IMPPAT Phytochemical information: 
Koenigine

Koenigine
Summary

SMILES: COc1cc2c(cc1O)[nH]c1c2cc(C)c2c1C=CC(O2)(C)C
InChI: InChI=1S/C19H19NO3/c1-10-7-13-12-8-16(22-4)15(21)9-14(12)20-17(13)11-5-6-19(2,3)23-18(10)11/h5-9,20-21H,1-4H3
InChIKey: CZZZOTXCAIDYOZ-UHFFFAOYSA-N
DeepSMILES: COcccccc6O)))[nH]cc5ccC)cc6C=CCO6)C)C
Scaffold Graph/Node/Bond level: C1=Cc2c(ccc3c2[nH]c2ccccc23)OC1
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CCCOC3CCC21
Scaffold Graph level: C1CCC2C(C1)CC1C3CCCCC3CCC21
Functional groups: cOC; cO; c[nH]c; cC=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Carbazoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Carbazole alkaloids
Synonymous chemical names:
koenigine, Koenigine
External chemical identifiers:
CID:CID_5318825; ChEBI:CHEBI:168437
Chemical structure download


Koenigine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.37
Log P RDKit 4.53
Topological polar surface area (Å2) RDKit 54.48
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 14
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.26
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
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 4


Koenigine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.694222


Koenigine
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 -5.14
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes