Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COC(C)(C)c1cncc(-c2nc3cc(F)c(F)cc3n2C2CC2)c1
InChiKey
SAGYZSXMVCNGKT-UHFFFAOYSA-N
Route Signature
7dde8c684cc38b6bb996edf844d3cfe7e3311576d8a6332b9ce1ea92362c1525
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_eed551c99f78807d4250baca",
"signature": "7dde8c684cc38b6bb996edf844d3cfe7e3311576d8a6332b9ce1ea92362c1525",
"contentHash": "3c474424057d4dd8b7a6fd52b0756abbd4242dcc080a63a835bb661e77e5f85d",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_15b49048f0273fa86e454726",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00781",
"moleculeId": "sa_fa80238b10595dc4d4dae3a8",
"smiles": "COC(C)(C)c1cncc(-c2nc3cc(F)c(F)cc3n2C2CC2)c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_fa80238b10595dc4d4dae3a8",
"inchikey": "SAGYZSXMVCNGKT-UHFFFAOYSA-N",
"smiles": "COC(C)(C)c1cncc(-c2nc3cc(F)c(F)cc3n2C2CC2)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9746",
"routeId": "sa_eed551c99f78807d4250baca",
"moleculeId": "sa_fa80238b10595dc4d4dae3a8",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_fa80238b10595dc4d4dae3a8",
"inchikey": "SAGYZSXMVCNGKT-UHFFFAOYSA-N",
"smiles": "COC(C)(C)c1cncc(-c2nc3cc(F)c(F)cc3n2C2CC2)c1"
},
"smiles": "COC(C)(C)c1cncc(-c2nc3cc(F)c(F)cc3n2C2CC2)c1",
"reactionStepId": "sa_0b98916cc106d4cbdce5b473",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130317057A1;0219;1454277\",\"rsmi\":\"I[CH3:1].[OH:2][C:3]([CH3:4])([CH3:5])[c:6]1[cH:7][n:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([cH:15][c:16]([F:17])[c:18]([F:19])[cH:20]3)[n:21]2[CH:22]2[CH2:23][CH2:24]2)[cH:25]1>C1CCOC1.CCOC(C)=O.[HH].[Na+]>[CH3:1][O:2][C:3]([CH3:4])([CH3:5])[c:6]1[cH:7][n:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([cH:15][c:16]([F:17])[c:18]([F:19])[cH:20]3)[n:21]2[CH:22]2[CH2:23][CH2:24]2)[cH:25]1\"},\"mapped_reaction_smiles\":\"I[CH3:1].[OH:2][C:3]([CH3:4])([CH3:5])[c:6]1[cH:7][n:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([cH:15][c:16]([F:17])[c:18]([F:19])[cH:20]3)[n:21]2[CH:22]2[CH2:23][CH2:24]2)[cH:25]1>C1CCOC1.CCOC(C)=O.[HH].[Na+]>[CH3:1][O:2][C:3]([CH3:4])([CH3:5])[c:6]1[cH:7][n:8][cH:9][c:10](-[c:11]2[n:12][c:13]3[c:14]([cH:15][c:16]([F:17])[c:18]([F:19])[cH:20]3)[n:21]2[CH:22]2[CH2:23][CH2:24]2)[cH:25]1\"}",
"reactionStep": {
"id": "sa_0b98916cc106d4cbdce5b473",
"reactionHash": "618439db2e5720ceb3bd6ac8c8c5ff2c382c9c3f9898c7027620599ae8ece6ec"
},
"children": [
{
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"routeId": "sa_eed551c99f78807d4250baca",
"moleculeId": "sa_bd70db4e0cb43aba9cd7606c",
"parentId": "9746",
"isLeaf": false,
"molecule": {
"id": "sa_bd70db4e0cb43aba9cd7606c",
"inchikey": "CAFMTLCLARMZDZ-UHFFFAOYSA-N",
"smiles": "CC(C)(O)c1cncc(-c2nc3cc(F)c(F)cc3n2C2CC2)c1"
},
"smiles": "CC(C)(O)c1cncc(-c2nc3cc(F)c(F)cc3n2C2CC2)c1",
"reactionStepId": "sa_ba65c97afe336bfdce4acd25",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130317057A1;0217;1454276\",\"rsmi\":\"O=[C:8]([c:7]1[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:24][n:23][cH:22]1)[NH:9][c:10]1[c:11]([NH:18][CH:19]2[CH2:20][CH2:21]2)[cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]1>CC(=O)O>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[c:11]([cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]3)[n:18]2[CH:19]2[CH2:20][CH2:21]2)[cH:22][n:23][cH:24]1\"},\"mapped_reaction_smiles\":\"O=[C:8]([c:7]1[cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:24][n:23][cH:22]1)[NH:9][c:10]1[c:11]([NH:18][CH:19]2[CH2:20][CH2:21]2)[cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]1>CC(=O)O>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][c:7](-[c:8]2[n:9][c:10]3[c:11]([cH:12][c:13]([F:14])[c:15]([F:16])[cH:17]3)[n:18]2[CH:19]2[CH2:20][CH2:21]2)[cH:22][n:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_ba65c97afe336bfdce4acd25",
