IMPPAT Phytochemical information: 
Koeniginequinone A

Koeniginequinone A
Summary

SMILES: COc1ccc2c(c1)[nH]c1c2C(=O)C(=CC1=O)C
InChI: InChI=1S/C14H11NO3/c1-7-5-11(16)13-12(14(7)17)9-4-3-8(18-2)6-10(9)15-13/h3-6,15H,1-2H3
InChIKey: FBXPHUZRLGTRFW-UHFFFAOYSA-N
DeepSMILES: COcccccc6)[nH]cc5C=O)C=CC6=O)))C
Scaffold Graph/Node/Bond level: O=C1C=CC(=O)c2c1[nH]c1ccccc21
Scaffold Graph/Node level: OC1CCC(O)C2C3CCCCC3NC12
Scaffold Graph level: CC1CCC(C)C2C1CC1CCCCC12
Functional groups: cOC; c[nH]c; CC1=CC(=O)ccC1=O
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:
koeniginequinone a
External chemical identifiers:
CID:CID_11264975; ChEMBL:CHEMBL496241; ChEBI:CHEBI:173738
Chemical structure download


Koeniginequinone A
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 241.25
Log P RDKit 2.5
Topological polar surface area (Å2) RDKit 59.16
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 18
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 12
Number of sp3 hybridized carbon atoms RDKit 2
Shape complexity RDKit 0.14
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


Koeniginequinone A
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 0.83


Koeniginequinone A
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.17
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No