Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4C(=O)NCCc4ccccc4)cc3)cc2)CC1
InChiKey
KUIXOBWOZQJOBU-UHFFFAOYSA-N
Route Signature
4a87838975ba5903b5484c1f518ba37f3ae3979882b09c00daf83a102b557556
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_b7f7279965a43775aa047969",
"signature": "4a87838975ba5903b5484c1f518ba37f3ae3979882b09c00daf83a102b557556",
"contentHash": "278a3b6b9a5647db8ebe9cbd685cd7f0054396772f142f6dc1584d1977285848",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_4439b7f72593aa32db1c03fc",
"benchmarkSetId": "7390a9c2522b1c81605e80a42a8de7c7ad9a5797d028633b54904bc78f091bb8",
"targetId": "n5-03485",
"moleculeId": "sa_24a3376fa1a03598e14e26ce",
"smiles": "CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4C(=O)NCCc4ccccc4)cc3)cc2)CC1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_24a3376fa1a03598e14e26ce",
"inchikey": "KUIXOBWOZQJOBU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4C(=O)NCCc4ccccc4)cc3)cc2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 10
},
"rootNode": {
"id": "2165",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_24a3376fa1a03598e14e26ce",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_24a3376fa1a03598e14e26ce",
"inchikey": "KUIXOBWOZQJOBU-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4C(=O)NCCc4ccccc4)cc3)cc2)CC1"
},
"smiles": "CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4C(=O)NCCc4ccccc4)cc3)cc2)CC1",
"reactionStepId": "sa_428422b18e3cd670d9e14e40",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150329502A1;0749;1785420\",\"rsmi\":\"Br[c:11]1[cH:12][cH:13][c:14](-[c:15]2[c:16]([C:17](=[O:18])[NH:19][CH2:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[c:28]([CH3:29])[n:30][o:31]2)[cH:32][cH:33]1.CC1(C)OB([c:10]2[cH:9][cH:8][c:7]([C:6]3([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:36][CH2:37]3)[cH:35][cH:34]2)OC1(C)C>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[c:16]([C:17](=[O:18])[NH:19][CH2:20][CH2:21][c:22]5[cH:23][cH:24][cH:25][cH:26][cH:27]5)[c:28]([CH3:29])[n:30][o:31]4)[cH:32][cH:33]3)[cH:34][cH:35]2)[CH2:36][CH2:37]1\"},\"mapped_reaction_smiles\":\"Br[c:11]1[cH:12][cH:13][c:14](-[c:15]2[c:16]([C:17](=[O:18])[NH:19][CH2:20][CH2:21][c:22]3[cH:23][cH:24][cH:25][cH:26][cH:27]3)[c:28]([CH3:29])[n:30][o:31]2)[cH:32][cH:33]1.CC1(C)OB([c:10]2[cH:9][cH:8][c:7]([C:6]3([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:36][CH2:37]3)[cH:35][cH:34]2)OC1(C)C>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[c:16]([C:17](=[O:18])[NH:19][CH2:20][CH2:21][c:22]5[cH:23][cH:24][cH:25][cH:26][cH:27]5)[c:28]([CH3:29])[n:30][o:31]4)[cH:32][cH:33]3)[cH:34][cH:35]2)[CH2:36][CH2:37]1\"}",
"reactionStep": {
"id": "sa_428422b18e3cd670d9e14e40",
"reactionHash": "7130a783b231a0a89559c9c25018c3f55ae8c1db26baf6e4e403da97a735631b"
},
"children": [
{
"id": "2166",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_b5c4b3d2309b93943e06c424",
"parentId": "2165",
"isLeaf": false,
"molecule": {
"id": "sa_b5c4b3d2309b93943e06c424",
"inchikey": "XEBHVYGBQSTVCP-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1C(=O)NCCc1ccccc1"
},
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1C(=O)NCCc1ccccc1",
"reactionStepId": "sa_088c0e0895923d92b4f4d631",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150329502A1;0748;1785419\",\"rsmi\":\"O[C:14]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:15].[NH2:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[C:14](=[O:15])[NH:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"},\"mapped_reaction_smiles\":\"O[C:14]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:15].[NH2:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1>>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[C:14](=[O:15])[NH:16][CH2:17][CH2:18][c:19]1[cH:20][cH:21][cH:22][cH:23][cH:24]1\"}",
"reactionStep": {
"id": "sa_088c0e0895923d92b4f4d631",
"reactionHash": "94704bdd853f41d256094b79a0fe962b74d25f1ce9f45c10fd6a8db0a2baf728"
},
"children": [
{
"id": "2167",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_363e920b67a918b840d580a4",
"parentId": "2166",
"isLeaf": true,
"molecule": {
"id": "sa_363e920b67a918b840d580a4",
"inchikey": "BHHGXPLMPWCGHP-UHFFFAOYSA-N",
"smiles": "NCCc1ccccc1"
},
"smiles": "NCCc1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2168",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_062a6f2c2748d6688da1dc5e",
"parentId": "2166",
"isLeaf": false,
"molecule": {
"id": "sa_062a6f2c2748d6688da1dc5e",
"inchikey": "GFLKZFOUAHOGJF-UHFFFAOYSA-N",
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1C(=O)O"
},
"smiles": "Cc1noc(-c2ccc(Br)cc2)c1C(=O)O",
"reactionStepId": "sa_7f591136601c708e2bacb2e8",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150329502A1;0596;1785344\",\"rsmi\":\"C[O:16][C:14]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:15]>CO.O.[Li+].O>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[C:14](=[O:15])[OH:16]\"},\"mapped_reaction_smiles\":\"C[O:16][C:14]([c:13]1[c:2]([CH3:1])[n:3][o:4][c:5]1-[c:6]1[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]1)=[O:15]>CO.O.[Li+].O>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([Br:10])[cH:11][cH:12]2)[c:13]1[C:14](=[O:15])[OH:16]\"}",
"reactionStep": {
"id": "sa_7f591136601c708e2bacb2e8",
"reactionHash": "201c2b499b6a3414478a716aeed26e4070f413b77bb86096be3574bad8408b4d"
},
"children": [
{
"id": "2169",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_6b8769c3f3913f5ef2cdffcf",
"parentId": "2168",
"isLeaf": true,
"molecule": {
"id": "sa_6b8769c3f3913f5ef2cdffcf",
"inchikey": "YVWJQDKQALEQHO-UHFFFAOYSA-N",
"smiles": "COC(=O)c1c(C)noc1-c1ccc(Br)cc1"
},
"smiles": "COC(=O)c1c(C)noc1-c1ccc(Br)cc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "2170",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_a3d949dc5dd8d24cf0cd26bd",
"parentId": "2165",
"isLeaf": false,
"molecule": {
"id": "sa_a3d949dc5dd8d24cf0cd26bd",
"inchikey": "ZYSWTQGHMDIKPH-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1(c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1"
},
"smiles": "CCOC(=O)C1(c2ccc(B3OC(C)(C)C(C)(C)O3)cc2)CC1",
"reactionStepId": "sa_4e94e2aa475e069ce152e0b6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150329502A1;0609;1785355\",\"rsmi\":\"Br[c:10]1[cH:9][cH:8][c:7]([C:6]2([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:22][CH2:23]2)[cH:21][cH:20]1.CC1(C)OB([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10]([B:11]3[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]3)[cH:20][cH:21]2)[CH2:22][CH2:23]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:9][cH:8][c:7]([C:6]2([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:22][CH2:23]2)[cH:21][cH:20]1.CC1(C)OB([B:11]2[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]2)OC1(C)C>C1COCCO1.CC(=O)O.Cl[Pd]Cl.[Fe+2].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10]([B:11]3[O:12][C:13]([CH3:14])([CH3:15])[C:16]([CH3:17])([CH3:18])[O:19]3)[cH:20][cH:21]2)[CH2:22][CH2:23]1\"}",
"reactionStep": {
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"children": [
{
"id": "2171",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "2170",
"isLeaf": true,
"molecule": {
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"inchikey": "IPWKHHSGDUIRAH-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C"
},
"smiles": "CC1(C)OB(B2OC(C)(C)C(C)(C)O2)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "2172",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_c26cf55f72230ea6fb30a0e7",
"parentId": "2170",
"isLeaf": false,
"molecule": {
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"inchikey": "KCCISTCYYRKGFF-UHFFFAOYSA-N",
"smiles": "CCOC(=O)C1(c2ccc(Br)cc2)CC1"
},
"smiles": "CCOC(=O)C1(c2ccc(Br)cc2)CC1",
"reactionStepId": "sa_807adfda012c62f3822fa7f7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150329502A1;0608;1785354\",\"rsmi\":\"O[C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[CH2:14][CH2:15]1.[CH3:1][CH2:2][OH:3]>O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[CH2:14][CH2:15]1\"},\"mapped_reaction_smiles\":\"O[C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[CH2:14][CH2:15]1.[CH3:1][CH2:2][OH:3]>O=S(=O)(O)O>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10]([Br:11])[cH:12][cH:13]2)[CH2:14][CH2:15]1\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"smiles": "O=C(O)C1(c2ccc(Br)cc2)CC1"
},
"smiles": "O=C(O)C1(c2ccc(Br)cc2)CC1",
"reactionStepId": "sa_eb3302bdd62a491b9d081711",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150329502A1;0607;1785353\",\"rsmi\":\"N#[C:2][C:4]1([c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[CH2:12][CH2:13]1.OCC[OH:1].[OH2:3]>[K+].O>[O:1]=[C:2]([OH:3])[C:4]1([c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[CH2:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"N#[C:2][C:4]1([c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[CH2:12][CH2:13]1.OCC[OH:1].[OH2:3]>[K+].O>[O:1]=[C:2]([OH:3])[C:4]1([c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[CH2:12][CH2:13]1\"}",
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"molecule": {
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"metadata": "{\"annotations\":{\"ID\":\"US20150329502A1;0606;1785352\",\"rsmi\":\"Br[CH2:11][CH2:12]Br.[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>CCCC[N+](CCCC)(CCCC)CCCC.Cc1ccccc1.O.Br.[K+].O>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]2)[CH2:11][CH2:12]1\"},\"mapped_reaction_smiles\":\"Br[CH2:11][CH2:12]Br.[N:1]#[C:2][CH2:3][c:4]1[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]1>CCCC[N+](CCCC)(CCCC)CCCC.Cc1ccccc1.O.Br.[K+].O>[N:1]#[C:2][C:3]1([c:4]2[cH:5][cH:6][c:7]([Br:8])[cH:9][cH:10]2)[CH2:11][CH2:12]1\"}",
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"children": [
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},
"smiles": "N#CCc1ccc(Br)cc1",
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{
"id": "2176",
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"molecule": {
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"inchikey": "PAAZPARNPHGIKF-UHFFFAOYSA-N",
"smiles": "BrCCBr"
},
"smiles": "BrCCBr",
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}
]
},
{
"id": "2177",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_daa2686ce35f5333036b911a",
"parentId": "2173",
"isLeaf": true,
"molecule": {
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"inchikey": "LYCAIKOWRPUZTN-UHFFFAOYSA-N",
"smiles": "OCCO"
},
"smiles": "OCCO",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
},
{
"id": "2178",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "2173",
"isLeaf": true,
"molecule": {
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"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
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"template": null,
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}
]
},
{
"id": "2179",
"routeId": "sa_b7f7279965a43775aa047969",
"moleculeId": "sa_afaca116b303dc7d01346819",
"parentId": "2172",
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}