IMPPAT Phytochemical information: 
8-Oxocoptisine

8-Oxocoptisine
Summary

SMILES: O=c1c2c(ccc3c2OCO3)cc2-c3c(CCn12)cc1c(c3)OCO1
InChI: InChI=1S/C19H13NO5/c21-19-17-11(1-2-14-18(17)25-9-22-14)5-13-12-7-16-15(23-8-24-16)6-10(12)3-4-20(13)19/h1-2,5-7H,3-4,8-9H2
InChIKey: UCAFJBSQKXVPDX-UHFFFAOYSA-N
DeepSMILES: O=ccccccc6OCO5)))))))cc-ccCCn%106)))cccc6)OCO5
Scaffold Graph/Node/Bond level: O=c1c2c3c(ccc2cc2n1CCc1cc4c(cc1-2)OCO4)OCO3
Scaffold Graph/Node level: OC1C2C(CCC3OCOC32)CC2C3CC4OCOC4CC3CCN12
Scaffold Graph level: CC1C2CCC3CC4CCCC4CC3C2CC2CCC3CCCC3C21
Functional groups: c=O; c1cOCO1; cn(c)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Isoquinolones and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Protoberberine alkaloids
Synonymous chemical names:
8-oxocoptisine
External chemical identifiers:
CID:CID_5245667; ChEMBL:CHEMBL3612189; ZINC:ZINC000013459011; SureChEMBL:SCHEMBL16168521; MolPort-039-338-894
Chemical structure download


8-Oxocoptisine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 335.32
Log P RDKit 2.68
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 6
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 15
Number of sp3 hybridized carbon atoms RDKit 4
Shape complexity RDKit 0.21
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
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 6


8-Oxocoptisine
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 0.632103


8-Oxocoptisine
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 -6.35
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No