Berberine

Identification

Name
Berberine
Accession Number
DB04115  (EXPT00672)
Type
Small Molecule
Groups
Approved, Investigational
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.

Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Berberine chlorideUOT4O1BYV8633-65-8VKJGBAJNNALVAV-UHFFFAOYSA-M
Berberine sulfate anhydrousFST3E667FF316-41-6OJVABJMSSDUECT-UHFFFAOYSA-L
Categories
UNII
0I8Y3P32UF
CAS number
2086-83-1
Weight
Average: 336.3612
Monoisotopic: 336.123583069
Chemical Formula
C20H18NO4
InChI Key
YBHILYKTIRIUTE-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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UHTH-type transcriptional regulator QacRNot AvailableStaphylococcus haemolyticus
UBaculoviral IAP repeat-containing protein 5Not AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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 References
Not Available
External Links
Human Metabolome Database
HMDB0003409
KEGG Drug
D00092
KEGG Compound
C00757
PubChem Compound
2353
PubChem Substance
46506051
ChemSpider
2263
BindingDB
50203126
ChEBI
16118
ChEMBL
CHEMBL295124
Therapeutic Targets Database
DNC000385
PharmGKB
PA165860812
HET
BER
Wikipedia
Berberine
PDB Entries
1jum / 2qvd / 3bti / 3d6y / 3np6 / 3r6r / 3vw2 / 4dbk / 5y0v

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingPreventionUlcerative Colitis (UC)1
1, 2CompletedTreatmentType 2 Diabetes Mellitus1
2CompletedTreatmentNonalcoholic Fatty Liver Disease1
2RecruitingTreatmentMixed hypercholesterolemia1
2, 3RecruitingTreatmentMetabolic Syndromes / Schizophrenia Spectrum and Other Psychotic Disorders / Schizophrenic Disorders1
3CompletedTreatmentMetabolic Syndromes / Type 2 Diabetes Mellitus1
4CompletedNot AvailableMetabolic Syndromes1
4CompletedTreatmentGastritis / Indigestion / Peptic Ulcers2
4CompletedTreatmentSchizophrenic Disorders / Therapeutics1
4Not Yet RecruitingTreatmentBacterial Infection Due to Helicobacter Pylori (H. Pylori) / Gastric Ulcer (GU) / Gastritis / Gastritis Chronic / Malignant Neoplasm of Stomach1
4Not Yet RecruitingTreatmentHyperglycemias1
4Not Yet RecruitingTreatmentUlcerative Colitis (UC)1
4RecruitingTreatmentChronic Kidney Disease (CKD) / Diabetes Mellitus (DM)1
4RecruitingTreatmentCoronary Artery Disease / Percutaneous Coronary Intervention1
Not AvailableCompletedTreatmentFemale / Metabolic Syndromes / Schizophrenic Disorders1
Not AvailableCompletedTreatmentSchizophrenic Disorders1
Not AvailableUnknown StatusTreatmentBMI >30 kg/m2 / Polycystic Ovaries Syndrome1
Not AvailableUnknown StatusTreatmentPolycystic Ovaries Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)145 °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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorInhibitor0.8933
CYP450 2C19 inhibitorNon-inhibitor0.7463
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000i-0009000000-19928d40d547cbbc26dc
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00di-0029000000-42f72c3da8025ad70c4d
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0103-0089000000-dbcf680bd232ed620a00
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-000i-0009000000-2993f75f22b9532dc39f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-000i-0009000000-1d4cdb20920f8c900320
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0079-0019000000-4995338b7526764bbad3
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-00dl-0059000000-ab35b8a7ec73f1063bb2
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-00fu-0089000000-09273e18fcd3186156f0
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-00di-0039000000-3a3f7eba3883c388e58c
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0006-0092000000-6f10979e1ecdd29611b1
LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , PositiveLC-MS/MSsplash10-0006-0090000000-bacf940c54361560b64b
LC-MS/MS Spectrum - LC-ESI-ITTOF (Shimadzu LC20A-IT-TOFMS) , PositiveLC-MS/MSsplash10-000i-0009000000-3d6d1928f5797f4633e4
LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , PositiveLC-MS/MSsplash10-000i-0009000000-6337ae6880e36d106adf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-0039000000-5d1ff6b7636484db90d1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-0059000000-131055c16d28a84b6130
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-9d8986d4bd9f3b6d634d
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0009000000-4459c8c8f7b607ad7b49
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dr-0019000000-a0c1c55261d223b09256
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00dl-0069000000-437bdc5509b367efef25
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0009000000-2993f75f22b9532dc39f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-0009000000-7308f7a2cd31283860f7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0079-0019000000-4995338b7526764bbad3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-0059000000-ab35b8a7ec73f1063bb2
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00fu-0089000000-09273e18fcd3186156f0
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-0039000000-3a3f7eba3883c388e58c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00dr-0019000000-60003f93e70ee242f1c4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00di-0019000000-14f0c8e22b0bd2c71ed0
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0019000000-390bf95ccd98952a4dbc
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-00di-0019000000-62c2ee4b84c5aed05853
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Protoberberine alkaloids and derivatives
Sub Class
Not Available
Direct Parent
Protoberberine alkaloids and derivatives
Alternative Parents
Isoquinolines and derivatives / Benzodioxoles / Anisoles / Alkyl aryl ethers / Pyridinium derivatives / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Acetals / Organopnictogen compounds
show 3 more
Substituents
Protoberberine skeleton / Isoquinoline / Benzodioxole / Anisole / Alkyl aryl ether / Pyridine / Pyridinium / Benzenoid / Heteroaromatic compound / Acetal
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heteropentacyclic compound, berberine alkaloid, alkaloid antibiotic, botanical anti-fungal agent (CHEBI:16118) / Alkaloids, Isoquinoline alkaloids (C00757) / a small molecule (BERBERINE)

Targets

Kind
Protein
Organism
Staphylococcus haemolyticus
Pharmacological action
Unknown
General Function
Transcription factor activity, sequence-specific dna binding
Specific Function
Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from...
Gene Name
qacR
Uniprot ID
P0A0N5
Uniprot Name
HTH-type transcriptional regulator QacR
Molecular Weight
22174.175 Da
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:17139284]
  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:17016423]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Multitasking protein that has dual roles in promoting cell proliferation and preventing apoptosis. Component of a chromosome passage protein complex (CPC) which is essential for chromosome alignmen...
Gene Name
BIRC5
Uniprot ID
O15392
Uniprot Name
Baculoviral IAP repeat-containing protein 5
Molecular Weight
16388.555 Da
References
  1. Wang Z, Guo X, Liu Z, Cui M, Song F, Liu S: Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry. J Mass Spectrom. 2008 Mar;43(3):327-35. [PubMed:17968851]

Drug created on June 13, 2005 07:24 / Updated on October 08, 2018 21:32