Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(-c3ccncc3C)cc2c1
InChiKey
YZTNDKMGURCHGM-UHFFFAOYSA-N
Route Signature
5185cea6d393b73fcbfe1a084f743e3cf3c9482606aa535e8f6b850ef1074119
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_756ebfdf3730a9343be14e6c",
"signature": "5185cea6d393b73fcbfe1a084f743e3cf3c9482606aa535e8f6b850ef1074119",
"contentHash": "19be4d632394b5849cfcb9c20118f5cacafc96450df7c12c0dc872d7aeb64625",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_d98d461d6c6b8c5d050858c5",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-01385",
"moleculeId": "sa_304fdbe3be812a2dbd47222c",
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(-c3ccncc3C)cc2c1",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_304fdbe3be812a2dbd47222c",
"inchikey": "YZTNDKMGURCHGM-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(-c3ccncc3C)cc2c1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10128",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_304fdbe3be812a2dbd47222c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_304fdbe3be812a2dbd47222c",
"inchikey": "YZTNDKMGURCHGM-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(-c3ccncc3C)cc2c1"
},
"smiles": "CCn1nc(-c2cnccn2)cc1-c1cnc2[nH]c(-c3ccncc3C)cc2c1",
"reactionStepId": "sa_a974ad71f56fdab56f50e17c",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0242;1383389\",\"rsmi\":\"CC1(C)OB([c:14]2[cH:15][n:16][c:17]3[nH:18][c:19](-[c:20]4[c:21]([CH3:22])[cH:23][n:24][cH:25][cH:26]4)[cH:27][c:28]3[cH:29]2)OC1(C)C.O=S(=O)(O[c:13]1[n:3]([CH2:2][CH3:1])[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12]1)C(F)(F)F>C1COCCO1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1-[c:14]1[cH:15][n:16][c:17]2[nH:18][c:19](-[c:20]3[c:21]([CH3:22])[cH:23][n:24][cH:25][cH:26]3)[cH:27][c:28]2[cH:29]1\"},\"mapped_reaction_smiles\":\"CC1(C)OB([c:14]2[cH:15][n:16][c:17]3[nH:18][c:19](-[c:20]4[c:21]([CH3:22])[cH:23][n:24][cH:25][cH:26]4)[cH:27][c:28]3[cH:29]2)OC1(C)C.O=S(=O)(O[c:13]1[n:3]([CH2:2][CH3:1])[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12]1)C(F)(F)F>C1COCCO1.Cl[Pd]Cl.O.O=C(O)O.[Fe+2].[K+].[K+]>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1-[c:14]1[cH:15][n:16][c:17]2[nH:18][c:19](-[c:20]3[c:21]([CH3:22])[cH:23][n:24][cH:25][cH:26]3)[cH:27][c:28]2[cH:29]1\"}",
"reactionStep": {
"id": "sa_a974ad71f56fdab56f50e17c",
"reactionHash": "0953cdaada5cd844c8e2d0e38ec259faf8202514a97ff5247687734257d8246f"
},
"children": [
{
"id": "10129",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_755d4c7a0ee3ac36e82de3ed",
"parentId": "10128",
"isLeaf": false,
"molecule": {
"id": "sa_755d4c7a0ee3ac36e82de3ed",
"inchikey": "NNGCGGMZCQOMDC-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1OS(=O)(=O)C(F)(F)F"
},
"smiles": "CCn1nc(-c2cnccn2)cc1OS(=O)(=O)C(F)(F)F",
"reactionStepId": "sa_097364cf1869d82a02fe90bc",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0176;1383355\",\"rsmi\":\"O=S(=O)(N(c1ccccc1)[S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21])C(F)(F)F.[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[OH:14]>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[O:14][S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21]\"},\"mapped_reaction_smiles\":\"O=S(=O)(N(c1ccccc1)[S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21])C(F)(F)F.[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[OH:14]>CN(C)C=O.[HH].[Na+]>[CH3:1][CH2:2][n:3]1[n:4][c:5](-[c:6]2[n:7][cH:8][cH:9][n:10][cH:11]2)[cH:12][c:13]1[O:14][S:15](=[O:16])(=[O:17])[C:18]([F:19])([F:20])[F:21]\"}",
"reactionStep": {
"id": "sa_097364cf1869d82a02fe90bc",
"reactionHash": "0514ac399fb47cca781b878c4eb7dbad13a618be019aaff86149b15bebd8853e"
},
"children": [
{
"id": "10130",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_24bc5b50442cd9e5fcf68f54",
"parentId": "10129",
"isLeaf": true,
"molecule": {
"id": "sa_24bc5b50442cd9e5fcf68f54",
"inchikey": "DIOHEXPTUTVCNX-UHFFFAOYSA-N",
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=S(=O)(N(c1ccccc1)S(=O)(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10131",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_7f1a52cb4b9227a266979d3a",
"parentId": "10129",
"isLeaf": true,
"molecule": {
"id": "sa_7f1a52cb4b9227a266979d3a",
"inchikey": "VFMDHVQHSBQJMV-UHFFFAOYSA-N",
"smiles": "CCn1nc(-c2cnccn2)cc1O"
},
"smiles": "CCn1nc(-c2cnccn2)cc1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10132",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_3284c1fc1aa7aef4a3e1ba57",
"parentId": "10128",
"isLeaf": false,
"molecule": {
"id": "sa_3284c1fc1aa7aef4a3e1ba57",
"inchikey": "PKYARSFBOIQKTC-UHFFFAOYSA-N",
"smiles": "Cc1cnccc1-c1cc2cc(B3OC(C)(C)C(C)(C)O3)cnc2[nH]1"
},
"smiles": "Cc1cnccc1-c1cc2cc(B3OC(C)(C)C(C)(C)O3)cnc2[nH]1",
"reactionStepId": "sa_028accfc9f4a1a674c3f1b6a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0241;1383388\",\"rsmi\":\"Br[c:8]1[cH:7][c:6]2[cH:5][c:4](-[c:3]3[c:2]([CH3:1])[cH:25][n:24][cH:23][cH:22]3)[nH:21][c:20]2[n:19][cH:18]1.CC1(C)OB([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.[K+]>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][c:6]3[cH:7][c:8]([B:9]4[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]4)[cH:18][n:19][c:20]3[nH:21]2)[cH:22][cH:23][n:24][cH:25]1\"},\"mapped_reaction_smiles\":\"Br[c:8]1[cH:7][c:6]2[cH:5][c:4](-[c:3]3[c:2]([CH3:1])[cH:25][n:24][cH:23][cH:22]3)[nH:21][c:20]2[n:19][cH:18]1.CC1(C)OB([B:9]2[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]2)OC1(C)C>C1COCCO1.CC(=O)O.[K+]>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][c:6]3[cH:7][c:8]([B:9]4[O:10][C:11]([CH3:12])([CH3:13])[C:14]([CH3:15])([CH3:16])[O:17]4)[cH:18][n:19][c:20]3[nH:21]2)[cH:22][cH:23][n:24][cH:25]1\"}",
"reactionStep": {
"id": "sa_028accfc9f4a1a674c3f1b6a",
"reactionHash": "c955b61cbb705cd7519454a141292e20d2dbb1da5730087a923aecc621a43830"
},
"children": [
{
"id": "10133",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_e6c301388ac142801d4af5a2",
"parentId": "10132",
"isLeaf": true,
"molecule": {
"id": "sa_e6c301388ac142801d4af5a2",
"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": "10134",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_76c91d82a643d82c00700632",
"parentId": "10132",
"isLeaf": false,
"molecule": {
"id": "sa_76c91d82a643d82c00700632",
"inchikey": "YYKZEYTVHBVOSU-UHFFFAOYSA-N",
"smiles": "Cc1cnccc1-c1cc2cc(Br)cnc2[nH]1"
},
"smiles": "Cc1cnccc1-c1cc2cc(Br)cnc2[nH]1",
"reactionStepId": "sa_ae2ad2566f9f7ec4859baa89",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0240;1383387\",\"rsmi\":\"[CH3:1][c:2]1[c:3]([C:4]#[C:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]2[NH2:13])[cH:14][cH:15][n:16][cH:17]1>CC(C)(C)O.CN1CCCC1=O.O.[K+]>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][c:6]3[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]3[nH:13]2)[cH:14][cH:15][n:16][cH:17]1\"},\"mapped_reaction_smiles\":\"[CH3:1][c:2]1[c:3]([C:4]#[C:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]2[NH2:13])[cH:14][cH:15][n:16][cH:17]1>CC(C)(C)O.CN1CCCC1=O.O.[K+]>[CH3:1][c:2]1[c:3](-[c:4]2[cH:5][c:6]3[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]3[nH:13]2)[cH:14][cH:15][n:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_ae2ad2566f9f7ec4859baa89",
"reactionHash": "5c2dcecee4aa95cdaec43daa9afd42ade9ce7ff9a23dfab3bb3210d95f99c6e1"
},
"children": [
{
"id": "10135",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_508db055ad793c954cad67bc",
"parentId": "10134",
"isLeaf": false,
"molecule": {
"id": "sa_508db055ad793c954cad67bc",
"inchikey": "ZYNIGHZWMKEJOH-UHFFFAOYSA-N",
"smiles": "Cc1cnccc1C#Cc1cc(Br)cnc1N"
},
"smiles": "Cc1cnccc1C#Cc1cc(Br)cnc1N",
"reactionStepId": "sa_e42a24a6b209e3186c33c500",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0239;1383386\",\"rsmi\":\"I[c:6]1[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]1[NH2:13].[CH3:1][c:2]1[c:3]([C:4]#[CH:5])[cH:14][cH:15][n:16][cH:17]1>CCN(CC)CC.CN(C)C=O.O.[Cu]I.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[c:3]([C:4]#[C:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]2[NH2:13])[cH:14][cH:15][n:16][cH:17]1\"},\"mapped_reaction_smiles\":\"I[c:6]1[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]1[NH2:13].[CH3:1][c:2]1[c:3]([C:4]#[CH:5])[cH:14][cH:15][n:16][cH:17]1>CCN(CC)CC.CN(C)C=O.O.[Cu]I.c1ccc([PH](c2ccccc2)(c2ccccc2)[Pd]([PH](c2ccccc2)(c2ccccc2)c2ccccc2)([PH](c2ccccc2)(c2ccccc2)c2ccccc2)[PH](c2ccccc2)(c2ccccc2)c2ccccc2)cc1>[CH3:1][c:2]1[c:3]([C:4]#[C:5][c:6]2[cH:7][c:8]([Br:9])[cH:10][n:11][c:12]2[NH2:13])[cH:14][cH:15][n:16][cH:17]1\"}",
"reactionStep": {
"id": "sa_e42a24a6b209e3186c33c500",
"reactionHash": "fc9c15ad7f005f87a1e6f8102d0e448dd452d02ba51674226c263f4eaef2de2d"
},
"children": [
{
"id": "10136",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_35846e2703ccea27cb532624",
"parentId": "10135",
"isLeaf": false,
"molecule": {
"id": "sa_35846e2703ccea27cb532624",
"inchikey": "UMXBMEVYOBWMBN-UHFFFAOYSA-N",
"smiles": "C#Cc1ccncc1C"
},
"smiles": "C#Cc1ccncc1C",
"reactionStepId": "sa_de2ba286e164233b357a5eed",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20130158049A1;0238;1383385\",\"rsmi\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[c:4]([CH3:5])[cH:6][n:7][cH:8][cH:9]1>CCOCC.CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[c:4]([CH3:5])[cH:6][n:7][cH:8][cH:9]1\"},\"mapped_reaction_smiles\":\"C[Si](C)(C)[C:1]#[C:2][c:3]1[c:4]([CH3:5])[cH:6][n:7][cH:8][cH:9]1>CCOCC.CO.O=C(O)O.[K+].[K+]>[CH:1]#[C:2][c:3]1[c:4]([CH3:5])[cH:6][n:7][cH:8][cH:9]1\"}",
"reactionStep": {
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"reactionHash": "15e0ac0e3aa7b5598a2d86525bd9de91d273a65917a0825b8cbf0a179ff9a93e"
},
"children": [
{
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"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_120dea2b0e022980f4cfc7b1",
"parentId": "10136",
"isLeaf": true,
"molecule": {
"id": "sa_120dea2b0e022980f4cfc7b1",
"inchikey": "JZEBKFGSLYUDMH-UHFFFAOYSA-N",
"smiles": "Cc1cnccc1C#C[Si](C)(C)C"
},
"smiles": "Cc1cnccc1C#C[Si](C)(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
},
{
"id": "10138",
"routeId": "sa_756ebfdf3730a9343be14e6c",
"moleculeId": "sa_9e6369b69104da7a237dd159",
"parentId": "10135",
"isLeaf": true,
"molecule": {
"id": "sa_9e6369b69104da7a237dd159",
"inchikey": "XPERZSKJGNUSHI-UHFFFAOYSA-N",
"smiles": "Nc1ncc(Br)cc1I"
},
"smiles": "Nc1ncc(Br)cc1I",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
}
]
}
}