IMPPAT Phytochemical information: 
Berberine chloride

Berberine chloride
Summary

SMILES: COc1c(OC)ccc2c1c[n+]1CCc3c(-c1c2)cc1c(c3)OCO1.[Cl-]
InChI: InChI=1S/C20H18NO4.ClH/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1
InChIKey: VKJGBAJNNALVAV-UHFFFAOYSA-M
DeepSMILES: COccOC))cccc6c[n+]CCcc-c6c%10))cccc6)OCO5.[Cl-]
Scaffold Graph/Node/Bond level: c1ccc2c[n+]3c(cc2c1)-c1cc2c(cc1CC3)OCO2
Scaffold Graph/Node level: C1CCC2CN3CCC4CC5OCOC5CC4C3CC2C1
Scaffold Graph level: C1CCC2CC3C(CCC4CC5CCCC5CC43)CC2C1
Functional groups: cOC; c[n+](c)C; c1cOCO1; [Cl-]
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Protoberberine alkaloids and derivatives
Synonymous chemical names:
berberine chloride
External chemical identifiers:
CID:CID_12456; ChEMBL:CHEMBL12089; ChEBI:CHEBI:31271; FDASRS:UOT4O1BYV8; SureChEMBL:SCHEMBL153906; MolPort-001-742-620
Chemical structure download


Berberine chloride
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 371.82
Log P RDKit 0.1
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 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


Berberine chloride
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 0.599193


Berberine chloride
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.43
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes


Berberine chloride
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_001663ENSG00000162607USP17398NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000822ENSG00000182866LCK3932ChEMBL
TAR_EXP_000802ENSG00000187486KCNJ113767ChEMBL
TAR_EXP_000798ENSG00000055118KCNH23757BindingDB, ChEMBL, NPASS
TAR_EXP_000041ENSG00000147955SIGMAR110280ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000081ENSG00000173198CYSLTR110800ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000127ENSG00000168539CHRM11128ChEMBL, NPASS
TAR_EXP_001837ENSG00000163394CCKAR886ChEMBL
TAR_EXP_000130ENSG00000181072CHRM21129ChEMBL
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000133ENSG00000133019CHRM31131ChEMBL
TAR_EXP_000137ENSG00000184984CHRM51133ChEMBL
TAR_EXP_000176ENSG00000166192SENP8123228BindingDB, ChEMBL, NPASS
TAR_EXP_000177ENSG00000183813CCR41233ChEMBL
TAR_EXP_000178ENSG00000160791CCR51234ChEMBL
TAR_EXP_000187ENSG00000118432CNR11268ChEMBL
TAR_EXP_000200ENSG00000163485ADORA1134ChEMBL
TAR_EXP_001669ENSG00000114812VIPR17433ChEMBL
TAR_EXP_000214ENSG00000282608ADORA3140ChEMBL
TAR_EXP_000215ENSG00000151414NEK7140609BindingDB, ChEMBL, NPASS
TAR_EXP_000222ENSG00000112062MAPK141432ChEMBL
TAR_EXP_000233ENSG00000171873ADRA1D146ChEMBL
TAR_EXP_000243ENSG00000150594ADRA2A150ChEMBL
TAR_EXP_000249ENSG00000274286ADRA2B151ChEMBL, NPASS
TAR_EXP_000250ENSG00000100448CTSG1511ChEMBL
TAR_EXP_000134ENSG00000180720CHRM41132ChEMBL
TAR_EXP_000861ENSG00000124089MC3R4159ChEMBL
TAR_EXP_000862ENSG00000166603MC4R4160ChEMBL
TAR_EXP_000863ENSG00000176136MC5R4161ChEMBL
TAR_EXP_001231ENSG00000102882MAPK35595ChEMBL
TAR_EXP_001230ENSG00000100030MAPK15594ChEMBL
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001191ENSG00000085377PREP5550BindingDB, NPASS
TAR_EXP_001186ENSG00000138814PPP3CA5530ChEMBL
TAR_EXP_001811ENSG00000138735PDE5A8654ChEMBL
TAR_EXP_001181ENSG00000166148AVPR1A552ChEMBL
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_001106ENSG00000085563ABCB15243ChEMBL
TAR_EXP_001007ENSG00000089041P2RX75027ChEMBL, NPASS
TAR_EXP_001003ENSG00000112038OPRM14988ChEMBL
TAR_EXP_001002ENSG00000082556OPRK14986ChEMBL
TAR_EXP_001001ENSG00000116329OPRD14985ChEMBL
TAR_EXP_000988ENSG00000185149NPY2R4887ChEMBL
TAR_EXP_000987ENSG00000164128NPY1R4886ChEMBL
TAR_EXP_001807ENSG00000196139AKR1C38644BindingDB
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, ChEMBL, NPASS
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_000888ENSG00000100985MMP94318ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_001289ENSG00000169403PTAFR5724ChEMBL
TAR_EXP_000255ENSG00000184160ADRA2C152ChEMBL, NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001320ENSG00000262418PTPRC5788ChEMBL
TAR_EXP_001339ENSG00000136238RAC15879ChEMBL, NPASS
TAR_EXP_001341ENSG00000002016RAD525893ChEMBL, NPASS
TAR_EXP_001343ENSG00000114200BCHE590BindingDB, ChEMBL, NPASS
TAR_EXP_001753ENSG00000137752CASP1834ChEMBL
TAR_EXP_001299ENSG00000073756PTGS25743ChEMBL
TAR_EXP_000258ENSG00000043591ADRB1153ChEMBL
TAR_EXP_000203ENSG00000128271ADORA2A135ChEMBL
TAR_EXP_000262ENSG00000140465CYP1A11543ChEMBL, NPASS
TAR_EXP_000515ENSG00000010810FYN2534ChEMBL
TAR_EXP_000461ENSG00000102755FLT12321ChEMBL
TAR_EXP_001519ENSG00000142319SLC6A36531ChEMBL
TAR_EXP_001518ENSG00000103546SLC6A26530ChEMBL
TAR_EXP_001461ENSG00000186350RXRA6256BindingDB, ChEMBL, NPASS
TAR_EXP_001458ENSG00000168398BDKRB2624ChEMBL
TAR_EXP_000455ENSG00000004139SARM123098ChEMBL, NPASS
TAR_EXP_000450ENSG00000004487KDM1A23028BindingDB
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000261ENSG00000169252ADRB2154ChEMBL
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000387ENSG00000141736ERBB22064ChEMBL
TAR_EXP_000357ENSG00000277571ELANE1991ChEMBL
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760ChEMBL
TAR_EXP_001520ENSG00000108576SLC6A46532ChEMBL
TAR_EXP_000733ENSG00000135914HTR2B3357ChEMBL, NPASS
TAR_EXP_000732ENSG00000102468HTR2A3356ChEMBL
TAR_EXP_000704ENSG00000113749HRH23274ChEMBL
TAR_EXP_000703ENSG00000196639HRH13269ChEMBL
TAR_EXP_000692ENSG00000113161HMGCR3156ChEMBL
TAR_EXP_000683ENSG00000197386HTT3064NPASS
TAR_EXP_001642ENSG00000121807CCR2729230ChEMBL
TAR_EXP_000339ENSG00000151617EDNRA1909ChEMBL
TAR_EXP_001631ENSG00000165409TSHR7253NPASS
TAR_EXP_001592ENSG00000059377TBXAS16916ChEMBL
TAR_EXP_000645ENSG00000113580NR3C12908ChEMBL, NPASS
TAR_EXP_001587ENSG00000115353TACR16869ChEMBL
TAR_EXP_001585ENSG00000075073TACR26865ChEMBL
TAR_EXP_001583ENSG00000006071ABCC86833ChEMBL, NPASS
TAR_EXP_001568ENSG00000168610STAT36774ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001599ENSG00000164362TERT7015BindingDB
TAR_EXP_000332ENSG00000180772AGTR2186ChEMBL
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL
TAR_EXP_000326ENSG00000151577DRD31814ChEMBL
TAR_EXP_000752ENSG00000142192APP351ChEMBL, NPASS
TAR_EXP_001727ENSG00000004948CALCR799ChEMBL
TAR_EXP_000760ENSG00000163464CXCR13577ChEMBL
TAR_EXP_000276ENSG00000272532CYP2D61565ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559ChEMBL
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL
TAR_EXP_000277ENSG00000130649CYP2E11571ChEMBL
TAR_EXP_001943ENSG00000070831CDC42998ChEMBL, NPASS
TAR_EXP_000265ENSG00000255974CYP2A61548ChEMBL
TAR_EXP_000761ENSG00000180871CXCR23579ChEMBL
TAR_EXP_000766ENSG00000131203IDO13620ChEMBL
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB
TAR_EXP_000263ENSG00000140505CYP1A21544ChEMBL
TAR_EXP_000267ENSG00000188778ADRB3155ChEMBL
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_000759ENSG00000169429CXCL83576BindingDB
TAR_EXP_000734ENSG00000147246HTR2C3358ChEMBL
TAR_EXP_000325ENSG00000149295DRD21813ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812ChEMBL
TAR_EXP_000738ENSG00000158748HTR63362ChEMBL
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000327ENSG00000069696DRD41815ChEMBL
TAR_EXP_001728ENSG00000176208ATAD579915NPASS