IMPPAT Phytochemical information: 
(-)-8-Oxocanadine

(-)-8-Oxocanadine
Summary

SMILES: O=C1N2CCc3c(C2Cc2c1c(O)c(cc2)O)cc1c(c3)OCO1
InChI: InChI=1S/C18H15NO5/c20-13-2-1-10-5-12-11-7-15-14(23-8-24-15)6-9(11)3-4-19(12)18(22)16(10)17(13)21/h1-2,6-7,12,20-21H,3-5,8H2
InChIKey: GKJXQIXFMHLUCW-UHFFFAOYSA-N
DeepSMILES: O=CNCCccC6Ccc%10cO)ccc6))O)))))))cccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1c2ccccc2CC2c3cc4c(cc3CCN12)OCO4
Scaffold Graph/Node level: OC1C2CCCCC2CC2C3CC4OCOC4CC3CCN12
Scaffold Graph level: CC1C2CCCCC2CC2C3CC4CCCC4CC3CCC12
Functional groups: cC(=O)N(C)C; cO; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Protoberberine alkaloids
Synonymous chemical names:
(-)-8-oxocanadine
External chemical identifiers:
CID:CID_86572845
Chemical structure download


(-)-8-Oxocanadine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 325.32
Log P RDKit 2.12
Topological polar surface area (Å2) RDKit 79.23
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.06
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.28
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 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


(-)-8-Oxocanadine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.72548


(-)-8-Oxocanadine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.42
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes