IMPPAT Phytochemical information: 
(S)-autumnaline

(S)-autumnaline
Summary

SMILES: COc1cc(CC[C@@H]2N(C)CCc3c2cc(O)c(c3)OC)cc(c1OC)O
InChI: InChI=1S/C21H27NO5/c1-22-8-7-14-11-19(25-2)17(23)12-15(14)16(22)6-5-13-9-18(24)21(27-4)20(10-13)26-3/h9-12,16,23-24H,5-8H2,1-4H3/t16-/m0/s1
InChIKey: GZUNPCNPOLOTLX-INIZCTEOSA-N
DeepSMILES: COcccCC[C@@H]NC)CCcc6ccO)cc6)OC)))))))))))))ccc6OC)))O
Scaffold Graph/Node/Bond level: c1ccc(CCC2NCCc3ccccc32)cc1
Scaffold Graph/Node level: C1CCC(CCC2NCCC3CCCCC32)CC1
Scaffold Graph level: C1CCC(CCC2CCCC3CCCCC32)CC1
Functional groups: cOC; CN(C)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Phenethylisoquinoline alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Phenethylisoquinoline alkaloids
Synonymous chemical names:
autumnaline
External chemical identifiers:
CID:CID_13878324; ChEBI:CHEBI:80672
Chemical structure download


(S)-autumnaline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 373.45
Log P RDKit 3.29
Topological polar surface area (Å2) RDKit 71.39
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
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 3


(S)-autumnaline
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 0.809698


(S)-autumnaline
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 -6.21
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No