Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
C[C@H]1CN(S(C)(=O)=O)C[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12
InChiKey
UUUHLLNUHQUDBU-GZMMTYOYSA-N
Route Signature
f4f8bc8c1aa05110e6bde709f325822d2bba2669c776e82f2917d4b5b9e4c7e0
Synthesis route with 5 steps (convergent)
Route tree structure (JSON format)
{
"route": {
"id": "sa_ae3601ed084ff02ae934f207",
"signature": "f4f8bc8c1aa05110e6bde709f325822d2bba2669c776e82f2917d4b5b9e4c7e0",
"contentHash": "afa8027288331f89747a388e1957deb153d4f4ad68a33dfcce51ee95bf30b5fe",
"length": 5,
"isConvergent": true
},
"target": {
"id": "sa_561254a2df5ecf81f668fec1",
"benchmarkSetId": "3895c2909c53593560c5ba610abc7e6df80513dfd8624165c560451735097d36",
"targetId": "n5-02114",
"moleculeId": "sa_26ed2bc52ee171198cc1f14b",
"smiles": "C[C@H]1CN(S(C)(=O)=O)C[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12",
"routeLength": 5,
"isConvergent": true,
"metadata": null,
"molecule": {
"id": "sa_26ed2bc52ee171198cc1f14b",
"inchikey": "UUUHLLNUHQUDBU-GZMMTYOYSA-N",
"smiles": "C[C@H]1CN(S(C)(=O)=O)C[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "10608",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_26ed2bc52ee171198cc1f14b",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_26ed2bc52ee171198cc1f14b",
"inchikey": "UUUHLLNUHQUDBU-GZMMTYOYSA-N",
"smiles": "C[C@H]1CN(S(C)(=O)=O)C[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12"
},
"smiles": "C[C@H]1CN(S(C)(=O)=O)C[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12",
"reactionStepId": "sa_1f023863510d57c9557dff21",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08987268B2;0974;1595386\",\"rsmi\":\"Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:9][C@H:10]1[NH:11][c:12]1[c:13]([C:14]([NH2:15])=[O:16])[cH:17][n:18][n:19]2[cH:20][c:21]([Br:22])[cH:23][c:24]12>CCN(C(C)C)C(C)C.ClCCl.I.O>[CH3:1][C@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][C@H:10]1[NH:11][c:12]1[c:13]([C:14]([NH2:15])=[O:16])[cH:17][n:18][n:19]2[cH:20][c:21]([Br:22])[cH:23][c:24]12\"},\"mapped_reaction_smiles\":\"Cl[S:5]([CH3:6])(=[O:7])=[O:8].[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:9][C@H:10]1[NH:11][c:12]1[c:13]([C:14]([NH2:15])=[O:16])[cH:17][n:18][n:19]2[cH:20][c:21]([Br:22])[cH:23][c:24]12>CCN(C(C)C)C(C)C.ClCCl.I.O>[CH3:1][C@H:2]1[CH2:3][N:4]([S:5]([CH3:6])(=[O:7])=[O:8])[CH2:9][C@H:10]1[NH:11][c:12]1[c:13]([C:14]([NH2:15])=[O:16])[cH:17][n:18][n:19]2[cH:20][c:21]([Br:22])[cH:23][c:24]12\"}",
"reactionStep": {
"id": "sa_1f023863510d57c9557dff21",
"reactionHash": "b7067d1ee6364915c1b6c728b5574b7557f65d4fb03f99b05c9cc9e8e4467c97"
},
"children": [
{
"id": "10609",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_2b3c4580ddaafc7cc8835b48",
"parentId": "10608",
"isLeaf": false,
"molecule": {
"id": "sa_2b3c4580ddaafc7cc8835b48",
"inchikey": "CKHWAIIGSRDBPN-OIBJUYFYSA-N",
"smiles": "C[C@H]1CNC[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12"
},
"smiles": "C[C@H]1CNC[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12",
"reactionStepId": "sa_012703fb0e8dec61ab80b3b6",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08987268B2;0928;1595372\",\"rsmi\":\"O=C(OCc1ccccc1)[N:4]1[CH2:3][C@H:2]([CH3:1])[C@H:6]([NH:7][c:8]2[c:9]([C:10]([NH2:11])=[O:12])[cH:13][n:14][n:15]3[cH:16][c:17]([Br:18])[cH:19][c:20]23)[CH2:5]1>CC#N.C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1N.C[Si](C)(C)I.NC(=O)c1cnn2cc(Br)cc2c1Cl>[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[NH:7][c:8]1[c:9]([C:10]([NH2:11])=[O:12])[cH:13][n:14][n:15]2[cH:16][c:17]([Br:18])[cH:19][c:20]12\"},\"mapped_reaction_smiles\":\"O=C(OCc1ccccc1)[N:4]1[CH2:3][C@H:2]([CH3:1])[C@H:6]([NH:7][c:8]2[c:9]([C:10]([NH2:11])=[O:12])[cH:13][n:14][n:15]3[cH:16][c:17]([Br:18])[cH:19][c:20]23)[CH2:5]1>CC#N.C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1N.C[Si](C)(C)I.NC(=O)c1cnn2cc(Br)cc2c1Cl>[CH3:1][C@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[NH:7][c:8]1[c:9]([C:10]([NH2:11])=[O:12])[cH:13][n:14][n:15]2[cH:16][c:17]([Br:18])[cH:19][c:20]12\"}",
"reactionStep": {
"id": "sa_012703fb0e8dec61ab80b3b6",
"reactionHash": "d949d1209208b43fe15d7758e2ee2223d3d0a69b27e8e52eec46861d3cd02e50"
},
"children": [
{
"id": "10610",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_c8ddde1d514b83c1764c5f5c",
"parentId": "10609",
"isLeaf": false,
"molecule": {
"id": "sa_c8ddde1d514b83c1764c5f5c",
"inchikey": "CWGUZDWSGIJRNW-SUMWQHHRSA-N",
"smiles": "C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12"
},
"smiles": "C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1Nc1c(C(N)=O)cnn2cc(Br)cc12",
"reactionStepId": "sa_d5ee9a625860e8adc4db1665",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08987268B2;0808;1595339\",\"rsmi\":\"Cl[c:18]1[c:19]([C:20]([NH2:21])=[O:22])[cH:23][n:24][n:25]2[cH:26][c:27]([Br:28])[cH:29][c:30]12.[CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C@H:16]1[NH2:17]>CC(=O)N(C)C.CCN(C(C)C)C(C)C>[CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C@H:16]1[NH:17][c:18]1[c:19]([C:20]([NH2:21])=[O:22])[cH:23][n:24][n:25]2[cH:26][c:27]([Br:28])[cH:29][c:30]12\"},\"mapped_reaction_smiles\":\"Cl[c:18]1[c:19]([C:20]([NH2:21])=[O:22])[cH:23][n:24][n:25]2[cH:26][c:27]([Br:28])[cH:29][c:30]12.[CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C@H:16]1[NH2:17]>CC(=O)N(C)C.CCN(C(C)C)C(C)C>[CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C@H:16]1[NH:17][c:18]1[c:19]([C:20]([NH2:21])=[O:22])[cH:23][n:24][n:25]2[cH:26][c:27]([Br:28])[cH:29][c:30]12\"}",
"reactionStep": {
"id": "sa_d5ee9a625860e8adc4db1665",
"reactionHash": "a5a0ae5614d987343daf94f7837a6f1f429486d42134cd91d67115a57cea09cb"
},
"children": [
{
"id": "10611",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_dd2f4a7d8b4d95d6d5d5299e",
"parentId": "10610",
"isLeaf": false,
"molecule": {
"id": "sa_dd2f4a7d8b4d95d6d5d5299e",
"inchikey": "CPJUWOTXCPVZOC-UHFFFAOYSA-N",
"smiles": "NC(=O)c1cnn2cc(Br)cc2c1Cl"
},
"smiles": "NC(=O)c1cnn2cc(Br)cc2c1Cl",
"reactionStepId": "sa_f32e767851aeb1c7f2a0af1d",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08987268B2;0612;1595274\",\"rsmi\":\"O=S(=O)(O)[OH:3].[N:1]#[C:2][c:4]1[c:5]([Cl:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][n:12]2[n:13][cH:14]1>>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([Cl:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][n:12]2[n:13][cH:14]1\"},\"mapped_reaction_smiles\":\"O=S(=O)(O)[OH:3].[N:1]#[C:2][c:4]1[c:5]([Cl:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][n:12]2[n:13][cH:14]1>>[NH2:1][C:2](=[O:3])[c:4]1[c:5]([Cl:6])[c:7]2[cH:8][c:9]([Br:10])[cH:11][n:12]2[n:13][cH:14]1\"}",
"reactionStep": {
"id": "sa_f32e767851aeb1c7f2a0af1d",
"reactionHash": "066737a265ee81025e61770b8ca8c4b5c2794784b8f9738a8aa654e27e49f598"
},
"children": [
{
"id": "10612",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_abb0f00ea0ed545ace6e84b3",
"parentId": "10611",
"isLeaf": false,
"molecule": {
"id": "sa_abb0f00ea0ed545ace6e84b3",
"inchikey": "HWAKDBSHORTLIK-UHFFFAOYSA-N",
"smiles": "N#Cc1cnn2cc(Br)cc2c1Cl"
},
"smiles": "N#Cc1cnn2cc(Br)cc2c1Cl",
