IMPPAT Phytochemical information: 
Oxynarcotine

Oxynarcotine
Summary

SMILES: CNCCc1cc2OCOc2c(c1CC(=O)c1ccc(c(c1C(=O)O)OC)OC)OC
InChI: InChI=1S/C22H25NO8/c1-23-8-7-12-9-17-21(31-11-30-17)19(28-3)14(12)10-15(24)13-5-6-16(27-2)20(29-4)18(13)22(25)26/h5-6,9,23H,7-8,10-11H2,1-4H3,(H,25,26)
InChIKey: GLKPKUBRBLNOSC-UHFFFAOYSA-N
DeepSMILES: CNCCcccOCOc5cc9CC=O)cccccc6C=O)O)))OC)))OC)))))))))OC
Scaffold Graph/Node/Bond level: O=C(Cc1ccc2c(c1)OCO2)c1ccccc1
Scaffold Graph/Node level: OC(CC1CCC2OCOC2C1)C1CCCCC1
Scaffold Graph level: CC(CC1CCC2CCCC2C1)C1CCCCC1
Functional groups: CNC; c1cOCO1; cC(C)=O; cC(=O)O; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Stilbenes
Synonymous chemical names:
nornarceine
External chemical identifiers:
CID:CID_5320347; ZINC:ZINC000014612405; SureChEMBL:SCHEMBL11790808
Chemical structure download


Oxynarcotine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 431.44
Log P RDKit 2.33
Topological polar surface area (Å2) RDKit 112.55
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 9
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 8
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 10
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 0
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


Oxynarcotine
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 Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.547356


Oxynarcotine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.92
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 No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes