Datasets:

jablonkagroup
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BBBP

The blood-brain barrier penetration (BBBP) dataset is designed for the modeling and prediction of barrier permeability. As a membrane separating circulating blood and brain extracellular fluid, the blood-brain barrier blocks most drugs, hormones, and neurotransmitters. Thus penetration of the barrier forms a long-standing issue in the development of drugs targeting the central nervous system. This dataset includes binary labels for over 2000 compounds on their permeability properties.

Curated by:
License: CC BY 4.0

Dataset Sources

Citation

BibTeX:

@article{doi:10.1021/ci300124c,
author = {Martins, Ines Filipa and Teixeira, Ana L. and Pinheiro, Luis and Falcao, Andre O.},
title = {A Bayesian Approach to in Silico Blood-Brain Barrier Penetration Modeling},
journal = {Journal of Chemical Information and Modeling},
volume = {52},
number = {6},
pages = {1686-1697},
year = {2012},
doi = {10.1021/ci300124c},
URL = {https://doi.org/10.1021/ci300124c},
eprint = {https://doi.org/10.1021/ci300124c}}

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text stringlengths 78 538	input stringlengths 78 538	answer_choices sequencelengths 0 0	correct_output_index float64
The chemical with the SMILES of [Cl].CC(C)NCC(O)COc1cccc2ccccc12 shows permeability through the membrane separating circulating blood and extracellular brain fluid.	The chemical with the SMILES of [Cl].CC(C)NCC(O)COc1cccc2ccccc12 shows permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of C(=O)(OC(C)(C)C)CCCc1ccc(cc1)N(CCCl)CCCl exhibits blood-brain barrier permeability.	The chemical with the SMILES of C(=O)(OC(C)(C)C)CCCc1ccc(cc1)N(CCCl)CCCl exhibits blood-brain barrier permeability.	[]	null
The compound with the SMILES of c12c3c(N4CCN(C)CC4)c(F)cc1c(c(C(O)=O)cn2C(C)CO3)=O displays permeability through the membrane separating circulating blood and extracellular brain fluid.	The compound with the SMILES of c12c3c(N4CCN(C)CC4)c(F)cc1c(c(C(O)=O)cn2C(C)CO3)=O displays permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of C1CCN(CC1)Cc1cccc(c1)OCCCNC(=O)C displays permeability through the membrane separating circulating blood and extracellular brain fluid.	The chemical with the SMILES of C1CCN(CC1)Cc1cccc(c1)OCCCNC(=O)C displays permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of Cc1onc(c2ccccc2Cl)c1C(=O)N[C@H]3[C@H]4SC(C)(C)[C@@H](N4C3=O)C(O)=O displays permeability through the blood-brain barrier.	The chemical with the SMILES of Cc1onc(c2ccccc2Cl)c1C(=O)N[C@H]3[C@H]4SC(C)(C)[C@@H](N4C3=O)C(O)=O displays permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SCC(=C(N3C2=O)C(O)=O)CSc4nnnn4C)c5ccc(O)cc5)C(=O)C1=O exhibits permeability through the blood-brain barrier.	The compound with the SMILES of CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SCC(=C(N3C2=O)C(O)=O)CSc4nnnn4C)c5ccc(O)cc5)C(=O)C1=O exhibits permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)c4c(O)cccc4[C@@]3(C)O)C(=O)[C@]2(O)C(=O)\C(=C(/O)NCN5CCCC5)C1=O displays blood-brain barrier permeability.	The compound with the SMILES of CN(C)[C@H]1[C@@H]2C[C@H]3C(=C(O)c4c(O)cccc4[C@@]3(C)O)C(=O)[C@]2(O)C(=O)\C(=C(/O)NCN5CCCC5)C1=O displays blood-brain barrier permeability.	[]	null
The chemical with the SMILES of Cn1c2CCC(Cn3ccnc3C)C(=O)c2c4ccccc14 exhibits permeability through the blood-brain barrier.	The chemical with the SMILES of Cn1c2CCC(Cn3ccnc3C)C(=O)c2c4ccccc14 exhibits permeability through the blood-brain barrier.	[]	null
The chemical with the SMILES of COc1ccc(cc1)[C@@H]2Sc3ccccc3N(CCN(C)C)C(=O)[C@@H]2OC(C)=O shows blood-brain barrier permeability.	The chemical with the SMILES of COc1ccc(cc1)[C@@H]2Sc3ccccc3N(CCN(C)C)C(=O)[C@@H]2OC(C)=O shows blood-brain barrier permeability.	[]	null
The compound with the SMILES of OCC(C)(O)c1onc(c2ncn3c2CN(C)C(c4c3cccc4Cl)=O)n1 exhibits no permeability through the membrane separating circulating blood and extracellular brain fluid.	The compound with the SMILES of OCC(C)(O)c1onc(c2ncn3c2CN(C)C(c4c3cccc4Cl)=O)n1 exhibits no permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of CC1=CN([C@H]2C[C@H](F)[C@@H](CO)O2)C(=O)NC1=O displays permeability through the membrane separating circulating blood and extracellular brain fluid.	The chemical with the SMILES of CC1=CN([C@H]2C[C@H](F)[C@@H](CO)O2)C(=O)NC1=O displays permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of C(Cl)Cl shows permeability through the blood-brain barrier.	The chemical with the SMILES of C(Cl)Cl shows permeability through the blood-brain barrier.	[]	null
The chemical with the SMILES of C1N(C(CC2CCCCC12)C(NC(C)(C)C)=O)CC(C(Cc1ccccc1)NC(C(NC(c1nc2c(cccc2)cc1)=O)CC(N)=O)=O)O exhibits blood-brain barrier permeability.	The chemical with the SMILES of C1N(C(CC2CCCCC12)C(NC(C)(C)C)=O)CC(C(Cc1ccccc1)NC(C(NC(c1nc2c(cccc2)cc1)=O)CC(N)=O)=O)O exhibits blood-brain barrier permeability.	[]	null
The chemical with the SMILES of CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c2ccccc2 shows blood-brain barrier permeability.	The chemical with the SMILES of CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c2ccccc2 shows blood-brain barrier permeability.	[]	null
The chemical with the SMILES of CCN1N=NN(CCN2CCC(CC2)(COC)N(C(=O)CC)c3ccccc3)C1=O shows blood-brain barrier permeability.	The chemical with the SMILES of CCN1N=NN(CCN2CCC(CC2)(COC)N(C(=O)CC)c3ccccc3)C1=O shows blood-brain barrier permeability.	[]	null
The compound with the SMILES of CN(C)C(=O)C(CCN1CCC(O)(CC1)c1ccc(Cl)cc1)(c1ccccc1)c1ccccc1 shows permeability through the blood-brain barrier.	The compound with the SMILES of CN(C)C(=O)C(CCN1CCC(O)(CC1)c1ccc(Cl)cc1)(c1ccccc1)c1ccccc1 shows permeability through the blood-brain barrier.	[]	null
The chemical with the SMILES of CN1C2CCC1CC(C2)OC(=O)[C@H](CO)c3ccccc3 exhibits permeability through the blood-brain barrier.	The chemical with the SMILES of CN1C2CCC1CC(C2)OC(=O)[C@H](CO)c3ccccc3 exhibits permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)[S](=O)(=O)NC(=O)NC3CCCCC3 exhibits permeability through the blood-brain barrier.	The compound with the SMILES of COc1ccc(Cl)cc1C(=O)NCCc2ccc(cc2)[S](=O)(=O)NC(=O)NC3CCCCC3 exhibits permeability through the blood-brain barrier.	[]	null
The chemical with the SMILES of Nc1nnc(c(N)n1)c2cccc(Cl)c2Cl shows permeability through the membrane separating circulating blood and extracellular brain fluid.	The chemical with the SMILES of Nc1nnc(c(N)n1)c2cccc(Cl)c2Cl shows permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of CCCC(C)C exhibits blood-brain barrier permeability.	The chemical with the SMILES of CCCC(C)C exhibits blood-brain barrier permeability.	[]	null
The chemical with the SMILES of c1cc2c(cc(CC3=CNC(=NC3=O)NCCSCc3oc(cc3)CN(C)C)cc2)cc1 exhibits no permeability through the membrane separating circulating blood and extracellular brain fluid.	The chemical with the SMILES of c1cc2c(cc(CC3=CNC(=NC3=O)NCCSCc3oc(cc3)CN(C)C)cc2)cc1 exhibits no permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The compound with the SMILES of CC(C)(C)NCC(O)COc1cccc2C[C@@H](O)[C@@H](O)Cc12 exhibits blood-brain barrier permeability.	The compound with the SMILES of CC(C)(C)NCC(O)COc1cccc2C[C@@H](O)[C@@H](O)Cc12 exhibits blood-brain barrier permeability.	[]	null
The compound with the SMILES of CCC(=O)N(c1ccccc1)C2(CCN(CCc3sccc3)CC2)COC exhibits permeability through the blood-brain barrier.	The compound with the SMILES of CCC(=O)N(c1ccccc1)C2(CCN(CCc3sccc3)CC2)COC exhibits permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CCNC(=NC#N)NCCSCc1c(cccn1)Br displays no blood-brain barrier permeability.	The compound with the SMILES of CCNC(=NC#N)NCCSCc1c(cccn1)Br displays no blood-brain barrier permeability.	[]	null
The chemical with the SMILES of CN(C)C(=O)Cc1n2cc(C)ccc2nc1c3ccc(C)cc3 shows permeability through the blood-brain barrier.	The chemical with the SMILES of CN(C)C(=O)Cc1n2cc(C)ccc2nc1c3ccc(C)cc3 shows permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CN1CCN(CC1)C2=C3C=CC=CC3=Nc4ccc(Cl)cc4N2 displays permeability through the blood-brain barrier.	The compound with the SMILES of CN1CCN(CC1)C2=C3C=CC=CC3=Nc4ccc(Cl)cc4N2 displays permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of FC(F)(F)c1c(Cl)nc(N2CCNCC2)cc1 exhibits permeability through the blood-brain barrier.	The compound with the SMILES of FC(F)(F)c1c(Cl)nc(N2CCNCC2)cc1 exhibits permeability through the blood-brain barrier.	[]	null
The chemical with the SMILES of O.CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)c4ccccc4)C(=O)C1=O shows blood-brain barrier permeability.	The chemical with the SMILES of O.CCN1CCN(C(=O)N[C@@H](C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C(O)=O)c4ccccc4)C(=O)C1=O shows blood-brain barrier permeability.	[]	null
The compound with the SMILES of CCCC(C)C1(CC)C(=O)NC(=O)NC1=O displays permeability through the blood-brain barrier.	The compound with the SMILES of CCCC(C)C1(CC)C(=O)NC(=O)NC1=O displays permeability through the blood-brain barrier.	[]	null
The chemical with the SMILES of C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc4C(=O)C(=CN1c24)C(O)=O displays blood-brain barrier permeability.	The chemical with the SMILES of C[C@H]1COc2c(N3CCN(C)CC3)c(F)cc4C(=O)C(=CN1c24)C(O)=O displays blood-brain barrier permeability.	[]	null
The compound with the SMILES of c1ccc(C(NCCCOc2cc(CN3CCCCC3)ccc2)=O)cc1 displays permeability through the blood-brain barrier.	The compound with the SMILES of c1ccc(C(NCCCOc2cc(CN3CCCCC3)ccc2)=O)cc1 displays permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CC(C)(C)OC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CS3)C exhibits permeability through the blood-brain barrier.	The compound with the SMILES of CC(C)(C)OC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CS3)C exhibits permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CCC(=O)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3 displays permeability through the blood-brain barrier.	The compound with the SMILES of CCC(=O)N(C1CCN(CC1)CCc2ccccc2)c3ccccc3 displays permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CCOC(=O)c1cncn1C(C)c2ccccc2 shows permeability through the blood-brain barrier.	The compound with the SMILES of CCOC(=O)c1cncn1C(C)c2ccccc2 shows permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of CN(C)c1cc(C2=NC(N)=NN2)ccn1 displays no permeability through the blood-brain barrier.	The compound with the SMILES of CN(C)c1cc(C2=NC(N)=NN2)ccn1 displays no permeability through the blood-brain barrier.	[]	null
The chemical with the SMILES of CN1CCN(CCCN2c3ccccc3Sc4ccc(Cl)cc24)CC1 shows permeability through the membrane separating circulating blood and extracellular brain fluid.	The chemical with the SMILES of CN1CCN(CCCN2c3ccccc3Sc4ccc(Cl)cc24)CC1 shows permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of IC1=C(N([H])[H])C=CC(C2=NC3=CC=C(O[H])C=C3S2)=C1 displays blood-brain barrier permeability.	The chemical with the SMILES of IC1=C(N([H])[H])C=CC(C2=NC3=CC=C(O[H])C=C3S2)=C1 displays blood-brain barrier permeability.	[]	null
The chemical with the SMILES of O=C(C)Nc1cc(c2csc(N=C(N)N)n2)ccc1 displays no permeability through the membrane separating circulating blood and extracellular brain fluid.	The chemical with the SMILES of O=C(C)Nc1cc(c2csc(N=C(N)N)n2)ccc1 displays no permeability through the membrane separating circulating blood and extracellular brain fluid.	[]	null
The chemical with the SMILES of CN1[C@H]2CCC[C@@H]1CC(C2)NC(=O)c3nn(C)c4ccccc34 exhibits permeability through the blood-brain barrier.	The chemical with the SMILES of CN1[C@H]2CCC[C@@H]1CC(C2)NC(=O)c3nn(C)c4ccccc34 exhibits permeability through the blood-brain barrier.	[]	null
The compound with the SMILES of C[S](=O)(=O)c1ccc(cc1)[C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl shows permeability through the blood-brain barrier.	The compound with the SMILES of C[S](=O)(=O)c1ccc(cc1)[C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl shows permeability through the blood-brain barrier.	[]	null