"reactionStepId": "sa_b2aa85038bdb5e2545963c38",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08987268B2;0611;1595273\",\"rsmi\":\"O=P(Cl)(Cl)[Cl:5].O[c:4]1[c:3]([C:2]#[N:1])[cH:13][n:12][n:11]2[c:6]1[cH:7][c:8]([Br:9])[cH:10]2>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[c:6]2[cH:7][c:8]([Br:9])[cH:10][n:11]2[n:12][cH:13]1\"},\"mapped_reaction_smiles\":\"O=P(Cl)(Cl)[Cl:5].O[c:4]1[c:3]([C:2]#[N:1])[cH:13][n:12][n:11]2[c:6]1[cH:7][c:8]([Br:9])[cH:10]2>>[N:1]#[C:2][c:3]1[c:4]([Cl:5])[c:6]2[cH:7][c:8]([Br:9])[cH:10][n:11]2[n:12][cH:13]1\"}",
"reactionStep": {
"id": "sa_b2aa85038bdb5e2545963c38",
"reactionHash": "6d107e6f0870fb2bc92127e33ab9e9d941e9079ebc8a2b8492fe254d4b67c259"
},
"children": [
{
"id": "10613",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_71d001c55e7ddf90716c8c57",
"parentId": "10612",
"isLeaf": true,
"molecule": {
"id": "sa_71d001c55e7ddf90716c8c57",
"inchikey": "DVIVVUSUTCHYGA-UHFFFAOYSA-N",
"smiles": "N#Cc1cnn2cc(Br)cc2c1O"
},
"smiles": "N#Cc1cnn2cc(Br)cc2c1O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "10614",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_312a7cd3d48a055e9bc98180",
"parentId": "10612",
"isLeaf": true,
"molecule": {
"id": "sa_312a7cd3d48a055e9bc98180",
"inchikey": "XHXFXVLFKHQFAL-UHFFFAOYSA-N",
"smiles": "O=P(Cl)(Cl)Cl"
},
"smiles": "O=P(Cl)(Cl)Cl",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10615",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_a538ca410f1833f7a9788be8",
"parentId": "10611",
"isLeaf": true,
"molecule": {
"id": "sa_a538ca410f1833f7a9788be8",
"inchikey": "QAOWNCQODCNURD-UHFFFAOYSA-N",
"smiles": "O=S(=O)(O)O"
},
"smiles": "O=S(=O)(O)O",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
}
]
},
{
"id": "10616",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_2080f62cc4dce2bd1467a658",
"parentId": "10610",
"isLeaf": false,
"molecule": {
"id": "sa_2080f62cc4dce2bd1467a658",
"inchikey": "ZSIMEKCEGXWPDZ-CMPLNLGQSA-N",
"smiles": "C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1N"
},
"smiles": "C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1N",
"reactionStepId": "sa_3439c3ff87f7364b555f52df",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US08987268B2;0644;1595288\",\"rsmi\":\"[N-]=[N+]=[N:17][C@H:16]1[C@@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1>CC#N.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C@H:16]1[NH2:17]\"},\"mapped_reaction_smiles\":\"[N-]=[N+]=[N:17][C@H:16]1[C@@H:2]([CH3:1])[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15]1>CC#N.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>[CH3:1][C@H:2]1[CH2:3][N:4]([C:5](=[O:6])[O:7][CH2:8][c:9]2[cH:10][cH:11][cH:12][cH:13][cH:14]2)[CH2:15][C@H:16]1[NH2:17]\"}",
"reactionStep": {
"id": "sa_3439c3ff87f7364b555f52df",
"reactionHash": "3ed6f1238c1abf99cb128e6c6e9bfd60e82e6eb296971a2dc82e582089cd95b9"
},
"children": [
{
"id": "10617",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_db788703838d7b24d12be3b2",
"parentId": "10616",
"isLeaf": true,
"molecule": {
"id": "sa_db788703838d7b24d12be3b2",
"inchikey": "WJDBVXAAUDUEMH-CMPLNLGQSA-N",
"smiles": "C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1N=[N+]=[N-]"
},
"smiles": "C[C@H]1CN(C(=O)OCc2ccccc2)C[C@H]1N=[N+]=[N-]",
"reactionStepId": null,
"template": null,
"metadata": null,
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}
]
}
]
}
]
},
{
"id": "10618",
"routeId": "sa_ae3601ed084ff02ae934f207",
"moleculeId": "sa_d2a31ea58046b00856f61ca5",
"parentId": "10608",
"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": []
}
]
}
}