Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cn1cc(-c2cc(Oc3ccc(NC(=O)N4CCN(C5CCOCC5)C4=O)nc3)ccn2)cn1
InChiKey
GBBAOXPAINQYPS-UHFFFAOYSA-N
Route Signature
a0e3cdbf3c164fb12da19058bc53f5c1b08892c749e8668cdf5c74c97b5f95b6
Synthesis route with 4 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_dcf1a3b64227d05ae7dee5ca",
"signature": "a0e3cdbf3c164fb12da19058bc53f5c1b08892c749e8668cdf5c74c97b5f95b6",
"contentHash": "f77c6aa4615e988e74cc5a3bec7a3e3413ec9b23ad3c3ea1d65a36028e021f8c",
"length": 4,
"isConvergent": true
},
"target": {
"id": "sa_20532f79b6f8cc12c66c5491",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00691",
"moleculeId": "sa_210e63d34240316f8ee0a5b4",
"smiles": "Cn1cc(-c2cc(Oc3ccc(NC(=O)N4CCN(C5CCOCC5)C4=O)nc3)ccn2)cn1",
"routeLength": 4,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_210e63d34240316f8ee0a5b4",
"inchikey": "GBBAOXPAINQYPS-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc(Oc3ccc(NC(=O)N4CCN(C5CCOCC5)C4=O)nc3)ccn2)cn1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9672",
"routeId": "sa_dcf1a3b64227d05ae7dee5ca",
"moleculeId": "sa_210e63d34240316f8ee0a5b4",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_210e63d34240316f8ee0a5b4",
"inchikey": "GBBAOXPAINQYPS-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc(Oc3ccc(NC(=O)N4CCN(C5CCOCC5)C4=O)nc3)ccn2)cn1"
},
"smiles": "Cn1cc(-c2cc(Oc3ccc(NC(=O)N4CCN(C5CCOCC5)C4=O)nc3)ccn2)cn1",
"reactionStepId": "sa_af3f3c233842e400d04922d3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315917A1;0382;1602010\",\"rsmi\":\"Cl[C:16](=[O:17])[N:18]1[CH2:19][CH2:20][N:21]([CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:28]1=[O:29].[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][n:13][c:14]([NH2:15])[cH:30][cH:31]3)[cH:32]2)[cH:33][n:34]1>ClCCl.O.c1ccncc1>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][n:13][c:14]([NH:15][C:16](=[O:17])[N:18]4[CH2:19][CH2:20][N:21]([CH:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)[C:28]4=[O:29])[cH:30][cH:31]3)[cH:32]2)[cH:33][n:34]1\"},\"mapped_reaction_smiles\":\"Cl[C:16](=[O:17])[N:18]1[CH2:19][CH2:20][N:21]([CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[C:28]1=[O:29].[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][n:13][c:14]([NH2:15])[cH:30][cH:31]3)[cH:32]2)[cH:33][n:34]1>ClCCl.O.c1ccncc1>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][n:13][c:14]([NH:15][C:16](=[O:17])[N:18]4[CH2:19][CH2:20][N:21]([CH:22]5[CH2:23][CH2:24][O:25][CH2:26][CH2:27]5)[C:28]4=[O:29])[cH:30][cH:31]3)[cH:32]2)[cH:33][n:34]1\"}",
"reactionStep": {
"id": "sa_af3f3c233842e400d04922d3",
"reactionHash": "ee4aac8b50e045d9ff3b6402a7baafdb77e731ed4f5f936c9c76b092920b50a3"
},
"children": [
{
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"routeId": "sa_dcf1a3b64227d05ae7dee5ca",
"moleculeId": "sa_d8675632fffa5c9fbcd3ddbe",
"parentId": "9672",
"isLeaf": false,
"molecule": {
"id": "sa_d8675632fffa5c9fbcd3ddbe",
"inchikey": "LFBKNPIKBTVNFO-UHFFFAOYSA-N",
"smiles": "O=C(Cl)N1CCN(C2CCOCC2)C1=O"
},
"smiles": "O=C(Cl)N1CCN(C2CCOCC2)C1=O",
"reactionStepId": "sa_18475700b2fd3028ab2b29fe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315917A1;0332;1601967\",\"rsmi\":\"Cl[C:2](=[O:1])[Cl:3].[NH:4]1[CH2:5][CH2:6][N:7]([CH:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[C:14]1=[O:15]>ClCCl.c1ccncc1>[O:1]=[C:2]([Cl:3])[N:4]1[CH2:5][CH2:6][N:7]([CH:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[C:14]1=[O:15]\"},\"mapped_reaction_smiles\":\"Cl[C:2](=[O:1])[Cl:3].[NH:4]1[CH2:5][CH2:6][N:7]([CH:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[C:14]1=[O:15]>ClCCl.c1ccncc1>[O:1]=[C:2]([Cl:3])[N:4]1[CH2:5][CH2:6][N:7]([CH:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[C:14]1=[O:15]\"}",
"reactionStep": {
"id": "sa_18475700b2fd3028ab2b29fe",
"reactionHash": "e8cfe6cf7afe71fc39a33633fcf51382a1d038bd1a539abe789dfcc137c5a78a"
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"children": [
{
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"moleculeId": "sa_6f5681379799953e8798c7ae",
"parentId": "9673",
"isLeaf": false,
"molecule": {
"id": "sa_6f5681379799953e8798c7ae",
"inchikey": "UXBQXHWLDXSYOW-UHFFFAOYSA-N",
"smiles": "OC1=NCCN1C1CCOCC1"
},
"smiles": "O=C1NCCN1C1CCOCC1",
"reactionStepId": "sa_3c857e0ac41985c3119978e7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20140315917A1;0331;1601966\",\"rsmi\":\"Cl[CH2:5][CH2:4][NH:3][C:2](=[O:1])[NH:6][CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1>C1CCOC1.[HH].[Na+]>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][N:6]1[CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1\"},\"mapped_reaction_smiles\":\"Cl[CH2:5][CH2:4][NH:3][C:2](=[O:1])[NH:6][CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1>C1CCOC1.[HH].[Na+]>[O:1]=[C:2]1[NH:3][CH2:4][CH2:5][N:6]1[CH:7]1[CH2:8][CH2:9][O:10][CH2:11][CH2:12]1\"}",
"reactionStep": {
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"molecule": {
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"inchikey": "NXJBTHHZRCQUDA-UHFFFAOYSA-N",
"smiles": "O=C(NCCCl)NC1CCOCC1"
},
"smiles": "O=C(NCCCl)NC1CCOCC1",
"reactionStepId": "sa_0e050af74b62a22bf9f7d017",
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"metadata": "{\"annotations\":{\"ID\":\"US20140315917A1;0330;1601965\",\"rsmi\":\"[NH2:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.[O:1]=[C:2]=[N:3][CH2:4][CH2:5][Cl:6]>C1CCOC1.Cc1ccccc1>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][Cl:6])[NH:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"[NH2:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1.[O:1]=[C:2]=[N:3][CH2:4][CH2:5][Cl:6]>C1CCOC1.Cc1ccccc1>[O:1]=[C:2]([NH:3][CH2:4][CH2:5][Cl:6])[NH:7][CH:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1\"}",
"reactionStep": {
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"isLeaf": true,
"molecule": {
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"inchikey": "AHVQYHFYQWKUKB-UHFFFAOYSA-N",
"smiles": "NC1CCOCC1"
},
"smiles": "NC1CCOCC1",
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"metadata": null,
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{
"id": "9677",
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"moleculeId": "sa_9892fc63675aa20069047c01",
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"molecule": {
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"inchikey": "BCMYXYHEMGPZJN-UHFFFAOYSA-N",
"smiles": "O=C=NCCCl"
},
"smiles": "O=C=NCCCl",
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},
{
"id": "9678",
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"isLeaf": true,
"molecule": {
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"inchikey": "YGYAWVDWMABLBF-UHFFFAOYSA-N",
"smiles": "O=C(Cl)Cl"
},
"smiles": "O=C(Cl)Cl",
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"template": null,
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]
},
{
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"molecule": {
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"inchikey": "VBWZRIVLGHLNHK-UHFFFAOYSA-N",
"smiles": "Cn1cc(-c2cc(Oc3ccc(N)nc3)ccn2)cn1"
},
"smiles": "Cn1cc(-c2cc(Oc3ccc(N)nc3)ccn2)cn1",
"reactionStepId": "sa_80567ef63c6ed09673bc985a",
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"metadata": "{\"annotations\":{\"ID\":\"US20140315917A1;0274;1601921\",\"rsmi\":\"O=[N+:15]([O-])[c:14]1[n:13][cH:12][c:11]([O:10][c:9]2[cH:8][cH:7][n:6][c:5](-[c:4]3[cH:3][n:2]([CH3:1])[n:20][cH:19]3)[cH:18]2)[cH:17][cH:16]1>CCO.O.Cl.[Fe].N>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][n:13][c:14]([NH2:15])[cH:16][cH:17]3)[cH:18]2)[cH:19][n:20]1\"},\"mapped_reaction_smiles\":\"O=[N+:15]([O-])[c:14]1[n:13][cH:12][c:11]([O:10][c:9]2[cH:8][cH:7][n:6][c:5](-[c:4]3[cH:3][n:2]([CH3:1])[n:20][cH:19]3)[cH:18]2)[cH:17][cH:16]1>CCO.O.Cl.[Fe].N>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][n:13][c:14]([NH2:15])[cH:16][cH:17]3)[cH:18]2)[cH:19][n:20]1\"}",
"reactionStep": {
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"molecule": {
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"smiles": "Cn1cc(-c2cc(Oc3ccc([N+](=O)[O-])nc3)ccn2)cn1"
},
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"reactionStepId": "sa_ab6d9127d4f868bce519d433",
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"metadata": "{\"annotations\":{\"ID\":\"US20140315917A1;0273;1601920\",\"rsmi\":\"CC1(C)OB([c:4]2[cH:3][n:2]([CH3:1])[n:22][cH:21]2)OC1(C)C.Cl[c:5]1[n:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[n:18][cH:19]2)[cH:20]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[n:18][cH:19]3)[cH:20]2)[cH:21][n:22]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:4]2[cH:3][n:2]([CH3:1])[n:22][cH:21]2)OC1(C)C.Cl[c:5]1[n:6][cH:7][cH:8][c:9]([O:10][c:11]2[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[n:18][cH:19]2)[cH:20]1>CN(C)C=O.O=C(O)O.[Cs+].[Cs+].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[n:6][cH:7][cH:8][c:9]([O:10][c:11]3[cH:12][cH:13][c:14]([N+:15](=[O:16])[O-:17])[n:18][cH:19]3)[cH:20]2)[cH:21][n:22]1\"}",
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{
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"smiles": "Oc1ccnc(Cl)c1",
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{
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},
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}
]
}
}