Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
OCCNC[C@H](Nc1cncc(-c2ccc3[nH]nc(F)c3c2)c1)c1ccccc1
InChiKey
RPWPZQWBUFBSCQ-NRFANRHFSA-N
Route Signature
32f07df921fd9b7f993b8c2ae8eac7bb5fcc77df244997c6d665bd22ff115e6b
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_297604db550aeefdd3b498ce",
"signature": "32f07df921fd9b7f993b8c2ae8eac7bb5fcc77df244997c6d665bd22ff115e6b",
"contentHash": "67c26543c17dd5797e9942a44797b214458751cc4a184a985d3e0b7115384265",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_84b718d9f750af554fb5d17d",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00864",
"moleculeId": "sa_6f6459a8495fd55a4c718ad5",
"smiles": "OCCNC[C@H](Nc1cncc(-c2ccc3[nH]nc(F)c3c2)c1)c1ccccc1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_6f6459a8495fd55a4c718ad5",
"inchikey": "RPWPZQWBUFBSCQ-NRFANRHFSA-N",
"smiles": "OCCNC[C@H](Nc1cncc(-c2ccc3[nH]nc(F)c3c2)c1)c1ccccc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9789",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_6f6459a8495fd55a4c718ad5",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_6f6459a8495fd55a4c718ad5",
"inchikey": "RPWPZQWBUFBSCQ-NRFANRHFSA-N",
"smiles": "OCCNC[C@H](Nc1cncc(-c2ccc3[nH]nc(F)c3c2)c1)c1ccccc1"
},
"smiles": "OCCNC[C@H](Nc1cncc(-c2ccc3[nH]nc(F)c3c2)c1)c1ccccc1",
"reactionStepId": "sa_ec92537617a0b2b7b58989cc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266878A1;0356;1758429\",\"rsmi\":\"O=[C:3]([CH2:2][OH:1])[NH:4][CH2:5][C@H:6]([NH:7][c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]3[nH:15][n:16][c:17]([F:18])[c:19]3[cH:20]2)[cH:21][n:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>C1CCOC1>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][C@H:6]([NH:7][c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]3[nH:15][n:16][c:17]([F:18])[c:19]3[cH:20]2)[cH:21][n:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"O=[C:3]([CH2:2][OH:1])[NH:4][CH2:5][C@H:6]([NH:7][c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]3[nH:15][n:16][c:17]([F:18])[c:19]3[cH:20]2)[cH:21][n:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1>C1CCOC1>[OH:1][CH2:2][CH2:3][NH:4][CH2:5][C@H:6]([NH:7][c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14]3[nH:15][n:16][c:17]([F:18])[c:19]3[cH:20]2)[cH:21][n:22][cH:23]1)[c:24]1[cH:25][cH:26][cH:27][cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_ec92537617a0b2b7b58989cc",
"reactionHash": "3ae75d0ac9aa059d49e547c73cd26a5c90bcf63ca5094d183252fa2e60e610d8"
},
"children": [
{
"id": "9790",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_41a6376e0388cd9c692d41ed",
"parentId": "9789",
"isLeaf": false,
"molecule": {
"id": "sa_41a6376e0388cd9c692d41ed",
"inchikey": "VKZPXVAKVGBVBB-FQEVSTJZSA-N",
"smiles": "O=C(CO)NC[C@H](Nc1cncc(-c2ccc3[nH]nc(F)c3c2)c1)c1ccccc1"
},
"smiles": "O=C(CO)NC[C@H](Nc1cncc(-c2ccc3[nH]nc(F)c3c2)c1)c1ccccc1",
"reactionStepId": "sa_ae03022e96af1a9494633bc6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266878A1;0355;1758428\",\"rsmi\":\"Br[c:11]1[cH:10][c:9]([NH:8][C@@H:7]([CH2:6][NH:5][C:2](=[O:1])[CH2:3][OH:4])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:24][n:23][cH:22]1.CC1(C)OB([c:12]2[cH:13][cH:14][c:15]3[nH:16][n:17][c:18]([F:19])[c:20]3[cH:21]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]([CH2:3][OH:4])[NH:5][CH2:6][C@H:7]([NH:8][c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]3[nH:16][n:17][c:18]([F:19])[c:20]3[cH:21]2)[cH:22][n:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"},\"mapped_reaction_smiles\":\"Br[c:11]1[cH:10][c:9]([NH:8][C@@H:7]([CH2:6][NH:5][C:2](=[O:1])[CH2:3][OH:4])[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[cH:24][n:23][cH:22]1.CC1(C)OB([c:12]2[cH:13][cH:14][c:15]3[nH:16][n:17][c:18]([F:19])[c:20]3[cH:21]2)OC1(C)C>C1COCCO1.O.O=C(O)O.[K+].[K+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]([CH2:3][OH:4])[NH:5][CH2:6][C@H:7]([NH:8][c:9]1[cH:10][c:11](-[c:12]2[cH:13][cH:14][c:15]3[nH:16][n:17][c:18]([F:19])[c:20]3[cH:21]2)[cH:22][n:23][cH:24]1)[c:25]1[cH:26][cH:27][cH:28][cH:29][cH:30]1\"}",
"reactionStep": {
"id": "sa_ae03022e96af1a9494633bc6",
"reactionHash": "e87bd0c43ffcdd2d1b84021d402b552212f1ca50f82dfa7f601b5687017f45b6"
},
"children": [
{
"id": "9791",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_f93cc46531ae9b8a39a47b5c",
"parentId": "9790",
"isLeaf": false,
"molecule": {
"id": "sa_f93cc46531ae9b8a39a47b5c",
"inchikey": "HICQYIDVMJLTRA-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc3[nH]nc(F)c3c2)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc3[nH]nc(F)c3c2)OC1(C)C",
"reactionStepId": "sa_4b09598d018f33b505ddd2cb",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266878A1;0289;1758394\",\"rsmi\":\"Br[c:6]1[cH:7][cH:8][c:9]2[nH:10][n:11][c:12]([F:13])[c:14]2[cH:15]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O[K].Cl[Pd]Cl.[CH]1[CH][CH]C(P(c2ccccc2)c2ccccc2)[CH]1.[CH]1[CH][CH]C(P(c2ccccc2)c2ccccc2)[CH]1.[Fe]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]3[nH:10][n:11][c:12]([F:13])[c:14]3[cH:15]2)[O:16][C:17]1([CH3:18])[CH3:19]\"},\"mapped_reaction_smiles\":\"Br[c:6]1[cH:7][cH:8][c:9]2[nH:10][n:11][c:12]([F:13])[c:14]2[cH:15]1.CC1(C)OB([B:5]2[O:4][C:2]([CH3:1])([CH3:3])[C:17]([CH3:18])([CH3:19])[O:16]2)OC1(C)C>C1COCCO1.CC(=O)O[K].Cl[Pd]Cl.[CH]1[CH][CH]C(P(c2ccccc2)c2ccccc2)[CH]1.[CH]1[CH][CH]C(P(c2ccccc2)c2ccccc2)[CH]1.[Fe]>[CH3:1][C:2]1([CH3:3])[O:4][B:5]([c:6]2[cH:7][cH:8][c:9]3[nH:10][n:11][c:12]([F:13])[c:14]3[cH:15]2)[O:16][C:17]1([CH3:18])[CH3:19]\"}",
"reactionStep": {
"id": "sa_4b09598d018f33b505ddd2cb",
"reactionHash": "29c64aea23aede00d97d31f757bc925a05ba7dc34118016f2c2a26e0071f0f3f"
},
"children": [
{
"id": "9792",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "9791",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9793",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_6f28616b737c72ed69a16193",
"parentId": "9791",
"isLeaf": true,
"molecule": {
"id": "sa_6f28616b737c72ed69a16193",
"inchikey": "YGAXEFQRZVEQAZ-UHFFFAOYSA-N",
"smiles": "Fc1n[nH]c2ccc(Br)cc12"
},
"smiles": "Fc1n[nH]c2ccc(Br)cc12",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9794",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_8dbf995ac1598b656e1cf37a",
"parentId": "9790",
"isLeaf": false,
"molecule": {
"id": "sa_8dbf995ac1598b656e1cf37a",
"inchikey": "WVFGJUAXCLTMCP-AWEZNQCLSA-N",
"smiles": "O=C(CO)NC[C@H](Nc1cncc(Br)c1)c1ccccc1"
},
"smiles": "O=C(CO)NC[C@H](Nc1cncc(Br)c1)c1ccccc1",
"reactionStepId": "sa_d976379d544356611042c99b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266878A1;0354;1758427\",\"rsmi\":\"O[C:2](=[O:1])[CH2:3][OH:4].[NH2:5][CH2:6][C@H:7]([NH:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][n:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F.O>[O:1]=[C:2]([CH2:3][OH:4])[NH:5][CH2:6][C@H:7]([NH:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][n:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1\"},\"mapped_reaction_smiles\":\"O[C:2](=[O:1])[CH2:3][OH:4].[NH2:5][CH2:6][C@H:7]([NH:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][n:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[PH](F)(F)(F)(F)F.O>[O:1]=[C:2]([CH2:3][OH:4])[NH:5][CH2:6][C@H:7]([NH:8][c:9]1[cH:10][c:11]([Br:12])[cH:13][n:14][cH:15]1)[c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1\"}",
"reactionStep": {
"id": "sa_d976379d544356611042c99b",
"reactionHash": "f97e1dd76abb78857c8f2d2902662bc708892173984269719d9eb15b04fe8b61"
},
"children": [
{
"id": "9795",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_9c35a45c65f1bbb724f9365f",
