Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
Cn1ccc2cc(Nc3ncc(C4CC4)cc3C(=O)O)cc(-c3ccc(-c4ccccc4)cc3)c21
InChiKey
WGYUKHHGAIEVLS-UHFFFAOYSA-N
Route Signature
7318cae939e83dcb863f3593dcf064066575a92602053f680120fcca89fa0119
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_7c2c35ed7b77656f0e71ed4f",
"signature": "7318cae939e83dcb863f3593dcf064066575a92602053f680120fcca89fa0119",
"contentHash": "2652df31b462bc3de95ade6ef3afd95de5bd3dad5e66a4a2eb70d3b56f5da4e1",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_675051673df77fb7b949eaec",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-00969",
"moleculeId": "sa_121b4287309f0bd7131f5817",
"smiles": "Cn1ccc2cc(Nc3ncc(C4CC4)cc3C(=O)O)cc(-c3ccc(-c4ccccc4)cc3)c21",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_121b4287309f0bd7131f5817",
"inchikey": "WGYUKHHGAIEVLS-UHFFFAOYSA-N",
"smiles": "Cn1ccc2cc(Nc3ncc(C4CC4)cc3C(=O)O)cc(-c3ccc(-c4ccccc4)cc3)c21"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "9832",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_121b4287309f0bd7131f5817",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_121b4287309f0bd7131f5817",
"inchikey": "WGYUKHHGAIEVLS-UHFFFAOYSA-N",
"smiles": "Cn1ccc2cc(Nc3ncc(C4CC4)cc3C(=O)O)cc(-c3ccc(-c4ccccc4)cc3)c21"
},
"smiles": "Cn1ccc2cc(Nc3ncc(C4CC4)cc3C(=O)O)cc(-c3ccc(-c4ccccc4)cc3)c21",
"reactionStepId": "sa_ef50dce3663db1546bbd87a7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150299189A1;1835;1774906\",\"rsmi\":\"C[O:13][C:11]([c:10]1[c:9]([NH:8][c:7]2[cH:6][c:5]3[cH:4][cH:3][n:2]([CH3:1])[c:35]3[c:22](-[c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[cH:33][cH:34]3)[cH:21]2)[n:20][cH:19][c:15]([CH:16]2[CH2:17][CH2:18]2)[cH:14]1)=[O:12]>C1CCOC1.CO.[Na+].O>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[c:10]([C:11](=[O:12])[OH:13])[cH:14][c:15]([CH:16]4[CH2:17][CH2:18]4)[cH:19][n:20]3)[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[cH:33][cH:34]3)[c:35]12\"},\"mapped_reaction_smiles\":\"C[O:13][C:11]([c:10]1[c:9]([NH:8][c:7]2[cH:6][c:5]3[cH:4][cH:3][n:2]([CH3:1])[c:35]3[c:22](-[c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[cH:33][cH:34]3)[cH:21]2)[n:20][cH:19][c:15]([CH:16]2[CH2:17][CH2:18]2)[cH:14]1)=[O:12]>C1CCOC1.CO.[Na+].O>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH:8][c:9]3[c:10]([C:11](=[O:12])[OH:13])[cH:14][c:15]([CH:16]4[CH2:17][CH2:18]4)[cH:19][n:20]3)[cH:21][c:22](-[c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][cH:32]4)[cH:33][cH:34]3)[c:35]12\"}",
"reactionStep": {
"id": "sa_ef50dce3663db1546bbd87a7",
"reactionHash": "8340e8371f2593f84e401743c4885aafb9ae5b98eae8db24d49f62dc326a7343"
},
"children": [
{
"id": "9833",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_6501b6c36b4a266c95efee74",
"parentId": "9832",
"isLeaf": false,
"molecule": {
"id": "sa_6501b6c36b4a266c95efee74",
"inchikey": "BHZABJRVEDSAQJ-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(C2CC2)cnc1Nc1cc(-c2ccc(-c3ccccc3)cc2)c2c(ccn2C)c1"
},
"smiles": "COC(=O)c1cc(C2CC2)cnc1Nc1cc(-c2ccc(-c3ccccc3)cc2)c2c(ccn2C)c1",
"reactionStepId": "sa_0ad2ed10e598e5968a87b502",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150299189A1;1832;1774905\",\"rsmi\":\"Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:36][c:32]([CH:33]2[CH2:34][CH2:35]2)[cH:31][n:30]1.[NH2:7][c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[c:23]2[c:24]([cH:25]1)[cH:26][cH:27][n:28]2[CH3:29]>Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[cH:21][cH:22]3)[c:23]3[c:24]([cH:25]2)[cH:26][cH:27][n:28]3[CH3:29])[n:30][cH:31][c:32]([CH:33]2[CH2:34][CH2:35]2)[cH:36]1\"},\"mapped_reaction_smiles\":\"Cl[c:6]1[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:36][c:32]([CH:33]2[CH2:34][CH2:35]2)[cH:31][n:30]1.[NH2:7][c:8]1[cH:9][c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[c:23]2[c:24]([cH:25]1)[cH:26][cH:27][n:28]2[CH3:29]>Cc1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(O)O.[Cs+].[Cs+].[Pd].[Pd]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([NH:7][c:8]2[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[cH:21][cH:22]3)[c:23]3[c:24]([cH:25]2)[cH:26][cH:27][n:28]3[CH3:29])[n:30][cH:31][c:32]([CH:33]2[CH2:34][CH2:35]2)[cH:36]1\"}",
"reactionStep": {
"id": "sa_0ad2ed10e598e5968a87b502",
"reactionHash": "14f47b437aaafef39f21f97d1bc2ac979644b3808842dc6a8455c8eb3f647d60"
},
"children": [
{
"id": "9834",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_47e1b96e71c2b7665b446c41",
"parentId": "9833",
"isLeaf": false,
"molecule": {
"id": "sa_47e1b96e71c2b7665b446c41",
"inchikey": "LYQIYWXYYOFZHD-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(C2CC2)cnc1Cl"
},
"smiles": "COC(=O)c1cc(C2CC2)cnc1Cl",
"reactionStepId": "sa_f26b515aff4ddcb185f9c4e9",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150299189A1;0546;1774665\",\"rsmi\":\"Br[c:10]1[cH:9][n:8][c:6]([Cl:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14]1.OB(O)[CH:11]1[CH2:12][CH2:13]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)O.CC(=O)O.CCOC(C)=O.Cc1ccccc1.O.O.O=P(O)(O)O.[K+].[K+].[K+].[Pd+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[n:8][cH:9][c:10]([CH:11]2[CH2:12][CH2:13]2)[cH:14]1\"},\"mapped_reaction_smiles\":\"Br[c:10]1[cH:9][n:8][c:6]([Cl:7])[c:5]([C:3]([O:2][CH3:1])=[O:4])[cH:14]1.OB(O)[CH:11]1[CH2:12][CH2:13]1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.CC(=O)O.CC(=O)O.CCOC(C)=O.Cc1ccccc1.O.O.O=P(O)(O)O.[K+].[K+].[K+].[Pd+2]>[CH3:1][O:2][C:3](=[O:4])[c:5]1[c:6]([Cl:7])[n:8][cH:9][c:10]([CH:11]2[CH2:12][CH2:13]2)[cH:14]1\"}",
"reactionStep": {
"id": "sa_f26b515aff4ddcb185f9c4e9",
"reactionHash": "4a9379571365e330e992fea1a81be4d70a27cb7483e040e44c56bad647ebf4fa"
},
"children": [
{
"id": "9835",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_977fc9ab6fdf7c40b5da3d78",
"parentId": "9834",
"isLeaf": true,
"molecule": {
"id": "sa_977fc9ab6fdf7c40b5da3d78",
"inchikey": "MOMQDEDQGJAKII-UHFFFAOYSA-N",
"smiles": "COC(=O)c1cc(Br)cnc1Cl"
},
"smiles": "COC(=O)c1cc(Br)cnc1Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9836",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_853be5f1c97fac6116cffa07",
"parentId": "9834",
"isLeaf": true,
"molecule": {
"id": "sa_853be5f1c97fac6116cffa07",
"inchikey": "WLVKDFJTYKELLQ-UHFFFAOYSA-N",
"smiles": "OB(O)C1CC1"
},
"smiles": "OB(O)C1CC1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "9837",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_c8baeb510448736fb91f9ae4",
"parentId": "9833",
"isLeaf": false,
"molecule": {
"id": "sa_c8baeb510448736fb91f9ae4",
"inchikey": "ZGRJBLVRXHUCHF-UHFFFAOYSA-N",
"smiles": "Cn1ccc2cc(N)cc(-c3ccc(-c4ccccc4)cc3)c21"
},
"smiles": "Cn1ccc2cc(N)cc(-c3ccc(-c4ccccc4)cc3)c21",
"reactionStepId": "sa_d798fd489751e737855f7f51",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150299189A1;0696;1774706\",\"rsmi\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]2[cH:4][cH:3][n:2]([CH3:1])[c:23]2[c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[cH:9]1>CCO.O.Cl.[Fe].N>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH2:8])[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[cH:21][cH:22]3)[c:23]12\"},\"mapped_reaction_smiles\":\"O=[N+:8]([O-])[c:7]1[cH:6][c:5]2[cH:4][cH:3][n:2]([CH3:1])[c:23]2[c:10](-[c:11]2[cH:12][cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][cH:22]2)[cH:9]1>CCO.O.Cl.[Fe].N>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([NH2:8])[cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[cH:16][cH:17][cH:18][cH:19][cH:20]4)[cH:21][cH:22]3)[c:23]12\"}",
"reactionStep": {
"id": "sa_d798fd489751e737855f7f51",
"reactionHash": "8a07962f1065ee084252b87ed421322a9abb8a1fece06ae836c7959dde09d7f7"
},
"children": [
{
"id": "9838",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_79683f75b643d30cc4331ce8",
"parentId": "9837",
"isLeaf": false,
"molecule": {
"id": "sa_79683f75b643d30cc4331ce8",
"inchikey": "JFXDKNWQZORWBW-UHFFFAOYSA-N",
"smiles": "Cn1ccc2cc([N+](=O)[O-])cc(-c3ccc(-c4ccccc4)cc3)c21"
},
"smiles": "Cn1ccc2cc([N+](=O)[O-])cc(-c3ccc(-c4ccccc4)cc3)c21",
"reactionStepId": "sa_839f809de89858123a18d8bf",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150299189A1;0693;1774705\",\"rsmi\":\"I[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[cH:23][cH:24]3)[c:25]12>CCOC(C)=O.CN(C)C=O.O.[HH].[Na+]>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[cH:23][cH:24]3)[c:25]12\"},\"mapped_reaction_smiles\":\"I[CH3:1].[nH:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[cH:23][cH:24]3)[c:25]12>CCOC(C)=O.CN(C)C=O.O.[HH].[Na+]>[CH3:1][n:2]1[cH:3][cH:4][c:5]2[cH:6][c:7]([N+:8](=[O:9])[O-:10])[cH:11][c:12](-[c:13]3[cH:14][cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[cH:23][cH:24]3)[c:25]12\"}",
"reactionStep": {
"id": "sa_839f809de89858123a18d8bf",
"reactionHash": "95c29f69978eeff37f6deb26aa98b149f30ac78374d91eceea2ba8bf106552d7"
},
"children": [
{
"id": "9839",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_82fdccf7d1cc329c9db73f21",
"parentId": "9838",
"isLeaf": true,
"molecule": {
"id": "sa_82fdccf7d1cc329c9db73f21",
"inchikey": "INQOMBQAUSQDDS-UHFFFAOYSA-N",
"smiles": "CI"
},
"smiles": "CI",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "9840",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_dbe2598c8b9380373f6ded6f",
"parentId": "9838",
"isLeaf": false,
"molecule": {
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"inchikey": "YWFZNYHRAKRSIA-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(-c2ccc(-c3ccccc3)cc2)c2[nH]ccc2c1"
},
"smiles": "O=[N+]([O-])c1cc(-c2ccc(-c3ccccc3)cc2)c2[nH]ccc2c1",
"reactionStepId": "sa_f12de8d430a82efbee8123d7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20150299189A1;0690;1774704\",\"rsmi\":\"I[c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:24][c:23]2[c:19]1[nH:20][cH:21][cH:22]2.OB(O)[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>C1COCCO1.CCOC(C)=O.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.Cl[Pd]Cl.O.O=P(O)(O)O.[K+].[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[c:19]2[nH:20][cH:21][cH:22][c:23]2[cH:24]1\"},\"mapped_reaction_smiles\":\"I[c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[cH:24][c:23]2[c:19]1[nH:20][cH:21][cH:22]2.OB(O)[c:7]1[cH:8][cH:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18]1>C1COCCO1.CCOC(C)=O.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.CN(C)c1ccc(P(C(C)(C)C)C(C)(C)C)cc1.Cl[Pd]Cl.O.O=P(O)(O)O.[K+].[K+].[K+]>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)[c:19]2[nH:20][cH:21][cH:22][c:23]2[cH:24]1\"}",
"reactionStep": {
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"reactionHash": "5b6c8283c13762998083d0bf3b8e60409bd9c947454c8994ff4628731a3ea8dc"
},
"children": [
{
"id": "9841",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_76f29812bdb49b14ac27001c",
"parentId": "9840",
"isLeaf": true,
"molecule": {
"id": "sa_76f29812bdb49b14ac27001c",
"inchikey": "MEKWUUDIPZOULX-UHFFFAOYSA-N",
"smiles": "O=[N+]([O-])c1cc(I)c2[nH]ccc2c1"
},
"smiles": "O=[N+]([O-])c1cc(I)c2[nH]ccc2c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "9842",
"routeId": "sa_7c2c35ed7b77656f0e71ed4f",
"moleculeId": "sa_0874b78a6139bfaeccd7e906",
"parentId": "9840",
"isLeaf": true,
"molecule": {
"id": "sa_0874b78a6139bfaeccd7e906",
"inchikey": "XPEIJWZLPWNNOK-UHFFFAOYSA-N",
"smiles": "OB(O)c1ccc(-c2ccccc2)cc1"
},
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}
}