IMPPAT Phytochemical information: 
Oxyberberine
Oxyberberine
Summary

SMILES: COc1c(OC)ccc2c1c(=O)n1c(-c3cc4OCOc4cc3CC1)c2
InChI: InChI=1S/C20H17NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9H,5-6,10H2,1-2H3
InChIKey: ZHYQCBCBTQWPLC-UHFFFAOYSA-N
DeepSMILES: COccOC))cccc6c=O)nc-cccOCOc5cc9CC%13)))))))))))c6
Scaffold Graph/Node/Bond level: O=c1c2ccccc2cc2n1CCc1cc3c(cc1-2)OCO3
Scaffold Graph/Node level: OC1C2CCCCC2CC2C3CC4OCOC4CC3CCN12
Scaffold Graph level: CC1C2CCCCC2CC2C3CC4CCCC4CC3CCC12
Functional groups: cOC; c=O; cn(c)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Isoquinolones and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Protoberberine alkaloids
Synonymous chemical names:
oxyberberine, oxyberberine (isoquinoline alkaloid), Oxyberberine, berlambine
External chemical identifiers:
CID:CID_11066; ChEMBL:CHEMBL11531; ZINC:ZINC000001604019; FDASRS:4A04YKB3FT; SureChEMBL:SCHEMBL229912; MolPort-006-069-431
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Oxyberberine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 351.36
Log P RDKit 2.97
Topological polar surface area (Å2) RDKit 58.92
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.25
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5
Oxyberberine
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 0.710399
Oxyberberine
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 -6.36
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes