [
{
"id": "10311",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_c97a351b3f30233ba0944101",
"parentId": "10310",
"isLeaf": false,
"molecule": {
"id": "sa_c97a351b3f30233ba0944101",
"inchikey": "DLWDXWOZJAFFFS-UHFFFAOYSA-N",
"smiles": "CC(C(=O)O)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O"
},
"smiles": "CC(C(=O)O)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O",
"reactionStepId": "sa_d9cbf7d9a3c826838c230f2c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;0718;1842671\",\"rsmi\":\"CC(C)(C)[O:5][C:3]([CH:2]([CH3:1])[n:6]1[cH:7][cH:8][c:9](-[c:10]2[c:11]([C:12]#[N:13])[cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[cH:19][c:20]1=[O:21])=[O:4]>O=C(O)C(F)(F)F>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[n:6]1[cH:7][cH:8][c:9](-[c:10]2[c:11]([C:12]#[N:13])[cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[cH:19][c:20]1=[O:21]\"},\"mapped_reaction_smiles\":\"CC(C)(C)[O:5][C:3]([CH:2]([CH3:1])[n:6]1[cH:7][cH:8][c:9](-[c:10]2[c:11]([C:12]#[N:13])[cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[cH:19][c:20]1=[O:21])=[O:4]>O=C(O)C(F)(F)F>[CH3:1][CH:2]([C:3](=[O:4])[OH:5])[n:6]1[cH:7][cH:8][c:9](-[c:10]2[c:11]([C:12]#[N:13])[cH:14][cH:15][c:16]([Cl:17])[cH:18]2)[cH:19][c:20]1=[O:21]\"}",
"reactionStep": {
"id": "sa_d9cbf7d9a3c826838c230f2c",
"reactionHash": "3544d82e402755200c772fcdb59b34c6908227e171121091bb89b9da116dea20"
},
"children": [
{
"id": "10312",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_3d5d8ba067e52710bab14f14",
"parentId": "10311",
"isLeaf": false,
"molecule": {
"id": "sa_3d5d8ba067e52710bab14f14",
"inchikey": "BSDXEYUDBXABHM-UHFFFAOYSA-N",
"smiles": "CC(C(=O)OC(C)(C)C)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O"
},
"smiles": "CC(C(=O)OC(C)(C)C)n1ccc(-c2cc(Cl)ccc2C#N)cc1=O",
"reactionStepId": "sa_be8ef2722b8af52071b8a560",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;0714;1842670\",\"rsmi\":\"Br[c:13]1[cH:12][cH:11][n:10]([CH:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:24](=[O:25])[cH:23]1.OB(O)[c:14]1[c:15]([C:16]#[N:17])[cH:18][cH:19][c:20]([Cl:21])[cH:22]1>c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[n:10]1[cH:11][cH:12][c:13](-[c:14]2[c:15]([C:16]#[N:17])[cH:18][cH:19][c:20]([Cl:21])[cH:22]2)[cH:23][c:24]1=[O:25]\"},\"mapped_reaction_smiles\":\"Br[c:13]1[cH:12][cH:11][n:10]([CH:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[c:24](=[O:25])[cH:23]1.OB(O)[c:14]1[c:15]([C:16]#[N:17])[cH:18][cH:19][c:20]([Cl:21])[cH:22]1>c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[n:10]1[cH:11][cH:12][c:13](-[c:14]2[c:15]([C:16]#[N:17])[cH:18][cH:19][c:20]([Cl:21])[cH:22]2)[cH:23][c:24]1=[O:25]\"}",
"reactionStep": {
"id": "sa_be8ef2722b8af52071b8a560",
"reactionHash": "1a31bba7d058a55ceb9bc7ea3def2a4d71f2e91f15ef64525acdc39b50733044"
},
"children": [
{
"id": "10313",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_724ea3850da2f11c10be42e7",
"parentId": "10312",
"isLeaf": true,
"molecule": {
"id": "sa_724ea3850da2f11c10be42e7",
"inchikey": "JXIINQQPEHZQAY-UHFFFAOYSA-N",
"smiles": "N#Cc1ccc(Cl)cc1B(O)O"
},
"smiles": "N#Cc1ccc(Cl)cc1B(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10314",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_c6394c9379cec0b9529f9483",
"parentId": "10312",
"isLeaf": false,
