Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCC(C)(CNC(=O)c1c(C)nn2c(OCc3c(F)cccc3Cl)cc(C)cc12)NC(=O)OC(C)(C)C
InChiKey
IEDWBHYMCIJHRG-UHFFFAOYSA-N
Route Signature
cbef83257df1964a087fd85556939ad30dc56c5cb8ea394dfa85589d3fafcd64
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_d9eace06b5c989f9811689c7",
"signature": "cbef83257df1964a087fd85556939ad30dc56c5cb8ea394dfa85589d3fafcd64",
"contentHash": "9f641c7385cf4cd29b446176f548ccb7a126ad27fd36a5e7961465954c6603c2",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_c27d51e6c15f78009df29e07",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01855",
"moleculeId": "sa_6c3cb712f64090e2a3a4bdd2",
"smiles": "CCCC(C)(CNC(=O)c1c(C)nn2c(OCc3c(F)cccc3Cl)cc(C)cc12)NC(=O)OC(C)(C)C",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_6c3cb712f64090e2a3a4bdd2",
"inchikey": "IEDWBHYMCIJHRG-UHFFFAOYSA-N",
"smiles": "CCCC(C)(CNC(=O)c1c(C)nn2c(OCc3c(F)cccc3Cl)cc(C)cc12)NC(=O)OC(C)(C)C"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10485",
"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_6c3cb712f64090e2a3a4bdd2",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6c3cb712f64090e2a3a4bdd2",
"inchikey": "IEDWBHYMCIJHRG-UHFFFAOYSA-N",
"smiles": "CCCC(C)(CNC(=O)c1c(C)nn2c(OCc3c(F)cccc3Cl)cc(C)cc12)NC(=O)OC(C)(C)C"
},
"smiles": "CCCC(C)(CNC(=O)c1c(C)nn2c(OCc3c(F)cccc3Cl)cc(C)cc12)NC(=O)OC(C)(C)C",
"reactionStepId": "sa_462534cb23915938cffa9fee",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160185775A1;1886;1900377\",\"rsmi\":\"O[C:8](=[O:9])[c:10]1[c:11]2[cH:12][c:13]([CH3:14])[cH:15][c:16]([O:17][CH2:18][c:19]3[c:20]([Cl:21])[cH:22][cH:23][cH:24][c:25]3[F:26])[n:27]2[n:28][c:29]1[CH3:30].[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([CH2:6][NH2:7])[NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38]>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([CH2:6][NH:7][C:8](=[O:9])[c:10]1[c:11]2[cH:12][c:13]([CH3:14])[cH:15][c:16]([O:17][CH2:18][c:19]3[c:20]([Cl:21])[cH:22][cH:23][cH:24][c:25]3[F:26])[n:27]2[n:28][c:29]1[CH3:30])[NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38]\"},\"mapped_reaction_smiles\":\"O[C:8](=[O:9])[c:10]1[c:11]2[cH:12][c:13]([CH3:14])[cH:15][c:16]([O:17][CH2:18][c:19]3[c:20]([Cl:21])[cH:22][cH:23][cH:24][c:25]3[F:26])[n:27]2[n:28][c:29]1[CH3:30].[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([CH2:6][NH2:7])[NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38]>C1CCOC1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.Cl.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([CH2:6][NH:7][C:8](=[O:9])[c:10]1[c:11]2[cH:12][c:13]([CH3:14])[cH:15][c:16]([O:17][CH2:18][c:19]3[c:20]([Cl:21])[cH:22][cH:23][cH:24][c:25]3[F:26])[n:27]2[n:28][c:29]1[CH3:30])[NH:31][C:32](=[O:33])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38]\"}",
"reactionStep": {
"id": "sa_462534cb23915938cffa9fee",
"reactionHash": "aa4268abe2a6e993a4ed4acd86caf40f04cf1c72c72e654f75b1cdf60c4567ea"
},
"children": [
{
"id": "10486",
"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_3ff7a85ec3be66e1e8cc7fc8",
"parentId": "10485",
"isLeaf": false,
"molecule": {
"id": "sa_3ff7a85ec3be66e1e8cc7fc8",
"inchikey": "KQVSNNHLRPHPRR-UHFFFAOYSA-N",
"smiles": "Cc1cc(OCc2c(F)cccc2Cl)n2nc(C)c(C(=O)O)c2c1"
},
"smiles": "Cc1cc(OCc2c(F)cccc2Cl)n2nc(C)c(C(=O)O)c2c1",
