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Identification
NameBerberine
Accession NumberDB04115  (EXPT00672)
TypeSmall Molecule
GroupsExperimental
Description

An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number2086-83-1
WeightAverage: 336.3612
Monoisotopic: 336.123583069
Chemical FormulaC20H18NO4
InChI KeyYBHILYKTIRIUTE-UHFFFAOYSA-N
InChI
InChI=1S/C20H18NO4/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/q+1
IUPAC Name
16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium
SMILES
COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassIsoquinolines and Derivatives
SubclassNot Available
Direct parentIsoquinolines and Derivatives
Alternative parentsBenzodioxoles; Anisoles; Alkyl Aryl Ethers; Pyridinium Derivatives; Polyamines; Acetals
Substituentsanisole; phenol ether; alkyl aryl ether; benzene; pyridinium; pyridine; acetal; polyamine; ether; organonitrogen compound
Classification descriptionThis compound belongs to the isoquinolines and derivatives. These are aromatic polycyclic compounds containing an isoquinoline moiety, which consists of a benzene ring fused to a pyridine ring and forming benzo[c]pyridine.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.5
Blood Brain Barrier + 0.9279
Caco-2 permeable + 0.8726
P-glycoprotein substrate Non-substrate 0.6002
P-glycoprotein inhibitor I Non-inhibitor 0.8782
P-glycoprotein inhibitor II Non-inhibitor 0.8435
Renal organic cation transporter Inhibitor 0.6035
CYP450 2C9 substrate Non-substrate 0.876
CYP450 2D6 substrate Non-substrate 0.5937
CYP450 3A4 substrate Substrate 0.6738
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Inhibitor 0.8933
CYP450 2C19 substrate Non-inhibitor 0.7463
CYP450 3A4 substrate Non-inhibitor 0.5873
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9003
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.9539
Biodegradation Not ready biodegradable 0.8408
Rat acute toxicity 2.7834 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8367
hERG inhibition (predictor II) Non-inhibitor 0.8734
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point145 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000354ALOGPS
logP-0.18ALOGPS
logP-1.3ChemAxon
logS-6ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.8 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity93.52 m3·mol-1ChemAxon
Polarizability36.92 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraMS/MSLC-MS1D NMR2D NMR
References
Synthesis Reference

Christopher W. Grote, Frank W. Moser, John E. Johnson, JR., “Berberine compounds and processes for the preparation of berberine compounds.” U.S. Patent US20100081821, issued April 01, 2010.

US20100081821
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00092
KEGG CompoundC00757
PubChem Compound2353
PubChem Substance46506051
ChEBI16118
ChEMBL
Therapeutic Targets DatabaseDNC000385
PharmGKBPA165860812
HETBER
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. HTH-type transcriptional regulator QacR

Kind: protein

Organism: Staphylococcus haemolyticus

Pharmacological action: unknown

Components

Name UniProt ID Details
HTH-type transcriptional regulator QacR P0A0N5 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23