IMPPAT Phytochemical information: 
Voaharine
Voaharine
Summary

SMILES: CC[C@@]12CN(CC[C@@]3(C(=O)C(=Nc4ccccc34)C1)O)C[C@@H]1[C@H]2O1
InChI: InChI=1S/C19H22N2O3/c1-2-18-9-14-16(22)19(23,12-5-3-4-6-13(12)20-14)7-8-21(11-18)10-15-17(18)24-15/h3-6,15,17,23H,2,7-11H2,1H3/t15-,17-,18+,19-/m1/s1
InChIKey: JYOSOFOPWRUQKW-OQIJWPOYSA-N
DeepSMILES: CC[C@@]CNCC[C@@]C=O)C=Ncccccc%106)))))))C9)))O))))C[C@@H][C@H]6O3
Scaffold Graph/Node/Bond level: O=C1C2=Nc3ccccc3C1CCN1CC(C2)C2OC2C1
Scaffold Graph/Node level: OC1C2CC3CN(CCC1C1CCCCC1N2)CC1OC31
Scaffold Graph level: CC1C2CC3CC(CCC1C1CCCCC1C2)CC1CC31
Functional groups: CN(C)C; cN=C(C)C(=O)C; CO; C[C@H]1O[C@H]1C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Quinolones and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
voaharine
External chemical identifiers:
CID:CID_101243263; ZINC:ZINC000169654737
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Voaharine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 326.4
Log P RDKit 1.8
Topological polar surface area (Å2) RDKit 65.43
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.58
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 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Voaharine
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 0.8
Voaharine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME 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 -7.71
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No