IMPPAT Phytochemical information: 
Epiberberine

Epiberberine
Summary

SMILES: COc1cc2-c3cc4ccc5c(c4c[n+]3CCc2cc1OC)OCO5
InChI: InChI=1S/C20H18NO4/c1-22-18-8-13-5-6-21-10-15-12(3-4-17-20(15)25-11-24-17)7-16(21)14(13)9-19(18)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
InChIKey: FPJQGFLUORYYPE-UHFFFAOYSA-N
DeepSMILES: COccc-cccccccc6c[n+]%10CCc%14cc%18OC))))))))))OCO5
Scaffold Graph/Node/Bond level: c1ccc2c(c1)CC[n+]1cc3c4c(ccc3cc1-2)OCO4
Scaffold Graph/Node level: C1CCC2C(C1)CCN1CC3C(CCC4OCOC43)CC21
Scaffold Graph level: C1CCC2C(C1)CCC1CC3C(CCC4CCCC43)CC12
Functional groups: cOC; c[n+](c)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
Synonymous chemical names:
Epiberberine, epiberberine
External chemical identifiers:
CID:CID_160876; ChEMBL:CHEMBL1197637; ZINC:ZINC000006017816; MolPort-039-052-346
Chemical structure download


Epiberberine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 336.37
Log P RDKit 3.1
Topological polar surface area (Å2) RDKit 40.8
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
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


Epiberberine
Drug-likeness
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 0.674491


Epiberberine
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 -5.78
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes


Epiberberine
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_000614ENSG00000087460GNAS2778NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000818ENSG00000187258NPSR1387129ChEMBL, NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000450ENSG00000004487KDM1A23028BindingDB, ChEMBL
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_000011ENSG00000126261UBA210054ChEMBL, NPASS
TAR_EXP_000012ENSG00000142230SAE110055BindingDB, ChEMBL
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_001663ENSG00000162607USP17398ChEMBL, NPASS
TAR_EXP_001650ENSG00000103275UBE2I7329BindingDB
TAR_EXP_001630ENSG00000074319TSG1017251ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001344ENSG00000132341RAN5901NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001139ENSG00000166851PLK15347NPASS
TAR_EXP_000361ENSG00000128394APOBEC3F200316NPASS
TAR_EXP_000119ENSG00000101751POLI11201ChEMBL, NPASS
TAR_EXP_000102ENSG00000091428RAPGEF411069NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000053ENSG00000079337RAPGEF310411NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS