Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
COCCOc1ccn2c(-c3ccc4cccc(OC5CCNCC5)c4n3)cnc2c1
InChiKey
RROPCZKHYUPTGO-UHFFFAOYSA-N
Route Signature
6adaab6c641cca3244b160aba69d35a60164d3f8efe82dcbcb2718e0e80f41d6
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_404397038244a0526929dec0",
"signature": "6adaab6c641cca3244b160aba69d35a60164d3f8efe82dcbcb2718e0e80f41d6",
"contentHash": "490931d3450b9f2f5ca6194e48e641e6a00de5ff4ad523881a806f391d11ece9",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_88366b426218b5909ae5104e",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00215",
"moleculeId": "sa_7d94523aa34c677e9eebe202",
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OC5CCNCC5)c4n3)cnc2c1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_7d94523aa34c677e9eebe202",
"inchikey": "RROPCZKHYUPTGO-UHFFFAOYSA-N",
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OC5CCNCC5)c4n3)cnc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12837",
"routeId": "sa_404397038244a0526929dec0",
"moleculeId": "sa_7d94523aa34c677e9eebe202",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_7d94523aa34c677e9eebe202",
"inchikey": "RROPCZKHYUPTGO-UHFFFAOYSA-N",
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OC5CCNCC5)c4n3)cnc2c1"
},
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OC5CCNCC5)c4n3)cnc2c1",
"reactionStepId": "sa_74481b20c7b870589278049c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029633A1;0299;830156\",\"rsmi\":\"CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][CH:17]([O:16][c:15]2[c:14]3[n:13][c:12](-[c:11]4[cH:10][n:9][c:8]5[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:31][cH:30][n:29]54)[cH:28][cH:27][c:26]3[cH:25][cH:24][cH:23]2)[CH2:22][CH2:21]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([O:16][CH:17]5[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]5)[cH:23][cH:24][cH:25][c:26]4[cH:27][cH:28]3)[n:29]2[cH:30][cH:31]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)OC(=O)[N:20]1[CH2:19][CH2:18][CH:17]([O:16][c:15]2[c:14]3[n:13][c:12](-[c:11]4[cH:10][n:9][c:8]5[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:31][cH:30][n:29]54)[cH:28][cH:27][c:26]3[cH:25][cH:24][cH:23]2)[CH2:22][CH2:21]1>ClCCl.O=C(O)C(F)(F)F>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([O:16][CH:17]5[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]5)[cH:23][cH:24][cH:25][c:26]4[cH:27][cH:28]3)[n:29]2[cH:30][cH:31]1\"}",
"reactionStep": {
"id": "sa_74481b20c7b870589278049c",
"reactionHash": "2af5f42b766ee9f4ad09355c23fe240be32358e0d30d5f53f7523c61eb2a9ccd"
},
"children": [
{
"id": "12838",
"routeId": "sa_404397038244a0526929dec0",
"moleculeId": "sa_20fa8d85363f438905ca5156",
"parentId": "12837",
"isLeaf": false,
"molecule": {
"id": "sa_20fa8d85363f438905ca5156",
"inchikey": "RKQWDKPRDFHCBK-UHFFFAOYSA-N",
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OC5CCN(C(=O)OC(C)(C)C)CC5)c4n3)cnc2c1"
},
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OC5CCN(C(=O)OC(C)(C)C)CC5)c4n3)cnc2c1",
"reactionStepId": "sa_b9d9c47d3077291eab775014",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029633A1;0298;830155\",\"rsmi\":\"O[c:15]1[c:14]2[n:13][c:12](-[c:11]3[cH:10][n:9][c:8]4[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:38][cH:37][n:36]43)[cH:35][cH:34][c:33]2[cH:32][cH:31][cH:30]1.[OH:16][CH:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1>C1CCOC1.CCOC(=O)N=NC(=O)OCC.CCOC(C)=O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([O:16][CH:17]5[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]5)[cH:30][cH:31][cH:32][c:33]4[cH:34][cH:35]3)[n:36]2[cH:37][cH:38]1\"},\"mapped_reaction_smiles\":\"O[c:15]1[c:14]2[n:13][c:12](-[c:11]3[cH:10][n:9][c:8]4[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:38][cH:37][n:36]43)[cH:35][cH:34][c:33]2[cH:32][cH:31][cH:30]1.[OH:16][CH:17]1[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1>C1CCOC1.CCOC(=O)N=NC(=O)OCC.CCOC(C)=O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([O:16][CH:17]5[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]5)[cH:30][cH:31][cH:32][c:33]4[cH:34][cH:35]3)[n:36]2[cH:37][cH:38]1\"}",
"reactionStep": {
"id": "sa_b9d9c47d3077291eab775014",
"reactionHash": "ac9c7092924ae76901a9af1335a338f8af9cc8bc80a56012b701e6a5c39607f9"
},
"children": [
{
"id": "12839",
"routeId": "sa_404397038244a0526929dec0",
"moleculeId": "sa_e227f714bc16457d74f3c20d",
"parentId": "12838",
"isLeaf": false,
"molecule": {
"id": "sa_e227f714bc16457d74f3c20d",
"inchikey": "MSLOSENVKADKAG-UHFFFAOYSA-N",
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(O)c4n3)cnc2c1"
},
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(O)c4n3)cnc2c1",
"reactionStepId": "sa_afb083e460c90482a4b89e9c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029633A1;0380;830186\",\"rsmi\":\"c1ccc(C[O:16][c:15]2[c:14]3[n:13][c:12](-[c:11]4[cH:10][n:9][c:8]5[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:25][cH:24][n:23]54)[cH:22][cH:21][c:20]3[cH:19][cH:18][cH:17]2)cc1>CO.O=CO.O=CO.N.O.O.[Pd+2]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([OH:16])[cH:17][cH:18][cH:19][c:20]4[cH:21][cH:22]3)[n:23]2[cH:24][cH:25]1\"},\"mapped_reaction_smiles\":\"c1ccc(C[O:16][c:15]2[c:14]3[n:13][c:12](-[c:11]4[cH:10][n:9][c:8]5[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:25][cH:24][n:23]54)[cH:22][cH:21][c:20]3[cH:19][cH:18][cH:17]2)cc1>CO.O=CO.O=CO.N.O.O.[Pd+2]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([OH:16])[cH:17][cH:18][cH:19][c:20]4[cH:21][cH:22]3)[n:23]2[cH:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_afb083e460c90482a4b89e9c",
"reactionHash": "0942dd0e9f0750a829f76ea4a2d7aa9e38dfcf45d1b8a67da7a12472614a8923"
},
"children": [
{
"id": "12840",
"routeId": "sa_404397038244a0526929dec0",
"moleculeId": "sa_30a9d775f3b021a2eda19b90",
"parentId": "12839",
"isLeaf": false,
"molecule": {
"id": "sa_30a9d775f3b021a2eda19b90",
"inchikey": "PXTSNPRXCQQAGI-UHFFFAOYSA-N",
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OCc5ccccc5)c4n3)cnc2c1"
},
"smiles": "COCCOc1ccn2c(-c3ccc4cccc(OCc5ccccc5)c4n3)cnc2c1",
"reactionStepId": "sa_a93432d46e7e134ba59911ab",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029633A1;0379;830185\",\"rsmi\":\"Cl[c:12]1[n:13][c:14]2[c:15]([O:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][cH:25][cH:26][c:27]2[cH:28][cH:29]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][cH:11][n:30]2[cH:31][cH:32]1>C1COCCO1.CC(=O)O.CC(=O)O.ClCCl.O.O=C(O)O.[K+].[K+].[Pd+2].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([O:16][CH2:17][c:18]5[cH:19][cH:20][cH:21][cH:22][cH:23]5)[cH:24][cH:25][cH:26][c:27]4[cH:28][cH:29]3)[n:30]2[cH:31][cH:32]1\"},\"mapped_reaction_smiles\":\"Cl[c:12]1[n:13][c:14]2[c:15]([O:16][CH2:17][c:18]3[cH:19][cH:20][cH:21][cH:22][cH:23]3)[cH:24][cH:25][cH:26][c:27]2[cH:28][cH:29]1.[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][cH:11][n:30]2[cH:31][cH:32]1>C1COCCO1.CC(=O)O.CC(=O)O.ClCCl.O.O=C(O)O.[K+].[K+].[Pd+2].c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][c:11](-[c:12]3[n:13][c:14]4[c:15]([O:16][CH2:17][c:18]5[cH:19][cH:20][cH:21][cH:22][cH:23]5)[cH:24][cH:25][cH:26][c:27]4[cH:28][cH:29]3)[n:30]2[cH:31][cH:32]1\"}",
"reactionStep": {
"id": "sa_a93432d46e7e134ba59911ab",
"reactionHash": "1941ab1fd35729f830c615501e6053b3df0e9fd901b8caa22d0ed82dc96cdda3"
},
"children": [
{
"id": "12841",
"routeId": "sa_404397038244a0526929dec0",
"moleculeId": "sa_a23fde89b0cb5b7605169d0d",
"parentId": "12840",
