IMPPAT Phytochemical information: 
Koeniginequinone B

Koeniginequinone B
Summary

SMILES: COc1cc2[nH]c3c(c2cc1OC)C(=O)C(=CC3=O)C
InChI: InChI=1S/C15H13NO4/c1-7-4-10(17)14-13(15(7)18)8-5-11(19-2)12(20-3)6-9(8)16-14/h4-6,16H,1-3H3
InChIKey: NIRRSVHUEHTZSM-UHFFFAOYSA-N
DeepSMILES: COccc[nH]ccc5cc9OC)))))C=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 b
External chemical identifiers:
CID:CID_11184822; ChEMBL:CHEMBL4575424; ZINC:ZINC000038340569; SureChEMBL:SCHEMBL17817043
Chemical structure download


Koeniginequinone B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 271.27
Log P RDKit 2.51
Topological polar surface area (Å2) RDKit 68.39
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
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 3
Shape complexity RDKit 0.2
Number of rotatable bonds RDKit 2
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 B
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.910808


Koeniginequinone B
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 -6.37
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