IMPPAT Phytochemical information: 
Aknadinine
Aknadinine
Summary

SMILES: COC1=C(OC)[C@@]23[C@](CC1=O)(CCN3C)c1c(CC2)ccc(c1O)OC
InChI: InChI=1S/C20H25NO5/c1-21-10-9-19-11-13(22)17(25-3)18(26-4)20(19,21)8-7-12-5-6-14(24-2)16(23)15(12)19/h5-6,23H,7-11H2,1-4H3/t19-,20+/m0/s1
InChIKey: XLWYWPDYNLZUJS-VQTJNVASSA-N
DeepSMILES: COC=COC))[C@][C@]CC6=O)))CCN5C))))ccCC6))cccc6O))OC
Scaffold Graph/Node/Bond level: O=C1C=CC23CCc4ccccc4C2(CCN3)C1
Scaffold Graph/Node level: OC1CCC23CCC4CCCCC4C2(CCN3)C1
Scaffold Graph level: CC1CCC23CCCC2(C1)C1CCCCC1CC3
Functional groups: COC(=C(OC)C(=O)C)C; CN(C)C; cO; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Hasubanan alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Hasubanan alkaloids|Isoquinoline alkaloids
Synonymous chemical names:
aknadine, 4-desmethylhasubanonine(same as aknadinine and hernanadoline), hernandoline, aknadinine
External chemical identifiers:
CID:CID_159966; ChEMBL:CHEMBL1098359
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Aknadinine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 359.42
Log P RDKit 2.14
Topological polar surface area (Å2) RDKit 68.23
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
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 9
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.55
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Aknadinine
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 0.891808
Aknadinine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.26
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 No
P-glycoprotein substrate SwissADME Yes