Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
c1ccc(-c2cc3cc(-c4ccncn4)c(-c4ccco4)nc3[nH]2)cc1
InChiKey
GMOSJDXQORTJOO-UHFFFAOYSA-N
Route Signature
83828207be748419b03c234ab7284cdf4e9334a359c65b11d64f268943fc7c3d
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_d627c8d44abb0306787a48cf",
"signature": "83828207be748419b03c234ab7284cdf4e9334a359c65b11d64f268943fc7c3d",
"contentHash": "9f0bab21d625b38b74967babf3b55c73b6de281dfb232113b3819a6c4aa97a89",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_c33885d14668057283551c26",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00015",
"moleculeId": "sa_760a6cd14775516e9b27d927",
"smiles": "c1ccc(-c2cc3cc(-c4ccncn4)c(-c4ccco4)nc3[nH]2)cc1",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_760a6cd14775516e9b27d927",
"inchikey": "GMOSJDXQORTJOO-UHFFFAOYSA-N",
"smiles": "c1ccc(-c2cc3cc(-c4ccncn4)c(-c4ccco4)nc3[nH]2)cc1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "12110",
"routeId": "sa_d627c8d44abb0306787a48cf",
"moleculeId": "sa_760a6cd14775516e9b27d927",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_760a6cd14775516e9b27d927",
"inchikey": "GMOSJDXQORTJOO-UHFFFAOYSA-N",
"smiles": "c1ccc(-c2cc3cc(-c4ccncn4)c(-c4ccco4)nc3[nH]2)cc1"
},
"smiles": "c1ccc(-c2cc3cc(-c4ccncn4)c(-c4ccco4)nc3[nH]2)cc1",
"reactionStepId": "sa_d6c67f3e4802c4b3635a7870",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0480;657450\",\"rsmi\":\"[cH:1]1[cH:2][cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][c:9](-[c:10]3[n:11][cH:12][n:13][cH:14][cH:15]3)[c:16](-[c:17]3[cH:18][cH:19][cH:20][o:21]3)[n:22][c:23]2[NH2:24])[cH:25][cH:26]1>CC(C)(C)O.CN1CCCC1=O.O.[K+]>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][c:7]3[cH:8][c:9](-[c:10]4[n:11][cH:12][n:13][cH:14][cH:15]4)[c:16](-[c:17]4[cH:18][cH:19][cH:20][o:21]4)[n:22][c:23]3[nH:24]2)[cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"[cH:1]1[cH:2][cH:3][c:4]([C:5]#[C:6][c:7]2[cH:8][c:9](-[c:10]3[n:11][cH:12][n:13][cH:14][cH:15]3)[c:16](-[c:17]3[cH:18][cH:19][cH:20][o:21]3)[n:22][c:23]2[NH2:24])[cH:25][cH:26]1>CC(C)(C)O.CN1CCCC1=O.O.[K+]>[cH:1]1[cH:2][cH:3][c:4](-[c:5]2[cH:6][c:7]3[cH:8][c:9](-[c:10]4[n:11][cH:12][n:13][cH:14][cH:15]4)[c:16](-[c:17]4[cH:18][cH:19][cH:20][o:21]4)[n:22][c:23]3[nH:24]2)[cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_d6c67f3e4802c4b3635a7870",
"reactionHash": "0ff351273ad21b95884a43a841f6f8cac94429f7d8583c295562f0652c323f94"
},
"children": [
{
"id": "12111",
"routeId": "sa_d627c8d44abb0306787a48cf",
"moleculeId": "sa_e7ac952cf2b6929d080ae7ad",
"parentId": "12110",
"isLeaf": false,
"molecule": {
"id": "sa_e7ac952cf2b6929d080ae7ad",
"inchikey": "IECLUNHLAHRITK-UHFFFAOYSA-N",
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1C#Cc1ccccc1"
},
"smiles": "Nc1nc(-c2ccco2)c(-c2ccncn2)cc1C#Cc1ccccc1",
"reactionStepId": "sa_06f87c5c385959be15200d94",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20090023763A1;0294;657401\",\"rsmi\":\"Br[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.[CH:19]#[C:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>C1CCOC1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[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[C:19]#[C:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1\"},\"mapped_reaction_smiles\":\"Br[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.[CH:19]#[C:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1>C1CCOC1.CCN(CC)CC.Cl[Pd](Cl)([PH](c1ccccc1)(c1ccccc1)c1ccccc1)[PH](c1ccccc1)(c1ccccc1)c1ccccc1.O.[Cu]I>[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[C:19]#[C:20][c:21]1[cH:22][cH:23][cH:24][cH:25][cH:26]1\"}",
"reactionStep": {
"id": "sa_06f87c5c385959be15200d94",
"reactionHash": "612bcd4902bcadef1ffc2104991dc6e999ffda7b5d079a143a7986c2f5eee562"
},
"children": [
{
"id": "12112",
"routeId": "sa_d627c8d44abb0306787a48cf",
"moleculeId": "sa_5fb824a36bac7ea89812a664",
"parentId": "12111",
"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": [
{
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"moleculeId": "sa_f30592c1184fb2dccf3c6b37",
"parentId": "12112",
"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": [
{
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"moleculeId": "sa_17eaff2a3d903a2746a88e0c",
"parentId": "12113",
"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": {
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"children": [
{
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"parentId": "12114",
"isLeaf": true,
"molecule": {
"id": "sa_daa2686ce35f5333036b911a",
"inchikey": "LYCAIKOWRPUZTN-UHFFFAOYSA-N",
"smiles": "OCCO"
},
"smiles": "OCCO",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "12116",
"routeId": "sa_d627c8d44abb0306787a48cf",
"moleculeId": "sa_dc72a5e4d0fad7c0aca75be8",
"parentId": "12114",
"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": {
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"reactionHash": "ab3d9f1a5d55711eab6f8e9fb81e3706917680d8f42198b3b64853fca6515fc9"
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"children": [
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"moleculeId": "sa_827eb7c244a9a2234b4b2013",
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"molecule": {
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"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\"}",
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"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",
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{
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"molecule": {
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"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
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}
]
},
{
"id": "12120",
"routeId": "sa_d627c8d44abb0306787a48cf",
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"parentId": "12116",
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"molecule": {
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"inchikey": "QGZKDVFQNNGYKY-UHFFFAOYSA-N",
"smiles": "N"
},
"smiles": "N",
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"metadata": null,
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"children": []
}
]
},
{
"id": "12121",
"routeId": "sa_d627c8d44abb0306787a48cf",
"moleculeId": "sa_106b35b8a76bbe73829a0a69",
"parentId": "12114",
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"molecule": {
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"inchikey": "XLYOFNOQVPJJNP-UHFFFAOYSA-N",
"smiles": "O"
},
"smiles": "O",
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"children": []
}
]
}
]
},
{
"id": "12122",
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"moleculeId": "sa_ccdcf23ac83e7a68bfa4f2e5",
"parentId": "12112",
"isLeaf": true,
"molecule": {
"id": "sa_ccdcf23ac83e7a68bfa4f2e5",
"inchikey": "PCLIMKBDDGJMGD-UHFFFAOYSA-N",
"smiles": "O=C1CCC(=O)N1Br"
},
"smiles": "O=C1CCC(=O)N1Br",
"reactionStepId": null,
"template": null,
"metadata": null,
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"children": []
}
]
},
{
"id": "12123",
"routeId": "sa_d627c8d44abb0306787a48cf",
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"parentId": "12111",
"isLeaf": true,
"molecule": {
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