IMPPAT Phytochemical information: 
Tuboxenine

Tuboxenine
Summary

SMILES: C[C@@H]1[C@]23CCCN4[C@@H]3[C@@]3([C@@]1(CC2)Nc1c3cccc1)CC4
InChI: InChI=1S/C19H24N2/c1-13-17-7-4-11-21-12-10-18(16(17)21)14-5-2-3-6-15(14)20-19(13,18)9-8-17/h2-3,5-6,13,16,20H,4,7-12H2,1H3/t13?,16-,17-,18+,19-/m0/s1
InChIKey: ZMNQOAJDBCBZSX-NKZCTWTRSA-N
DeepSMILES: C[C@@H][C@@]CCCN[C@@H]6[C@@][C@@]9CC%10))Ncc5cccc6))))))))CC5
Scaffold Graph/Node/Bond level: c1ccc2c(c1)NC13CCC4(CCCN5CCC21C54)C3
Scaffold Graph/Node level: C1CCC2C(C1)NC13CCC4(CCCN5CCC21C54)C3
Scaffold Graph level: C1CCC2C(C1)CC13CCC4(CCCC5CCC21C54)C3
Functional groups: cNC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidospermatan-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
tuboxenine, Tuboxenine
External chemical identifiers:
CID:CID_101104094
Chemical structure download


Tuboxenine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 280.42
Log P RDKit 3.39
Topological polar surface area (Å2) RDKit 15.27
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 2
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.68
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6


Tuboxenine
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 0.78


Tuboxenine
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 -5.51
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes