IMPPAT Phytochemical information: 
5-(4,5-Dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,2,3-trimethyl-3,4-dihydroisoquinolin-2-ium-6-ol

5-(4,5-Dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,2,3-trimethyl-3,4-dihydroisoquinolin-2-ium-6-ol
Summary

SMILES: COc1cc(O)c(c2c1C(=[N+](C)C(C2)C)C)c1c(C)cc(c2c1cccc2OC)OC
InChI: InChI=1S/C26H29NO4/c1-14-11-21(30-6)26-17(9-8-10-20(26)29-5)23(14)25-18-12-15(2)27(4)16(3)24(18)22(31-7)13-19(25)28/h8-11,13,15H,12H2,1-7H3/p+1
InChIKey: APRMONYQVUUJSI-UHFFFAOYSA-O
DeepSMILES: COcccO)ccc6C=[N+]C)CC6)C)))C))))ccC)cccc6cccc6OC))))))))OC
Scaffold Graph/Node/Bond level: C1=[NH+]CCc2c1cccc2-c1cccc2ccccc12
Scaffold Graph/Node level: C1CCC2C(C1)CCCC2C1CCCC2CNCCC21
Scaffold Graph level: C1CCC2C(C1)CCCC2C1CCCC2CCCCC21
Functional groups: cOC; cO; cC(C)=[N+](C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Naphthylisoquinolines
Synonymous chemical names:
ancistrocladinine
External chemical identifiers:
CID:CID_375959
Chemical structure download


5-(4,5-Dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,2,3-trimethyl-3,4-dihydroisoquinolin-2-ium-6-ol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 420.53
Log P RDKit 4.94
Topological polar surface area (Å2) RDKit 50.93
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 26
Number of heavy atoms RDKit 31
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.04
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 17
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
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


5-(4,5-Dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,2,3-trimethyl-3,4-dihydroisoquinolin-2-ium-6-ol
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 Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.61


5-(4,5-Dimethoxy-2-methylnaphthalen-1-yl)-8-methoxy-1,2,3-trimethyl-3,4-dihydroisoquinolin-2-ium-6-ol
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.49
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes