IMPPAT Phytochemical information: 
Bargustanine
Bargustanine
Summary

SMILES: COc1cc2CCN([C@H](c2c(c1O)Oc1cc2CN(C)CCc2cc1OC)[C@@H](c1ccc(c(c1)O)O)O)C
InChI: InChI=1S/C29H34N2O7/c1-30-9-7-16-12-22(36-3)23(14-19(16)15-30)38-29-25-17(13-24(37-4)28(29)35)8-10-31(2)26(25)27(34)18-5-6-20(32)21(33)11-18/h5-6,11-14,26-27,32-35H,7-10,15H2,1-4H3/t26-,27-/m1/s1
InChIKey: AYINLWLMPMZNKE-KAYWLYCHSA-N
DeepSMILES: COcccCCN[C@H]c6cc%10O))OcccCNC)CCc6cc%10OC)))))))))))))))[C@@H]cccccc6)O))O)))))O)))C
Scaffold Graph/Node/Bond level: c1ccc(CC2NCCc3cccc(Oc4ccc5c(c4)CNCC5)c32)cc1
Scaffold Graph/Node level: C1CCC(CC2NCCC3CCCC(OC4CCC5CCNCC5C4)C32)CC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCC(CC4CCC5CCCCC5C4)C32)CC1
Functional groups: cOC; cO; CO; CN(C)C; cOc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Benzylisoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
bargustanine
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Bargustanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 522.6
Log P RDKit 3.86
Topological polar surface area (Å2) RDKit 115.09
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 29
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.07
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 18
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5
Bargustanine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.36
Bargustanine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.39
Number of PAINS structural alerts SwissADME 1
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 No