"reactionStepId": "sa_3d0ff5a087c205cbdd71eb1d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160185775A1;1883;1900376\",\"rsmi\":\"CC[O:8][C:6]([c:5]1[c:4]2[cH:3][c:2]([CH3:1])[cH:24][c:13]([O:14][CH2:15][c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[F:23])[n:12]2[n:11][c:9]1[CH3:10])=[O:7]>C1COCCO1.CS(C)=O.[Na+].O>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([C:6](=[O:7])[OH:8])[c:9]([CH3:10])[n:11][n:12]2[c:13]([O:14][CH2:15][c:16]2[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]2[F:23])[cH:24]1\"},\"mapped_reaction_smiles\":\"CC[O:8][C:6]([c:5]1[c:4]2[cH:3][c:2]([CH3:1])[cH:24][c:13]([O:14][CH2:15][c:16]3[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]3[F:23])[n:12]2[n:11][c:9]1[CH3:10])=[O:7]>C1COCCO1.CS(C)=O.[Na+].O>[CH3:1][c:2]1[cH:3][c:4]2[c:5]([C:6](=[O:7])[OH:8])[c:9]([CH3:10])[n:11][n:12]2[c:13]([O:14][CH2:15][c:16]2[c:17]([Cl:18])[cH:19][cH:20][cH:21][c:22]2[F:23])[cH:24]1\"}",
"reactionStep": {
"id": "sa_3d0ff5a087c205cbdd71eb1d",
"reactionHash": "d481109a4fc42e6f6b4075c1ec29970542ff427adb6fb4018a667b85b6a681b4"
},
"children": [
{
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"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_44e2584abbab8a6909b32c81",
"parentId": "10486",
"isLeaf": false,
"molecule": {
"id": "sa_44e2584abbab8a6909b32c81",
"inchikey": "ZLSFSRGMWRYLJR-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(C)nn2c(OCc3c(F)cccc3Cl)cc(C)cc12"
},
"smiles": "CCOC(=O)c1c(C)nn2c(OCc3c(F)cccc3Cl)cc(C)cc12",
"reactionStepId": "sa_ace48b1a61dd32ca4e0ec130",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160185775A1;1879;1900375\",\"rsmi\":\"O[CH2:14][c:15]1[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]1[F:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([OH:13])[n:23]2[n:24][c:25]1[CH3:26]>C1CCOC1.CC(C)OC(=O)N=NC(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][CH2:14][c:15]3[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]3[F:22])[n:23]2[n:24][c:25]1[CH3:26]\"},\"mapped_reaction_smiles\":\"O[CH2:14][c:15]1[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]1[F:22].[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([OH:13])[n:23]2[n:24][c:25]1[CH3:26]>C1CCOC1.CC(C)OC(=O)N=NC(=O)OC(C)C.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][CH2:14][c:15]3[c:16]([Cl:17])[cH:18][cH:19][cH:20][c:21]3[F:22])[n:23]2[n:24][c:25]1[CH3:26]\"}",
"reactionStep": {
"id": "sa_ace48b1a61dd32ca4e0ec130",
"reactionHash": "afb73b3ce17bd2fe363dfc61b694f6f0b17854893b4b8bfe134c654aa832652e"
},
"children": [
{
"id": "10488",
"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_20fe2936cb5beecb48eb3622",
"parentId": "10487",
"isLeaf": false,
"molecule": {
"id": "sa_20fe2936cb5beecb48eb3622",
"inchikey": "VUNIYQYBUJOEGW-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(C)nn2c(O)cc(C)cc12"
},
"smiles": "CCOC(=O)c1c(C)nn2c(O)cc(C)cc12",
"reactionStepId": "sa_abe04d65a9df092d81e99b3e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160185775A1;1356;1900313\",\"rsmi\":\"c1ccc(C[O:13][c:12]2[cH:11][c:9]([CH3:10])[cH:8][c:7]3[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:16]([CH3:17])[n:15][n:14]32)cc1>C1=CCCCC1.CCO.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([OH:13])[n:14]2[n:15][c:16]1[CH3:17]\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:13][c:12]2[cH:11][c:9]([CH3:10])[cH:8][c:7]3[c:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[c:16]([CH3:17])[n:15][n:14]32)cc1>C1=CCCCC1.CCO.[Pd]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([OH:13])[n:14]2[n:15][c:16]1[CH3:17]\"}",
"reactionStep": {
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"reactionHash": "046378323ba5f431c3a538e91152fabc7443a80542af1b88ee0fe1836d90361e"
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"children": [
{
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"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_a27a4c5067b9b7c07c4b6f0e",
"parentId": "10488",
