IMPPAT Phytochemical information: 
Skimmianine

Skimmianine
Summary

SMILES: COc1ccc2c(c1OC)nc1c(c2OC)cco1
InChI: InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3
InChIKey: SLSIBLKBHNKZTB-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC)))nccc6OC)))cco5
Scaffold Graph/Node/Bond level: c1ccc2nc3occc3cc2c1
Scaffold Graph/Node level: C1CCC2NC3OCCC3CC2C1
Scaffold Graph level: C1CCC2CC3CCCC3CC2C1
Functional groups: cOC; cnc; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Quinolines and derivatives
ClassyFire Subclass: Furanoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids|Anthranilic acid alkaloids
NP Classifier Class: Quinoline alkaloids
Synonymous chemical names:
skimmiamine, chloroxylonine, skimmianine, Skimmianine
External chemical identifiers:
CID:CID_6760; ChEMBL:CHEMBL21396; ChEBI:CHEBI:9172; ZINC:ZINC000000035525; FDASRS:4E1KLC380B; SureChEMBL:SCHEMBL893654; MolPort-000-742-994
Chemical structure download


Skimmianine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 259.26
Log P RDKit 3.01
Topological polar surface area (Å2) RDKit 53.72
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 19
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 11
Number of sp3 hybridized carbon atoms RDKit 3
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 3
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


Skimmianine
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 0.723303


Skimmianine
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 -5.87
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 Yes
P-glycoprotein substrate SwissADME No