Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CNCc1ccc(-c2cc3cc(F)cc(C(=O)OC)c3o2)cc1
InChiKey
BLYMUYQRQBBAIA-UHFFFAOYSA-N
Route Signature
315cf43cff61dfd54eaf4fdcf7546ce1453e0a862506bf595a3070148c3b2db3
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_bc03d163561915e623cb282e",
"signature": "315cf43cff61dfd54eaf4fdcf7546ce1453e0a862506bf595a3070148c3b2db3",
"contentHash": "e7aafd9ff3e8b4beb0e87b49cfe3dc2b199f5304b728f491e15d1cfc5bd42eed",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_fd68b01c298fff076b7f4468",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02614",
"moleculeId": "sa_80bb364668f2a52bea25b5b6",
"smiles": "CNCc1ccc(-c2cc3cc(F)cc(C(=O)OC)c3o2)cc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_80bb364668f2a52bea25b5b6",
"inchikey": "BLYMUYQRQBBAIA-UHFFFAOYSA-N",
"smiles": "CNCc1ccc(-c2cc3cc(F)cc(C(=O)OC)c3o2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10794",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_80bb364668f2a52bea25b5b6",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_80bb364668f2a52bea25b5b6",
"inchikey": "BLYMUYQRQBBAIA-UHFFFAOYSA-N",
"smiles": "CNCc1ccc(-c2cc3cc(F)cc(C(=O)OC)c3o2)cc1"
},
"smiles": "CNCc1ccc(-c2cc3cc(F)cc(C(=O)OC)c3o2)cc1",
"reactionStepId": "sa_11f16621a95f3e8b51972634",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150018542A1;0094;1640122\",\"rsmi\":\"C[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[c:11]([o:12]2)[c:13]([C:14](=[O:15])[O:16][CH3:17])[cH:18][c:19]([F:20])[cH:21]3)[cH:22][cH:23]1>C#Cc1ccc(CNC)cc1.COC(=O)c1cc(F)cc(I)c1O>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[c:11]([o:12]2)[c:13]([C:14](=[O:15])[O:16][CH3:17])[cH:18][c:19]([F:20])[cH:21]3)[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"C[N:2]([CH3:1])[CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[c:11]([o:12]2)[c:13]([C:14](=[O:15])[O:16][CH3:17])[cH:18][c:19]([F:20])[cH:21]3)[cH:22][cH:23]1>C#Cc1ccc(CNC)cc1.COC(=O)c1cc(F)cc(I)c1O>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][cH:6][c:7](-[c:8]2[cH:9][c:10]3[c:11]([o:12]2)[c:13]([C:14](=[O:15])[O:16][CH3:17])[cH:18][c:19]([F:20])[cH:21]3)[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_11f16621a95f3e8b51972634",
"reactionHash": "4d0e160cf313a314c432596c771b6fe64005524bb9e1d774ebc55491f62c6247"
},
"children": [
{
"id": "10795",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_2d6ae571e172c965ead360cb",
"parentId": "10794",
"isLeaf": false,
"molecule": {
"id": "sa_2d6ae571e172c965ead360cb",
"inchikey": "AEXDUHBLXUNIJF-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(F)cc2cc(-c3ccc(CN(C)C)cc3)oc12"
},
"smiles": "COC(=O)c1cc(F)cc2cc(-c3ccc(CN(C)C)cc3)oc12",
"reactionStepId": "sa_69ad81abc4a6739ebb14982b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150018542A1;0079;1640117\",\"rsmi\":\"I[c:10]1[cH:9][c:7]([F:8])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]1[OH:12].[C:13]([c:14]1[cH:15][cH:16][c:17]([CH2:18][N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1)#[CH:24]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]2[c:11]1[o:12][c:13](-[c:14]1[cH:15][cH:16][c:17]([CH2:18][N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1)[cH:24]2\"},\"mapped_reaction_smiles\":\"I[c:10]1[cH:9][c:7]([F:8])[cH:6][c:5]([C:3]([O:2][CH3:1])=[O:4])[c:11]1[OH:12].[C:13]([c:14]1[cH:15][cH:16][c:17]([CH2:18][N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1)#[CH:24]>CCN(CC)CC.CCOC(C)=O.CN(C)C=O.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]2[c:11]1[o:12][c:13](-[c:14]1[cH:15][cH:16][c:17]([CH2:18][N:19]([CH3:20])[CH3:21])[cH:22][cH:23]1)[cH:24]2\"}",
"reactionStep": {
"id": "sa_69ad81abc4a6739ebb14982b",
"reactionHash": "5bdad9639bad9cd53932d57bc7398a123a24b1ee53cb9bfd2297c90dfaa93f51"
},
"children": [
{
"id": "10796",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_09ce82b7a226e21d13416aa3",
"parentId": "10795",
"isLeaf": false,
"molecule": {
"id": "sa_09ce82b7a226e21d13416aa3",
"inchikey": "IFXZRANXDFXZPF-UHFFFAOYSA-N",
"smiles": "C#Cc1ccc(CN(C)C)cc1"
},
"smiles": "C#Cc1ccc(CN(C)C)cc1",
"reactionStepId": "sa_5a45e74a5e2b1122e202afe7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150018542A1;0076;1640116\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1>CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1>CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][N:8]([CH3:9])[CH3:10])[cH:11][cH:12]1\"}",
"reactionStep": {
"id": "sa_5a45e74a5e2b1122e202afe7",
"reactionHash": "d607cb18d747c41dfd5b2c4a54ee3d53bacd2628d66a823174e06b85250653f2"
},
"children": [
{
"id": "10797",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_e184e92bb0af6f903aad1155",
"parentId": "10796",
"isLeaf": false,
"molecule": {
"id": "sa_e184e92bb0af6f903aad1155",
"inchikey": "NINVWUVVSVOPDI-UHFFFAOYSA-N",
"smiles": "CN(C)Cc1ccc(C#C[Si](C)(C)C)cc1"
},
"smiles": "CN(C)Cc1ccc(C#C[Si](C)(C)C)cc1",
