Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCCNC(=O)COc1c(-c2ccc3c(c2)CNC3=O)ccc(OC(F)F)c1OC
InChiKey
FPBRXXOGNMLHSF-UHFFFAOYSA-N
Route Signature
5b91821eb4c32adcaad7f15342203fd74e9ae3b6b73273448a538606a18f5bff
Synthesis route with 7 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_36b29e58905c0308c4be871d",
"signature": "5b91821eb4c32adcaad7f15342203fd74e9ae3b6b73273448a538606a18f5bff",
"contentHash": "e377dee40c69414039e59dff758a211416bec8dd80cb7608bb5d83c8c7b6a1ad",
"length": 7,
"isConvergent": false
},
"target": {
"id": "sa_08ab3c629d8d427f70fa7a22",
"benchmarkSetId": "61e696668b63e77d7c2a29c0821768e1c383de8313852d6e995224859494442e",
"targetId": "n5-00358",
"moleculeId": "sa_f14ac392c4a002ff390eeea1",
"smiles": "CCCNC(=O)COc1c(-c2ccc3c(c2)CNC3=O)ccc(OC(F)F)c1OC",
"routeLength": 7,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f14ac392c4a002ff390eeea1",
"inchikey": "FPBRXXOGNMLHSF-UHFFFAOYSA-N",
"smiles": "CCCNC(=O)COc1c(-c2ccc3c(c2)CNC3=O)ccc(OC(F)F)c1OC"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "13147",
"routeId": "sa_36b29e58905c0308c4be871d",
"moleculeId": "sa_f14ac392c4a002ff390eeea1",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f14ac392c4a002ff390eeea1",
"inchikey": "FPBRXXOGNMLHSF-UHFFFAOYSA-N",
"smiles": "CCCNC(=O)COc1c(-c2ccc3c(c2)CNC3=O)ccc(OC(F)F)c1OC"
},
"smiles": "CCCNC(=O)COc1c(-c2ccc3c(c2)CNC3=O)ccc(OC(F)F)c1OC",
"reactionStepId": "sa_3b9b46a0c8a5e9686321e131",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09051290B2;1023;1626544\",\"rsmi\":\"Br[c:20]1[c:9]([O:8][CH2:7][C:5]([NH:4][CH2:3][CH2:2][CH3:1])=[O:6])[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19]1.CC1(C)OB([c:21]2[cH:22][cH:23][c:24]3[c:29]([cH:30]2)[CH2:28][NH:27][C:25]3=[O:26])OC1(C)C>CN(C)C=O.O=C(O)O.[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][O:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19][c:20]1-[c:21]1[cH:22][cH:23][c:24]2[c:29]([cH:30]1)[CH2:28][NH:27][C:25]2=[O:26]\"},\"mapped_reaction_smiles\":\"Br[c:20]1[c:9]([O:8][CH2:7][C:5]([NH:4][CH2:3][CH2:2][CH3:1])=[O:6])[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19]1.CC1(C)OB([c:21]2[cH:22][cH:23][c:24]3[c:29]([cH:30]2)[CH2:28][NH:27][C:25]3=[O:26])OC1(C)C>CN(C)C=O.O=C(O)O.[Cs+].[Cs+].[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][O:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19][c:20]1-[c:21]1[cH:22][cH:23][c:24]2[c:29]([cH:30]1)[CH2:28][NH:27][C:25]2=[O:26]\"}",
"reactionStep": {
"id": "sa_3b9b46a0c8a5e9686321e131",
"reactionHash": "a85f0f76eb85f3a2780272921694acdd3da3369ff93165c845ccdc4f88edacc6"
},
"children": [
{
"id": "13148",
"routeId": "sa_36b29e58905c0308c4be871d",
"moleculeId": "sa_a29e5082725cdef061672311",
"parentId": "13147",
"isLeaf": true,
"molecule": {
"id": "sa_a29e5082725cdef061672311",
"inchikey": "CLACMCLRELMFLJ-UHFFFAOYSA-N",
"smiles": "CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C"
},
"smiles": "CC1(C)OB(c2ccc3c(c2)CNC3=O)OC1(C)C",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "13149",
"routeId": "sa_36b29e58905c0308c4be871d",
"moleculeId": "sa_8349c2b6927bc9dc5a2f3040",
"parentId": "13147",
"isLeaf": false,
"molecule": {
"id": "sa_8349c2b6927bc9dc5a2f3040",
"inchikey": "LGLDCZOPDNQVNF-UHFFFAOYSA-N",
"smiles": "CCCNC(=O)COc1c(Br)ccc(OC(F)F)c1OC"
},
"smiles": "CCCNC(=O)COc1c(Br)ccc(OC(F)F)c1OC",
"reactionStepId": "sa_63a04a4ace959137f3c54bfe",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09051290B2;1022;1626543\",\"rsmi\":\"O[C:5](=[O:6])[CH2:7][O:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19][c:20]1[Br:21].[CH3:1][CH2:2][CH2:3][NH2:4]>CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.ClCCl.O.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][O:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19][c:20]1[Br:21]\"},\"mapped_reaction_smiles\":\"O[C:5](=[O:6])[CH2:7][O:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19][c:20]1[Br:21].[CH3:1][CH2:2][CH2:3][NH2:4]>CCN(CC)CC.CCN=C=NCCCN(C)C.Cl.ClCCl.O.On1nnc2ccccc21>[CH3:1][CH2:2][CH2:3][NH:4][C:5](=[O:6])[CH2:7][O:8][c:9]1[c:10]([O:11][CH3:12])[c:13]([O:14][CH:15]([F:16])[F:17])[cH:18][cH:19][c:20]1[Br:21]\"}",
"reactionStep": {
"id": "sa_63a04a4ace959137f3c54bfe",
"reactionHash": "9b57a3c4c52b5f7c27d75cd6270e11b72e785d2699edfd66b3f9a6afc78b3e28"
},
"children": [
{
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"routeId": "sa_36b29e58905c0308c4be871d",
"moleculeId": "sa_d7f130279c6bf513f6af9d73",
"parentId": "13149",
"isLeaf": false,
"molecule": {
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"inchikey": "TZMNBTSWHWYOGK-UHFFFAOYSA-N",
"smiles": "COc1c(OC(F)F)ccc(Br)c1OCC(=O)O"
},
"smiles": "COc1c(OC(F)F)ccc(Br)c1OCC(=O)O",
"reactionStepId": "sa_aefc0ce0dbfd6c292185c4c1",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09051290B2;1021;1626542\",\"rsmi\":\"CC[O:9][C:7]([CH2:6][O:5][c:4]1[c:3]([O:2][CH3:1])[c:14]([O:15][CH:16]([F:17])[F:18])[cH:13][cH:12][c:10]1[Br:11])=[O:8]>C1CCOC1.O.[Li+].O>[CH3:1][O:2][c:3]1[c:4]([O:5][CH2:6][C:7](=[O:8])[OH:9])[c:10]([Br:11])[cH:12][cH:13][c:14]1[O:15][CH:16]([F:17])[F:18]\"},\"mapped_reaction_smiles\":\"CC[O:9][C:7]([CH2:6][O:5][c:4]1[c:3]([O:2][CH3:1])[c:14]([O:15][CH:16]([F:17])[F:18])[cH:13][cH:12][c:10]1[Br:11])=[O:8]>C1CCOC1.O.[Li+].O>[CH3:1][O:2][c:3]1[c:4]([O:5][CH2:6][C:7](=[O:8])[OH:9])[c:10]([Br:11])[cH:12][cH:13][c:14]1[O:15][CH:16]([F:17])[F:18]\"}",
"reactionStep": {
"id": "sa_aefc0ce0dbfd6c292185c4c1",
"reactionHash": "df0ddf0be6e9d1e16e421d30f0f7c7bdd4a86a49b4dd6447cafe30f938a64743"
},
"children": [
{
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"routeId": "sa_36b29e58905c0308c4be871d",
"moleculeId": "sa_f83508879d8b48c8b1cd4a3b",
"parentId": "13150",
"isLeaf": false,
"molecule": {
"id": "sa_f83508879d8b48c8b1cd4a3b",
"inchikey": "XBRGEQSIUCJLGL-UHFFFAOYSA-N",
"smiles": "CCOC(=O)COc1c(Br)ccc(OC(F)F)c1OC"
},
"smiles": "CCOC(=O)COc1c(Br)ccc(OC(F)F)c1OC",
"reactionStepId": "sa_68f7b1e09742596099afc420",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09051290B2;1020;1626541\",\"rsmi\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[c:9]([O:10][CH3:11])[c:12]([O:13][CH:14]([F:15])[F:16])[cH:17][cH:18][c:19]1[Br:20]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[c:9]([O:10][CH3:11])[c:12]([O:13][CH:14]([F:15])[F:16])[cH:17][cH:18][c:19]1[Br:20]\"},\"mapped_reaction_smiles\":\"Br[CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].[OH:7][c:8]1[c:9]([O:10][CH3:11])[c:12]([O:13][CH:14]([F:15])[F:16])[cH:17][cH:18][c:19]1[Br:20]>CC#N.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][O:7][c:8]1[c:9]([O:10][CH3:11])[c:12]([O:13][CH:14]([F:15])[F:16])[cH:17][cH:18][c:19]1[Br:20]\"}",
"reactionStep": {
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"children": [
{
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"isLeaf": true,
"molecule": {
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"smiles": "CCOC(=O)CBr"
},
"smiles": "CCOC(=O)CBr",
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{
"id": "13153",
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"molecule": {
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"inchikey": "VHOCBRYWMZWVBC-UHFFFAOYSA-N",
"smiles": "COc1c(OC(F)F)ccc(Br)c1O"
},
"smiles": "COc1c(OC(F)F)ccc(Br)c1O",
"reactionStepId": "sa_9c2506b93b706c8e890623a7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09051290B2;0944;1626501\",\"rsmi\":\"COC[O:5][c:4]1[c:3]([O:2][CH3:1])[c:10]([O:11][CH:12]([F:13])[F:14])[cH:9][cH:8][c:6]1[Br:7]>CO.Cl>[CH3:1][O:2][c:3]1[c:4]([OH:5])[c:6]([Br:7])[cH:8][cH:9][c:10]1[O:11][CH:12]([F:13])[F:14]\"},\"mapped_reaction_smiles\":\"COC[O:5][c:4]1[c:3]([O:2][CH3:1])[c:10]([O:11][CH:12]([F:13])[F:14])[cH:9][cH:8][c:6]1[Br:7]>CO.Cl>[CH3:1][O:2][c:3]1[c:4]([OH:5])[c:6]([Br:7])[cH:8][cH:9][c:10]1[O:11][CH:12]([F:13])[F:14]\"}",
"reactionStep": {
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"children": [
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"molecule": {
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"inchikey": "TWSVOIBPNWYHSL-UHFFFAOYSA-N",
"smiles": "COCOc1c(Br)ccc(OC(F)F)c1OC"
},
"smiles": "COCOc1c(Br)ccc(OC(F)F)c1OC",
"reactionStepId": "sa_5ed8bd6cd67d3776e6785b60",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US09051290B2;0915;1626489\",\"rsmi\":\"Cl[CH:12]([F:13])[F:14].[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([OH:11])[c:15]1[O:16][CH3:17]>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([O:11][CH:12]([F:13])[F:14])[c:15]1[O:16][CH3:17]\"},\"mapped_reaction_smiles\":\"Cl[CH:12]([F:13])[F:14].[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([OH:11])[c:15]1[O:16][CH3:17]>CN(C)C=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([O:11][CH:12]([F:13])[F:14])[c:15]1[O:16][CH3:17]\"}",
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"children": [
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"molecule": {
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"inchikey": "MOCOIAKQJPKKJC-UHFFFAOYSA-N",
"smiles": "COCOc1c(Br)ccc(O)c1OC"
},
"smiles": "COCOc1c(Br)ccc(O)c1OC",
"reactionStepId": "sa_29f045c84e2fcb507e9ab49e",
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"metadata": "{\"annotations\":{\"ID\":\"US09051290B2;0914;1626488\",\"rsmi\":\"Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([OH:11])[c:12]1[O:13][CH3:14]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([OH:11])[c:12]1[O:13][CH3:14]\"},\"mapped_reaction_smiles\":\"Cl[CH2:3][O:2][CH3:1].[OH:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([OH:11])[c:12]1[O:13][CH3:14]>CC(C)=O.O=C(O)O.[K+].[K+]>[CH3:1][O:2][CH2:3][O:4][c:5]1[c:6]([Br:7])[cH:8][cH:9][c:10]([OH:11])[c:12]1[O:13][CH3:14]\"}",
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{
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"smiles": "COc1c(O)ccc(Br)c1O"
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{
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"smiles": "FC(F)Cl"
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}
]
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]
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]
}
]
},
{
"id": "13159",
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"molecule": {
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"smiles": "CCCN"
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"smiles": "CCCN",
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]
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]
}
}