"parentId": "9794",
"isLeaf": true,
"molecule": {
"id": "sa_9c35a45c65f1bbb724f9365f",
"inchikey": "AEMRFAOFKBGASW-UHFFFAOYSA-N",
"smiles": "O=C(O)CO"
},
"smiles": "O=C(O)CO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9796",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_f49277c947e7a5fe372e4377",
"parentId": "9794",
"isLeaf": false,
"molecule": {
"id": "sa_f49277c947e7a5fe372e4377",
"inchikey": "FUQRWWNSHSOGQF-ZDUSSCGKSA-N",
"smiles": "NC[C@H](Nc1cncc(Br)c1)c1ccccc1"
},
"smiles": "NC[C@H](Nc1cncc(Br)c1)c1ccccc1",
"reactionStepId": "sa_c0c8eaf58cb9de6ae4045687",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266878A1;0318;1758406\",\"rsmi\":\"O=C1c2ccccc2C(=O)[N:1]1[CH2:2][C@H:3]([NH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][n:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>CCO.NN.O.O>[NH2:1][CH2:2][C@H:3]([NH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][n:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O=C1c2ccccc2C(=O)[N:1]1[CH2:2][C@H:3]([NH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][n:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1>CCO.NN.O.O>[NH2:1][CH2:2][C@H:3]([NH:4][c:5]1[cH:6][c:7]([Br:8])[cH:9][n:10][cH:11]1)[c:12]1[cH:13][cH:14][cH:15][cH:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_c0c8eaf58cb9de6ae4045687",
"reactionHash": "16a069505471e6ebc76c6d58618a44aeb2663d5c32001f9227fb485aaa952a4c"
},
"children": [
{
"id": "9797",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_e4e4b06b0d9625c2ee3d3e00",
"parentId": "9796",
"isLeaf": false,
"molecule": {
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"inchikey": "BBGIWSXOONHDIR-IBGZPJMESA-N",
"smiles": "O=C1c2ccccc2C(=O)N1C[C@H](Nc1cncc(Br)c1)c1ccccc1"
},
"smiles": "O=C1c2ccccc2C(=O)N1C[C@H](Nc1cncc(Br)c1)c1ccccc1",
"reactionStepId": "sa_85217d01a08fa230e42b841c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150266878A1;0316;1758405\",\"rsmi\":\"O[CH2:12][C@H:13]([NH:14][c:15]1[cH:16][c:17]([Br:18])[cH:19][n:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>C1CCOC1.CCOC(=O)N=NC(=O)OCC.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][C@H:13]([NH:14][c:15]1[cH:16][c:17]([Br:18])[cH:19][n:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1\"},\"mapped_reaction_smiles\":\"O[CH2:12][C@H:13]([NH:14][c:15]1[cH:16][c:17]([Br:18])[cH:19][n:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1.[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[NH:11]1>C1CCOC1.CCOC(=O)N=NC(=O)OCC.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[O:1]=[C:2]1[c:3]2[cH:4][cH:5][cH:6][cH:7][c:8]2[C:9](=[O:10])[N:11]1[CH2:12][C@H:13]([NH:14][c:15]1[cH:16][c:17]([Br:18])[cH:19][n:20][cH:21]1)[c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1\"}",
"reactionStep": {
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"reactionHash": "e472cdd149a216460c3443d259507474284b30b50841d69d1a1d281f0d40fe83"
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"children": [
{
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"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_55c000779ce0b3d5072b008b",
"parentId": "9797",
"isLeaf": true,
"molecule": {
"id": "sa_55c000779ce0b3d5072b008b",
"inchikey": "XKJCHHZQLQNZHY-UHFFFAOYSA-N",
"smiles": "O=C1N=C(O)c2ccccc21"
},
"smiles": "O=C1NC(=O)c2ccccc21",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9799",
"routeId": "sa_297604db550aeefdd3b498ce",
"moleculeId": "sa_8860f16c89bcecc69f9540e1",
"parentId": "9797",
"isLeaf": true,
"molecule": {
"id": "sa_8860f16c89bcecc69f9540e1",
"inchikey": "XSDKZHAOTWDLQC-ZDUSSCGKSA-N",
"smiles": "OC[C@H](Nc1cncc(Br)c1)c1ccccc1"
},
"smiles": "OC[C@H](Nc1cncc(Br)c1)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
}
]
}
]
}
]
}
]
}
}