"reactionStepId": "sa_9c39c14f3fcf52f6b86cee04",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150018542A1;0073;1640115\",\"rsmi\":\"I[c:8]1[cH:7][cH:6][c:5]([CH2:4][N:2]([CH3:1])[CH3:3])[cH:16][cH:15]1.[CH:9]#[C:10][Si:11]([CH3:12])([CH3:13])[CH3:14]>C1CCOC1.CCN(CC)CC.Cl[Pd]Cl.[Cu]I.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16]1\"},\"mapped_reaction_smiles\":\"I[c:8]1[cH:7][cH:6][c:5]([CH2:4][N:2]([CH3:1])[CH3:3])[cH:16][cH:15]1.[CH:9]#[C:10][Si:11]([CH3:12])([CH3:13])[CH3:14]>C1CCOC1.CCN(CC)CC.Cl[Pd]Cl.[Cu]I.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([C:9]#[C:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[cH:15][cH:16]1\"}",
"reactionStep": {
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"reactionHash": "d11065503e0193ce5fd036b1e3116cb3eb6dfbd79e1cac6e192a7a319a090f9e"
},
"children": [
{
"id": "10798",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "10797",
"isLeaf": true,
"molecule": {
"id": "sa_95a9277ba0d873f43bb42b7f",
"inchikey": "CWMFRHBXRUITQE-UHFFFAOYSA-N",
"smiles": "C#C[Si](C)(C)C"
},
"smiles": "C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10799",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_ad25396595684e0426cafef2",
"parentId": "10797",
"isLeaf": false,
"molecule": {
"id": "sa_ad25396595684e0426cafef2",
"inchikey": "OFXGJTFUMSIQPF-UHFFFAOYSA-N",
"smiles": "CN(C)Cc1ccc(I)cc1"
},
"smiles": "CN(C)Cc1ccc(I)cc1",
"reactionStepId": "sa_9075a68131da67fbb01972e9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150018542A1;0070;1640114\",\"rsmi\":\"Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1\"},\"mapped_reaction_smiles\":\"Br[CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1.[CH3:1][NH:2][CH3:3]>>[CH3:1][N:2]([CH3:3])[CH2:4][c:5]1[cH:6][cH:7][c:8]([I:9])[cH:10][cH:11]1\"}",
"reactionStep": {
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"reactionHash": "4c8ed1d9be965e365167871cb1b4a03d105aeb7b8c32f6aaed6ea72eb43d923e"
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"children": [
{
"id": "10800",
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"parentId": "10799",
"isLeaf": true,
"molecule": {
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"inchikey": "BQTRMYJYYNQQGK-UHFFFAOYSA-N",
"smiles": "BrCc1ccc(I)cc1"
},
"smiles": "BrCc1ccc(I)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "10801",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_e2676e5c7c9d7a020ed1780e",
"parentId": "10799",
"isLeaf": true,
"molecule": {
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"inchikey": "ROSDSFDQCJNGOL-UHFFFAOYSA-N",
"smiles": "CNC"
},
"smiles": "CNC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "10802",
"routeId": "sa_bc03d163561915e623cb282e",
"moleculeId": "sa_b8e919f4c32120f0e4b3d8ec",
"parentId": "10795",
"isLeaf": false,
"molecule": {
"id": "sa_b8e919f4c32120f0e4b3d8ec",
"inchikey": "SPCXJKWATXURQS-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(F)cc(I)c1O"
},
"smiles": "COC(=O)c1cc(F)cc(I)c1O",
"reactionStepId": "sa_7b616aa5a98598f21f28f050",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150018542A1;0067;1640113\",\"rsmi\":\"O=C1CCC(=O)N1[I:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:12]1[OH:13]>CCOC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([I:11])[c:12]1[OH:13]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[I:11].[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:12]1[OH:13]>CCOC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][c:10]([I:11])[c:12]1[OH:13]\"}",
"reactionStep": {
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"reactionHash": "0edde6798437301eb26872ef8de410d1e936431ccc3f1cb93eb38a1e7f225aee"
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"children": [
{
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"moleculeId": "sa_688a13dc1e155a64c8031cf3",
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"molecule": {
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"inchikey": "DGHBWVVOJLVMFF-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(F)ccc1O"
},
"smiles": "COC(=O)c1cc(F)ccc1O",
"reactionStepId": "sa_254516f651bef2416448b661",
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"metadata": "{\"annotations\":{\"ID\":\"US20150018542A1;0064;1640112\",\"rsmi\":\"O[C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[OH:12].[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[OH:12]\"},\"mapped_reaction_smiles\":\"O[C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[OH:12].[CH3:1][OH:2]>O=S(=O)(O)O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([F:8])[cH:9][cH:10][c:11]1[OH:12]\"}",
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"children": [
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"molecule": {
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{
"id": "10805",
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"molecule": {
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"smiles": "CO"
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}
]
},
{
"id": "10806",
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"molecule": {
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"inchikey": "LQZMLBORDGWNPD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1I"
},
"smiles": "O=C1CCC(=O)N1I",
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]
}
]
}
}