IMPPAT Phytochemical information: 
Capnoidine
Capnoidine
Summary

SMILES: CN1CCc2c([C@@H]1[C@@H]1OC(=O)c3c1ccc1c3OCO1)cc1c(c2)OCO1
InChI: InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18-/m1/s1
InChIKey: IYGYMKDQCDOMRE-QZTJIDSGSA-N
DeepSMILES: CNCCcc[C@@H]6[C@@H]OC=O)cc5cccc6OCO5)))))))))))))cccc6)OCO5
Scaffold Graph/Node/Bond level: O=C1OC(C2NCCc3cc4c(cc32)OCO4)c2ccc3c(c21)OCO3
Scaffold Graph/Node level: OC1OC(C2NCCC3CC4OCOC4CC32)C2CCC3OCOC3C12
Scaffold Graph level: CC1CC(C2CCCC3CC4CCCC4CC32)C2CCC3CCCC3C12
Functional groups: CN(C)C; cC(=O)OC; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Phthalide isoquinolines
NP Classifier Biosynthetic pathway: Alkaloids|Polyketides
NP Classifier Superclass: Tyrosine alkaloids|Cyclic polyketides
NP Classifier Class: Isoquinoline alkaloids|Phthalide derivatives|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
(-) adlumidine, (-)-adlumidine
External chemical identifiers:
CID:CID_120698; ChEMBL:CHEMBL1437488; ChEBI:CHEBI:68991; ZINC:ZINC000019899010; FDASRS:LV8QH3HB1R
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Capnoidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 367.36
Log P RDKit 2.58
Topological polar surface area (Å2) RDKit 66.46
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 7
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 13
Number of sp3 hybridized carbon atoms RDKit 7
Shape complexity RDKit 0.35
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
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
Capnoidine
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 0.717905
Capnoidine
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 -6.69
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No