Unnamed: 0
int64 0
445k
| level_0
int64 0
1.94M
| index
float64 0
1.81M
⌀ | original_rxn
stringlengths 104
2.67k
| fragments
stringlengths 6
161
⌀ | source
stringlengths 11
26
| year
int64 1.98k
2.02k
| mapped_rxn
stringlengths 110
2.63k
| confidence
float64 0
1
| canonical_rxn_with_fragment_info
stringlengths 25
599
| canonical_rxn
stringlengths 25
599
| ID
stringlengths 17
32
| reaction_hash
stringlengths 56
56
| reactants
stringlengths 55
1.33k
| products
stringlengths 51
1.3k
| retro_template
stringlengths 46
417
| template_hash
stringclasses 1k
values | selectivity
float64 0
1
| outcomes
float64 1
15
| reagents
stringlengths 1
370
⌀ | labels
int64 0
999
|
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
5,191 | 27,025 | 38,813 | [NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[Na+].[Br:14][CH2:15][C:16](Br)=[O:17]>C(O)(=O)C>[OH:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:1][C:16](=[O:17])[CH2:15][Br:14] | |f:1.2| | US04081474_ | 1,978 | Br[C:2](=[O:1])[CH2:3][Br:4].CC(=O)O.CC(=O)[O-].[NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]1.[Na+]>>[O:1]=[C:2]([CH2:3][Br:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]1 | 0.941797 | CC(=O)O.CC(=O)[O-]~[Na+].Nc1cccc(O)c1.O=C(Br)CBr>>O=C(CBr)Nc1cccc(O)c1 | CC(=O)O.CC(=O)[O-].Nc1cccc(O)c1.O=C(Br)CBr.[Na+]>>O=C(CBr)Nc1cccc(O)c1 | US04081474_grants | 755e8ecffd18aeb142a8cb9a1836ba94950edc5c35826ffbd5abdf89 | Br[C:2](=[O:1])[CH2:3][Br:4].CC(=O)O.CC(=O)[O-].[NH2:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]1.[Na+] | [O:1]=[C:2]([CH2:3][Br:4])[NH:5][c:6]1[cH:7][cH:8][cH:9][c:10]([OH:11])[cH:12]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[c:5])>>(Br-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[c:5]) | 8ab04841592f589cf1861a16fea6663af1db3cbfa5e5cb1096e666bd | 1 | 1 | CC(=O)O.CC(=O)[O-].[Na+] | 442 |
7,279 | 37,373 | 58,685 | [C:1]([C:4](=[O:17])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=1)=[O:6])([OH:3])=[O:2]>[Pd].CO>[C:1]([C:4](=[O:17])[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([NH2:14])[CH:9]=1)=[O:6])([OH:3])=[O:2] | null | US04165365_ | 1,979 | CO.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[C:10](=[O:11])[C:12](=[O:13])[OH:14])[cH:15]1.[Pd]>>[NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[C:10](=[O:11])[C:12](=[O:13])[OH:14])[cH:15]1 | 0.93706 | CO.O=C(O)C(=O)C(=O)Nc1cccc([N+](=O)[O-])c1.[Pd]>>Nc1cccc(NC(=O)C(=O)C(=O)O)c1 | CO.O=C(O)C(=O)C(=O)Nc1cccc([N+](=O)[O-])c1.[Pd]>>Nc1cccc(NC(=O)C(=O)C(=O)O)c1 | US04165365_grants | ef4c3d32c587829caeb680517c923030139498cfe18fe3604bce2f30 | CO.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[C:10](=[O:11])[C:12](=[O:13])[OH:14])[cH:15]1.[Pd] | [NH2:1][c:2]1[cH:3][cH:4][cH:5][c:6]([NH:7][C:8](=[O:9])[C:10](=[O:11])[C:12](=[O:13])[OH:14])[cH:15]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd] | 1 |
295,921 | 963,717 | 1,621,430 | Br[C:2]1[C:3]([O:10][CH:11]([F:13])[F:12])=[N:4][CH:5]=[C:6]([CH2:8][Br:9])[CH:7]=1.[Cl:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1>>[Br:9][CH2:8][C:6]1[CH:7]=[C:2]([C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:14])[CH:20]=2)[C:3]([O:10][CH:11]([F:13])[F:12])=[N:4][CH:5]=1 | null | US09040692B2_0417 | 2,015 | Br[c:12]1[c:5]([O:4][CH:2]([F:1])[F:3])[n:6][cH:7][c:8]([CH2:9][Br:10])[cH:11]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1>>[F:1][CH:2]([F:3])[O:4][c:5]1[n:6][cH:7][c:8]([CH2:9][Br:10])[cH:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1 | 0.726311 | FC(F)Oc1ncc(CBr)cc1Br.OB(O)c1cccc(Cl)c1>>FC(F)Oc1ncc(CBr)cc1-c1cccc(Cl)c1 | FC(F)Oc1ncc(CBr)cc1Br.OB(O)c1cccc(Cl)c1>>FC(F)Oc1ncc(CBr)cc1-c1cccc(Cl)c1 | US09040692B2_0417grants | 10a99b5ab94c2207a095f763536861bbe90ae89aac56ee184ed1d9fe | Br[c:12]1[c:5]([O:4][CH:2]([F:1])[F:3])[n:6][cH:7][c:8]([CH2:9][Br:10])[cH:11]1.OB(O)[c:13]1[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1 | [F:1][CH:2]([F:3])[O:4][c:5]1[n:6][cH:7][c:8]([CH2:9][Br:10])[cH:11][c:12]1-[c:13]1[cH:14][cH:15][cH:16][c:17]([Cl:18])[cH:19]1 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[c:2])-[c;H0;D3;+0:5](:[c:6]):[c:7])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]:[#7;a:4]).(O-B(-O)-[c;H0;D3;+0:5](:[c:6]):[c:7]) | d9e3b3a2cfe6e8e4f2db101af24fed0e1646b47d310510c8f6dc03e2 | 1 | 1 | null | 833 |
425,403 | 1,807,749 | null | [C:1]1([C:7]2([CH3:24])[CH2:12][N:11]([CH2:13][CH:14]([OH:21])[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:10](=[O:22])[N:9]([CH3:23])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.CN(C=O)C.[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl.O>[C:1]1([C:7]2([CH3:24])[CH2:8][N:9]([CH3:23])[C:10](=[O:22])[N:11]([CH2:13][C:14](=[O:21])[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:12]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1 | |f:2.3.4| | US20150376136A1_0476 | 2,015 | CN(C)C=O.ClCCl.O.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([C:6]2=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][N:13]([CH2:14][CH:15]([OH:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C:23]1=[O:24].c1cc[nH+]cc1.c1cc[nH+]cc1>>[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([C:6]2=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][N:13]([CH2:14][C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C:23]1=[O:24] | 0.846559 | CN(C)C=O.CN1CC(C)(C2=CCCCC2)CN(CC(O)c2ccccc2)C1=O.ClCCl.O.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-]~c1cc[nH+]cc1~c1cc[nH+]cc1>>CN1CC(C)(C2=CCCCC2)CN(CC(=O)c2ccccc2)C1=O | CN(C)C=O.CN1CC(C)(C2=CCCCC2)CN(CC(O)c2ccccc2)C1=O.ClCCl.O.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].c1cc[nH+]cc1.c1cc[nH+]cc1>>CN1CC(C)(C2=CCCCC2)CN(CC(=O)c2ccccc2)C1=O | US20150376136A1_0476apps | 1a4edd7c8f332426227d459c162ea59c96b7cbc7c20ca2af5117b751 | CN(C)C=O.ClCCl.O.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].[CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([C:6]2=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][N:13]([CH2:14][CH:15]([OH:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C:23]1=[O:24].c1cc[nH+]cc1.c1cc[nH+]cc1 | [CH3:1][N:2]1[CH2:3][C:4]([CH3:5])([C:6]2=[CH:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH2:12][N:13]([CH2:14][C:15](=[O:16])[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[C:23]1=[O:24] | ([C:1]-[C;H0;D3;+0:2](=[O;H0;D1;+0:3])-[c:4])>>([C:1]-[CH;D3;+0:2](-[OH;D1;+0:3])-[c:4]) | e3761dd8779ed2c76826399776efc0a057df5223967be1430eab4eb1 | 1 | 1 | CN(C)C=O.ClCCl.O.O=[Cr](=O)([O-])O[Cr](=O)(=O)[O-].c1cc[nH+]cc1.c1cc[nH+]cc1 | 32 |