Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(NC3CCCC3)c2)cc1
InChiKey
ZGQFMRKGMPUTDW-UHFFFAOYSA-N
Route Signature
6e64cbd56277302548e9ac3e10ae293b2b439f8ad2c3cc9fbba8e5100e3f69da
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_198eb3e76adae9ddb0b22046",
"signature": "6e64cbd56277302548e9ac3e10ae293b2b439f8ad2c3cc9fbba8e5100e3f69da",
"contentHash": "abfd7d3f684156d3fe190993770f196a914f28b707cbbd0055ac74e113c0c4ef",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_82fe7c892743ee89c8d5d88f",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00170",
"moleculeId": "sa_5829ee1f17b50b6277e46df9",
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(NC3CCCC3)c2)cc1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_5829ee1f17b50b6277e46df9",
"inchikey": "ZGQFMRKGMPUTDW-UHFFFAOYSA-N",
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(NC3CCCC3)c2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12626",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_5829ee1f17b50b6277e46df9",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_5829ee1f17b50b6277e46df9",
"inchikey": "ZGQFMRKGMPUTDW-UHFFFAOYSA-N",
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(NC3CCCC3)c2)cc1"
},
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(NC3CCCC3)c2)cc1",
"reactionStepId": "sa_a999979ae7b4e5cb7e993a72",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070287721A1;0556;525140\",\"rsmi\":\"F[c:23]1[cH:22][c:21](-[c:20]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:34][cH:33]3)[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]32)[cH:32][cH:31][n:30]1.[NH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]3[c:20]2-[c:21]2[cH:22][c:23]([NH:24][CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[n:30][cH:31][cH:32]2)[cH:33][cH:34]1\"},\"mapped_reaction_smiles\":\"F[c:23]1[cH:22][c:21](-[c:20]2[c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:34][cH:33]3)[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]32)[cH:32][cH:31][n:30]1.[NH2:24][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]3[c:20]2-[c:21]2[cH:22][c:23]([NH:24][CH:25]3[CH2:26][CH2:27][CH2:28][CH2:29]3)[n:30][cH:31][cH:32]2)[cH:33][cH:34]1\"}",
"reactionStep": {
"id": "sa_a999979ae7b4e5cb7e993a72",
"reactionHash": "aedc7ebf38c47a75f65d94ac367025d8a492cff5f5b8a265208a4f7ddc9b88c9"
},
"children": [
{
"id": "12627",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_882a71327a5153424650c51e",
"parentId": "12626",
"isLeaf": true,
"molecule": {
"id": "sa_882a71327a5153424650c51e",
"inchikey": "NISGSNTVMOOSJQ-UHFFFAOYSA-N",
"smiles": "NC1CCCC1"
},
"smiles": "NC1CCCC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12628",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_4c65882b4ea97acc822e7782",
"parentId": "12626",
"isLeaf": false,
"molecule": {
"id": "sa_4c65882b4ea97acc822e7782",
"inchikey": "WZNLDODEGLUOEA-UHFFFAOYSA-N",
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(F)c2)cc1"
},
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2-c2ccnc(F)c2)cc1",
"reactionStepId": "sa_e475109fd1c5869483b8445a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070287721A1;0555;525139\",\"rsmi\":\"Br[c:20]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:29][cH:28]2)[n:7][n:8]2[c:9]([NH:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][cH:18][c:19]21.OB(O)[c:21]1[cH:22][c:23]([F:24])[n:25][cH:26][cH:27]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]3[c:20]2-[c:21]2[cH:22][c:23]([F:24])[n:25][cH:26][cH:27]2)[cH:28][cH:29]1\"},\"mapped_reaction_smiles\":\"Br[c:20]1[c:6](-[c:5]2[cH:4][cH:3][c:2]([F:1])[cH:29][cH:28]2)[n:7][n:8]2[c:9]([NH:10][CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15]3)[cH:16][cH:17][cH:18][c:19]21.OB(O)[c:21]1[cH:22][c:23]([F:24])[n:25][cH:26][cH:27]1>>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]3[c:20]2-[c:21]2[cH:22][c:23]([F:24])[n:25][cH:26][cH:27]2)[cH:28][cH:29]1\"}",
"reactionStep": {
"id": "sa_e475109fd1c5869483b8445a",
"reactionHash": "c6b05ddf51fe25ecf484fea04a5a98658f8bc843bbc391b7754eafaac2adfcf1"
},
"children": [
{
"id": "12629",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_041891661be36cacd76a6156",
"parentId": "12628",
"isLeaf": false,
"molecule": {
"id": "sa_041891661be36cacd76a6156",
"inchikey": "JPCHUGJACCMNKC-UHFFFAOYSA-N",
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2Br)cc1"
},
"smiles": "Fc1ccc(-c2nn3c(NC4CCCC4)cccc3c2Br)cc1",
"reactionStepId": "sa_d7f8d9301e51e1671166cf70",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070287721A1;0551;525136\",\"rsmi\":\"Cl[c:9]1[n:8]2[n:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:23][cH:22]3)[c:20]([Br:21])[c:19]2[cH:18][cH:17][cH:16]1.[NH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1>CC(=O)O.CC(=O)O.CCOCC.Cc1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]3[c:20]2[Br:21])[cH:22][cH:23]1\"},\"mapped_reaction_smiles\":\"Cl[c:9]1[n:8]2[n:7][c:6](-[c:5]3[cH:4][cH:3][c:2]([F:1])[cH:23][cH:22]3)[c:20]([Br:21])[c:19]2[cH:18][cH:17][cH:16]1.[NH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]1>CC(=O)O.CC(=O)O.CCOCC.Cc1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd+2].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([NH:10][CH:11]4[CH2:12][CH2:13][CH2:14][CH2:15]4)[cH:16][cH:17][cH:18][c:19]3[c:20]2[Br:21])[cH:22][cH:23]1\"}",
"reactionStep": {
"id": "sa_d7f8d9301e51e1671166cf70",
"reactionHash": "7ba0181c64774cef301ad7b3d5c0b65e55180cf7eebf61a6e299ed600feb5f4f"
},
"children": [
{
"id": "12630",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_f970bce2ce5ccd4ed8e4612f",
"parentId": "12629",
"isLeaf": false,
"molecule": {
"id": "sa_f970bce2ce5ccd4ed8e4612f",
"inchikey": "JVDQDOUMMGFLNG-UHFFFAOYSA-N",
"smiles": "Fc1ccc(-c2nn3c(Cl)cccc3c2Br)cc1"
},
"smiles": "Fc1ccc(-c2nn3c(Cl)cccc3c2Br)cc1",
"reactionStepId": "sa_8fcad397607a180170531210",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070287721A1;0550;525135\",\"rsmi\":\"O=C1CCC(=O)N1[Br:16].[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[cH:15]2)[cH:17][cH:18]1>C1CCOC1.CCOCC.O=C(O)O.[Na+]>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[c:15]2[Br:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:16].[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[cH:15]2)[cH:17][cH:18]1>C1CCOC1.CCOCC.O=C(O)O.[Na+]>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[c:15]2[Br:16])[cH:17][cH:18]1\"}",
"reactionStep": {
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"reactionHash": "f7c89a69d05cd8b01d98ccc9483aa54430ff9b78ee8f71d286b9f28beddfbfce"
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"children": [
{
"id": "12631",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_369cad38a889cc69f62a441b",
"parentId": "12630",
"isLeaf": false,
"molecule": {
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"inchikey": "ATENWFZPEVYXTK-UHFFFAOYSA-N",
"smiles": "Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1"
},
"smiles": "Fc1ccc(-c2cc3cccc(Cl)n3n2)cc1",
"reactionStepId": "sa_d5e7929afa94169c2a6eabf8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070287721A1;0472;525115\",\"rsmi\":\"O[N:7]=[C:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]1)[CH2:15][c:14]1[n:8][c:9]([Cl:10])[cH:11][cH:12][cH:13]1>CCN(CC)CC.COCCOC.Cl[Fe]Cl.O=C(OC(=O)C(F)(F)F)C(F)(F)F>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[cH:15]2)[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"O[N:7]=[C:6]([c:5]1[cH:4][cH:3][c:2]([F:1])[cH:17][cH:16]1)[CH2:15][c:14]1[n:8][c:9]([Cl:10])[cH:11][cH:12][cH:13]1>CCN(CC)CC.COCCOC.Cl[Fe]Cl.O=C(OC(=O)C(F)(F)F)C(F)(F)F>[F:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[c:9]([Cl:10])[cH:11][cH:12][cH:13][c:14]3[cH:15]2)[cH:16][cH:17]1\"}",
"reactionStep": {
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"reactionHash": "b21b7e50748e4f500ab666f9276724e2592887806fda86c5ab413f21d29a2dc5"
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"children": [
{
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"moleculeId": "sa_45cc7be655f17052c9fea66d",
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"molecule": {
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"inchikey": "IXPKAIUODGJXTC-UHFFFAOYSA-N",
"smiles": "ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1"
},
"smiles": "ON=C(Cc1cccc(Cl)n1)c1ccc(F)cc1",
"reactionStepId": "sa_6a7f039979422ea32fffe696",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070287721A1;0471;525114\",\"rsmi\":\"O=[C:3]([CH2:4][c:5]1[n:6][c:7]([Cl:8])[cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.[OH:1][NH2:2]>CO.Cl.[Na+].O>[OH:1][N:2]=[C:3]([CH2:4][c:5]1[n:6][c:7]([Cl:8])[cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=[C:3]([CH2:4][c:5]1[n:6][c:7]([Cl:8])[cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1.[OH:1][NH2:2]>CO.Cl.[Na+].O>[OH:1][N:2]=[C:3]([CH2:4][c:5]1[n:6][c:7]([Cl:8])[cH:9][cH:10][cH:11]1)[c:12]1[cH:13][cH:14][c:15]([F:16])[cH:17][cH:18]1\"}",
"reactionStep": {
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"reactionHash": "c897e5cf11a1e1c7b70c8a0347df0e9b034a8720e0f85e731e78697abcd9b485"
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"children": [
{
"id": "12633",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_04a18e3f07bde82ca29399ee",
"parentId": "12632",
"isLeaf": true,
"molecule": {
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"inchikey": "AVXURJPOCDRRFD-UHFFFAOYSA-N",
"smiles": "NO"
},
"smiles": "NO",
"reactionStepId": null,
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"metadata": null,
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},
{
"id": "12634",
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"moleculeId": "sa_a6e79891ddf425c1ff59bb61",
"parentId": "12632",
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"molecule": {
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"inchikey": "ZMPCHEOJUQKYBJ-UHFFFAOYSA-N",
"smiles": "O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1"
},
"smiles": "O=C(Cc1cccc(Cl)n1)c1ccc(F)cc1",
"reactionStepId": "sa_35351b3c69eb29b4603b4b2c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20070287721A1;0470;525113\",\"rsmi\":\"CCO[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1.[CH3:3][c:4]1[n:5][c:6]([Cl:7])[cH:8][cH:9][cH:10]1>C1CCOC1.C[Si](C)(C)N[Si](C)(C)C.[Li+]>[O:1]=[C:2]([CH2:3][c:4]1[n:5][c:6]([Cl:7])[cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1\"},\"mapped_reaction_smiles\":\"CCO[C:2](=[O:1])[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1.[CH3:3][c:4]1[n:5][c:6]([Cl:7])[cH:8][cH:9][cH:10]1>C1CCOC1.C[Si](C)(C)N[Si](C)(C)C.[Li+]>[O:1]=[C:2]([CH2:3][c:4]1[n:5][c:6]([Cl:7])[cH:8][cH:9][cH:10]1)[c:11]1[cH:12][cH:13][c:14]([F:15])[cH:16][cH:17]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_5feb842f8f0d05424e7de046",
"parentId": "12634",
"isLeaf": true,
"molecule": {
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"inchikey": "GXZDYRYYNXYPMQ-UHFFFAOYSA-N",
"smiles": "Cc1cccc(Cl)n1"
},
"smiles": "Cc1cccc(Cl)n1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12636",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_27b6986b16a701ba65cd2948",
"parentId": "12634",
"isLeaf": true,
"molecule": {
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"inchikey": "UMPRJGKLMUDRHL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)c1ccc(F)cc1"
},
"smiles": "CCOC(=O)c1ccc(F)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "12637",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "12630",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "12638",
"routeId": "sa_198eb3e76adae9ddb0b22046",
"moleculeId": "sa_882a71327a5153424650c51e",
"parentId": "12629",
"isLeaf": true,
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