IMPPAT Phytochemical information: 
Homolycorine

Homolycorine
Summary

SMILES: COc1cc2[C@@H]3[C@@H](CC=C4[C@H]3N(C)CC4)OC(=O)c2cc1OC
InChI: InChI=1S/C18H21NO4/c1-19-7-6-10-4-5-13-16(17(10)19)11-8-14(21-2)15(22-3)9-12(11)18(20)23-13/h4,8-9,13,16-17H,5-7H2,1-3H3/t13-,16-,17-/m1/s1
InChIKey: WXZAKVLYZHWSNF-KBRIMQKVSA-N
DeepSMILES: COccc[C@@H][C@@H]CC=C[C@H]6NC)CC5)))))))OC=O)c6cc%10OC
Scaffold Graph/Node/Bond level: O=C1OC2CC=C3CCNC3C2c2ccccc21
Scaffold Graph/Node level: OC1OC2CCC3CCNC3C2C2CCCCC12
Scaffold Graph level: CC1CC2CCC3CCCC3C2C2CCCCC12
Functional groups: cOC; CC=C(C)C; CN(C)C; cC(=O)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Amaryllidaceae alkaloids
ClassyFire Subclass: Homolycorine-type amaryllidaceae alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Amarylidaceae alkaloids
Synonymous chemical names:
homolycorine
External chemical identifiers:
CID:CID_160473; ChEMBL:CHEMBL1221973; SureChEMBL:SCHEMBL4373999
Chemical structure download


Homolycorine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 315.37
Log P RDKit 2.36
Topological polar surface area (Å2) RDKit 48
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
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


Homolycorine
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 0.619247


Homolycorine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.83
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No