Compounds > 5,6-dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride
Page last updated: 2024-12-06

5,6-dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID SourceID
PubMed CID72703
CHEMBL ID1223099
CHEBI ID175111
MeSH IDM0298344

Synonyms (32)

Synonym
berberrubine, dihydrate
15401-69-1
benzo[g]-1,6-a]quinolizium, 5,6-dihydro-9-hydroxy-10-methoxy-, chloride,
nsc-96347
berbinium,8,13,13a-tetradehydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-, chloride
CHEBI:175111
17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-ol;chloride
beberrubine chloride
CHEMBL1223099
berberrubine hydrochloride
benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-, chloride
berberrubine chloride
9-berberoline chloride
5,6-dihydro-9-hydroxy-10-methoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium chloride
beroline chloride
berbinium, 7,8,13,13a-tetradehydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-, chloride
NSC96347 ,
nsc 96347
AKOS025149081
AC-34896
9-hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
FT-0697742
9-hydroxy-10-methoxy-5,6-dihydro-[1,3]dioxolo-[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
doi:10.14272/gyfsyevkfoolfz-uhfffaoysa-n.1
10.14272/GYFSYEVKFOOLFZ-UHFFFAOYSA-N.1
berberrubine chloride pound>>beroline chloride
BCP29956
berberrubine (chloride)
CS-0009733
HY-125850
CCG-268127
AS-77884

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"In order to enhance oral bioavailability of berberine (BBR) for its cholesterol-lowering efficacy in vivo, a series of ester or ether prodrugs of berberrubine (M1), which is an active metabolite of BBR after first-pass metabolism, were designed, semi-synthesized, and evaluated."( Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine.
Deng, HB; Jiang, JD; Kong, WJ; Li, Y; Li, YH; Ren, G; Song, DQ; Wang, YM; Wang, YX; Yang, P; You, XF, 2010)		0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
alkaloidAny of the naturally occurring, basic nitrogen compounds (mostly heterocyclic) occurring mostly in the plant kingdom, but also found in bacteria, fungi, and animals. By extension, certain neutral compounds biogenetically related to basic alkaloids are also classed as alkaloids. Amino acids, peptides, proteins, nucleotides, nucleic acids, amino sugars and antibiotics are not normally regarded as alkaloids. Compounds in which the nitrogen is exocyclic (dopamine, mescaline, serotonin, etc.) are usually classed as amines rather than alkaloids.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID11386121-Octanol-water distribution coefficient, log D of the compound at pH 4.5 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID723297Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Jan-01, Volume: 23, Issue:1
Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives: a lipophilic substitute role.
AID590169Antiviral activity against 0.05 MOI Human immunodeficiency virus 1 NL4.3 infected in human CEM cells expressing green fluorescent protein assessed as p24 antigen production at 15.52 uM measured 7 days post infection by ELISA2011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Synthesis of 9-substituted derivatives of berberine as anti-HIV agents.
AID1138630Dissociation constant, pKa of the compound2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID590166Antiviral activity against 0.05 MOI Human immunodeficiency virus 1 NL4.3 infected in human CEM cells expressing green fluorescent protein assessed as p24 antigen production measured 7 days post infection by ELISA2011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Synthesis of 9-substituted derivatives of berberine as anti-HIV agents.
AID723296Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Jan-01, Volume: 23, Issue:1
Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives: a lipophilic substitute role.
AID11386111-Octanol-water distribution coefficient, log D of the compound at pH 6 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID1138603Solubility of the compound in sodium phosphate buffer at pH 6 at 25 degC after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID11386051-Octanol-water partition coefficient, log P of the compound at pH 8.6 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID11386101-Octanol-water distribution coefficient, log D of the compound at pH 7 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID11386081-Octanol-water partition coefficient, log P of the compound at pH 4.5 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID11386071-Octanol-water partition coefficient, log P of the compound at pH 6 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID1138613Binding affinity to bovine serum albumin by fluorescence quenching assay2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID11386091-Octanol-water distribution coefficient, log D of the compound at pH 8.6 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID723295Cytotoxicity against human HT-29 cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Jan-01, Volume: 23, Issue:1
Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives: a lipophilic substitute role.
AID1138601Solubility of the compound in sodium phosphate buffer at pH 8.6 at 25 degC after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID590346Inhibition of Human immunodeficiency virus 1 NL4.3 reverse transcriptase activity at 20 ug/ml2011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Synthesis of 9-substituted derivatives of berberine as anti-HIV agents.
AID723293Cytotoxicity against human HT-29 cells after 48 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, Jan-01, Volume: 23, Issue:1
Synthesis and anticancer activity of a novel series of 9-O-substituted berberine derivatives: a lipophilic substitute role.
AID590167Therapeutic index, ratio of CC50 for human CEM cells expressing green fluorescent protein to EC50 for Human immunodeficiency virus 1 NL4.32011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Synthesis of 9-substituted derivatives of berberine as anti-HIV agents.
AID11386061-Octanol-water partition coefficient, log P of the compound at pH 7 after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID694188Increase in AMPKalpha phosphorylation in human HepG2 cells at 10 uM after 4 hrs by Western blot analysis relative to untreated control2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Synthesis and structure-activity relationship of berberine analogues in LDLR up-regulation and AMPK activation.
AID1703587Antioxidant activity assessed as radical scavenging activity incubated for 20 mins by DPPH assay based UV spectrophotometer analysis2020European journal of medicinal chemistry, Oct-01, Volume: 203Discovery of novel berberine derivatives with balanced cholinesterase and prolyl oligopeptidase inhibition profile.
AID1138602Solubility of the compound in sodium phosphate buffer at pH 7 at 25 degC after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID590165Cytotoxicity against human CEM cells expressing green fluorescent protein after 48 hrs by MTT assay2011European journal of medicinal chemistry, Apr, Volume: 46, Issue:4
Synthesis of 9-substituted derivatives of berberine as anti-HIV agents.
AID1138604Solubility of the compound in sodium phosphate buffer at pH 4.5 at 25 degC after 1 week by HPLC-ESIMS/MS analysis2014Journal of natural products, Apr-25, Volume: 77, Issue:4
Berberine and its metabolites: relationship between physicochemical properties and plasma levels after administration to human subjects.
AID501764Lipophilicity, log P of the compound2010Bioorganic & medicinal chemistry, Sep-01, Volume: 18, Issue:17
Design, synthesis, and cholesterol-lowering efficacy for prodrugs of berberrubine.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's5 (83.33)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 13.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index13.26 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index5.21 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (13.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
tacrine
Tacrine: A cholinesterase inhibitor that crosses the blood-brain barrier. Tacrine has been used to counter the effects of muscle relaxants, as a respiratory stimulant, and in the treatment of Alzheimer's disease and other central nervous system disorders.. tacrine : A member of the class of acridines that is 1,2,3,4-tetrahydroacridine substituted by an amino group at position 9. It is used in the treatment of Alzheimer's disease.		2.2510acridines;
aromatic amine		EC 3.1.1.7 (acetylcholinesterase) inhibitor
donepezil
Donepezil: An indan and piperidine derivative that acts as a selective and reversible inhibitor of ACETYLCHOLINESTERASE. Donepezil is highly selective for the central nervous system and is used in the management of mild to moderate DEMENTIA in ALZHEIMER DISEASE.. donepezil : A racemate comprising equimolar amounts of (R)- and (S)-donepezil. A centrally acting reversible acetylcholinesterase inhibitor, its main therapeutic use is in the treatment of Alzheimer's disease where it is used to increase cortical acetylcholine.. 2-[(1-benzylpiperidin-4-yl)methyl]-5,6-dimethoxyindan-1-one : A member of the class of indanones that is 5,6-dimethoxyindan-1-one which is substituted at position 2 by an (N-benzylpiperidin-4-yl)methyl group.		2.2510aromatic ether;
indanones;
piperidines;
racemate		EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
nootropic agent
furosemide
Furosemide: A benzoic-sulfonamide-furan. It is a diuretic with fast onset and short duration that is used for EDEMA and chronic RENAL INSUFFICIENCY.. furosemide : A chlorobenzoic acid that is 4-chlorobenzoic acid substituted by a (furan-2-ylmethyl)amino and a sulfamoyl group at position 2 and 5 respectively. It is a diuretic used in the treatment of congestive heart failure.		2.2510chlorobenzoic acid;
furans;
sulfonamide		environmental contaminant;
loop diuretic;
xenobiotic
nevirapine
Nevirapine: A potent, non-nucleoside reverse transcriptase inhibitor used in combination with nucleoside analogues for treatment of HIV INFECTIONS and AIDS.. nevirapine : A dipyridodiazepine that is 5,11-dihydro-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepine which is substituted by methyl, oxo, and cyclopropyl groups at positions 4, 6, and 11, respectively. A non-nucleoside reverse transcriptase inhibitor with activity against HIV-1, it is used in combination with other antiretrovirals for the treatment of HIV infection.		2.0610cyclopropanes;
dipyridodiazepine		antiviral drug;
HIV-1 reverse transcriptase inhibitor
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.2510acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
Berberine chloride (TN)
[no description available]		3.3460organic molecular entity
canadine
canadine: RN given refers to cpd without isomeric designation; structure. canadine : A berberine alkaloid that is 5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline substituted by methoxy groups at positions 9 and 10.		2.0610aromatic ether;
berberine alkaloid;
organic heteropentacyclic compound;
oxacycle
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.0610azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid
[no description available]		2.2510chromanol;
monocarboxylic acid;
phenols		antioxidant;
ferroptosis inhibitor;
neuroprotective agent;
radical scavenger;
Wnt signalling inhibitor
tetrahydropalmatine
[no description available]		2.0610an (S)-7,8,13,14-tetrahydroprotoberberine;
berberine alkaloid;
organic heterotetracyclic compound		adrenergic agent;
dopaminergic antagonist;
non-narcotic analgesic
rivastigmine
[no description available]		2.2510carbamate ester;
tertiary amino compound		cholinergic drug;
EC 3.1.1.8 (cholinesterase) inhibitor;
neuroprotective agent
jatrorrhizine chloride
[no description available]		2.4820
cefuroxime
[no description available]		2.25103-(carbamoyloxymethyl)cephalosporin;
furans;
oxime O-ether		drug allergen
pseudoberberine
pseudoberberine: structure in first source		2.0710
piroxicam
[no description available]		2.2510benzothiazine;
monocarboxylic acid amide;
pyridines		analgesic;
antirheumatic drug;
cyclooxygenase 1 inhibitor;
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor;
non-steroidal anti-inflammatory drug
ConditionIndicatedRelationship StrengthStudiesTrials
Hyperlipemia
[description not available]		02.0510
Hyperlipidemias
Conditions with excess LIPIDS in the blood.		02.0510