IMPPAT Phytochemical information: 
9-O-Demethylhomolycorine
9-O-Demethylhomolycorine
Summary

SMILES: COc1cc2[C@@H]3[C@@H](CC=C4[C@H]3N(C)CC4)OC(=O)c2cc1O
InChI: InChI=1S/C17H19NO4/c1-18-6-5-9-3-4-13-15(16(9)18)10-8-14(21-2)12(19)7-11(10)17(20)22-13/h3,7-8,13,15-16,19H,4-6H2,1-2H3/t13-,15-,16-/m1/s1
InChIKey: VLDOBKJPRUQEEC-FVQBIDKESA-N
DeepSMILES: COccc[C@@H][C@@H]CC=C[C@H]6NC)CC5)))))))OC=O)c6cc%10O
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; cO
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:
9-o-demethyl homolycorine, 9-o-demethylhomolycorine, 9-demethylhomolycorine
External chemical identifiers:
CID:CID_388787; ChEMBL:CHEMBL1979251; ChEBI:CHEBI:31154; ZINC:ZINC000004102398
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
9-O-Demethylhomolycorine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 301.34
Log P RDKit 2.06
Topological polar surface area (Å2) RDKit 59
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 17
Number of heavy atoms RDKit 22
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 0.18
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.47
Number of rotatable bonds RDKit 1
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
9-O-Demethylhomolycorine
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 0.635361
9-O-Demethylhomolycorine
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 -6.98
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 Yes