Benchmark Sets
Browse retrosynthesis benchmark datasets with ground truth routes
| Name | Description | Targets | Stock |
|---|---|---|---|
SMILES
CCc1c(NC(=S)NCCN)ccc2ocnc12
InChiKey
BOTATBVDXIPEQD-UHFFFAOYSA-N
Route Signature
0d7f3f90082bc11e900bb4e7c51c45d772e9e4f9014703370cba02ec7411344f
Synthesis route with 9 steps
Route tree structure (JSON format)
{
"route": {
"id": "sa_7b564b090a671b02590f8495",
"signature": "0d7f3f90082bc11e900bb4e7c51c45d772e9e4f9014703370cba02ec7411344f",
"contentHash": "0df3a396f5dd42e66de8ce042c1dd341edc949c9c6675ab5619ebf5bd8916a7e",
"length": 9,
"isConvergent": false
},
"target": {
"id": "sa_91387f6e420a39418983c0d0",
"benchmarkSetId": "a82783729b577c36f2e09a2b6fdd55ae9542aed5546571d67ef9cb74dc21f70a",
"targetId": "n5-00172",
"moleculeId": "sa_f4bc2f631eb73eaad3af7b8c",
"smiles": "CCc1c(NC(=S)NCCN)ccc2ocnc12",
"routeLength": 9,
"isConvergent": false,
"metadata": null,
"molecule": {
"id": "sa_f4bc2f631eb73eaad3af7b8c",
"inchikey": "BOTATBVDXIPEQD-UHFFFAOYSA-N",
"smiles": "CCc1c(NC(=S)NCCN)ccc2ocnc12"
},
"hasAcceptableRoutes": true,
"acceptableRoutesCount": 1
},
"rootNode": {
"id": "17809",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_f4bc2f631eb73eaad3af7b8c",
"parentId": null,
"isLeaf": false,
"molecule": {
"id": "sa_f4bc2f631eb73eaad3af7b8c",
"inchikey": "BOTATBVDXIPEQD-UHFFFAOYSA-N",
"smiles": "CCc1c(NC(=S)NCCN)ccc2ocnc12"
},
"smiles": "CCc1c(NC(=S)NCCN)ccc2ocnc12",
"reactionStepId": "sa_892d62f7bac2b58b73666b0b",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481957\",\"rsmi\":\"[CH3:1][CH2:2][c:3]1[c:4]([N:5]=[C:6]=[S:7])[cH:12][cH:13][c:14]2[c:15]1[n:16][cH:17][o:18]2.[NH2:8][CH2:9][CH2:10][NH2:11]>Cc1ccccc1>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[S:7])[NH:8][CH2:9][CH2:10][NH2:11])[cH:12][cH:13][c:14]2[c:15]1[n:16][cH:17][o:18]2\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][c:3]1[c:4]([N:5]=[C:6]=[S:7])[cH:12][cH:13][c:14]2[c:15]1[n:16][cH:17][o:18]2.[NH2:8][CH2:9][CH2:10][NH2:11]>Cc1ccccc1>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[S:7])[NH:8][CH2:9][CH2:10][NH2:11])[cH:12][cH:13][c:14]2[c:15]1[n:16][cH:17][o:18]2\"}",
"reactionStep": {
"id": "sa_892d62f7bac2b58b73666b0b",
"reactionHash": "fc25eb3cc4e765af3cdabae14d6997aa986e90f79e616f74b5c5e8800a9137b8"
},
"children": [
{
"id": "17810",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_9d6e2e22f9d099e672c3b9fa",
"parentId": "17809",
"isLeaf": true,
"molecule": {
"id": "sa_9d6e2e22f9d099e672c3b9fa",
"inchikey": "PIICEJLVQHRZGT-UHFFFAOYSA-N",
"smiles": "NCCN"
},
"smiles": "NCCN",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17811",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_dd14618c30aee21e698aad4a",
"parentId": "17809",
"isLeaf": false,
"molecule": {
"id": "sa_dd14618c30aee21e698aad4a",
"inchikey": "QSDCXPZKZWBTBC-UHFFFAOYSA-N",
"smiles": "CCc1c(N=C=S)ccc2ocnc12"
},
"smiles": "CCc1c(N=C=S)ccc2ocnc12",
