IMPPAT Phytochemical information: 
Aknadicine

Aknadicine
Summary

SMILES: COC1=C(OC)[C@]23[C@](CC1=O)(CCN2)c1c(CC3)ccc(c1O)OC
InChI: InChI=1S/C19H23NO5/c1-23-13-5-4-11-6-7-19-17(25-3)16(24-2)12(21)10-18(19,8-9-20-19)14(11)15(13)22/h4-5,20,22H,6-10H2,1-3H3/t18-,19+/m0/s1
InChIKey: KTRLYLXLXTXHPM-RBUKOAKNSA-N
DeepSMILES: COC=COC))[C@][C@]CC6=O)))CCN5)))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; CNC; 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:
aknadicine
External chemical identifiers:
CID:CID_442156; ChEBI:CHEBI:2529
Chemical structure download


Aknadicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 345.4
Log P RDKit 1.79
Topological polar surface area (Å2) RDKit 77.02
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 25
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 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.53
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


Aknadicine
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.87


Aknadicine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.51
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes