IMPPAT Phytochemical information: 
Bicuculline
Bicuculline
Summary

SMILES: CN1CCc2c([C@H]1[C@@H]1OC(=O)c3c1ccc1c3OCO1)cc1c(c2)OCO1
InChI: InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1
InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N
DeepSMILES: CNCCcc[C@H]6[C@@H]OC=O)cc5cccc6OCO5)))))))))))))cccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1OC(C2NCCc3cc4c(cc32)OCO4)c2ccc3c(c21)OCO3
Scaffold Graph/Node level: OC1OC(C2NCCC3CC4OCOC4CC32)C2CCC3OCOC3C12
Scaffold Graph level: CC1CC(C2CCCC3CC4CCCC4CC32)C2CCC3CCCC3C12
Functional groups: CN(C)C; cC(=O)OC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Phthalide isoquinolines
NP Classifier Biosynthetic pathway: Alkaloids|Polyketides
NP Classifier Superclass: Tyrosine alkaloids|Cyclic polyketides
NP Classifier Class: Isoquinoline alkaloids|Phthalide derivatives|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
bicuculline, (+)-bicuculline, d-bicuculline
External chemical identifiers:
CID:CID_10237; ChEMBL:CHEMBL417990; ChEBI:CHEBI:3092; ZINC:ZINC000019899011; FDASRS:Y37615DVKC; SureChEMBL:SCHEMBL8222; MolPort-001-728-112
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bicuculline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 367.36
Log P RDKit 2.58
Topological polar surface area (Å2) RDKit 66.46
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Bicuculline
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.717905
Bicuculline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.69
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Bicuculline
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000532ENSG00000163285GABRG12565ChEMBL
TAR_EXP_000531ENSG00000102287GABRE2564ChEMBL
TAR_EXP_000535ENSG00000094755GABRP2568ChEMBL
TAR_EXP_001225ENSG00000268089GABRQ55879ChEMBL
TAR_EXP_000554ENSG00000101347SAMHD125939ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269BindingDB
TAR_EXP_000534ENSG00000182256GABRG32567ChEMBL
TAR_EXP_000533ENSG00000113327GABRG22566ChEMBL
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001472ENSG00000153253SCN3A6328ChEMBL, NPASS
TAR_EXP_001471ENSG00000136531SCN2A6326ChEMBL
TAR_EXP_001470ENSG00000144285SCN1A6323ChEMBL
TAR_EXP_000530ENSG00000187730GABRD2563ChEMBL
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_000528ENSG00000145864GABRB22561ChEMBL
TAR_EXP_000527ENSG00000163288GABRB12560ChEMBL
TAR_EXP_000529ENSG00000166206GABRB32562ChEMBL
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000525ENSG00000186297GABRA52558BindingDB, ChEMBL
TAR_EXP_000524ENSG00000109158GABRA42557ChEMBL
TAR_EXP_000523ENSG00000011677GABRA32556BindingDB, ChEMBL
TAR_EXP_000522ENSG00000151834GABRA22555ChEMBL
TAR_EXP_000521ENSG00000022355GABRA12554BindingDB, ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000526ENSG00000145863GABRA62559BindingDB, ChEMBL, NPASS