berberrubine profile

Berberrubine is a quaternary ammonium alkaloid that has been isolated from various plants, including Berberis vulgaris and Coptis chinensis. It is known for its diverse pharmacological activities, including anti-inflammatory, antioxidant, and anticancer properties. The synthesis of berberrubine can be achieved through various chemical reactions, often involving modifications of existing berberine derivatives. Studies have shown that berberrubine exhibits significant anti-inflammatory effects by inhibiting the production of inflammatory mediators like prostaglandins and leukotrienes. Its antioxidant properties are attributed to its ability to scavenge free radicals and protect cells from oxidative damage. Furthermore, berberrubine has demonstrated potential anticancer activity by inducing apoptosis in cancer cells and inhibiting their proliferation. The compound's potential therapeutic applications have spurred research interest in understanding its mechanisms of action and exploring its clinical utility in various diseases.'

berberrubine: RN refers to chloride salt; a protoberberine alkaloid antitumor agent which exhibits topoisomerase II poison activity as well as catalytic inhibition activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	72704
CHEMBL ID	203135
SCHEMBL ID	910779
MeSH ID	M0298347

Synonym
beroline
benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
berberrubin
NCI60_042148
benzo[g]benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
berberrubine
CHEMBL203135
17388-19-1
chileninone
MLS002472969
smr001397076
SCHEMBL910779
DTXSID90169675
6847-93-4 (inner salt)
9-berberoline
AKOS037514567
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
benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 5,6-dihydro-9-hydroxy-10-methoxy-
10-methoxy-5,6-dihydrobenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium-9-ol
berbinium, 7,8,13,13a-tetradehydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-
5,6-dihydro-9-hydroxy-10-methoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium
ZZT5GBZ8KE

Excerpt	Reference	Relevance
"Berberrubine is an isoquinoline alkaloid isolated from Berberis vulgaris L, and it is readily derived from berberine. "	( Pharmacokinetics in rats and tissue distribution in mouse of berberrubine by UPLC-MS/MS. Deng, M; Fan, M; Gao, Z; Hu, L; Lu, M; Ma, J; Wang, S; Wang, X; Ye, T, 2015)	2.1

Excerpt	Reference	Relevance
" Moreover, in vitro assessment clearly showed BRB had a toxic effect on renal cell lines, while the primary metabolite, berberrubine-9-O-β-d-glucuronide (BRBG), did not show any obvious toxicity."	( High fat diet aggravates the nephrotoxicity of berberrubine by influencing on its pharmacokinetic profile. Aa, J; Fei, F; Feng, S; Fu, F; Geng, J; Guo, J; He, J; Liao, X; Sun, R; Wang, G; Wang, H; Wang, J; Xie, Y; Yang, N; Zhao, Y; Zhen, L; Zhu, X, 2016)	0.9

Excerpt	Reference	Relevance
"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)	0.8
" However, the plasma concentration of BBR is very low after oral administration for the reason that BBR is poorly absorbed and rapidly metabolized."	( Berberine metabolites could induce low density lipoprotein receptor up-regulation to exert lipid-lowering effects in human hepatoma cells. Bin, W; Cao, S; Kang, N; Qiu, F; Wang, Y; Xu, P; Yan, J; Zhou, Y, 2014)	0.4
" The absolute bioavailability of berberrubine was determined to be 31."	( Pharmacokinetics in rats and tissue distribution in mouse of berberrubine by UPLC-MS/MS. Deng, M; Fan, M; Gao, Z; Hu, L; Lu, M; Ma, J; Wang, S; Wang, X; Ye, T, 2015)	0.94
" However, BBR exhibits low bioavailability due to its extensive metabolism and limited absorption."	( Berberrubine attenuates potassium oxonate- and hypoxanthine-induced hyperuricemia by regulating urate transporters and JAK2/STAT3 signaling pathway. Chen, J; Huang, Z; Jiang, L; Li, Y; Lin, G; Lin, Z; Liu, Y; Mai, L; Su, Z; Xie, J; Xu, L; Yu, Q, 2021)	2.06

Excerpt	Relevance	Reference
" Sixteen metabolites, including 10 Phase I and six Phase II metabolites were identified and clarified after dosing in vivo."	( Excretion of berberine and its metabolites in oral administration in rats. Chen, SN; Feng, R; Fu, J; He, CY; He, WY; Huang, M; Jiang, JD; Ma, C; Ma, JY; Shou, JW; Tan, XS; Wang, Y; Zhao, ZX, 2013)	0.39
" In summary, BB exerted similar effect to its analogue BBR and positive control in attenuating DSS-induced UC with much lower dosage and similar mechanism."	( Berberrubine attenuates mucosal lesions and inflammation in dextran sodium sulfate-induced colitis in mice. Chen, JP; Huang, YF; Li, HL; Qu, C; Su, ZR; Xu, LQ; Xu, YF; Yi, TG; Yu, XT; Zeng, HF; Zhang, XJ; Zheng, L, 2018)	1.92

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
WRN	Homo sapiens (human)	Potency	50.1187	0.1683	31.2583	100.0000	AID651768
GLS protein	Homo sapiens (human)	Potency	10.0000	0.3548	7.9355	39.8107	AID624170
TDP1 protein	Homo sapiens (human)	Potency	29.0929	0.0008	11.3822	44.6684	AID686978
apical membrane antigen 1, AMA1	Plasmodium falciparum 3D7	Potency	4.4668	0.7079	12.1943	39.8107	AID720542
parathyroid hormone/parathyroid hormone-related peptide receptor precursor	Homo sapiens (human)	Potency	44.6684	3.5481	19.5427	44.6684	AID743266
serine/threonine-protein kinase PLK1	Homo sapiens (human)	Potency	29.9349	0.1683	16.4040	67.0158	AID720504
Rap guanine nucleotide exchange factor 3	Homo sapiens (human)	Potency	70.7946	6.3096	60.2008	112.2020	AID720709
Rap guanine nucleotide exchange factor 4	Homo sapiens (human)	Potency	89.1251	3.9811	46.7448	112.2020	AID720708
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
angiogenesis	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
adaptive immune response	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathway	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
associative learning	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
Rap protein signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of actin cytoskeleton organization	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
negative regulation of syncytium formation by plasma membrane fusion	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
intracellular signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of GTPase activity	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of angiogenesis	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of angiogenesis	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of protein export from nucleus	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of stress fiber assembly	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of phosphatidylinositol 3-kinase/protein kinase B signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
positive regulation of syncytium formation by plasma membrane fusion	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
establishment of endothelial barrier	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
cellular response to cAMP	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
Ras protein signal transduction	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
regulation of insulin secretion	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
adaptive immune response	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
G protein-coupled receptor signaling pathway	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathway	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
calcium-ion regulated exocytosis	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
regulation of exocytosis	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
insulin secretion	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
positive regulation of insulin secretion	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
regulation of synaptic vesicle cycle	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
Ras protein signal transduction	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
regulation of insulin secretion	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
guanyl-nucleotide exchange factor activity	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
protein binding	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
protein domain specific binding	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
cAMP binding	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
guanyl-nucleotide exchange factor activity	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
protein binding	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
cAMP binding	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
protein-macromolecule adaptor activity	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
small GTPase binding	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
cortical actin cytoskeleton	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
plasma membrane	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
microvillus	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
endomembrane system	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
membrane	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
lamellipodium	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
filopodium	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
extracellular exosome	Rap guanine nucleotide exchange factor 3	Homo sapiens (human)
cytosol	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
plasma membrane	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
membrane	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
hippocampal mossy fiber to CA3 synapse	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
plasma membrane	Rap guanine nucleotide exchange factor 4	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay ID	Title	Year	Journal	Article
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5	Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID269178	Antifungal activity against Cryptococcus neoformans ATCC 36556 by broth microdilution method	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
AID656692	Therapeutic index, ratio of TD50 for human fibroblast cell to ID 50 for Toxoplasma gondii ATCC 50839	2012	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8	Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.
AID656690	Antiparasitic activity against Toxoplasma gondii ATCC 50839 infected in human fibroblasts assessed as inhibition of replication of tachyzoites after 4 days by bacterial beta-galactosidase assay	2012	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8	Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.
AID269172	Antifungal activity against Candida albicans ATCC 10231 by broth microdilution method	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
AID1101184	Antifungal activity against Blumeria graminis f. sp. tritici on wheat plant assessed as disease control at 100 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101179	Antifungal activity against Zymoseptoria tritici on wheat plant at 25 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101173	Herbicidal activity against Lemna minor (common duckweed) at 1 ppm after 9 days relative to control	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101177	Antifungal activity against Magnaporthe oryzae on rice plant at 25 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101183	Antifungal activity against Phaeosphaeria nodorum on wheat plant assessed as disease control at 100 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101175	Antifungal activity against Ustilago maydis on rice plant at 25 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID269174	Antifungal activity against Candida lusitaniae ATCC 42720 by broth microdilution method	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
AID262001	Binding affinity to sulfonylurea receptor in pancreatic islet beta cell membranes	2006	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 16, Issue:5	Synthesis and antihyperglycemic evaluation of various protoberberine derivatives.
AID261998	Reduction of blood glucose level in alloxan induced diabetic mice at 200 mg/kg	2006	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 16, Issue:5	Synthesis and antihyperglycemic evaluation of various protoberberine derivatives.
AID269177	Antifungal activity against Aspergillus terreus ATCC 46941 by broth microdilution method	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
AID1101180	Antifungal activity against Phaeosphaeria nodorum on wheat plant at 25 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101174	Herbicidal activity against Agrostis stolonifera var. palustris at 1 ppm after 9 days relative to control	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID262000	Antibacterial activity against Escherichia coli upto 50 ug/mL	2006	Bioorganic & medicinal chemistry letters, Mar-01, Volume: 16, Issue:5	Synthesis and antihyperglycemic evaluation of various protoberberine derivatives.
AID656691	Cytotoxicity against human fibroblasts assessed as cell viability by microplate reader	2012	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 22, Issue:8	Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.
AID1101181	Antifungal activity against Puccinia recondita on wheat plant assessed as disease control at 100 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID269176	Antifungal activity against Aspergillus fumigatus ATCC 16424 by broth microdilution method	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
AID269175	Antifungal activity against Candida krusei ATCC 6258 by broth microdilution method	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
AID269173	Antifungal activity against Candida tropicalis ATCC 13803 by broth microdilution method	2006	Bioorganic & medicinal chemistry letters, Aug-01, Volume: 16, Issue:15	Synthesis of 13-(substituted benzyl) berberine and berberrubine derivatives as antifungal agents.
AID1101176	Antifungal activity against Phytophthora infestans on rice plant at 25 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101178	Antifungal activity against Rhizoctonia solani on rice plant at 25 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
