Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[Si](C)(C)C#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1N
InChiKey
VGVQBWXKQOXLIP-UHFFFAOYSA-N
Route Signature
078f5943ac8954e54e382104b7609f37b1baf7c884627276c56783118cfaa839
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_a5cb8c239bb82ce08180b113",
"signature": "078f5943ac8954e54e382104b7609f37b1baf7c884627276c56783118cfaa839",
"contentHash": "6658ec7ddb445d4d15c7efb23fb71c8cce4c27e8f1acc614a104ad46284f4452",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_498be99afe4922429ea0a4e7",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-02807",
"moleculeId": "sa_0971560f3074121f6aec376b",
"smiles": "C[Si](C)(C)C#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1N",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_0971560f3074121f6aec376b",
"inchikey": "VGVQBWXKQOXLIP-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)C#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1N"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "14875",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_0971560f3074121f6aec376b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_0971560f3074121f6aec376b",
"inchikey": "VGVQBWXKQOXLIP-UHFFFAOYSA-N",
"smiles": "C[Si](C)(C)C#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1N"
},
"smiles": "C[Si](C)(C)C#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1N",
"reactionStepId": "sa_64e2acc097e11b7a9b54a812",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0290;657400\",\"rsmi\":\"Br[c:7]1[cH:8][c:9](-[c:10]2[n:11][cH:12][n:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][o:21]2)[n:22][c:23]1[NH2:24].[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6]>C1CCOC1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][c:9](-[c:10]2[n:11][cH:12][n:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][o:21]2)[n:22][c:23]1[NH2:24]\"},\"mapped_reaction_smiles\":\"Br[c:7]1[cH:8][c:9](-[c:10]2[n:11][cH:12][n:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][o:21]2)[n:22][c:23]1[NH2:24].[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[CH:6]>C1CCOC1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[CH3:1][Si:2]([CH3:3])([CH3:4])[C:5]#[C:6][c:7]1[cH:8][c:9](-[c:10]2[n:11][cH:12][n:13][cH:14][cH:15]2)[c:16](-[c:17]2[cH:18][cH:19][cH:20][o:21]2)[n:22][c:23]1[NH2:24]\"}",
"reactionStep": {
"id": "sa_64e2acc097e11b7a9b54a812",
"reactionHash": "e78af7bff249df14ac056f479201309bc4caed8d38c219fa692e6cd319a28b65"
},
"children": [
{
"id": "14876",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_95a9277ba0d873f43bb42b7f",
"parentId": "14875",
"isLeaf": true,
"molecule": {
"id": "sa_95a9277ba0d873f43bb42b7f",
"inchikey": "CWMFRHBXRUITQE-UHFFFAOYSA-N",
"smiles": "C#C[Si](C)(C)C"
},
"smiles": "C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14877",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_5fb824a36bac7ea89812a664",
"parentId": "14875",
"isLeaf": false,
"molecule": {
"id": "sa_5fb824a36bac7ea89812a664",
"inchikey": "JGADJJZAXIBPDI-UHFFFAOYSA-N",
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1Br"
},
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1Br",
"reactionStepId": "sa_0255879e80cb153de6d35092",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0286;657399\",\"rsmi\":\"O=C1CCC(=O)N1[Br:19].[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][cH:18]1>CS(C)=O.O>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][c:18]1[Br:19]\"},\"mapped_reaction_smiles\":\"O=C1CCC(=O)N1[Br:19].[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][cH:18]1>CS(C)=O.O>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][c:18]1[Br:19]\"}",
"reactionStep": {
"id": "sa_0255879e80cb153de6d35092",
"reactionHash": "d7cf99ba52872d8f826bfbc53e84c873c2e01811fc99901678dbd274b52f249e"
},
"children": [
{
"id": "14878",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_f30592c1184fb2dccf3c6b37",
"parentId": "14877",
"isLeaf": false,
"molecule": {
"id": "sa_f30592c1184fb2dccf3c6b37",
"inchikey": "KHOBIMMEBWRRDE-UHFFFAOYSA-N",
"smiles": "Nc1ccc(-c2ccncn2)c(-c2ccco2)n1"
},
"smiles": "Nc1ccc(-c2ccncn2)c(-c2ccco2)n1",
"reactionStepId": "sa_005e183d04a0ab577de1698c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0282;657398\",\"rsmi\":\"O=C(O)[c:18]1[c:2]([NH2:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17]1>CCOCC.[Cu].c1ccc2ncccc2c1>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][cH:18]1\"},\"mapped_reaction_smiles\":\"O=C(O)[c:18]1[c:2]([NH2:1])[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17]1>CCOCC.[Cu].c1ccc2ncccc2c1>[NH2:1][c:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][cH:8][o:9]2)[c:10](-[c:11]2[n:12][cH:13][n:14][cH:15][cH:16]2)[cH:17][cH:18]1\"}",
"reactionStep": {
"id": "sa_005e183d04a0ab577de1698c",
"reactionHash": "605ede0c257c0cddd67e4caf1d28b0234acedbfd0646bbb95a608834673233d4"
},
"children": [
{
"id": "14879",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_17eaff2a3d903a2746a88e0c",
"parentId": "14878",
"isLeaf": false,
"molecule": {
"id": "sa_17eaff2a3d903a2746a88e0c",
"inchikey": "OBWNVVYNNFZHJS-UHFFFAOYSA-N",
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1C(=O)O"
},
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1C(=O)O",
"reactionStepId": "sa_05c79ff65a016b4305625333",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0190;657378\",\"rsmi\":\"N#[C:4][c:3]1[c:2]([NH2:1])[n:21][c:15](-[c:16]2[cH:17][cH:18][cH:19][o:20]2)[c:8](-[c:9]2[n:10][cH:11][n:12][cH:13][cH:14]2)[cH:7]1.OCC[OH:6].[OH2:5]>Cl.[K+]>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8](-[c:9]2[n:10][cH:11][n:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][o:20]2)[n:21]1\"},\"mapped_reaction_smiles\":\"N#[C:4][c:3]1[c:2]([NH2:1])[n:21][c:15](-[c:16]2[cH:17][cH:18][cH:19][o:20]2)[c:8](-[c:9]2[n:10][cH:11][n:12][cH:13][cH:14]2)[cH:7]1.OCC[OH:6].[OH2:5]>Cl.[K+]>[NH2:1][c:2]1[c:3]([C:4](=[O:5])[OH:6])[cH:7][c:8](-[c:9]2[n:10][cH:11][n:12][cH:13][cH:14]2)[c:15](-[c:16]2[cH:17][cH:18][cH:19][o:20]2)[n:21]1\"}",
"reactionStep": {
"id": "sa_05c79ff65a016b4305625333",
"reactionHash": "cf83d82e4fb7c41cf02b1141e5035bea8a332b8b9d9a399726f46ad82cd59f80"
},
"children": [
{
"id": "14880",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_daa2686ce35f5333036b911a",
"parentId": "14879",
"isLeaf": true,
"molecule": {
"id": "sa_daa2686ce35f5333036b911a",
"inchikey": "LYCAIKOWRPUZTN-UHFFFAOYSA-N",
"smiles": "OCCO"
},
"smiles": "OCCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14881",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_dc72a5e4d0fad7c0aca75be8",
"parentId": "14879",
"isLeaf": false,
"molecule": {
"id": "sa_dc72a5e4d0fad7c0aca75be8",
"inchikey": "PHMOIECSADXENL-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1N"
},
"smiles": "N#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1N",
"reactionStepId": "sa_e8ea7cd2c15d8328a367ebf2",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0186;657377\",\"rsmi\":\"Cl[c:4]1[c:3]([C:2]#[N:1])[cH:20][c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[n:6]1.[NH3:5]>CCO>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"Cl[c:4]1[c:3]([C:2]#[N:1])[cH:20][c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[n:6]1.[NH3:5]>CCO>[N:1]#[C:2][c:3]1[c:4]([NH2:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[cH:20]1\"}",
"reactionStep": {
"id": "sa_e8ea7cd2c15d8328a367ebf2",
"reactionHash": "ab3d9f1a5d55711eab6f8e9fb81e3706917680d8f42198b3b64853fca6515fc9"
},
"children": [
{
"id": "14882",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_827eb7c244a9a2234b4b2013",
"parentId": "14881",
"isLeaf": false,
"molecule": {
"id": "sa_827eb7c244a9a2234b4b2013",
"inchikey": "GNZYVOQZDXRVAN-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1Cl"
},
"smiles": "N#Cc1cc(-c2ccncn2)c(-c2ccco2)nc1Cl",
"reactionStepId": "sa_16ad3ab55daddd670c0e882c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0182;657376\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:5].O=[c:4]1[c:3]([C:2]#[N:1])[cH:20][c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[nH:6]1>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[cH:20]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:5].O=[c:4]1[c:3]([C:2]#[N:1])[cH:20][c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[nH:6]1>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][o:12]2)[c:13](-[c:14]2[n:15][cH:16][n:17][cH:18][cH:19]2)[cH:20]1\"}",
"reactionStep": {
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"reactionHash": "9c6ddb6d4ad937280ee1d183886ecb9dd607820e81f1b40abaf48ffe015dbc6f"
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"children": [
{
"id": "14883",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_1105c91c86a31949e21840bf",
"parentId": "14882",
"isLeaf": true,
"molecule": {
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"inchikey": "STIHXOOJWFVYHP-UHFFFAOYSA-N",
"smiles": "N#Cc1cc(-c2ccncn2)c(-c2ccco2)[nH]c1=O"
},
"smiles": "N#Cc1cc(-c2ccncn2)c(-c2ccco2)[nH]c1=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "14884",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "14882",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "14885",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_c9679fdd876f32f86b77fb69",
"parentId": "14881",
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"molecule": {
"id": "sa_c9679fdd876f32f86b77fb69",
"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "14886",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "14879",
"isLeaf": true,
"molecule": {
"id": "sa_106b35b8a76bbe73829a0a69",
"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
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"children": []
}
]
}
]
},
{
"id": "14887",
"routeId": "sa_a5cb8c239bb82ce08180b113",
"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "14877",
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"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
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"metadata": null,
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"children": []
}
]
}
]
}
}