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"molecule": {
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"inchikey": "RBQBHSAPCBWXIU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1c(C)nn2c(OCc3ccccc3)cc(C)cc12"
},
"smiles": "CCOC(=O)c1c(C)nn2c(OCc3ccccc3)cc(C)cc12",
"reactionStepId": "sa_febe4ea167690ac539ffc984",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20160185775A1;1351;1900312\",\"rsmi\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]#[C:23][CH3:24].[cH:7]1[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n+:21]1[NH2:22]>CN(C)C=O.Cc1cc(C)c(S(=O)(=O)O)c(C)c1.O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21]2[n:22][c:23]1[CH3:24]\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]#[C:23][CH3:24].[cH:7]1[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][CH2:14][c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[n+:21]1[NH2:22]>CN(C)C=O.Cc1cc(C)c(S(=O)(=O)O)c(C)c1.O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[c:7]2[cH:8][c:9]([CH3:10])[cH:11][c:12]([O:13][CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[n:21]2[n:22][c:23]1[CH3:24]\"}",
"reactionStep": {
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"children": [
{
"id": "10490",
"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_eb64de2eefbd5d0d02fc96bb",
"parentId": "10489",
"isLeaf": true,
"molecule": {
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"inchikey": "AHBYNNBJXHBKBF-UHFFFAOYSA-N",
"smiles": "Cc1cc[n+](N)c(OCc2ccccc2)c1"
},
"smiles": "Cc1cc[n+](N)c(OCc2ccccc2)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
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{
"id": "10491",
"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_8c3c2264df80e4f76227f158",
"parentId": "10489",
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"molecule": {
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"inchikey": "FCJJZKCJURDYNF-UHFFFAOYSA-N",
"smiles": "CC#CC(=O)OCC"
},
"smiles": "CC#CC(=O)OCC",
"reactionStepId": null,
"template": null,
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}
]
}
]
},
{
"id": "10492",
"routeId": "sa_d9eace06b5c989f9811689c7",
"moleculeId": "sa_96647ff8668f6c24b4c310b4",
"parentId": "10487",
"isLeaf": true,
"molecule": {
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"inchikey": "ZZFCUESFXBCRSC-UHFFFAOYSA-N",
"smiles": "OCc1c(F)cccc1Cl"
},
"smiles": "OCc1c(F)cccc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
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]
},
{
"id": "10493",
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"moleculeId": "sa_43823bf2ed2b19847beacaf0",
"parentId": "10485",
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"molecule": {
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"inchikey": "UIPGQYPLCLBMBU-UHFFFAOYSA-N",
"smiles": "CCCC(C)(CN)NC(=O)OC(C)(C)C"
},
"smiles": "CCCC(C)(CN)NC(=O)OC(C)(C)C",
"reactionStepId": "sa_36279818be9e1f6c1d25104c",
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"metadata": "{\"annotations\":{\"ID\":\"US20160185775A1;1934;1900390\",\"rsmi\":\"[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([C:6]#[N:7])[NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]>CC(C)(C)O.CO.[Ni]>[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([CH2:6][NH2:7])[NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([C:6]#[N:7])[NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]>CC(C)(C)O.CO.[Ni]>[CH3:1][CH2:2][CH2:3][C:4]([CH3:5])([CH2:6][NH2:7])[NH:8][C:9](=[O:10])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15]\"}",
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]
}
}