B3DB_classification_index
stringlengths
21
24
compound_name
stringlengths
1
325
IUPAC_name
stringlengths
4
616
SMILES
stringlengths
1
382
CID
float64
11
155M
logBB
float64
-2.69
1.64
BBB+/BBB-
class label
2 classes
Inchi
stringlengths
11
785
threshold
float64
-1
-1
reference
stringclasses
772 values
group
stringclasses
1 value
comments
stringclasses
2 values
ClusterNo
int64
1
211
MolCount
int64
1
2.21k
B3DB_classification_1
sulphasalazine
2-hydroxy-5-[[4-(pyridin-2-ylsulfamoyl)phenyl]diazenyl]benzoic acid
O=C(O)c1cc(N=Nc2ccc(S(=O)(=O)Nc3ccccn3)cc2)ccc1O
5,339
-2.69
0BBB-
InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)
null
R2|R2|R25|R46|
training
null
1
2,208
B3DB_classification_23
raloxifene
[6-hydroxy-2-(4-hydroxyphenyl)-1-benzothiophen-3-yl]-[4-(2-piperidin-1-ylethoxy)phenyl]methanone
O=C(c1ccc(OCCN2CCCCC2)cc1)c1c(-c2ccc(O)cc2)sc2cc(O)ccc12
5,035
-1.81
0BBB-
InChI=1S/C28H27NO4S/c30-21-8-4-20(5-9-21)28-26(24-13-10-22(31)18-25(24)34-28)27(32)19-6-11-23(12-7-19)33-17-16-29-14-2-1-3-15-29/h4-13,18,30-31H,1-3,14-17H2
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_25
chlorambucil
4-[4-[bis(2-chloroethyl)amino]phenyl]butanoic acid
O=C(O)CCCc1ccc(N(CCCl)CCCl)cc1
2,708
-1.7
0BBB-
InChI=1S/C14H19Cl2NO2/c15-8-10-17(11-9-16)13-6-4-12(5-7-13)2-1-3-14(18)19/h4-7H,1-3,8-11H2,(H,18,19)
null
R18|R26|R27|R2|R2|R5|R8|R17|R21|R25|R27|R27|R35|R36|R39|R43|R46|R47|R49|R40|
training
null
1
2,208
B3DB_classification_28
flurbiprofen
2-(3-fluoro-4-phenylphenyl)propanoic acid
CC(C(=O)O)c1ccc(-c2ccccc2)c(F)c1
3,394
-1.68
0BBB-
InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)
null
R2|R2|R18|R20|R25|R26|R27|R46|
training
null
1
2,208
B3DB_classification_30
d-mannitol
(2r,3r,4r,5r)-hexane-1,2,3,4,5,6-hexol
OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
6,251
-1.6
0BBB-
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4-,5-,6-/m1/s1
null
R31|R8|R21|
training
null
1
2,208
B3DB_classification_31
mannitol (d-mannitol)
hexane-1,2,3,4,5,6-hexol
OCC(O)C(O)C(O)C(O)CO
453
-1.6
0BBB-
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2
null
R2|R2|R3|R18|R25|R26|R27|R27|R38|R40|R41|R43|R46|R47|
training
null
1
2,208
B3DB_classification_32
compound 34
n-[3-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]phenyl]acetamide
CC(=O)Nc1cccc(-c2csc(N=C(N)N)n2)c1
14,022,511
-1.57
0BBB-
InChI=1S/C12H13N5OS/c1-7(18)15-9-4-2-3-8(5-9)10-6-19-12(16-10)17-11(13)14/h2-6H,1H3,(H,15,18)(H4,13,14,16,17)
null
R2|R2|R8|R40|R3|R3|R12|R18|R25|R26|R27|R35|R36|R38|R38|R41|R41|R43|R46|R47|R48|R49|R49|R4|
training
null
1
2,208
B3DB_classification_35
chebi: 145922
1-cyano-3-[3-[2-(diaminomethylideneamino)-1,3-thiazol-4-yl]phenyl]-2-methylguanidine
CN=C(NC#N)Nc1cccc(-c2csc(N=C(N)N)n2)c1
14,022,519
-1.54
0BBB-
InChI=1S/C13H14N8S/c1-17-12(18-7-14)19-9-4-2-3-8(5-9)10-6-22-13(20-10)21-11(15)16/h2-6H,1H3,(H2,17,18,19)(H4,15,16,20,21)
null
R2|R2|R2|R2|R3|R3|R8|R12|R18|R21|R25|R25|R26|R27|R27|R35|R36|R38|R38|R40|R41|R41|R43|R46|R46|R47|R48|R49|R4|R41|
training
null
1
2,208
B3DB_classification_36
guanidinothiazol analogue 17 ac1lbibi -- pubmed
2-[4-(3,4-dihydroxyphenyl)-1,3-thiazol-2-yl]guanidine
NC(N)=Nc1nc(-c2ccc(O)c(O)c2)cs1
536,278
-1.54
0BBB-
InChI=1S/C10H10N4O2S/c11-9(12)14-10-13-6(4-17-10)5-1-2-7(15)8(16)3-5/h1-4,15-16H,(H4,11,12,13,14)
null
R47|
training
null
1
2,208
B3DB_classification_40
chembl151192
n-[2-[4-[3-(ethylamino)pyridin-2-yl]piperazine-1-carbonyl]-1h-indol-5-yl]methanesulfonamide
CCNc1cccnc1N1CCN(C(=O)c2cc3cc(NS(C)(=O)=O)ccc3[nH]2)CC1
468,305
-1.52
0BBB-
InChI=1S/C21H26N6O3S/c1-3-22-18-5-4-8-23-20(18)26-9-11-27(12-10-26)21(28)19-14-15-13-16(25-31(2,29)30)6-7-17(15)24-19/h4-8,13-14,22,24-25H,3,9-12H2,1-2H3
null
R46|
training
null
1
2,208
B3DB_classification_43
baclofen
4-amino-3-(4-chlorophenyl)butanoic acid
NCC(CC(=O)O)c1ccc(Cl)cc1
2,284
-1.52
0BBB-
InChI=1S/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14)
null
R2|R2|R25|R46|
training
null
1
2,208
B3DB_classification_46
imatinib
4-[(4-methylpiperazin-1-yl)methyl]-n-[4-methyl-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]phenyl]benzamide
Cc1ccc(NC(=O)c2ccc(CN3CCN(C)CC3)cc2)cc1Nc1nccc(-c2cccnc2)n1
5,291
-1.5
0BBB-
InChI=1S/C29H31N7O/c1-21-5-10-25(18-27(21)34-29-31-13-11-26(33-29)24-4-3-12-30-19-24)32-28(37)23-8-6-22(7-9-23)20-36-16-14-35(2)15-17-36/h3-13,18-19H,14-17,20H2,1-2H3,(H,32,37)(H,31,33,34)
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_49
4-hydroxyalprazolam
8-chloro-1-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-ol
Cc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2O
182,017
-1.48
0BBB-
InChI=1S/C17H13ClN4O/c1-10-20-21-16-17(23)19-15(11-5-3-2-4-6-11)13-9-12(18)7-8-14(13)22(10)16/h2-9,17,23H,1H3
null
R2|R2|R8|R12|R21|R25|R27|R40|R43|R46|R47|
training
null
1
2,208
B3DB_classification_51