"reactionStepId": "sa_31148bdec2094c86e092d8aa",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481956\",\"rsmi\":\"[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:8][cH:9][c:10]2[c:11]1[n:12][cH:13][o:14]2.c1ccc(O[C:6](Oc2ccccn2)=[S:7])nc1>ClCCl>[CH3:1][CH2:2][c:3]1[c:4]([N:5]=[C:6]=[S:7])[cH:8][cH:9][c:10]2[c:11]1[n:12][cH:13][o:14]2\"},\"mapped_reaction_smiles\":\"[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:8][cH:9][c:10]2[c:11]1[n:12][cH:13][o:14]2.c1ccc(O[C:6](Oc2ccccn2)=[S:7])nc1>ClCCl>[CH3:1][CH2:2][c:3]1[c:4]([N:5]=[C:6]=[S:7])[cH:8][cH:9][c:10]2[c:11]1[n:12][cH:13][o:14]2\"}",
"reactionStep": {
"id": "sa_31148bdec2094c86e092d8aa",
"reactionHash": "ce396a6bfb5b9a5f9d33b9c59cf68f1bf3f23041e7be36a5335fe11116342131"
},
"children": [
{
"id": "17812",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_4532ee8352faffbed122f8f4",
"parentId": "17811",
"isLeaf": true,
"molecule": {
"id": "sa_4532ee8352faffbed122f8f4",
"inchikey": "IKYOVSVBLHGFMA-UHFFFAOYSA-N",
"smiles": "S=C(Oc1ccccn1)Oc1ccccn1"
},
"smiles": "S=C(Oc1ccccn1)Oc1ccccn1",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17813",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_46787f67470dc7de8aebcd9b",
"parentId": "17811",
"isLeaf": false,
"molecule": {
"id": "sa_46787f67470dc7de8aebcd9b",
"inchikey": "JATKUHHROMUUBS-UHFFFAOYSA-N",
"smiles": "CCc1c(N)ccc2ocnc12"
},
"smiles": "CCc1c(N)ccc2ocnc12",
"reactionStepId": "sa_4c888c743ff193a4f8fdcc8e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481955\",\"rsmi\":\"O=C(C(F)(F)F)[NH:5][c:4]1[c:3]([CH2:2][CH3:1])[c:9]2[c:8]([cH:7][cH:6]1)[o:12][cH:11][n:10]2>CCOC(C)=O.CO.O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:8]2[c:9]1[n:10][cH:11][o:12]2\"},\"mapped_reaction_smiles\":\"O=C(C(F)(F)F)[NH:5][c:4]1[c:3]([CH2:2][CH3:1])[c:9]2[c:8]([cH:7][cH:6]1)[o:12][cH:11][n:10]2>CCOC(C)=O.CO.O.O=C(O)O.[K+].[K+]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:8]2[c:9]1[n:10][cH:11][o:12]2\"}",
"reactionStep": {
"id": "sa_4c888c743ff193a4f8fdcc8e",
"reactionHash": "cf20f946bc096a3798db44f0e81acd478372d144e7335b6b7ebaaab594f5a5c6"
},
"children": [
{
"id": "17814",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_b4bb4c48c7a30abd5c56d9c0",
"parentId": "17813",
"isLeaf": false,
"molecule": {
"id": "sa_b4bb4c48c7a30abd5c56d9c0",
"inchikey": "KQUQIGONUQSYDX-UHFFFAOYSA-N",
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc2ocnc12"
},
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc2ocnc12",
"reactionStepId": "sa_4b63781237799ae46fce3c86",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481954\",\"rsmi\":\"CCO[CH:17](OCC)OCC.[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([OH:18])[c:15]1[NH2:16]>CO.Cl>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]2[c:15]1[n:16][cH:17][o:18]2\"},\"mapped_reaction_smiles\":\"CCO[CH:17](OCC)OCC.[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([OH:18])[c:15]1[NH2:16]>CO.Cl>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]2[c:15]1[n:16][cH:17][o:18]2\"}",
"reactionStep": {
"id": "sa_4b63781237799ae46fce3c86",
"reactionHash": "57a219038ae625850701c46b5fc226bf6b148a6376b6dd4f7da30ff00bac1acc"
},
"children": [
{
"id": "17815",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_dc98236d967ab0cdbd0fcd04",
"parentId": "17814",
"isLeaf": true,
"molecule": {
"id": "sa_dc98236d967ab0cdbd0fcd04",
"inchikey": "GKASDNZWUGIAMG-UHFFFAOYSA-N",
"smiles": "CCOC(OCC)OCC"
},
"smiles": "CCOC(OCC)OCC",
"reactionStepId": null,
"template": null,
"metadata": null,
"reactionStep": null,
"children": []
},
{
"id": "17816",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_9a2c627429e9de7091a2ee66",
"parentId": "17814",
"isLeaf": false,
"molecule": {
"id": "sa_9a2c627429e9de7091a2ee66",
"inchikey": "LTAKARCJBJKWCI-UHFFFAOYSA-N",
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc(O)c1N"
},
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc(O)c1N",
"reactionStepId": "sa_cfc821d56188ea1d1501bdc7",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481953\",\"rsmi\":\"O=[N+:17]([O-])[c:16]1[c:3]([CH2:2][CH3:1])[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]1[OH:15]>CO.O=C(Nc1ccccc1O)C(F)(F)F.[Pd]>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([OH:15])[c:16]1[NH2:17]\"},\"mapped_reaction_smiles\":\"O=[N+:17]([O-])[c:16]1[c:3]([CH2:2][CH3:1])[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]1[OH:15]>CO.O=C(Nc1ccccc1O)C(F)(F)F.[Pd]>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([OH:15])[c:16]1[NH2:17]\"}",
"reactionStep": {
"id": "sa_cfc821d56188ea1d1501bdc7",
"reactionHash": "7c192e322ac0bbb8a607f706f1832e6ec47f21bec24bc0e6d8641ee65eaeb1b2"
},
"children": [
{
"id": "17817",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_aaa3cabc1bd3b534b66975e3",
"parentId": "17816",
"isLeaf": false,
"molecule": {
"id": "sa_aaa3cabc1bd3b534b66975e3",
"inchikey": "JBMJHCSHVZNEDC-UHFFFAOYSA-N",
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc(O)c1[N+](=O)[O-]"
},
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc(O)c1[N+](=O)[O-]",
"reactionStepId": "sa_3335e9c08b7816e4ace83376",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481952\",\"rsmi\":\"C[O:15][c:14]1[cH:13][cH:12][c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[c:3]([CH2:2][CH3:1])[c:16]1[N+:17](=[O:18])[O-:19]>BrB(Br)Br.CO.ClCCl.O>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([OH:15])[c:16]1[N+:17](=[O:18])[O-:19]\"},\"mapped_reaction_smiles\":\"C[O:15][c:14]1[cH:13][cH:12][c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[c:3]([CH2:2][CH3:1])[c:16]1[N+:17](=[O:18])[O-:19]>BrB(Br)Br.CO.ClCCl.O>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([OH:15])[c:16]1[N+:17](=[O:18])[O-:19]\"}",
"reactionStep": {
"id": "sa_3335e9c08b7816e4ace83376",
"reactionHash": "ba5c4a8ac72b2789e964fa46b0d22e6f041db9c2b98c4f201933f0722a65b5a0"
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"children": [
{
"id": "17818",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_72b00fa0ab79f8158b3a0a3a",
"parentId": "17817",
"isLeaf": false,
"molecule": {
"id": "sa_72b00fa0ab79f8158b3a0a3a",
"inchikey": "DDRLTKBSMZJARP-UHFFFAOYSA-N",
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc(OC)c1[N+](=O)[O-]"
},
"smiles": "CCc1c(NC(=O)C(F)(F)F)ccc(OC)c1[N+](=O)[O-]",
"reactionStepId": "sa_976def415d0159d29a7e1f7e",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481951\",\"rsmi\":\"O=C(O[C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])C(F)(F)F.[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]1[N+:18](=[O:19])[O-:20]>CCN(CC)CC.Cl.ClCCl>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]1[N+:18](=[O:19])[O-:20]\"},\"mapped_reaction_smiles\":\"O=C(O[C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])C(F)(F)F.[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]1[N+:18](=[O:19])[O-:20]>CCN(CC)CC.Cl.ClCCl>[CH3:1][CH2:2][c:3]1[c:4]([NH:5][C:6](=[O:7])[C:8]([F:9])([F:10])[F:11])[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]1[N+:18](=[O:19])[O-:20]\"}",
"reactionStep": {
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"reactionHash": "a69fc038ec30efe1534985878c336e7a27f068e54f781b33ec991bd7789212f7"
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"children": [
{
"id": "17819",
"routeId": "sa_7b564b090a671b02590f8495",
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"molecule": {
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"inchikey": "QAEDZJGFFMLHHQ-UHFFFAOYSA-N",
"smiles": "O=C(OC(=O)C(F)(F)F)C(F)(F)F"
},
"smiles": "O=C(OC(=O)C(F)(F)F)C(F)(F)F",
"reactionStepId": null,
"template": null,
"metadata": null,
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},
{
"id": "17820",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_304df1267288301ee17ebe7b",
"parentId": "17818",
"isLeaf": false,
"molecule": {
"id": "sa_304df1267288301ee17ebe7b",
"inchikey": "WFUYAAWWVMWGEF-UHFFFAOYSA-N",
"smiles": "CCc1c(N)ccc(OC)c1[N+](=O)[O-]"
},
"smiles": "CCc1c(N)ccc(OC)c1[N+](=O)[O-]",
"reactionStepId": "sa_d710a0bc534716a1ecacee1a",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481950\",\"rsmi\":\"O=[N+:5]([O-])[c:4]1[c:3]([CH2:2][CH3:1])[c:11]([N+:12](=[O:13])[O-:14])[c:8]([O:9][CH3:10])[cH:7][cH:6]1>CO.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]1[N+:12](=[O:13])[O-:14]\"},\"mapped_reaction_smiles\":\"O=[N+:5]([O-])[c:4]1[c:3]([CH2:2][CH3:1])[c:11]([N+:12](=[O:13])[O-:14])[c:8]([O:9][CH3:10])[cH:7][cH:6]1>CO.O=C(O)O.[Na+].[Na+]>[CH3:1][CH2:2][c:3]1[c:4]([NH2:5])[cH:6][cH:7][c:8]([O:9][CH3:10])[c:11]1[N+:12](=[O:13])[O-:14]\"}",
"reactionStep": {
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"reactionHash": "efd4028fd37bf55462fd6852c70ebb58781bb9823eed0828031cf940e4c99afb"
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"children": [
{
"id": "17821",
"routeId": "sa_7b564b090a671b02590f8495",
"moleculeId": "sa_31f08a92f20553637bb019f9",
"parentId": "17820",
"isLeaf": false,
"molecule": {
"id": "sa_31f08a92f20553637bb019f9",
"inchikey": "JEZHIWJEZSKGSL-UHFFFAOYSA-N",
"smiles": "CCc1c([N+](=O)[O-])ccc(OC)c1[N+](=O)[O-]"
},
"smiles": "CCc1c([N+](=O)[O-])ccc(OC)c1[N+](=O)[O-]",
"reactionStepId": "sa_4af89caa5ea79b9ae1817060",
"template": null,
"metadata": "{\"annotations\":{\"ID\":\"US06110952;;481949\",\"rsmi\":\"O[N+:5](=[O:6])[O-:7].[CH3:1][CH2:2][c:3]1[cH:4][cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]1[N+:14](=[O:15])[O-:16]>CC(=O)O.O=S(=O)(O)O>[CH3:1][CH2:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]1[N+:14](=[O:15])[O-:16]\"},\"mapped_reaction_smiles\":\"O[N+:5](=[O:6])[O-:7].[CH3:1][CH2:2][c:3]1[cH:4][cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]1[N+:14](=[O:15])[O-:16]>CC(=O)O.O=S(=O)(O)O>[CH3:1][CH2:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][cH:9][c:10]([O:11][CH3:12])[c:13]1[N+:14](=[O:15])[O-:16]\"}",
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