IMPPAT Phytochemical information: 
(-)-Argemonine

(-)-Argemonine
Summary

SMILES: COc1cc2c(cc1OC)C[C@@H]1N([C@H]2Cc2c1cc(c(c2)OC)OC)C
InChI: InChI=1S/C21H25NO4/c1-22-16-6-12-8-18(23-2)20(25-4)10-14(12)17(22)7-13-9-19(24-3)21(26-5)11-15(13)16/h8-11,16-17H,6-7H2,1-5H3/t16-,17-/m0/s1
InChIKey: QEOWCPFWLCIQSL-IRXDYDNUSA-N
DeepSMILES: COcccccc6OC))))C[C@@H]N[C@H]6Ccc6cccc6)OC)))OC))))))))C
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC1NC2Cc2ccccc21
Scaffold Graph/Node level: C1CCC2C(C1)CC1NC2CC2CCCCC21
Scaffold Graph level: C1CCC2C(C1)CC1CC2CC2CCCCC21
Functional groups: cOC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Pavine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids
Synonymous chemical names:
argemonine
External chemical identifiers:
CID:CID_442168; ChEBI:CHEBI:80; ZINC:ZINC000026771533
Chemical structure download


(-)-Argemonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 355.43
Log P RDKit 3.55
Topological polar surface area (Å2) RDKit 40.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 4
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 4


(-)-Argemonine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.84


(-)-Argemonine
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 -6.15
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes