Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CC(C)(C)OC(=O)NC1(c2ccnc(Br)c2)CC1
InChiKey
RDUISJDOWOIILY-UHFFFAOYSA-N
Route Signature
a1803196c5e474c7fd5cb2585c3da198026edb6c3f6dbba8c1d06c85e5f32255
Synthesis route with 6 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_40849d589c00ba631dbbd80b",
"signature": "a1803196c5e474c7fd5cb2585c3da198026edb6c3f6dbba8c1d06c85e5f32255",
"contentHash": "59c4f8ae66ff7ed53cd42da94de71ea2208f8fa84cbf57a6332d6185a2eba4f6",
"length": 6,
"isConvergent": false
},
"target": {
"id": "sa_0e3a28125c1a052243fb6725",
"benchmarkSetId": "f925e688d731a0ad4e3aa6a505df094f6d3ca64ce3facc312bc5f64731921b33",
"targetId": "n5-00285",
"moleculeId": "sa_da6bf671cc533a4a072ed57e",
"smiles": "CC(C)(C)OC(=O)NC1(c2ccnc(Br)c2)CC1",
"routeLength": 6,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_da6bf671cc533a4a072ed57e",
"inchikey": "RDUISJDOWOIILY-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1(c2ccnc(Br)c2)CC1"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 2
},
"rootNode": {
"id": "3832",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_da6bf671cc533a4a072ed57e",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_da6bf671cc533a4a072ed57e",
"inchikey": "RDUISJDOWOIILY-UHFFFAOYSA-N",
"smiles": "CC(C)(C)OC(=O)NC1(c2ccnc(Br)c2)CC1"
},
"smiles": "CC(C)(C)OC(=O)NC1(c2ccnc(Br)c2)CC1",
"reactionStepId": "sa_f50132c6a353fd19b842a1e3",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120270870A1;0175;1289472\",\"rsmi\":\"O[C:6](=[O:7])[C:9]1([c:10]2[cH:11][c:12]([Br:13])[n:14][cH:15][cH:16]2)[CH2:17][CH2:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].[N-]=[N+]=[N:8]P(=O)(c1ccccc1)c1ccccc1>CCN(CC)CC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([c:10]2[cH:11][c:12]([Br:13])[n:14][cH:15][cH:16]2)[CH2:17][CH2:18]1\"},\"mapped_reaction_smiles\":\"O[C:6](=[O:7])[C:9]1([c:10]2[cH:11][c:12]([Br:13])[n:14][cH:15][cH:16]2)[CH2:17][CH2:18]1.[CH3:1][C:2]([CH3:3])([CH3:4])[OH:5].[N-]=[N+]=[N:8]P(=O)(c1ccccc1)c1ccccc1>CCN(CC)CC>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[NH:8][C:9]1([c:10]2[cH:11][c:12]([Br:13])[n:14][cH:15][cH:16]2)[CH2:17][CH2:18]1\"}",
"reactionStep": {
"id": "sa_f50132c6a353fd19b842a1e3",
"reactionHash": "3d024e73a961a4c309b835ac1da9026d5fd47a9b7134c747c6a7bb7ff4438c96"
},
"children": [
{
"id": "3833",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_339f109b29d21e95632a74f6",
"parentId": "3832",
"isLeaf": true,
"molecule": {
"id": "sa_339f109b29d21e95632a74f6",
"inchikey": "DKGAVHZHDRPRBM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)O"
},
"smiles": "CC(C)(C)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3834",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_4ef1c6416628b1f9a93030b0",
"parentId": "3832",
"isLeaf": false,
"molecule": {
"id": "sa_4ef1c6416628b1f9a93030b0",
"inchikey": "IPHJRNBPNWSYIK-UHFFFAOYSA-N",
"smiles": "O=C(O)C1(c2ccnc(Br)c2)CC1"
},
"smiles": "O=C(O)C1(c2ccnc(Br)c2)CC1",
"reactionStepId": "sa_ca4ea73bae93f6d98ae2b41b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120270870A1;0174;1289471\",\"rsmi\":\"CC(C)(C)[OH:3].[O:1]=[CH:2][C:4]1([c:5]2[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]2)[CH2:12][CH2:13]1>CC=C(C)C.O.O.O=P(O)(O)O.[Na+].[Na+].[O-][Cl+]O>[O:1]=[C:2]([OH:3])[C:4]1([c:5]2[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]2)[CH2:12][CH2:13]1\"},\"mapped_reaction_smiles\":\"CC(C)(C)[OH:3].[O:1]=[CH:2][C:4]1([c:5]2[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]2)[CH2:12][CH2:13]1>CC=C(C)C.O.O.O=P(O)(O)O.[Na+].[Na+].[O-][Cl+]O>[O:1]=[C:2]([OH:3])[C:4]1([c:5]2[cH:6][c:7]([Br:8])[n:9][cH:10][cH:11]2)[CH2:12][CH2:13]1\"}",
"reactionStep": {
"id": "sa_ca4ea73bae93f6d98ae2b41b",
"reactionHash": "d3eab22c450c2dedf24f57b4f32217dfad9684361126df79ee209e277e43ec28"
},
"children": [
{
"id": "3835",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_339f109b29d21e95632a74f6",
"parentId": "3834",
"isLeaf": true,
"molecule": {
"id": "sa_339f109b29d21e95632a74f6",
"inchikey": "DKGAVHZHDRPRBM-UHFFFAOYSA-N",
"smiles": "CC(C)(C)O"
},
"smiles": "CC(C)(C)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3836",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_e0fe1e81eb80ba4a6fd9dd8e",
"parentId": "3834",
"isLeaf": false,
"molecule": {
"id": "sa_e0fe1e81eb80ba4a6fd9dd8e",
"inchikey": "WZFYOHARLCOXOL-UHFFFAOYSA-N",
"smiles": "O=CC1(c2ccnc(Br)c2)CC1"
},
"smiles": "O=CC1(c2ccnc(Br)c2)CC1",
"reactionStepId": "sa_1b44b71e8535c5a454230e44",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120270870A1;0173;1289470\",\"rsmi\":\"CCOC(C)=[O:1].N#[C:2][C:3]1([c:4]2[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]2)[CH2:11][CH2:12]1>CC(C)C[AlH]CC(C)C.Cc1ccccc1.O=S(=O)(O)O>[O:1]=[CH:2][C:3]1([c:4]2[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]2)[CH2:11][CH2:12]1\"},\"mapped_reaction_smiles\":\"CCOC(C)=[O:1].N#[C:2][C:3]1([c:4]2[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]2)[CH2:11][CH2:12]1>CC(C)C[AlH]CC(C)C.Cc1ccccc1.O=S(=O)(O)O>[O:1]=[CH:2][C:3]1([c:4]2[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]2)[CH2:11][CH2:12]1\"}",
"reactionStep": {
"id": "sa_1b44b71e8535c5a454230e44",
"reactionHash": "7badcf76656859d60f7a778b7b4368f81278b08b7a1def43fb87ede3588f690a"
},
"children": [
{
"id": "3837",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_654614044932a5d04a690b3c",
"parentId": "3836",
"isLeaf": false,
"molecule": {
"id": "sa_654614044932a5d04a690b3c",
"inchikey": "HKLRZPZCPJJBTP-UHFFFAOYSA-N",
"smiles": "N#CC1(c2ccnc(Br)c2)CC1"
},
"smiles": "N#CC1(c2ccnc(Br)c2)CC1",
"reactionStepId": "sa_01caeba23551a91f9a0d2cd6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120270870A1;0172;1289469\",\"rsmi\":\"Br[CH2:11][CH2:12]Br.[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]1>CCOC(C)=O.CCOCC.CS(C)=O.O.[HH].[Na+]>[N:1]#[C:2][C:3]1([c:4]2[cH:5][c:6]([Br:7])[n: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][c:6]([Br:7])[n:8][cH:9][cH:10]1>CCOC(C)=O.CCOCC.CS(C)=O.O.[HH].[Na+]>[N:1]#[C:2][C:3]1([c:4]2[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]2)[CH2:11][CH2:12]1\"}",
"reactionStep": {
"id": "sa_01caeba23551a91f9a0d2cd6",
"reactionHash": "4cfc74ba0f07fa40c6980708f4547ef9de04693c28957e28953895ff71eebc64"
},
"children": [
{
"id": "3838",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_17fe34ec56218f473432e26a",
"parentId": "3837",
"isLeaf": true,
"molecule": {
"id": "sa_17fe34ec56218f473432e26a",
"inchikey": "PAAZPARNPHGIKF-UHFFFAOYSA-N",
"smiles": "BrCCBr"
},
"smiles": "BrCCBr",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3839",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_dc95b3cf898e288ed1bf8541",
"parentId": "3837",
"isLeaf": false,
"molecule": {
"id": "sa_dc95b3cf898e288ed1bf8541",
"inchikey": "PBNYXTKBDQXJFM-UHFFFAOYSA-N",
"smiles": "N#CCc1ccnc(Br)c1"
},
"smiles": "N#CCc1ccnc(Br)c1",
"reactionStepId": "sa_fd480db702d90ef259a706a5",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120270870A1;0171;1289468\",\"rsmi\":\"CS(=O)(=O)O[CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]1.[N:1]#[CH:2]>CCO.CCOC(C)=O.O.O=C(O)O.[K+].[Na+]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]1\"},\"mapped_reaction_smiles\":\"CS(=O)(=O)O[CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]1.[N:1]#[CH:2]>CCO.CCOC(C)=O.O.O=C(O)O.[K+].[Na+]>[N:1]#[C:2][CH2:3][c:4]1[cH:5][c:6]([Br:7])[n:8][cH:9][cH:10]1\"}",
"reactionStep": {
"id": "sa_fd480db702d90ef259a706a5",
"reactionHash": "4201894ff02174b899375327a168b80212adff7dab4ac6af25c86a7d40728317"
},
"children": [
{
"id": "3840",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_5995aff3aeff665a1f3e984d",
"parentId": "3839",
"isLeaf": true,
"molecule": {
"id": "sa_5995aff3aeff665a1f3e984d",
"inchikey": "LELOWRISYMNNSU-UHFFFAOYSA-N",
"smiles": "C#N"
},
"smiles": "C#N",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3841",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_b364015de177f24b2a05ad2b",
"parentId": "3839",
"isLeaf": false,
"molecule": {
"id": "sa_b364015de177f24b2a05ad2b",
"inchikey": "ZBZXPEHGUNVRFC-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)OCc1ccnc(Br)c1"
},
"smiles": "CS(=O)(=O)OCc1ccnc(Br)c1",
"reactionStepId": "sa_08eef563a0bb4337d64a1add",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US20120270870A1;0170;1289467\",\"rsmi\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][c:7]1[cH:8][c:9]([Br:10])[n:11][cH:12][cH:13]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][c:9]([Br:10])[n:11][cH:12][cH:13]1\"},\"mapped_reaction_smiles\":\"Cl[S:2]([CH3:1])(=[O:3])=[O:4].[OH:5][CH2:6][c:7]1[cH:8][c:9]([Br:10])[n:11][cH:12][cH:13]1>CCN(C(C)C)C(C)C.ClCCl>[CH3:1][S:2](=[O:3])(=[O:4])[O:5][CH2:6][c:7]1[cH:8][c:9]([Br:10])[n:11][cH:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_08eef563a0bb4337d64a1add",
"reactionHash": "8c0735769271a1b1d32f0d1bf0c0f2fae4a92a526cac38a3f70bcd48d429139b"
},
"children": [
{
"id": "3842",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_d7eff4bbca5871edd726cc2c",
"parentId": "3841",
"isLeaf": true,
"molecule": {
"id": "sa_d7eff4bbca5871edd726cc2c",
"inchikey": "IQNUGAFIKDRYRP-UHFFFAOYSA-N",
"smiles": "OCc1ccnc(Br)c1"
},
"smiles": "OCc1ccnc(Br)c1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "3843",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "3841",
"isLeaf": true,
"molecule": {
"id": "sa_d2a31ea58046b00856f61ca5",
"inchikey": "QARBMVPHQWIHKH-UHFFFAOYSA-N",
"smiles": "CS(=O)(=O)Cl"
},
"smiles": "CS(=O)(=O)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
}
]
},
{
"id": "3844",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_6bf30f725089b74d691fc82c",
"parentId": "3836",
"isLeaf": true,
"molecule": {
"id": "sa_6bf30f725089b74d691fc82c",
"inchikey": "XEKOWRVHYACXOJ-UHFFFAOYSA-N",
"smiles": "CCOC(C)=O"
},
"smiles": "CCOC(C)=O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
]
},
{
"id": "3845",
"routeId": "sa_40849d589c00ba631dbbd80b",
"moleculeId": "sa_b2e7e70131d8726a166b6104",
"parentId": "3832",
"isLeaf": true,
"molecule": {
"id": "sa_b2e7e70131d8726a166b6104",
"inchikey": "MKRTXPORKIRPDG-UHFFFAOYSA-N",
"smiles": "[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1"
},
"smiles": "[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
}
}