"isLeaf": false,
"molecule": {
"id": "sa_a23fde89b0cb5b7605169d0d",
"inchikey": "KDBADDXDBJFAAO-UHFFFAOYSA-N",
"smiles": "COCCOc1ccn2ccnc2c1"
},
"smiles": "COCCOc1ccn2ccnc2c1",
"reactionStepId": "sa_0b81709123e6e42789fa5ca5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029633A1;0285;830145\",\"rsmi\":\"O=[CH:10][CH2:11]Cl.[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[n:12][cH:13][cH:14]1>C1CCOC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][cH:11][n:12]2[cH:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O=[CH:10][CH2:11]Cl.[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[n:12][cH:13][cH:14]1>C1CCOC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]2[n:9][cH:10][cH:11][n:12]2[cH:13][cH:14]1\"}",
"reactionStep": {
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"reactionHash": "ff9253df5248db98eda589f267ea49468fcdf06bfe799335180d44c06018f9d2"
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"children": [
{
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"moleculeId": "sa_611c4156e3f1139a7f57da6b",
"parentId": "12841",
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"molecule": {
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"inchikey": "HBBYDTFNQNAFJA-UHFFFAOYSA-N",
"smiles": "COCCOc1ccnc(N)c1"
},
"smiles": "COCCOc1ccnc(N)c1",
"reactionStepId": "sa_c965d5a5c9af990ee90d7fc4",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20100029633A1;0284;830144\",\"rsmi\":\"C[Si](C)(C)[NH:9][Si](C)(C)C.Cl[c:8]1[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:12][cH:11][n:10]1>C1CCOC1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.Cl.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Li+].[Pd].[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[n:10][cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[NH:9][Si](C)(C)C.Cl[c:8]1[cH:7][c:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])[cH:12][cH:11][n:10]1>C1CCOC1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.Cl.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Li+].[Pd].[Pd]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([NH2:9])[n:10][cH:11][cH:12]1\"}",
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"smiles": "C[Si](C)(C)N[Si](C)(C)C"
},
"smiles": "C[Si](C)(C)N[Si](C)(C)C",
"reactionStepId": null,
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},
{
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"smiles": "COCCOc1ccnc(Cl)c1",
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"metadata": "{\"annotations\":{\"ID\":\"US20100029633A1;0283;830143\",\"rsmi\":\"O=[N+]([O-])[c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11][cH:12]1.[CH3:1][O:2][CH2:3][CH2:4][OH:5]>CC(C)(C)O.[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11][cH:12]1\"},\"mapped_reaction_smiles\":\"O=[N+]([O-])[c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11][cH:12]1.[CH3:1][O:2][CH2:3][CH2:4][OH:5]>CC(C)(C)O.[K+]>[CH3:1][O:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][c:8]([Cl:9])[n:10][cH:11][cH:12]1\"}",
"reactionStep": {
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"children": [
{
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"molecule": {
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"inchikey": "LIEPVGBDUYKPLC-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1ccnc(Cl)c1"
},
"smiles": "O=[N+]([O-])c1ccnc(Cl)c1",
"reactionStepId": null,
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},
{
"id": "12846",
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"molecule": {
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"smiles": "COCCO"
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}
]
}
]
},
{
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