Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
O=C(O)c1cc(Cl)c2nccn2c1-c1cccc(F)c1
InChiKey
FGIDRPYFFGVNOS-UHFFFAOYSA-N
Route Signature
558d44a8e1b0434c8dbdaee978477fe15fc3ec2175cf427d41aad029d0b0e851
Synthesis route with 8 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a8cdb404725d72adb109b9f6",
"signature": "558d44a8e1b0434c8dbdaee978477fe15fc3ec2175cf427d41aad029d0b0e851",
"contentHash": "bfd23c8184b10efcf49b3480809324c1c63500793f9969ecbff2e99e683a8bcb",
"length": 8,
"isConvergent": false
},
"target": {
"id": "sa_c28de5f7d79cb2a30e39d8fb",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n5-00207",
"moleculeId": "sa_048095e3c2340bfa5c5b95cc",
"smiles": "O=C(O)c1cc(Cl)c2nccn2c1-c1cccc(F)c1",
"routeLength": 8,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_048095e3c2340bfa5c5b95cc",
"inchikey": "FGIDRPYFFGVNOS-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(Cl)c2nccn2c1-c1cccc(F)c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17824",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_048095e3c2340bfa5c5b95cc",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_048095e3c2340bfa5c5b95cc",
"inchikey": "FGIDRPYFFGVNOS-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(Cl)c2nccn2c1-c1cccc(F)c1"
},
"smiles": "O=C(O)c1cc(Cl)c2nccn2c1-c1cccc(F)c1",
"reactionStepId": "sa_41c74ce61c631021f8b4b591",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0418;1129210\",\"rsmi\":\"C[O:3][C:2](=[O:1])[c:4]1[c:5](-[c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][cH:12]2)[n:13]2[cH:14][cH:15][n:16][c:17]2[c:18]([Cl:19])[cH:20]1>C1CCOC1.Cl.O.[Na+].O>[O:1]=[C:2]([OH:3])[c:4]1[c:5](-[c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][cH:12]2)[n:13]2[cH:14][cH:15][n:16][c:17]2[c:18]([Cl:19])[cH:20]1\"},\"mapped_reaction_smiles\":\"C[O:3][C:2](=[O:1])[c:4]1[c:5](-[c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][cH:12]2)[n:13]2[cH:14][cH:15][n:16][c:17]2[c:18]([Cl:19])[cH:20]1>C1CCOC1.Cl.O.[Na+].O>[O:1]=[C:2]([OH:3])[c:4]1[c:5](-[c:6]2[cH:7][c:8]([F:9])[cH:10][cH:11][cH:12]2)[n:13]2[cH:14][cH:15][n:16][c:17]2[c:18]([Cl:19])[cH:20]1\"}",
"reactionStep": {
"id": "sa_41c74ce61c631021f8b4b591",
"reactionHash": "644487b619a15ea2bcc86c1914b0cc1bb2cc344766d99591e083fcb1eb5cdaa0"
},
"children": [
{
"id": "17825",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_e2231d6b931a32b9dba7046e",
"parentId": "17824",
"isLeaf": false,
"molecule": {
"id": "sa_e2231d6b931a32b9dba7046e",
"inchikey": "KYNLGBPQCDRISR-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)c2nccn2c1-c1cccc(F)c1"
},
"smiles": "COC(=O)c1cc(Cl)c2nccn2c1-c1cccc(F)c1",
"reactionStepId": "sa_3bb89d450148eaa0bb55cd94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0416;1129209\",\"rsmi\":\"O=[CH:16][CH2:15]Cl.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:18]([NH2:17])[c:19]([Cl:20])[cH:21]1>CCO.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14]2[cH:15][cH:16][n:17][c:18]2[c:19]([Cl:20])[cH:21]1\"},\"mapped_reaction_smiles\":\"O=[CH:16][CH2:15]Cl.[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:18]([NH2:17])[c:19]([Cl:20])[cH:21]1>CCO.O>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14]2[cH:15][cH:16][n:17][c:18]2[c:19]([Cl:20])[cH:21]1\"}",
"reactionStep": {
"id": "sa_3bb89d450148eaa0bb55cd94",
"reactionHash": "9c92431adfa8862975f6ef48a09269c741740517e47326c963c82fbdcca93e8c"
},
"children": [
{
"id": "17826",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_39e6e4b9f78844a3f394fe85",
"parentId": "17825",
"isLeaf": false,
"molecule": {
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"inchikey": "HEMRZJFICMWYQP-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)c(N)nc1-c1cccc(F)c1"
},
"smiles": "COC(=O)c1cc(Cl)c(N)nc1-c1cccc(F)c1",