"molecule": {
"id": "sa_c6394c9379cec0b9529f9483",
"inchikey": "KTOXWPNIJZRTSA-UHFFFAOYSA-N",
"smiles": "CC(C(=O)OC(C)(C)C)n1ccc(Br)cc1=O"
},
"smiles": "CC(C(=O)OC(C)(C)C)n1ccc(Br)cc1=O",
"reactionStepId": "sa_8fbce3e2bd7c057f0db41166",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;0710;1842669\",\"rsmi\":\"Br[CH:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].[nH:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]1=[O:17]>>[CH3:1][CH:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[n:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]1=[O:17]\"},\"mapped_reaction_smiles\":\"Br[CH:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9].[nH:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]1=[O:17]>>[CH3:1][CH:2]([C:3](=[O:4])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[n:10]1[cH:11][cH:12][c:13]([Br:14])[cH:15][c:16]1=[O:17]\"}",
"reactionStep": {
"id": "sa_8fbce3e2bd7c057f0db41166",
"reactionHash": "3a637566af21495a317e86f66b75db59e4f3a4c8ef7e0d640125984b688770eb"
},
"children": [
{
"id": "10315",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_185bba11e4d3a107adb41c94",
"parentId": "10314",
"isLeaf": true,
"molecule": {
"id": "sa_185bba11e4d3a107adb41c94",
"inchikey": "CVAWKJKISIPBOD-UHFFFAOYSA-N",
"smiles": "CC(Br)C(=O)OC(C)(C)C"
},
"smiles": "CC(Br)C(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "10316",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_a4aa79dd099dd5a536affd69",
"parentId": "10314",
"isLeaf": true,
"molecule": {
"id": "sa_a4aa79dd099dd5a536affd69",
"inchikey": "SSLMGOKTIUIZLY-UHFFFAOYSA-N",
"smiles": "Oc1cc(Br)ccn1"
},
"smiles": "O=c1cc(Br)cc[nH]1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "10317",
"routeId": "sa_732d1803fcb43491d70b9da5",
"moleculeId": "sa_61a23b377325be244d0cfb44",
"parentId": "10310",
"isLeaf": false,
"molecule": {
"id": "sa_61a23b377325be244d0cfb44",
"inchikey": "RWABPDVDFAXYRW-UHFFFAOYSA-N",
"smiles": "Cn1c(=O)c2ccc(N)cc2n1C(=O)OC(C)(C)C"
},
"smiles": "Cn1c(=O)c2ccc(N)cc2n1C(=O)OC(C)(C)C",
"reactionStepId": "sa_3fc940878d3b4f2fb4e7b9dc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160052884A1;0621;1842653\",\"rsmi\":\"O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]2[c:3](=[O:4])[n:2]([CH3:1])[n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:11]2[cH:10]1>CCO.[Pd]>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]2[n:12]1[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"O=[N+:9]([O-])[c:8]1[cH:7][cH:6][c:5]2[c:3](=[O:4])[n:2]([CH3:1])[n:12]([C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[c:11]2[cH:10]1>CCO.[Pd]>[CH3:1][n:2]1[c:3](=[O:4])[c:5]2[cH:6][cH:7][c:8]([NH2:9])[cH:10][c:11]2[n:12]1[C:13](=[O:14])[O:15][C:16]([CH3:17])([CH3:18])[CH3:19]\"}",
"reactionStep": {
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"reactionHash": "977f16301c97c9ff66e644a37ffae094e7475879003a6c6e58a2a54ff7d6c40d"
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"children": [
{
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"molecule": {
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"inchikey": "BIWMJZIRVCQBRG-UHFFFAOYSA-N",
"smiles": "Cn1c(=O)c2ccc([N+](=O)[O-])cc2n1C(=O)OC(C)(C)C"
},
"smiles": "Cn1c(=O)c2ccc([N+](=O)[O-])cc2n1C(=O)OC(C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
}
}