atenolol
null
CC(C)NC(O)COc1ccc(CC(N)=O)cc1
null
-1.42
0BBB-
InChI=1S/C13H20N2O3/c1-9(2)15-13(17)8-18-11-5-3-10(4-6-11)7-12(14)16/h3-6,9,13,15,17H,7-8H2,1-2H3,(H2,14,16)
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_61
4-aminobenzoic acid
4-aminobenzoic acid
Nc1ccc(C(=O)O)cc1
978
-1.4
0BBB-
InChI=1S/C7H7NO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,8H2,(H,9,10)
null
R47|
training
null
1
2,208
B3DB_classification_62
null
null
CCOc1ccc(C(=O)c2cccc3ccccc23)c2ccccc12
null
-1.39
0BBB-
InChI=1S/C23H18O2/c1-2-25-22-15-14-21(18-11-5-6-12-19(18)22)23(24)20-13-7-9-16-8-3-4-10-17(16)20/h3-15H,2H2,1H3
null
R2|R2|R25|R27|R46|
training
null
1
2,208
B3DB_classification_66
benzoylecgonine
null
CN1[C@H]2CC[C@H]1[C@@H](CC(=O)O)[C@@H](OC(=O)c1ccccc1)C2
null
-1.35
0BBB-
InChI=1S/C17H21NO4/c1-18-12-7-8-14(18)13(10-16(19)20)15(9-12)22-17(21)11-5-3-2-4-6-11/h2-6,12-15H,7-10H2,1H3,(H,19,20)/t12-,13+,14-,15-/m0/s1
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_68
dcka
5,7-dichloro-4-oxo-1h-quinoline-2-carboxylic acid
O=C(O)c1cc(=O)c2c(Cl)cc(Cl)cc2[nH]1
1,779
-1.33
0BBB-
InChI=1S/C10H5Cl2NO3/c11-4-1-5(12)9-6(2-4)13-7(10(15)16)3-8(9)14/h1-3H,(H,13,14)(H,15,16)
null
R20|
training
null
1
2,208
B3DB_classification_70
salbutamol
4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)phenol
CC(C)(C)NCC(O)c1ccc(O)c(CO)c1
2,083
-1.3
0BBB-
InChI=1S/C13H21NO3/c1-13(2,3)14-7-12(17)9-4-5-11(16)10(6-9)8-15/h4-6,12,14-17H,7-8H2,1-3H3
null
R3|R18|R25|R26|R27|R38|R41|R46|R47|R2|R2|R27|R40|R8|R21|R27|R43|R12|R31|R35|R39|R5|
training
null
1
2,208
B3DB_classification_81
yg19
2-(4-phenyl-1,3-thiazol-2-yl)ethanamine
NCCc1nc(-c2ccccc2)cs1
1,497,794
-1.3
0BBB-
InChI=1S/C11H12N2S/c12-7-6-11-13-10(8-14-11)9-4-2-1-3-5-9/h1-5,8H,6-7,12H2
null
R35|R36|R43|R48|R49|R4|R8|R21|R27|R2|R2|R12|R25|R46|R48|
training
null
1
2,208
B3DB_classification_83
diclofenac
2-[2-(2,6-dichloroanilino)phenyl]acetic acid
O=C(O)Cc1ccccc1Nc1c(Cl)cccc1Cl
3,033
-1.3
0BBB-
InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_86
α-hydroxyalprazolam (alpha-hydroxyalprazolam)
(8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanol
OCc1nnc2n1-c1ccc(Cl)cc1C(c1ccccc1)=NC2
162,244
-1.3
0BBB-
InChI=1S/C17H13ClN4O/c18-12-6-7-14-13(8-12)17(11-4-2-1-3-5-11)19-9-15-20-21-16(10-23)22(14)15/h1-8,23H,9-10H2
null
R5|R8|R21|R27|R2|R2|R12|R25|R35|R40|R46|R47|R43|
training
null
1
2,208
B3DB_classification_89
p-phenylbenzoic acid
4-phenylbenzoic acid
O=C(O)c1ccc(-c2ccccc2)cc1
66,724
-1.26
0BBB-
InChI=1S/C13H10O2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9H,(H,14,15)
null
R2|R2|R8|R21|R25|R27|R41|R43|R46|R47|R40|R3|R38|
training
null
1
2,208
B3DB_classification_103
bufotenine
3-[2-(dimethylamino)ethyl]-1h-indol-5-ol
CN(C)CCc1c[nH]c2ccc(O)cc12
10,257
-1.19
0BBB-
InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_104
y12
[2-acetyloxy-4-[(e)-3-oxo-3-(2-phenylethylamino)prop-1-enyl]phenyl] acetate
CC(=O)Oc1ccc(/C=C/C(=O)NCCc2ccccc2)cc1OC(C)=O
11,957,394
-1.17
0BBB-
InChI=1S/C21H21NO5/c1-15(23)26-19-10-8-18(14-20(19)27-16(2)24)9-11-21(25)22-13-12-17-6-4-3-5-7-17/h3-11,14H,12-13H2,1-2H3,(H,22,25)/b11-9+
null
R11|
training
null
1
2,208
B3DB_classification_106
72801-60-6
2-[4-(3-aminophenyl)-1,3-thiazol-2-yl]guanidine
NC(N)=Nc1nc(-c2cccc(N)c2)cs1
14,022,509
-1.15
0BBB-
InChI=1S/C10H11N5S/c11-7-3-1-2-6(4-7)8-5-16-10(14-8)15-9(12)13/h1-5H,11H2,(H4,12,13,14,15)
null
R18|R26|R27|R4|R2|R2|R3|R3|R8|R12|R21|R25|R27|R35|R36|R38|R40|R41|R43|R46|R47|R48|R49|R49|
training
null
1
2,208
B3DB_classification_114
sulpiride
n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide
CCN1CCCC1CNC(=O)c1cc(S(N)(=O)=O)ccc1OC
5,355
-1.11
0BBB-
InChI=1S/C15H23N3O4S/c1-3-18-8-4-5-11(18)10-17-15(19)13-9-12(23(16,20)21)6-7-14(13)22-2/h6-7,9,11H,3-5,8,10H2,1-2H3,(H,17,19)(H2,16,20,21)
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_115
salicylic acid (2-hydroxybenzoic acid)
2-hydroxybenzoic acid
O=C(O)c1ccccc1O
338
-1.1
0BBB-
InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
null
R3|R41|R38|R40|R50|R8|R21|R27|R2|R2|R27|R3|R5|R11|R12|R17|R18|R25|R26|R27|R35|R36|R39|R43|R46|R47|R48|R49|R49|R4|R31|
training
null
1
2,208
B3DB_classification_124
zolmitriptan
(4s)-4-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,3-oxazolidin-2-one
CN(C)CCc1c[nH]c2ccc(C[C@H]3COC(=O)N3)cc12
60,857
-1.04
0BBB-
InChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_128
139264-82-7
4-[[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]methyl]-1,3-oxazolidin-2-one
CN(C)CCc1c[nH]c2ccc(CC3COC(=O)N3)cc12
5,731
-1.01
0BBB-
InChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)
null
R47|
training
null
1
2,208
B3DB_classification_129
fexofenadine (allegra)
2-[4-[1-hydroxy-4-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]butyl]phenyl]-2-methylpropanoic acid
CC(C)(C(=O)O)c1ccc(C(O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1
3,348
-1
1BBB+
InChI=1S/C32H39NO4/c1-31(2,30(35)36)25-17-15-24(16-18-25)29(34)14-9-21-33-22-19-28(20-23-33)32(37,26-10-5-3-6-11-26)27-12-7-4-8-13-27/h3-8,10-13,15-18,28-29,34,37H,9,14,19-23H2,1-2H3,(H,35,36)
null
R18|R26|R27|R2|R2|R8|R40|R4|R21|R25|R27|R46|R50|R47|
training
null
1
2,208
B3DB_classification_130
proc-19m
null
CC(C)(C)c1ccc(C(=O)N2CCN(c3ccc(OCCCN4CCCCC4)cc3)C(=O)C2)cc1
null
-1
1BBB+
InChI=1S/C29H39N3O3/c1-29(2,3)24-10-8-23(9-11-24)28(34)31-19-20-32(27(33)22-31)25-12-14-26(15-13-25)35-21-7-18-30-16-5-4-6-17-30/h8-15H,4-7,16-22H2,1-3H3
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_142
chembl3264225
(e)-3-[3,4-bis(2-hydroxyethoxy)phenyl]-n-[2-(2-methylindol-1-yl)ethyl]prop-2-enamide
Cc1cc2ccccc2n1CCNC(=O)/C=C/c1ccc(OCCO)c(OCCO)c1
86,765,134
-1
1BBB+
InChI=1S/C24H28N2O5/c1-18-16-20-4-2-3-5-21(20)26(18)11-10-25-24(29)9-7-19-6-8-22(30-14-12-27)23(17-19)31-15-13-28/h2-9,16-17,27-28H,10-15H2,1H3,(H,25,29)/b9-7+
null
R47|
training
null
1
2,208
B3DB_classification_146
chembl1185227
4-[4-(azetidine-1-carbonyl)benzoyl]-1-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperazin-2-one
O=C(c1ccc(C(=O)N2CCN(c3ccc(OC4CCN(C5CCC5)CC4)cc3)C(=O)C2)cc1)N1CCC1
15,986,375
-1
1BBB+
InChI=1S/C30H36N4O4/c35-28-21-33(30(37)23-7-5-22(6-8-23)29(36)32-15-2-16-32)19-20-34(28)25-9-11-26(12-10-25)38-27-13-17-31(18-14-27)24-3-1-4-24/h5-12,24,27H,1-4,13-21H2
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_149
anabet
5-[3-(tert-butylamino)-2-hydroxypropoxy]-1,2,3,4-tetrahydronaphthalene-2,3-diol
CC(C)(C)NCC(O)COc1cccc2c1CC(O)C(O)C2
4,411
-0.95
1BBB+
InChI=1S/C17H27NO4/c1-17(2,3)18-9-12(19)10-22-16-6-4-5-11-7-14(20)15(21)8-13(11)16/h4-6,12,14-15,18-21H,7-10H2,1-3H3
null
R2|R2|R25|R46|
training
null
1
2,208
B3DB_classification_154
chembl243790
6-(4-ethylsulfonylphenyl)-5-[4-(2-piperidin-1-ylethoxy)phenoxy]naphthalen-2-ol
CCS(=O)(=O)c1ccc(-c2ccc3cc(O)ccc3c2Oc2ccc(OCCN3CCCCC3)cc2)cc1
10,324,755
-0.92
1BBB+
InChI=1S/C31H33NO5S/c1-2-38(34,35)28-14-6-23(7-15-28)29-16-8-24-22-25(33)9-17-30(24)31(29)37-27-12-10-26(11-13-27)36-21-20-32-18-4-3-5-19-32/h6-17,22,33H,2-5,18-21H2,1H3
null
R47|
training
null
1
2,208
B3DB_classification_155
atenolol
2-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
CC(C)NCC(O)COc1ccc(CC(N)=O)cc1
2,249
-0.9
1BBB+
InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)
null
R36|R43|R47|R5|R8|R21|R27|R4|R40|R50|R2|R2|R27|R12|R31|R35|R39|R46|R25|R41|R3|R38|R44|
training
null
1
2,208
B3DB_classification_157
glibenclamide
5-chloro-n-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
COc1ccc(Cl)cc1C(=O)NCCc1ccc(S(=O)(=O)NC(=O)NC2CCCCC2)cc1
3,488
-0.9
1BBB+
InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
null
R2|R2|R25|R46|
training
null
1
2,208
B3DB_classification_165
sulfamethoxypyridazine
4-amino-n-(6-methoxypyridazin-3-yl)benzenesulfonamide
COc1ccc(NS(=O)(=O)c2ccc(N)cc2)nn1
5,330
-0.85
1BBB+
InChI=1S/C11H12N4O3S/c1-18-11-7-6-10(13-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,15)
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_167
chembl357268
benzyl n-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate
Nc1ccccc1NC(=O)c1ccc(CNC(=O)OCc2ccccc2)cc1
5,044
-0.85
1BBB+
InChI=1S/C22H21N3O3/c23-19-8-4-5-9-20(19)25-21(26)18-12-10-16(11-13-18)14-24-22(27)28-15-17-6-2-1-3-7-17/h1-13H,14-15,23H2,(H,24,27)(H,25,26)
null
R47|
training
null
1
2,208
B3DB_classification_171
ly2066948
6-(4-methylsulfonylphenyl)-5-[4-(2-piperidin-1-ylethoxy)phenoxy]naphthalen-2-ol
CS(=O)(=O)c1ccc(-c2ccc3cc(O)ccc3c2Oc2ccc(OCCN3CCCCC3)cc2)cc1
5,327,043
-0.81
1BBB+
InChI=1S/C30H31NO5S/c1-37(33,34)27-13-5-22(6-14-27)28-15-7-23-21-24(32)8-16-29(23)30(28)36-26-11-9-25(10-12-26)35-20-19-31-17-3-2-4-18-31/h5-16,21,32H,2-4,17-20H2,1H3
null
R47|
training
null
1
2,208
B3DB_classification_172
domperidone
6-chloro-3-[1-[3-(2-oxo-3h-benzimidazol-1-yl)propyl]piperidin-4-yl]-1h-benzimidazol-2-one
O=c1[nH]c2ccccc2n1CCCN1CCC(n2c(=O)[nH]c3cc(Cl)ccc32)CC1
3,151
-0.8
1BBB+
InChI=1S/C22H24ClN5O2/c23-15-6-7-20-18(14-15)25-22(30)28(20)16-8-12-26(13-9-16)10-3-11-27-19-5-2-1-4-17(19)24-21(27)29/h1-2,4-7,14,16H,3,8-13H2,(H,24,29)(H,25,30)
null
R27|R47|R3|R18|R26|R38|R41|R40|R8|R21|R27|R2|R2|R5|R25|R36|R39|R46|R49|
training
null
1
2,208
B3DB_classification_177
compound 4b [pmid: 16099654]
n-(2-ethyltetrazol-5-yl)-9h-xanthene-9-carboxamide
CCn1nnc(NC(=O)C2c3ccccc3Oc3ccccc32)n1
9,923,127
-0.8
1BBB+
InChI=1S/C17H15N5O2/c1-2-22-20-17(19-21-22)18-16(23)15-11-7-3-5-9-13(11)24-14-10-6-4-8-12(14)15/h3-10,15H,2H2,1H3,(H,18,20,23)
null
R47|
training
null
1
2,208
B3DB_classification_178
compound 13
2-[[5-chloro-2-[4-[(4-methylpiperazin-1-yl)methyl]anilino]pyrimidin-4-yl]amino]-n,n-dimethylbenzenesulfonamide
CN1CCN(Cc2ccc(Nc3ncc(Cl)c(Nc4ccccc4S(=O)(=O)N(C)C)n3)cc2)CC1
56,839,178
-0.8
1BBB+
InChI=1S/C24H30ClN7O2S/c1-30(2)35(33,34)22-7-5-4-6-21(22)28-23-20(25)16-26-24(29-23)27-19-10-8-18(9-11-19)17-32-14-12-31(3)13-15-32/h4-11,16H,12-15,17H2,1-3H3,(H2,26,27,28,29)
null
R20|
training
null
1
2,208
B3DB_classification_180
risperidone-9-oh
null
Cc1nc2n(c(=O)c1CCN1CCC(c3coc4cc(F)ccc34)CC1)CCCC2O
null
-0.8
1BBB+
InChI=1S/C24H28FN3O3/c1-15-18(24(30)28-9-2-3-21(29)23(28)26-15)8-12-27-10-6-16(7-11-27)20-14-31-22-13-17(25)4-5-19(20)22/h4-5,13-14,16,21,29H,2-3,6-12H2,1H3
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_181
levodopa
(2s)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
N[C@@H](Cc1ccc(O)c(O)c1)C(=O)O
6,047
-0.8
1BBB+
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
null
R5|R21|R8|R39|
training
null
1
2,208
B3DB_classification_182
d-phenylalanine-l-proline
null
N[C@H](Cc1ccccc1)C(=O)ON1CCC[C@H]1C(=O)O
null
-0.8
1BBB+
InChI=1S/C14H18N2O4/c15-11(9-10-5-2-1-3-6-10)14(19)20-16-8-4-7-12(16)13(17)18/h1-3,5-6,11-12H,4,7-9,15H2,(H,17,18)/t11-,12+/m1/s1
null
R2|R2|R25|R46|
training
null
1
2,208
B3DB_classification_191
n-methylthiazolium-dcka
null
Cc1c(CCOC(=O)c2cc(=O)c3c(Cl)cc(Cl)cc3[nH]2)sc[n+]1C
null
-0.78
1BBB+
InChI=1S/C17H14Cl2N2O3S/c1-9-15(25-8-21(9)2)3-4-24-17(23)13-7-14(22)16-11(19)5-10(18)6-12(16)20-13/h5-8H,3-4H2,1-2H3/p+1
null
R2|R2|R20|R25|R46|
training
null
1
2,208
B3DB_classification_192
levodopa
2-amino-3-(3,4-dihydroxyphenyl)propanoic acid
NC(Cc1ccc(O)c(O)c1)C(=O)O
836
-0.77
1BBB+
InChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)
null
R27|R43|R2|R2|R12|R25|R35|R46|R47|R40|
training
null
1
2,208
B3DB_classification_193
chembl244000
6-(4-hydroxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)phenoxy]naphthalen-2-ol
Oc1ccc(-c2ccc3cc(O)ccc3c2Oc2ccc(OCCN3CCCCC3)cc2)cc1
9,848,501
-0.77
1BBB+
InChI=1S/C29H29NO4/c31-23-7-4-21(5-8-23)27-14-6-22-20-24(32)9-15-28(22)29(27)34-26-12-10-25(11-13-26)33-19-18-30-16-2-1-3-17-30/h4-15,20,31-32H,1-3,16-19H2
null
R47|
training
null
1
2,208
B3DB_classification_205
alfentanil, rapifen
null
CCCC(=O)N(c1ccccc1)C1(COC)CCN(CCn2nnn(CC)c2=O)CC1
null
-0.71
1BBB+
InChI=1S/C22H34N6O3/c1-4-9-20(29)28(19-10-7-6-8-11-19)22(18-31-3)12-14-25(15-13-22)16-17-27-21(30)26(5-2)23-24-27/h6-8,10-11H,4-5,9,12-18H2,1-3H3
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_215
verapamil
2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
COc1ccc(CCN(C)CCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC
2,520
-0.7
1BBB+
InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3
null
R3|R5|R11|R12|R17|R25|R35|R36|R43|R46|R47|R49|R49|R2|R2|R27|R21|R27|R8|R50|R40|R41|R38|R18|R26|R27|R3|
training
null
1
2,208
B3DB_classification_216
dexverapamil
(2r)-2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]-2-propan-2-ylpentanenitrile
COc1ccc(CCN(C)CCC[C@](C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC
65,808
-0.7
1BBB+
InChI=1S/C27H38N2O4/c1-20(2)27(19-28,22-10-12-24(31-5)26(18-22)33-7)14-8-15-29(3)16-13-21-9-11-23(30-4)25(17-21)32-6/h9-12,17-18,20H,8,13-16H2,1-7H3/t27-/m1/s1
null
R48|
training
null
1
2,208
B3DB_classification_217
chembl239099
4-[4-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]-3-oxopiperazine-1-carbonyl]benzonitrile
N#Cc1ccc(C(=O)N2CCN(c3ccc(OC4CCN(C5CCC5)CC4)cc3)C(=O)C2)cc1
15,987,108
-0.7
1BBB+
InChI=1S/C27H30N4O3/c28-18-20-4-6-21(7-5-20)27(33)30-16-17-31(26(32)19-30)23-8-10-24(11-9-23)34-25-12-14-29(15-13-25)22-2-1-3-22/h4-11,22,25H,1-3,12-17,19H2
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_218
paliperidone
3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-9-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one
Cc1nc2n(c(=O)c1CCN1CCC(c3noc4cc(F)ccc34)CC1)CCCC2O
115,237
-0.7
1BBB+
InChI=1S/C23H27FN4O3/c1-14-17(23(30)28-9-2-3-19(29)22(28)25-14)8-12-27-10-6-15(7-11-27)21-18-5-4-16(24)13-20(18)31-26-21/h4-5,13,15,19,29H,2-3,6-12H2,1H3
null
R2|R2|R8|R3|R12|R21|R25|R27|R36|R38|R39|R41|R43|R46|R47|R49|R20|
training
null
1
2,208
B3DB_classification_219
granisetron
1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide
CN1C2CCCC1CC(NC(=O)c1nn(C)c3ccccc13)C2
3,510
-0.69
1BBB+
InChI=1S/C18H24N4O/c1-21-13-6-5-7-14(21)11-12(10-13)19-18(23)17-15-8-3-4-9-16(15)22(2)20-17/h3-4,8-9,12-14H,5-7,10-11H2,1-2H3,(H,19,23)
null
R2|R2|R8|R21|R25|R27|R43|R46|R47|R36|
training
null
1
2,208
B3DB_classification_222
7-hydroxy risperidone
3-[2-[4-(6-fluoro-1,2-benzoxazol-3-yl)piperidin-1-yl]ethyl]-7-hydroxy-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one
Cc1nc2n(c(=O)c1CCN1CCC(c3noc4cc(F)ccc34)CC1)CC(O)CC2
475,100
-0.67
1BBB+
InChI=1S/C23H27FN4O3/c1-14-18(23(30)28-13-17(29)3-5-21(28)25-14)8-11-27-9-6-15(7-10-27)22-19-4-2-16(24)12-20(19)31-26-22/h2,4,12,15,17,29H,3,5-11,13H2,1H3
null
R2|R2|R8|R40|R21|R27|
training
null
1
2,208
B3DB_classification_239
norverapamil
2-(3,4-dimethoxyphenyl)-5-[2-(3,4-dimethoxyphenyl)ethylamino]-2-propan-2-ylpentanenitrile
COc1ccc(CCNCCCC(C#N)(c2ccc(OC)c(OC)c2)C(C)C)cc1OC
104,972
-0.64
1BBB+
InChI=1S/C26H36N2O4/c1-19(2)26(18-27,21-9-11-23(30-4)25(17-21)32-6)13-7-14-28-15-12-20-8-10-22(29-3)24(16-20)31-5/h8-11,16-17,19,28H,7,12-15H2,1-6H3
null
R12|R21|R25|R27|R43|R46|R47|R2|R2|R8|R40|
training
null
1
2,208
B3DB_classification_242
null
null
CC(=O)Cc1ccc(C(=O)Nc2cc(-c3cccs3)ccc2N)cc1
null
-0.62
1BBB+
InChI=1S/C20H18N2O2S/c1-13(23)11-14-4-6-15(7-5-14)20(24)22-18-12-16(8-9-17(18)21)19-3-2-10-25-19/h2-10,12H,11,21H2,1H3,(H,22,24)
null
R47|
training
null
1
2,208
B3DB_classification_249
chembl239299
4-(2,4-difluorobenzoyl)-1-[4-[3-[(2r)-2-methylpyrrolidin-1-yl]propoxy]phenyl]piperazin-2-one
C[C@@H]1CCCN1CCCOc1ccc(N2CCN(C(=O)c3ccc(F)cc3F)CC2=O)cc1
12,001,199
-0.6
1BBB+
InChI=1S/C25H29F2N3O3/c1-18-4-2-11-28(18)12-3-15-33-21-8-6-20(7-9-21)30-14-13-29(17-24(30)31)25(32)22-10-5-19(26)16-23(22)27/h5-10,16,18H,2-4,11-15,17H2,1H3/t18-/m1/s1
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_253
s-licarbizine
5-hydroxy-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
NC(=O)N1c2ccccc2CC(O)c2ccccc21
114,709
-0.59
1BBB+
InChI=1S/C15H14N2O2/c16-15(19)17-12-7-3-1-5-10(12)9-14(18)11-6-2-4-8-13(11)17/h1-8,14,18H,9H2,(H2,16,19)
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_255
tacedinaline
4-acetamido-n-(2-aminophenyl)benzamide
CC(=O)Nc1ccc(C(=O)Nc2ccccc2N)cc1
2,746
-0.58
1BBB+
InChI=1S/C15H15N3O2/c1-10(19)17-12-8-6-11(7-9-12)15(20)18-14-5-3-2-4-13(14)16/h2-9H,16H2,1H3,(H,17,19)(H,18,20)
null
R47|
training
null
1
2,208
B3DB_classification_256
tipr-dcka
null
C/C(=C(\CCOC(=O)c1cc(=O)c2c(Cl)cc(Cl)cc2[nH]1)SSC(C)C)N(C=O)Cc1cnc(C)nc1N
null
-0.57
1BBB+
InChI=1S/C25H27Cl2N5O4S2/c1-13(2)37-38-22(14(3)32(12-33)11-16-10-29-15(4)30-24(16)28)5-6-36-25(35)20-9-21(34)23-18(27)7-17(26)8-19(23)31-20/h7-10,12-13H,5-6,11H2,1-4H3,(H,31,34)(H2,28,29,30)/b22-14-
null
R20|R2|R2|R25|R46|
training
null
1
2,208
B3DB_classification_257
chembl390020
6-(3-hydroxyphenyl)-5-[4-(2-piperidin-1-ylethoxy)phenoxy]naphthalen-2-ol
Oc1cccc(-c2ccc3cc(O)ccc3c2Oc2ccc(OCCN3CCCCC3)cc2)c1
12,074,176
-0.57
1BBB+
InChI=1S/C29H29NO4/c31-23-6-4-5-21(19-23)27-13-7-22-20-24(32)8-14-28(22)29(27)34-26-11-9-25(10-12-26)33-18-17-30-15-2-1-3-16-30/h4-14,19-20,31-32H,1-3,15-18H2
null
R47|
training
null
1
2,208
B3DB_classification_261
bmsp
1-(4-bromophenyl)-8-[4-(4-fluorophenyl)-4-oxobutyl]-3-methyl-1,3,8-triazaspiro[4.5]decan-4-one
CN1CN(c2ccc(Br)cc2)C2(CCN(CCCC(=O)c3ccc(F)cc3)CC2)C1=O
13,497,177
-0.55
1BBB+
InChI=1S/C24H27BrFN3O2/c1-27-17-29(21-10-6-19(25)7-11-21)24(23(27)31)12-15-28(16-13-24)14-2-3-22(30)18-4-8-20(26)9-5-18/h4-11H,2-3,12-17H2,1H3
null
R40|R2|R2|R3|R25|R38|R41|R43|R46|R47|
training
null
1
2,208
B3DB_classification_262
practolol
n-[4-[(2s)-2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]acetamide
CC(=O)Nc1ccc(OC[C@@H](O)CNC(C)C)cc1
443,371
-0.55
1BBB+
InChI=1S/C14H22N2O3/c1-10(2)15-8-13(18)9-19-14-6-4-12(5-7-14)16-11(3)17/h4-7,10,13,15,18H,8-9H2,1-3H3,(H,16,17)/t13-/m0/s1
null
R2|R2|R25|R46|
training
null
1
2,208
B3DB_classification_264
pregabalin
3-(aminomethyl)-5-methylhexanoic acid
CC(C)CC(CN)CC(=O)O
4,715,169
-0.54
1BBB+
InChI=1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_270
eletriptan
5-[2-(benzenesulfonyl)ethyl]-3-[[(2s)-1-methylpyrrolidin-2-yl]methyl]-1h-indole
CN1CCC[C@H]1Cc1c[nH]c2ccc(CCS(=O)(=O)c3ccccc3)cc12
25,273,626
-0.52
1BBB+
InChI=1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m0/s1
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_271
tg4-155
(e)-n-[2-(2-methylindol-1-yl)ethyl]-3-(3,4,5-trimethoxyphenyl)prop-2-enamide
COc1cc(/C=C/C(=O)NCCn2c(C)cc3ccccc32)cc(OC)c1OC
5,886,965
-0.52
1BBB+
InChI=1S/C23H26N2O4/c1-16-13-18-7-5-6-8-19(18)25(16)12-11-24-22(26)10-9-17-14-20(27-2)23(29-4)21(15-17)28-3/h5-10,13-15H,11-12H2,1-4H3,(H,24,26)/b10-9+
null
R47|
training
null
1
2,208
B3DB_classification_277
faha
6-[(2-fluoroacetyl)amino]-n-phenylhexanamide
O=C(CF)NCCCCCC(=O)Nc1ccccc1
11,995,317
-0.51
1BBB+
InChI=1S/C14H19FN2O2/c15-11-14(19)16-10-6-2-5-9-13(18)17-12-7-3-1-4-8-12/h1,3-4,7-8H,2,5-6,9-11H2,(H,16,19)(H,17,18)
null
R47|
training
null
1
2,208
B3DB_classification_278
50-78-2
2-acetyloxybenzoate
CC(=O)Oc1ccccc1C(=O)O
2,244
-0.5
1BBB+
InChI=1S/C9H8O4/c1-6(10)13-8-5-3-2-4-7(8)9(11)12/h2-5H,1H3,(H,11,12)
null
R4|R8|R21|R27|R2|R2|R27|R5|R11|R12|R17|R18|R25|R26|R27|R35|R36|R39|R43|R46|R47|R48|R49|R49|
training
null
1
2,208
B3DB_classification_282
melphalan
2-amino-3-[4-[bis(2-chloroethyl)amino]phenyl]propanoic acid
NC(Cc1ccc(N(CCCl)CCCl)cc1)C(=O)O
4,053
-0.5
1BBB+
InChI=1S/C13H18Cl2N2O2/c14-5-7-17(8-6-15)11-3-1-10(2-4-11)9-12(16)13(18)19/h1-4,12H,5-9,16H2,(H,18,19)
null
R2|R2|R25|R27|R46|
training
null
1
2,208
B3DB_classification_288
phenothiazine
n,n-dimethyl-3-(5-oxophenothiazin-10-yl)propan-1-amine
CN(C)CCCN1c2ccccc2[S+]([O-])c2ccccc21
547,559
-0.48
1BBB+
InChI=1S/C17H20N2OS/c1-18(2)12-7-13-19-14-8-3-5-10-16(14)21(20)17-11-6-4-9-15(17)19/h3-6,8-11H,7,12-13H2,1-2H3
null
R21|R25|R27|R43|R47|R4|R2|R2|R8|R27|R40|
training
null
1
2,208
B3DB_classification_292
skb30 (npropylacetamide33npiperidinylmethylphenoxy)
n-[3-[3-(piperidin-1-ylmethyl)phenoxy]propyl]acetamide
CC(=O)NCCCOc1cccc(CN2CCCCC2)c1
9,971,484
-0.46
1BBB+
InChI=1S/C17H26N2O2/c1-15(20)18-9-6-12-21-17-8-5-7-16(13-17)14-19-10-3-2-4-11-19/h5,7-8,13H,2-4,6,9-12,14H2,1H3,(H,18,20)
null
R2|R2|R8|R27|R40|R3|R3|R18|R21|R25|R26|R27|R27|R35|R36|R38|R38|R41|R41|R43|R46|R47|R48|R49|R49|R4|
training
null
1
2,208
B3DB_classification_294
naratriptan
n-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethanesulfonamide
CNS(=O)(=O)CCc1ccc2[nH]cc(C3CCN(C)CC3)c2c1
4,440
-0.46
1BBB+
InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
null
R18|R26|R27|R47|
training
null
1
2,208
B3DB_classification_295
chembl239975
4-(4-fluorobenzoyl)-1-[4-(3-piperidin-1-ylpropoxy)phenyl]piperazin-2-one
O=C(c1ccc(F)cc1)N1CCN(c2ccc(OCCCN3CCCCC3)cc2)C(=O)C1
15,986,917
-0.46
1BBB+
InChI=1S/C25H30FN3O3/c26-21-7-5-20(6-8-21)25(31)28-16-17-29(24(30)19-28)22-9-11-23(12-10-22)32-18-4-15-27-13-2-1-3-14-27/h5-12H,1-4,13-19H2
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_296
flesinoxan
4-fluoro-n-[2-[4-[2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl]ethyl]benzamide
O=C(NCCN1CCN(c2cccc3c2OCC(CO)O3)CC1)c1ccc(F)cc1
9,844,747
-0.45
1BBB+
InChI=1S/C22H26FN3O4/c23-17-6-4-16(5-7-17)22(28)24-8-9-25-10-12-26(13-11-25)19-2-1-3-20-21(19)29-15-18(14-27)30-20/h1-7,18,27H,8-15H2,(H,24,28)
null
R27|R43|R46|R47|R2|R2|R27|R25|R40|
training
null
1
2,208
B3DB_classification_297
flesinoxan
4-fluoro-n-[2-[4-[(2s)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-5-yl]piperazin-1-yl]ethyl]benzamide
O=C(NCCN1CCN(c2cccc3c2OC[C@H](CO)O3)CC1)c1ccc(F)cc1
57,347
-0.45
1BBB+
InChI=1S/C22H26FN3O4/c23-17-6-4-16(5-7-17)22(28)24-8-9-25-10-12-26(13-11-25)19-2-1-3-20-21(19)29-15-18(14-27)30-20/h1-7,18,27H,8-15H2,(H,24,28)/t18-/m0/s1
null
R21|R8|
training
null
1
2,208
B3DB_classification_298
salicyluric acid (salicylurate)
2-[(2-hydroxybenzoyl)amino]acetic acid
O=C(O)CNC(=O)c1ccccc1O
10,253
-0.44
1BBB+
InChI=1S/C9H9NO4/c11-7-4-2-1-3-6(7)9(14)10-5-8(12)13/h1-4,11H,5H2,(H,10,14)(H,12,13)
null
R2|R2|R8|R11|R12|R18|R21|R25|R26|R27|R27|R27|R35|R36|R39|R43|R46|R47|R40|
training
null
1
2,208
B3DB_classification_301
besp
1-(4-bromophenyl)-3-ethyl-8-[4-(4-fluorophenyl)-4-oxobutyl]-1,3,8-triazaspiro[4.5]decan-4-one
CCN1CN(c2ccc(Br)cc2)C2(CCN(CCCC(=O)c3ccc(F)cc3)CC2)C1=O
13,497,179
-0.43
1BBB+
InChI=1S/C25H29BrFN3O2/c1-2-29-18-30(22-11-7-20(26)8-12-22)25(24(29)32)13-16-28(17-14-25)15-3-4-23(31)19-5-9-21(27)10-6-19/h5-12H,2-4,13-18H2,1H3
null
R2|R2|R8|R27|R40|R3|R25|R38|R41|R43|R47|
training
null
1
2,208
B3DB_classification_309
sumatriptan
1-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]-n-methylmethanesulfonamide
CNS(=O)(=O)Cc1ccc2[nH]cc(CCN(C)C)c2c1
5,358
-0.4
1BBB+
InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
null
R18|R26|R27|R47|R2|R2|R25|R27|R46|
training
null
1
2,208
B3DB_classification_310
carteolol
5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydro-1h-quinolin-2-one
CC(C)(C)NCC(O)COc1cccc2c1CCC(=O)N2
2,583
-0.4
1BBB+
InChI=1S/C16H24N2O3/c1-16(2,3)17-9-11(19)10-21-14-6-4-5-13-12(14)7-8-15(20)18-13/h4-6,11,17,19H,7-10H2,1-3H3,(H,18,20)
null
R18|R26|R27|R40|R3|R25|R38|R41|R46|R47|R8|R21|R27|R43|
training
null
1
2,208
B3DB_classification_313
probenecid
4-(dipropylsulfamoyl)benzoic acid
CCCN(CCC)S(=O)(=O)c1ccc(C(=O)O)cc1
4,911
-0.4
1BBB+
InChI=1S/C13H19NO4S/c1-3-9-14(10-4-2)19(17,18)12-7-5-11(6-8-12)13(15)16/h5-8H,3-4,9-10H2,1-2H3,(H,15,16)
null
R2|R2|R25|R27|R46|
training
null
1
2,208
B3DB_classification_314
mesoridazine
10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine
CN1CCCCC1CCN1c2ccccc2Sc2ccc([S+](C)[O-])cc21
4,078
-0.4
1BBB+
InChI=1S/C21H26N2OS2/c1-22-13-6-5-7-16(22)12-14-23-18-8-3-4-9-20(18)25-21-11-10-17(26(2)24)15-19(21)23/h3-4,8-11,15-16H,5-7,12-14H2,1-2H3
null
R5|R11|R12|R20|R25|R35|R36|R39|R43|R47|R2|R2|R27|R8|R21|R27|R40|R4|
training
null
1
2,208
B3DB_classification_315
compound 3a [pmid: 16099654]
n-(5-methyl-1,2,4-oxadiazol-3-yl)-9h-xanthene-9-carboxamide
Cc1nc(NC(=O)C2c3ccccc3Oc3ccccc32)no1
44,573,698
-0.4
1BBB+
InChI=1S/C17H13N3O3/c1-10-18-17(20-23-10)19-16(21)15-11-6-2-4-8-13(11)22-14-9-5-3-7-12(14)15/h2-9,15H,1H3,(H,19,20,21)
null
R47|
training
null
1
2,208
B3DB_classification_317
chembl1190347
4-(4-chlorobenzoyl)-1-[4-(1-cyclobutylpiperidin-4-yl)oxyphenyl]piperazin-2-one
O=C(c1ccc(Cl)cc1)N1CCN(c2ccc(OC3CCN(C4CCC4)CC3)cc2)C(=O)C1
15,986,644
-0.4
1BBB+
InChI=1S/C26H30ClN3O3/c27-20-6-4-19(5-7-20)26(32)29-16-17-30(25(31)18-29)22-8-10-23(11-9-22)33-24-12-14-28(15-13-24)21-2-1-3-21/h4-11,21,24H,1-3,12-18H2
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_324
escitalopram
(1s)-1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile
CN(C)CCC[C@@]1(c2ccc(F)cc2)OCc2cc(C#N)ccc21
146,570
-0.37
1BBB+
InChI=1S/C20H21FN2O/c1-23(2)11-3-10-20(17-5-7-18(21)8-6-17)19-9-4-15(13-22)12-16(19)14-24-20/h4-9,12H,3,10-11,14H2,1-2H3/t20-/m0/s1
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_325
chembl243571
4-[6-hydroxy-1-[4-(2-piperidin-1-ylethoxy)phenoxy]naphthalen-2-yl]-n,n-dimethylbenzenesulfonamide
CN(C)S(=O)(=O)c1ccc(-c2ccc3cc(O)ccc3c2Oc2ccc(OCCN3CCCCC3)cc2)cc1
44,427,370
-0.37
1BBB+
InChI=1S/C31H34N2O5S/c1-32(2)39(35,36)28-14-6-23(7-15-28)29-16-8-24-22-25(34)9-17-30(24)31(29)38-27-12-10-26(11-13-27)37-21-20-33-18-4-3-5-19-33/h6-17,22,34H,3-5,18-21H2,1-2H3
null
R47|
training
null
1
2,208
B3DB_classification_328
mesoridazine
null
CC(=O)C1CSc2ccccc2N1CCC1CCCCN1C
null
-0.36
1BBB+
InChI=1S/C18H26N2OS/c1-14(21)17-13-22-18-9-4-3-8-16(18)20(17)12-10-15-7-5-6-11-19(15)2/h3-4,8-9,15,17H,5-7,10-13H2,1-2H3
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_329
[(2r,9s)-2-carbamoyl-9-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl] acetate
[(2r,9s)-2-carbamoyl-9-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenyl] acetate
CC(=O)O[C@H]1Cc2ccccc2[C@@H](C(N)=O)c2ccccc21
29,939,457
-0.34
1BBB+
InChI=1S/C18H17NO3/c1-11(20)22-16-10-12-6-2-3-7-13(12)17(18(19)21)15-9-5-4-8-14(15)16/h2-9,16-17H,10H2,1H3,(H2,19,21)/t16-,17+/m0/s1
null
R8|
training
null
1
2,208
B3DB_classification_330
schembl11119364
5,6-dimethyl-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
CC1c2ccccc2N(C(N)=O)c2ccccc2C1C
70,517,986
-0.34
1BBB+
InChI=1S/C17H18N2O/c1-11-12(2)14-8-4-6-10-16(14)19(17(18)20)15-9-5-3-7-13(11)15/h3-12H,1-2H3,(H2,18,20)
null
R2|R2|R8|R27|
training
null
1
2,208
B3DB_classification_331
carbamazepine, 9,10-epoxide
3-oxatetracyclo[10.4.0.02,4.05,10]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
NC(=O)C1c2ccccc2C2OC2c2ccccc21
91,751,467
-0.34
1BBB+
InChI=1S/C16H13NO2/c17-16(18)13-9-5-1-3-7-11(9)14-15(19-14)12-8-4-2-6-10(12)13/h1-8,13-15H,(H2,17,18)
null
R2|R2|R27|
training
null
1
2,208
B3DB_classification_332
cbz-epo
11-azatetracyclo[10.4.0.02,4.05,10]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
NC(=O)N1c2ccccc2C2CC2c2ccccc21
12,323,381
-0.34
1BBB+
InChI=1S/C16H14N2O/c17-16(19)18-14-7-3-1-5-10(14)12-9-13(12)11-6-2-4-8-15(11)18/h1-8,12-13H,9H2,(H2,17,19)
null
R3|R38|R41|R43|
training
null
1
2,208
B3DB_classification_333
null
null
NC(=O)[C@H]1c2ccccc2[C@H]2O[C@H]2c2ccccc21
null
-0.34
1BBB+
InChI=1S/C16H13NO2/c17-16(18)13-9-5-1-3-7-11(9)14-15(19-14)12-8-4-2-6-10(12)13/h1-8,13-15H,(H2,17,18)/t13-,14+,15-
null
R48|
training
null
1
2,208
B3DB_classification_335
risperidone
null
Cc1nc2n(c(=O)c1CCN1CCC(c3coc4cc(F)ccc34)CC1)CCCC2
null
-0.32
1BBB+
InChI=1S/C24H28FN3O2/c1-16-19(24(29)28-10-3-2-4-23(28)26-16)9-13-27-11-7-17(8-12-27)21-15-30-22-14-18(25)5-6-20(21)22/h5-6,14-15,17H,2-4,7-13H2,1H3
null
R18|R26|R27|
training
null
1
2,208
B3DB_classification_337
acetaminophen (p-acetamidophenol)
n-(4-hydroxyphenyl)acetamide
CC(=O)Nc1ccc(O)cc1
1,983
-0.3
1BBB+
InChI=1S/C8H9NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5,11H,1H3,(H,9,10)
null
R4|R40|R50|R18|R26|R27|R8|R21|R27|R2|R2|R3|R27|R38|R41|R47|R12|R17|R25|R35|R36|R39|R43|R46|R48|R49|R49|R5|R42|R44|
training
null
1
2,208
B3DB_classification_338
betahistine (y-g 14)
n-methyl-2-pyridin-2-ylethanamine
CNCCc1ccccn1
2,366
-0.3
1BBB+
InChI=1S/C8H12N2/c1-9-7-5-8-4-2-3-6-10-8/h2-4,6,9H,5,7H2,1H3
null
R12|R20|R25|R46|R48|R2|R2|R27|R50|R40|R8|R21|R27|R3|R35|R36|R38|R41|R43|R47|R48|R49|R4|R42|
training
null
1
2,208
B3DB_classification_339
theophylline
1,3-dimethyl-7h-purine-2,6-dione
Cn1c(=O)c2[nH]cnc2n(C)c1=O
2,153
-0.3
1BBB+
InChI=1S/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
null
R4|R47|R3|R38|R41|R40|R50|R2|R2|R27|R8|R21|R27|R8|R2|R2|R27|R5|R12|R17|R18|R20|R25|R26|R27|R31|R43|R46|R48|R49|R49|R42|
training
null
1
2,208
B3DB_classification_340
b-096
3-oxa-11-azatetracyclo[10.4.0.02,4.05,10]hexadeca-1(16),5,7,9,12,14-hexaene-11-carboxamide
NC(=O)N1c2ccccc2C2OC2c2ccccc21
2,555
-0.3
1BBB+
InChI=1S/C15H12N2O2/c16-15(18)17-11-7-3-1-5-9(11)13-14(19-13)10-6-2-4-8-12(10)17/h1-8,13-14H,(H2,16,18)
null
R12|R25|R36|R46|R40|R2|R2|R27|R8|R11|R18|R21|R26|R27|R27|R35|R39|R43|R47|R49|R49|R5|
training
null
1
2,208
B3DB_classification_341
dichloromethane
dichloromethane
ClCCl
6,344
-0.3
1BBB+
InChI=1S/CH2Cl2/c2-1-3/h1H2
null
R25|R41|R3|R38|R46|R47|R40|R2|R2|R27|R8|R21|R27|R12|R18|R26|R27|R35|R39|R43|R5|
training
null
1
2,208

Blood-Brain Barrier Database (B3DB)

The Blood-Brain Barrier Database (B3DB) is a large benchmark dataset compiled from 50 published resources (as summarized at raw_data/raw_data_summary.tsv) and categorized based on the consistency between different experimental references/measurements. This dataset was published in Scientific Data and a mirror of the theochem/B3DB the official Github repo where it is occasionally uploaded with new experimental data. Scientists who would like to contribute data should contact the database's maintainers (e.g., by creating a new Issue in the database).

A subset of the molecules in B3DB has numerical logBB values (1058 compounds), while the whole dataset has categorical (BBB+ or BBB-) BBB permeability labels (7807 compounds). Some physicochemical properties of the molecules are also provided.

Quickstart Usage

Load a dataset in python

Each subset can be loaded into python using the Huggingface datasets library. First, from the command line install the datasets library

$ pip install datasets

then, from within python load the datasets library

>>> import datasets

and load one of the B3DB datasets, e.g.,

>>> B3DB_classification = datasets.load_dataset("maomlab/B3DB", name = "B3DB_classification")
Downloading readme: 100%|████████████████████████| 4.40k/4.40k [00:00<00:00, 1.35MB/s]
Downloading data: 100%|██████████████████████████| 680k/680k [00:00<00:00, 946kB/s]
Downloading data: 100%|██████████████████████████| 2.11M/2.11M [00:01<00:00, 1.28MB/s]
Generating test split: 100%|█████████████████████| 1951/1951 [00:00<00:00, 20854.95 examples/s]
Generating train split: 100%|████████████████████| 5856/5856 [00:00<00:00, 144260.80 examples/s]

and inspecting the loaded dataset

>>> B3DB_classification
B3DB_classification
DatasetDict({
  test: Dataset({
     features: ['B3DB_classification_index', 'compound_name', 'IUPAC_name', 'SMILES', 'CID', 'logBB', 'BBB+/BBB-', 'Inchi', 'threshold', 'reference', 'group', 'comments', 'ClusterNo', 'MolCount'],
     num_rows: 1951
  })
  train: Dataset({
      features: ['B3DB_classification_index', 'compound_name', 'IUPAC_name', 'SMILES', 'CID', 'logBB', 'BBB+/BBB-', 'Inchi', 'threshold', 'reference', 'group', 'comments', 'ClusterNo', 'MolCount'],
      num_rows: 5856
  })
})

Use a dataset to train a model

One way to use the dataset is through the MolFlux package developed by Exscientia. First, from the command line, install MolFlux library with catboost and rdkit support

pip install 'molflux[catboost,rdkit]'

then load, featurize, split, fit, and evaluate the a catboost model

import json
from datasets import load_dataset
from molflux.datasets import featurise_dataset
from molflux.features import load_from_dicts as load_representations_from_dicts
from molflux.splits import load_from_dict as load_split_from_dict
from molflux.modelzoo import load_from_dict as load_model_from_dict
from molflux.metrics import load_suite

split_dataset = load_dataset('maomlab/B3DB', name = 'B3DB_classification')

split_featurised_dataset = featurise_dataset(
  split_dataset,
  column = "SMILES",
  representations = load_representations_from_dicts([{"name": "morgan"}, {"name": "maccs_rdkit"}]))

model = load_model_from_dict({
    "name": "cat_boost_classifier",
    "config": {
        "x_features": ['SMILES::morgan', 'SMILES::maccs_rdkit'],
        "y_features": ['BBB+/BBB-']}})

model.train(split_featurised_dataset["train"])
preds = model.predict(split_featurised_dataset["test"])

classification_suite = load_suite("classification")

scores = classification_suite.compute(
    references=split_featurised_dataset["test"]['BBB+/BBB-'],
    predictions=preds["cat_boost_classifier::BBB+/BBB-"])

About the DB3B

Features of B3DB

  1. The largest dataset with numerical and categorical values for Blood-Brain Barrier small molecules (to the best of our knowledge, as of February 25, 2021).

  2. Inclusion of stereochemistry information with isomeric SMILES with chiral specifications if available. Otherwise, canonical SMILES are used.

  3. Characterization of uncertainty of experimental measurements by grouping the collected molecular data records.

  4. Extended datasets for numerical and categorical data with precomputed physicochemical properties using mordred.

Data splits

The original B3DB dataset does not define splits, so here we have used the Realistic Split method described in (Martin et al., 2018).

Citation

Please use the following citation in any publication using our B3DB dataset:

@article{Meng_A_curated_diverse_2021,
author = {Meng, Fanwang and Xi, Yang and Huang, Jinfeng and Ayers, Paul W.},
doi = {10.1038/s41597-021-01069-5},
journal = {Scientific Data},
number = {289},
title = {A curated diverse molecular database of blood-brain barrier permeability with chemical descriptors},
volume = {8},
year = {2021},
url = {https://www.nature.com/articles/s41597-021-01069-5},
publisher = {Springer Nature}
}
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