"reactionStepId": "sa_4b693161d1f630dca16fb8f6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0414;1129208\",\"rsmi\":\"COc1ccc(C[NH:16][c:15]2[n:14][c:6](-[c:7]3[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]3)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:19][c:17]2[Cl:18])cc1OC>O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH2:16])[c:17]([Cl:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"COc1ccc(C[NH:16][c:15]2[n:14][c:6](-[c:7]3[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]3)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:19][c:17]2[Cl:18])cc1OC>O=C(O)C(F)(F)F>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH2:16])[c:17]([Cl:18])[cH:19]1\"}",
"reactionStep": {
"id": "sa_4b693161d1f630dca16fb8f6",
"reactionHash": "38f1fccd337ce4c4dafeb0ad69de185b0efef249bd9ff0b6af994b737b813f6e"
},
"children": [
{
"id": "17827",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_360169724088108f0ea167a5",
"parentId": "17826",
"isLeaf": false,
"molecule": {
"id": "sa_360169724088108f0ea167a5",
"inchikey": "QMKVTYBHGTWQFK-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)c(NCc2ccc(OC)c(OC)c2)nc1-c1cccc(F)c1"
},
"smiles": "COC(=O)c1cc(Cl)c(NCc2ccc(OC)c(OC)c2)nc1-c1cccc(F)c1",
"reactionStepId": "sa_b687fbdcdb555ccc17db00a4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0412;1129207\",\"rsmi\":\"Cl[c:15]1[n:14][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][c:28]1[Cl:29].[NH2:16][CH2:17][c:18]1[cH:19][c:20]([O:21][CH3:22])[c:23]([O:24][CH3:25])[cH:26][cH:27]1>CCO>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH2:17][c:18]2[cH:19][c:20]([O:21][CH3:22])[c:23]([O:24][CH3:25])[cH:26][cH:27]2)[c:28]([Cl:29])[cH:30]1\"},\"mapped_reaction_smiles\":\"Cl[c:15]1[n:14][c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:30][c:28]1[Cl:29].[NH2:16][CH2:17][c:18]1[cH:19][c:20]([O:21][CH3:22])[c:23]([O:24][CH3:25])[cH:26][cH:27]1>CCO>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([NH:16][CH2:17][c:18]2[cH:19][c:20]([O:21][CH3:22])[c:23]([O:24][CH3:25])[cH:26][cH:27]2)[c:28]([Cl:29])[cH:30]1\"}",
"reactionStep": {
"id": "sa_b687fbdcdb555ccc17db00a4",
"reactionHash": "a0a039c578eb5ccad427466a0858643482539697808cbb246b2a4917dd6721dd"
},
"children": [
{
"id": "17828",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_75f92177e0d6bad3f11108b3",
"parentId": "17827",
"isLeaf": false,
"molecule": {
"id": "sa_75f92177e0d6bad3f11108b3",
"inchikey": "CZDOBLDMZXWLQL-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)c(Cl)nc1-c1cccc(F)c1"
},
"smiles": "COC(=O)c1cc(Cl)c(Cl)nc1-c1cccc(F)c1",
"reactionStepId": "sa_b2304ea22985a50463d93ffc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0410;1129206\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:16].[O-][n+:14]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:19][c:17]([Cl:18])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:16].[O-][n+:14]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:19][c:17]([Cl:18])[cH:15]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][c:15]([Cl:16])[c:17]([Cl:18])[cH:19]1\"}",
"reactionStep": {
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"reactionHash": "57e6bfbf302d1f849a9a90a9c29bcd4b991e99efcd1e6793be0bc8122d5f6dc8"
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"children": [
{
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"moleculeId": "sa_cceb26d671e471f8a9fc4bee",
"parentId": "17828",
"isLeaf": false,
"molecule": {
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"smiles": "COC(=O)c1cc(Cl)c[n+]([O-])c1-c1cccc(F)c1"
},
"smiles": "COC(=O)c1cc(Cl)c[n+]([O-])c1-c1cccc(F)c1",
"reactionStepId": "sa_def74638718fda2092d49054",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0383;1129195\",\"rsmi\":\"CC(=O)O[OH:15].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][cH:16][c:17]([Cl:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n+:14]([O-:15])[cH:16][c:17]([Cl:18])[cH:19]1\"},\"mapped_reaction_smiles\":\"CC(=O)O[OH:15].[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][cH:16][c:17]([Cl:18])[cH:19]1>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n+:14]([O-:15])[cH:16][c:17]([Cl:18])[cH:19]1\"}",
"reactionStep": {
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"children": [
{
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"moleculeId": "sa_c0a42f51dad7e5d573ab2028",
"parentId": "17829",
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"molecule": {
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"inchikey": "GNPHDRNWTIFENV-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Cl)cnc1-c1cccc(F)c1"
},
"smiles": "COC(=O)c1cc(Cl)cnc1-c1cccc(F)c1",
"reactionStepId": "sa_94e30ce3fa8ec36e53090e02",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0381;1129194\",\"rsmi\":\"Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][c:16]([Cl:17])[cH:15][n:14]1.OB(O)[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]1>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][cH:15][c:16]([Cl:17])[cH:18]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:18][c:16]([Cl:17])[cH:15][n:14]1.OB(O)[c:7]1[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]1>C1COCCO1.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6](-[c:7]2[cH:8][c:9]([F:10])[cH:11][cH:12][cH:13]2)[n:14][cH:15][c:16]([Cl:17])[cH:18]1\"}",
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"children": [
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"molecule": {
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"smiles": "COC(=O)c1cc(Cl)cnc1Cl"
},
"smiles": "COC(=O)c1cc(Cl)cnc1Cl",
"reactionStepId": "sa_7fe7742b38ef84b9d6300b71",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20110281884A1;0379;1129193\",\"rsmi\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[n:8][cH:9][c:10]([Cl:11])[cH:12]1>CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[n:8][cH:9][c:10]([Cl:11])[cH:12]1\"},\"mapped_reaction_smiles\":\"O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[n:8][cH:9][c:10]([Cl:11])[cH:12]1>CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[n:8][cH:9][c:10]([Cl:11])[cH:12]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "OKKJLVBELUTLKV-UHFFFAOYSA-N",
"smiles": "CO"
},
"smiles": "CO",
"reactionStepId": null,
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"metadata": null,
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"children": []
},
{
"id": "17833",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_21e2fd5627589493fad3f06d",
"parentId": "17831",
"isLeaf": true,
"molecule": {
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"inchikey": "SXQSMLIMBNMUNB-UHFFFAOYSA-N",
"smiles": "O=C(O)c1cc(Cl)cnc1Cl"
},
"smiles": "O=C(O)c1cc(Cl)cnc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "17834",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_be0c91163c72215e9ccf02c0",
"parentId": "17830",
"isLeaf": true,
"molecule": {
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"inchikey": "KNXQDJCZSVHEIW-UHFFFAOYSA-N",
"smiles": "OB(O)c1cccc(F)c1"
},
"smiles": "OB(O)c1cccc(F)c1",
"reactionStepId": null,
"template": null,
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}
]
},
{
"id": "17835",
"routeId": "sa_a8cdb404725d72adb109b9f6",
"moleculeId": "sa_fdfcbdb78f2667746f1fedbd",
"parentId": "17829",
"isLeaf": true,
"molecule": {
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"inchikey": "KFSLWBXXFJQRDL-UHFFFAOYSA-N",
"smiles": "CC(=O)OO"
},
"smiles": "CC(=O)OO",
"reactionStepId": null,
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