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Drug

D0251 | Berberine

Molecular Formula C20H18NO4+
Molecular Weight 336.4
Structure
State solid
Description protoberberine group of benzylisoquinoline alkaloids found in plants; under ultraviolet light, berberine shows a strong yellow fluorescence

Toxicity Dose Time Species Model Method Action Positive criterion Reference
TRANSMEMBRANE POTENTIAL 25 μM 6, 24 hr K1735-M2 mouse melanoma cells TMRM decrease 327
OPENING OF PERMEABILITY TRANSITION PORE (PTP) 31.2 nmol/mg isolated rat muscle mitochondria evaluate mitochondrial calcium loading capacity using the fluorescence probe Calcium Green 5N induce 327
OXYGEN CONSUMPTION RATE (OCR) 1-10 µM isolated rat muscle mitochondria Clark type oxygen electrode (Strathkelvin Instruments) decrease 328
BASAL RESPIRATION 3 μM zebrafish XFe24 Extracellular Flux Analyzer Negative 88
BASAL RESPIRATION 3 μM zebrafish XFe24 Extracellular Flux Analyzer Negative 88
P/O RATIO ( ADP/O) 6.7, 16.7 nmol/mg Protein Male Wistar rats (10 weeks old) isolated rat muscle mitochondria Clark type oxygen electrode (Strathkelvin Instruments) Negative 327
GLUCOSE GALACTOSE IC50 RATIO 7 LUHMES (Lund human mesencephalic) cells Glc–Gal–NeuriTox assay EC25(NA) [Glc/Gal] 326
ENERGY CHARGE 25 μM 48, 72 hr K1735-M2 mouse melanoma cells An acid extraction procedure was used to evaluate the intracellular concentration of adenine nucleotides. Adenine nucleotides were separated by reverse-phase high-performance liquid chromatography. Quantification was achieved by employing ATP, ADP, and AMP standard curves. decrease p< 0.05 vs. control for each time of incubation 327
ATP/ADP RATIO 10 μM 24 hr K1735-M2 mouse melanoma cells An acid extraction procedure was used to evaluate the intracellular concentration of adenine nucleotides. Adenine nucleotides were separated by reverse-phase high-performance liquid chromatography. Quantification was achieved by employing ATP, ADP, and AMP standard curves. decrease p< 0.05 vs. control for each time of incubation 327
SWELLING isolated rat muscle mitochondria decrease of absorbance at 540 nm with a Jasco V-560 spectrophotometer increase 327
OXIDATIVE STRESS 25 μM 6, 24 hr K1735-M2 mouse melanoma cells CM-H2DCFDA (DCF), a fluorescent probe for oxidative stress (epifluorescence microscope) increase 327

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 1-10 µM isolated rat muscle mitochondria Clark type oxygen electrode (Strathkelvin Instruments) inhibit 328
NADH:ubiquinone reductase 7 LUHMES (Lund human mesencephalic) cells Glc–Gal–NeuriTox assay EC25(NA) [Glc/Gal] 326
5'-AMP-activated protein kinase catalytic subunit alpha-2 10 mol/l mouse embryonic fibroblasts (MEFs) immunoblotting activate 328


  • 086B831 0I8Y3P32UF 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium
    2086-83-1 3,4-dimethoxy-6,7-dihydro-[1,3]dioxolo[4,5-g]pyrido[2,1-a]isoquinolin-5-ylium 3-[3-(2-ethyl-1,3-thiazol-4-yl)phenyl]-5-{2-[(4-methylphenyl)sulfonyl]ethyl}-1,2,4-oxadiazole
    316-41-6 34MD1011DM 5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium chloride
    5,6-dihydro-9,10-dimethoxy-benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium
    9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetrahydroberbinium 9,10-Dimethoxy-5,6-dihydro-7lambda~5~-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
    9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium 9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ylium chloride
    9,10-Dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium 9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium 9,10-dimethoxy-5,6-dihydro-2H-1,3-dioxoleno[4,5-g]isoquinolino[3,2-a]isoquinol ine
    9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium AB0106411 AC-117
    ACon1_001957 AKOS002141363 BBL029198
    BCBcMAP01_000112 BDBM50203126 BERBINIUM, 7,8,13,13a-TETRAHYDRO-9,10-DIMETHOXY-2,3-(METHYLENEDIOXY)-
    BPBio1_000476 BRD-K14796088-003-06-0 BRD-K14796088-003-17-7
    BRN 3570374 BSPBio_000432 BSPBio_002156
    Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy- Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy- Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy- (9CI)
    Benzylpenicillin benzathine, Antibiotic for Culture Media Use Only Berbamine sulphate acid Berberal
    Berbericine Berberin Berberinechloride
    Berbinium Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)- Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-, chloride
    C00757 C20H18NO4 CAS-633-65-8
    CCG-35898 CHEBI:16118 CHEMBL12089
    CHEMBL295124 CS-0009734 CTK6J4626
    Coptis rhizome DB-050153 DB04115
    DTXSID9043857 DivK1c_000265 EINECS 218-229-1
    FT-0603587 GNF-PF-4545 HMS3561D13
    HY-N0716 IDI1_000265 InChI=1/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+
    KBio1_000265 KBio2_001590 KBio2_004158
    KBio2_006726 KBio3_001656 KBioGR_001230
    KBioSS_001590 LS-43472 MCULE-8261808830
    MEGxp0_001923 Majarine N1368
    NCGC00016526-01 NCGC00016526-02 NCGC00016526-03
    NCGC00016526-04 NCGC00016526-05 NCGC00016526-06
    NCGC00016526-07 NCGC00016526-08 NCGC00016526-11
    NCGC00091896-03 NCI60_001050 NCI60_001224
    NCI60_004319 NCIMech_000354 NINDS_000265
    NSC646666 Prestwick0_000586 Prestwick1_000586
    Prestwick2_000586 Prestwick3_000586 Q-200701
    Q-200702 Q176525 SBI-0051613.P002
    SCHEMBL25632 SDCCGMLS-0066718.P001 SMP1_000298
    SPBio_000708 SPBio_002651 SR-01000711827-5
    ST055798 STK870320 Spectrum2_000894
    Spectrum3_000618 Spectrum4_000785 Spectrum5_001458
    Spectrum_001110 Thalsine UNII-0I8Y3P32UF
    UPCMLD-DP032 UPCMLD-DP032:001 Umbellatin
    Umbellatine Umbellatine (6CI) W-2449
    YBHILYKTIRIUTE-UHFFFAOYSA-N ZINC3779067 berberine
    berberine dimer chloride cid_12456
    inverted exclamation markY97%

    DrugBank Name Berberine
    DrugBank DB04115
    CAS Number 141433-60-5, 2086-83-1, 4263-84-7, 633-65-8, 633-66-9
    PubChem Compound 2353
    KEGG Compound ID C00757
    KEGG Drug D00092
    PubChem.Substance 46506051
    ChEBI 16118
    PharmGKB PA165860812
    ChemSpider 2263
    BindingDB 50203126.0
    TTD DNC000385
    Wikipedia Berberine
    HET BER