IMPPAT Phytochemical information: 
Losbanine
Losbanine
Summary

SMILES: OC(=O)[C@]1(COCC=C2[C@@H]1CCNC2)c1cc2c([nH]1)cccc2
InChI: InChI=1S/C18H20N2O3/c21-17(22)18(16-9-12-3-1-2-4-15(12)20-16)11-23-8-6-13-10-19-7-5-14(13)18/h1-4,6,9,14,19-20H,5,7-8,10-11H2,(H,21,22)/t14-,18-/m0/s1
InChIKey: NCJBMKOLGAKGTI-KSSFIOAISA-N
DeepSMILES: OC=O)[C@]COCC=C[C@@H]7CCNC6))))))))))cccc[nH]5)cccc6
Scaffold Graph/Node/Bond level: C1=C2CNCCC2C(c2cc3ccccc3[nH]2)COC1
Scaffold Graph/Node level: C1CCC2NC(C3COCCC4CNCCC43)CC2C1
Scaffold Graph level: C1CCC2CC(C3CCCCC4CCCCC43)CC2C1
Functional groups: CC(=O)O; COC; CC=C(C)C; CNC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carboline alkaloids
Synonymous chemical names:
losbanine, 6,7-seco-6-norangustilobine B(losbanine), Losbanine
External chemical identifiers:
CID:CID_101589339
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Losbanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 312.37
Log P RDKit 2.06
Topological polar surface area (Å2) RDKit 74.35
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.39
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Losbanine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.74
Losbanine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very 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 -9.26
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