AID1101182	Antifungal activity against Phytophthora infestans on potato plant assessed as disease control at 100 ppm after 24 hr	2000	Bioscience, biotechnology, and biochemistry, Sep, Volume: 64, Issue:9	Fungicidal and herbicidal activities of berberine related alkaloids.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (1.79)	18.2507
2000's	13 (23.21)	29.6817
2010's	28 (50.00)	24.3611
2020's	14 (25.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	56 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
bromide Bromides: Salts of hydrobromic acid, HBr, with the bromine atom in the 1- oxidation state. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	2.31	1	halide anion; monoatomic bromine
hydrogen Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.	7.41	1	elemental hydrogen; elemental molecule; gas molecular entity	antioxidant; electron donor; food packaging gas; fuel; human metabolite
uric acid Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.	2.31	1	uric acid	Escherichia coli metabolite; human metabolite; mouse metabolite
berberine [no description available]	5.34	50	alkaloid antibiotic; berberine alkaloid; botanical anti-fungal agent; organic heteropentacyclic compound	antilipemic drug; antineoplastic agent; antioxidant; EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor; EC 1.21.3.3 (reticuline oxidase) inhibitor; EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor; EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor; EC 2.7.11.10 (IkappaB kinase) inhibitor; EC 3.1.1.4 (phospholipase A2) inhibitor; EC 3.1.1.7 (acetylcholinesterase) inhibitor; EC 3.1.1.8 (cholinesterase) inhibitor; EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor; EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; geroprotector; hypoglycemic agent; metabolite; potassium channel blocker
oxonic acid Oxonic Acid: Antagonist of urate oxidase.	2.31	1	1,3,5-triazines; monocarboxylic acid
trimethoprim Trimethoprim: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM, SULFAMETHOXAZOLE DRUG COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.. trimethoprim : An aminopyrimidine antibiotic whose structure consists of pyrimidine 2,4-diamine and 1,2,3-trimethoxybenzene moieties linked by a methylene bridge.	2.07	1	aminopyrimidine; methoxybenzenes	antibacterial drug; diuretic; drug allergen; EC 1.5.1.3 (dihydrofolate reductase) inhibitor; environmental contaminant; xenobiotic
quinazolines Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.	2.25	1	azaarene; mancude organic heterobicyclic parent; ortho-fused heteroarene; quinazolines
hydrazine diamine : Any polyamine that contains two amino groups.	7.31	1	azane; hydrazines	EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
dihydroberberine dihydroberberine: structure in first source	2.07	1	alkaloid
bicuculline Bicuculline: An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.. bicuculline : A benzylisoquinoline alkaloid that is 6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinoline which is substituted at the 5-pro-S position by a (6R)-8-oxo-6,8-dihydrofuro[3,4-e][1,3]benzodioxol-6-yl group. A light-sensitive competitive antagonist of GABAA receptors. It was originally identified in 1932 in plant alkaloid extracts and has been isolated from Dicentra cucullaria, Adlumia fungosa, Fumariaceae, and several Corydalis species.	2.05	1	benzylisoquinoline alkaloid; isoquinoline alkaloid; isoquinolines	agrochemical; central nervous system stimulant; GABA-gated chloride channel antagonist; GABAA receptor antagonist; neurotoxin
jkl 1073a 8-oxoberberine: structure given in first source	2.07	1
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.11	1	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
Berberine chloride (TN) [no description available]	2.71	3	organic molecular entity
palmatine burasaine: structure in first source	2.84	3	berberine alkaloid; organic heterotetracyclic compound	plant metabolite
canadine, (s)-isomer (S)-canadine : The (S)-enantiomer of canadine.	2.45	2	an (S)-7,8,13,14-tetrahydroprotoberberine; canadine	plant metabolite
tetradecanoylphorbol acetate Tetradecanoylphorbol Acetate: A phorbol ester found in CROTON OIL with very effective tumor promoting activity. It stimulates the synthesis of both DNA and RNA.. phorbol ester : Esters of phorbol, originally found in croton oil (from Croton tiglium, of the family Euphorbiaceae). A number of phorbol esters possess activity as tumour promoters and activate the mechanisms associated with cell growth. Some of these are used in experiments as activators of protein kinase C.. phorbol 13-acetate 12-myristate : A phorbol ester that is phorbol in which the hydroxy groups at the cyclopropane ring juction (position 13) and the adjacent carbon (position 12) have been converted into the corresponding acetate and myristate esters. It is a major active constituent of the seed oil of Croton tiglium. It has been used as a tumour promoting agent for skin carcinogenesis in rodents and is associated with increased cell proliferation of malignant cells. However its function is controversial since a decrease in cell proliferation has also been observed in several cancer cell types.	2.11	1	acetate ester; diester; phorbol ester; tertiary alpha-hydroxy ketone; tetradecanoate ester	antineoplastic agent; apoptosis inducer; carcinogenic agent; mitogen; plant metabolite; protein kinase C agonist; reactive oxygen species generator
etoposide [no description available]	1.99	1	beta-D-glucoside; furonaphthodioxole; organic heterotetracyclic compound	antineoplastic agent; DNA synthesis inhibitor
1-methyl-4-phenylpyridinium 1-Methyl-4-phenylpyridinium: An active neurotoxic metabolite of 1-METHYL-4-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE. The compound reduces dopamine levels, inhibits the biosynthesis of catecholamines, depletes cardiac norepinephrine and inactivates tyrosine hydroxylase. These and other toxic effects lead to cessation of oxidative phosphorylation, ATP depletion, and cell death. The compound, which is related to PARAQUAT, has also been used as an herbicide.. N-methyl-4-phenylpyridinium : A pyridinium ion that is N-methylpyridinium having a phenyl substituent at the 4-position.	2.13	1	pyridinium ion	apoptosis inducer; herbicide; human xenobiotic metabolite; neurotoxin
columbamine [no description available]	2.52	2	berberine alkaloid; organic heterotetracyclic compound
coptisine coptisine: RN given refers to parent cpd	8.01	4	alkaloid	metabolite
jatrorrhizine jatrorrhizine: isolated from bark of Enantia chlorantha (Annonaceae); structure given in first source	3.33	6	alkaloid
gliquidone gliquidone: structure; RN given refers to parent cpd	2.03	1	isoquinolines
corydaline [no description available]	2.13	1	isoquinoline alkaloid; isoquinolines
protoberberine protoberberine: a benzyltetrahydroisoquinoline derivative that appears as an isoquinoline annelated (adjoined) with a naphthylene; the nitrogen is typically quarternary; nitidine is annelated differently; RN given refers to parent cpd	8.17	5
evodiamine [no description available]	2.25	1	beta-carbolines
epiberberine epiberberine: isolated in plants of Coptis from China	2.82	3
tetrahydrojateorrhizine corypalmine: from Corydalis chaerophylla (Fumariaceae); structure in first source	2.05	1
demethyleneberberine demethyleneberberine: structure in first source	3.16	5
potassium oxonate potassium oxonate: used to induce hyperuricemia in mice	7.31	1	organic molecular entity
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.11	1
thalifendine thalifendine: structure in first source	2.98	4
dinoprostone prostaglandin E2 : Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.	2.11	1	prostaglandins E	human metabolite; mouse metabolite; oxytocic
vitamin k semiquinone radical vitamin K semiquinone radical: found in active preparations of vitamin K-dependent carboxylase. vitamin K : Any member of a group of fat-soluble 2-methyl-1,4-napthoquinones that exhibit biological activity against vitamin K deficiency. Vitamin K is required for the synthesis of prothrombin and certain other blood coagulation factors.	2.6	1
amphotericin b Amphotericin B: Macrolide antifungal antibiotic produced by Streptomyces nodosus obtained from soil of the Orinoco river region of Venezuela.. amphotericin B : A macrolide antibiotic used to treat potentially life-threatening fungal infections.	2.03	1	antibiotic antifungal drug; macrolide antibiotic; polyene antibiotic	antiamoebic agent; antiprotozoal drug; bacterial metabolite
mocetinostat mocetinostat: undergoing phase II clinical trials for treatment of cancer. mocetinostat : A benzamide obtained by formal condensation of the carboxy group of 4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an orally active and isotype-selective HDAC inhibitor which exhibits antitumour activity (IC50 = 0.15, 0.29, 1.66 and 0.59 muM for HDAC1, HDAC2, HDAC3 and HDAC11).	2.17	1	aminopyrimidine; benzamides; pyridines; secondary amino compound; secondary carboxamide; substituted aniline	antineoplastic agent; apoptosis inducer; autophagy inducer; cardioprotective agent; EC 3.5.1.98 (histone deacetylase) inhibitor; hepatotoxic agent
interleukin-8 Interleukin-8: A member of the CXC chemokine family that plays a role in the regulation of the acute inflammatory response. It is secreted by variety of cell types and induces CHEMOTAXIS of NEUTROPHILS and other inflammatory cells.	7.03	1
silybin Silybin: The major active component of silymarin flavonoids extracted from seeds of the MILK THISTLE, Silybum marianum; it is used in the treatment of HEPATITIS; LIVER CIRRHOSIS; and CHEMICAL AND DRUG INDUCED LIVER INJURY, and has antineoplastic activity; silybins A and B are diastereomers.	2.06	1
hypoxanthine [no description available]	7.31	1	nucleobase analogue; oxopurine; purine nucleobase	fundamental metabolite
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.63	2	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger

Condition	Relationship Strength	Studies
Alloxan Diabetes [description not available]	2.47	2
Innate Inflammatory Response [description not available]	2.8	3
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	7.8	3
Carcinogenesis The origin, production or development of cancer through genotypic and phenotypic changes which upset the normal balance between cell proliferation and cell death. Carcinogenesis generally requires a constellation of steps, which may occur quickly or over a period of many years.	2.31	1
Carcinoma, Non-Small Cell Lung [description not available]	2.31	1
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.31	1
Acute Liver Injury, Drug-Induced [description not available]	2.69	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.63	2
Kidney Diseases Pathological processes of the KIDNEY or its component tissues.	2.31	1
Hyperuricemia Excessive URIC ACID or urate in blood as defined by its solubility in plasma at 37 degrees C; greater than 0.42mmol per liter (7.0mg/dL) in men or 0.36mmol per liter (6.0mg/dL) in women. This condition is caused by overproduction of uric acid or impaired renal clearance. Hyperuricemia can be acquired, drug-induced or genetically determined (LESCH-NYHAN SYNDROME). It is associated with HYPERTENSION and GOUT.	7.31	1
Chemical and Drug Induced Liver Injury A spectrum of clinical liver diseases ranging from mild biochemical abnormalities to ACUTE LIVER FAILURE, caused by drugs, drug metabolites, herbal and dietary supplements and chemicals from the environment.	2.69	2
Blood Clot [description not available]	3.52	4
Thrombosis Formation and development of a thrombus or blood clot in the blood vessel.	3.52	4
Colorectal Cancer [description not available]	7.48	2
Colorectal Neoplasms Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.	2.48	2
B16 Melanoma [description not available]	2.25	1
Colitis Inflammation of the COLON section of the large intestine (INTESTINE, LARGE), usually with symptoms such as DIARRHEA (often with blood and mucus), ABDOMINAL PAIN, and FEVER.	7.17	1
Hepatocellular Carcinoma [description not available]	2.1	1
Cancer of Liver [description not available]	2.48	2
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.1	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.48	2
Diabetes Mellitus, Adult-Onset [description not available]	2.1	1
Insulin Sensitivity [description not available]	2.1	1
Diabetes Mellitus, Type 2 A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.	2.1	1
Insulin Resistance Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.	2.1	1
Blood Poisoning [description not available]	2.11	1
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.11	1
Fibrosarcoma A sarcoma derived from deep fibrous tissue, characterized by bundles of immature proliferating fibroblasts with variable collagen formation, which tends to invade locally and metastasize by the bloodstream. (Stedman, 25th ed)	2.11	1
Kidney Failure A severe irreversible decline in the ability of kidneys to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism.	2.13	1
Renal Insufficiency Conditions in which the KIDNEYS perform below the normal level in the ability to remove wastes, concentrate URINE, and maintain ELECTROLYTE BALANCE; BLOOD PRESSURE; and CALCIUM metabolism. Renal insufficiency can be classified by the degree of kidney damage (as measured by the level of PROTEINURIA) and reduction in GLOMERULAR FILTRATION RATE.	2.13	1
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.15	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.15	1
Hyperlipemia [description not available]	2.05	1
Hyperlipidemias Conditions with excess LIPIDS in the blood.	2.05	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	2.06	1

berberrubine

Description

Cross-References

Synonyms (22)

Research Excerpts

Overview

Toxicity

Bioavailability

Dosage Studied

Protein Targets (8)

Potency Measurements

Biological Processes (26)

Molecular Functions (6)

Ceullar Components (10)

Bioassays (36)

Research

Studies (56)

Market Indicators

Research Demand Index: 26.95

Study Types

berberrubine

Description

Cross-References

Synonyms (22)

Research Excerpts

Overview

Toxicity

Bioavailability

Dosage Studied

Protein Targets (8)

Potency Measurements

Biological Processes (26)

Molecular Functions (6)

Ceullar Components (10)

Bioassays (36)

Research

Studies (56)

Market Indicators

Research Demand Index: 26.95

Study Types

Related Drugs (39)

Related Conditions (35)