IMPPAT Phytochemical information: 
Bisnordihydrotoxyferine
Bisnordihydrotoxyferine
Summary

SMILES: C/C=C\1/CN2CC[C@@]34[C@@H]2C[C@@H]1C1=CN2c5ccccc5[C@]56[C@@H]2C(=CN([C@H]31)c1c4cccc1)[C@H]1C[C@@H]6N(CC5)C/C/1=C/C
InChI: InChI=1S/C38H40N4/c1-3-23-19-39-15-13-37-29-9-5-8-12-32(29)42-22-28-26-18-34-38(14-16-40(34)20-24(26)4-2)30-10-6-7-11-31(30)41(36(28)38)21-27(35(37)42)25(23)17-33(37)39/h3-12,21-22,25-26,33-36H,13-20H2,1-2H3/b23-3-,24-4-,27-21-,28-22-/t25-,26-,33-,34-,35-,36-,37+,38+/m0/s1
InChIKey: XISKMNBBUQQBBE-SWFQZPKUSA-N
DeepSMILES: C/C=C/CNCC[C@@][C@@H]5C[C@@H]/9C=CNcccccc6[C@@][C@@H]9C=CN[C@H]%19%15)cc%20cccc6))))))))[C@H]C[C@@H]6NCC9))C/C/6=C/C
Scaffold Graph/Node/Bond level: C=C1CN2CCC34c5ccccc5N5C=C6C7CC8N(CCC89c8ccccc8N(C=C(C1CC23)C54)C69)CC7=C
Scaffold Graph/Node level: CC1CN2CCC34C5CCCCC5N5CC6C7CC8N(CCC89C8CCCCC8N(CC(C1CC23)C54)C69)CC7C
Scaffold Graph level: CC1CC2CCC34C2CC1C1CC2C5CCCCC5C56CCC7CC(C)C(CC75)C(CC(C5CCCCC53)C14)C26
Functional groups: C/C=C(/C)C; CN(C)C; cN(C)C=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Strychnos alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Strychnos type
Synonymous chemical names:
bisnordihydrotoxiferine
External chemical identifiers:
CID:CID_21628627; ChEMBL:CHEMBL403151
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bisnordihydrotoxyferine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 552.77
Log P RDKit 6.13
Topological polar surface area (Å2) RDKit 12.96
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 38
Number of heavy atoms RDKit 42
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 18
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 7
Number of aliphatic rings RDKit 9
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 11
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 6
Number of Smallest Set of Smallest Rings (SSSR) RDKit 11
Bisnordihydrotoxyferine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36
Bisnordihydrotoxyferine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.65
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes