IMPPAT Phytochemical information: 
Akuammiline

Akuammiline
Summary

SMILES: COC(=O)C1(COC(=O)C)[C@@H]2C[C@H]3C4=Nc5c([C@@]14CCN3C/C/2=C/C)cccc5
InChI: InChI=1S/C23H26N2O4/c1-4-15-12-25-10-9-22-16-7-5-6-8-18(16)24-20(22)19(25)11-17(15)23(22,21(27)28-3)13-29-14(2)26/h4-8,17,19H,9-13H2,1-3H3/b15-4-/t17?,19-,22?,23?/m0/s1
InChIKey: QBHALCZZZWCCLV-KDXAUCRISA-N
DeepSMILES: COC=O)CCOC=O)C))))[C@@H]C[C@H]C=Ncc[C@@]95CCN9C/C/%13=C/C))))))))cccc6
Scaffold Graph/Node/Bond level: C=C1CN2CCC34CC1CC2C3=Nc1ccccc14
Scaffold Graph/Node level: CC1CN2CCC34CC1CC2C3NC1CCCCC14
Scaffold Graph level: CC1CC2CCC34CC1CC2C3CC1CCCCC14
Functional groups: COC(C)=O; cN=C(C)C; CN(C)C; C/C=C(/C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
akuammiline
External chemical identifiers:
CID:CID_9977936; MolPort-039-338-257
Chemical structure download


Akuammiline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 394.47
Log P RDKit 2.79
Topological polar surface area (Å2) RDKit 68.2
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.52
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5


Akuammiline
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 0.58


Akuammiline
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 -7.66
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
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