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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot 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-13λ⁵-azapentacyclo[11.8.0.0²,¹⁰.0⁴,⁸.0¹⁵,²⁰]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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtoberberine alkaloids and derivatives
Sub ClassNot Available
Direct ParentProtoberberine alkaloids and derivatives
Alternative Parents
Substituents
  • Protoberberine skeleton
  • Isoquinoline
  • Benzodioxole
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Pyridinium
  • Pyridine
  • Heteroaromatic compound
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption-0.5
Blood Brain Barrier+0.9279
Caco-2 permeable+0.8726
P-glycoprotein substrateNon-substrate0.6002
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.8435
Renal organic cation transporterInhibitor0.6035
CYP450 2C9 substrateNon-substrate0.876
CYP450 2D6 substrateNon-substrate0.5937
CYP450 3A4 substrateSubstrate0.6738
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 substrateNon-inhibitor0.907
CYP450 2D6 substrateInhibitor0.8933
CYP450 2C19 substrateNon-inhibitor0.7463
CYP450 3A4 substrateNon-inhibitor0.5873
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9003
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9539
BiodegradationNot ready biodegradable0.8408
Rat acute toxicity2.7834 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8367
hERG inhibition (predictor II)Non-inhibitor0.8734
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point145 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.000354 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
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