"reactionHash": "75297b50308cb4649f13b471f13fbb7f3076f61b0fdfa1141e90050cc168f3b1"
},
"children": [
{
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"routeId": "sa_eed551c99f78807d4250baca",
"moleculeId": "sa_9aad6e2d3e1a685dd357d91d",
"parentId": "9747",
"isLeaf": false,
"molecule": {
"id": "sa_9aad6e2d3e1a685dd357d91d",
"inchikey": "LECQGJSSQIHPMB-UHFFFAOYSA-N",
"smiles": "CC(C)(O)c1cncc(C(=O)Nc2cc(F)c(F)cc2NC2CC2)c1"
},
"smiles": "CC(C)(O)c1cncc(C(=O)Nc2cc(F)c(F)cc2NC2CC2)c1",
"reactionStepId": "sa_b4cf3154b179d898ca03da24",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130317057A1;0215;1454275\",\"rsmi\":\"O[C:10]([c:9]1[cH:8][n:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:25]1)=[O:11].[NH2:12][c:13]1[c:14]([NH:15][CH:16]2[CH2:17][CH2:18]2)[cH:19][c:20]([F:21])[c:22]([F:23])[cH:24]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F.On1nnc2cccnc21>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][n:7][cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]2[c:14]([NH:15][CH:16]3[CH2:17][CH2:18]3)[cH:19][c:20]([F:21])[c:22]([F:23])[cH:24]2)[cH:25]1\"},\"mapped_reaction_smiles\":\"O[C:10]([c:9]1[cH:8][n:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:25]1)=[O:11].[NH2:12][c:13]1[c:14]([NH:15][CH:16]2[CH2:17][CH2:18]2)[cH:19][c:20]([F:21])[c:22]([F:23])[cH:24]1>CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.ClCCl.F[PH](F)(F)(F)(F)F.On1nnc2cccnc21>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][n:7][cH:8][c:9]([C:10](=[O:11])[NH:12][c:13]2[c:14]([NH:15][CH:16]3[CH2:17][CH2:18]3)[cH:19][c:20]([F:21])[c:22]([F:23])[cH:24]2)[cH:25]1\"}",
"reactionStep": {
"id": "sa_b4cf3154b179d898ca03da24",
"reactionHash": "0d75a429198b0ce58420dab7eae9767386fae9ff344cd4e7e78d522084ab301a"
},
"children": [
{
"id": "9749",
"routeId": "sa_eed551c99f78807d4250baca",
"moleculeId": "sa_c3aec7b4cf0cf04e6af6c4b7",
"parentId": "9748",
"isLeaf": false,
"molecule": {
"id": "sa_c3aec7b4cf0cf04e6af6c4b7",
"inchikey": "RZEODQGBDQOYAI-UHFFFAOYSA-N",
"smiles": "Nc1cc(F)c(F)cc1NC1CC1"
},
"smiles": "Nc1cc(F)c(F)cc1NC1CC1",
"reactionStepId": "sa_b537f3d0939d5a48e593c726",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130317057A1;0211;1454273\",\"rsmi\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8][c:9]1[NH:10][CH:11]1[CH2:12][CH2:13]1>CO.[Pd]>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8][c:9]1[NH:10][CH:11]1[CH2:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"O=[N+:1]([O-])[c:2]1[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8][c:9]1[NH:10][CH:11]1[CH2:12][CH2:13]1>CO.[Pd]>[NH2:1][c:2]1[cH:3][c:4]([F:5])[c:6]([F:7])[cH:8][c:9]1[NH:10][CH:11]1[CH2:12][CH2:13]1\"}",
"reactionStep": {
"id": "sa_b537f3d0939d5a48e593c726",
"reactionHash": "12b2241ae2cbf82dccb6599f0483d3545c695ba22f8669afb7c9334f1a668168"
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"children": [
{
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"routeId": "sa_eed551c99f78807d4250baca",
"moleculeId": "sa_e61beaac657c040c3abb8269",
"parentId": "9749",
"isLeaf": false,
"molecule": {
"id": "sa_e61beaac657c040c3abb8269",
"inchikey": "XDTLZKOZOUBESV-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(F)c(F)cc1NC1CC1"
},
"smiles": "O=[N+]([O-])c1cc(F)c(F)cc1NC1CC1",
"reactionStepId": "sa_1e911f7bf9818a7045ce4e75",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130317057A1;0209;1454272\",\"rsmi\":\"F[c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:15][c:13]([F:14])[c:11]([F:12])[cH:10]1.[NH2:6][CH:7]1[CH2:8][CH2:9]1>ClCCl.O=C(O)O.F.[K+].[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH:7]2[CH2:8][CH2:9]2)[cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]1\"},\"mapped_reaction_smiles\":\"F[c:5]1[c:4]([N+:2](=[O:1])[O-:3])[cH:15][c:13]([F:14])[c:11]([F:12])[cH:10]1.[NH2:6][CH:7]1[CH2:8][CH2:9]1>ClCCl.O=C(O)O.F.[K+].[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[c:5]([NH:6][CH:7]2[CH2:8][CH2:9]2)[cH:10][c:11]([F:12])[c:13]([F:14])[cH:15]1\"}",
"reactionStep": {
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"reactionHash": "f69b87b67f5bc84c0246fba69035f1d2d8c0fb350726bb3c20a4737ab5482bc1"
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"children": [
{
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"moleculeId": "sa_f7b02628c6b00fb9d50a0f6c",
"parentId": "9750",
"isLeaf": true,
"molecule": {
"id": "sa_f7b02628c6b00fb9d50a0f6c",
"inchikey": "HTJDQJBWANPRPF-UHFFFAOYSA-N",
"smiles": "NC1CC1"
},
"smiles": "NC1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9752",
"routeId": "sa_eed551c99f78807d4250baca",
"moleculeId": "sa_fadc0d9ef69de1d7a7b56b6e",
"parentId": "9750",
"isLeaf": true,
"molecule": {
"id": "sa_fadc0d9ef69de1d7a7b56b6e",
"inchikey": "ROJNMGYMBLNTPK-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(F)c(F)cc1F"
},
"smiles": "O=[N+]([O-])c1cc(F)c(F)cc1F",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "9753",
"routeId": "sa_eed551c99f78807d4250baca",
"moleculeId": "sa_a2ab8772e4a28797d3166b24",
"parentId": "9748",
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"molecule": {
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"inchikey": "ZHMCIHCFHJXTTG-UHFFFAOYSA-N",
"smiles": "CC(C)(O)c1cncc(C(=O)O)c1"
},
"smiles": "CC(C)(O)c1cncc(C(=O)O)c1",
"reactionStepId": "sa_fd515ab95802c16291ac7539",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130317057A1;0213;1454274\",\"rsmi\":\"C[O:12][C:10]([c:9]1[cH:8][n:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:13]1)=[O:11]>CO.[Na+].O>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][n:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13]1\"},\"mapped_reaction_smiles\":\"C[O:12][C:10]([c:9]1[cH:8][n:7][cH:6][c:5]([C:2]([CH3:1])([CH3:3])[OH:4])[cH:13]1)=[O:11]>CO.[Na+].O>[CH3:1][C:2]([CH3:3])([OH:4])[c:5]1[cH:6][n:7][cH:8][c:9]([C:10](=[O:11])[OH:12])[cH:13]1\"}",
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"children": [
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"molecule": {
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"inchikey": "UPVZUVYISQEBGY-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cncc(C(C)(C)O)c1"
},
"smiles": "COC(=O)c1cncc(C(C)(C)O)c1",
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},
{
"id": "9755",
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"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
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"molecule": {
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"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
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"smiles": "CI",
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]
}
}