SID11112431

ID: ALA295124

Chembl Id: CHEMBL295124

Max Phase: Phase

Molecular Formula: C20H18NO4+

Molecular Weight: 336.37

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: Berbericine | Berberin | Berberine | Berberone | Majarine | Thalsine | Umbellatin | Umbellatine

Synonyms from Alternative Forms(13): Berberine chloride | Berberine hydrochloride | Berberinum | GNF-Pf-4545 | NSC-163088 | NSC-646666 | Berberine sulfate | Berberine sulfate (2:1) | Berberine sulfate anhydrous | Berberine sulphate | Erben | Neutral berberine sulfate | NSC-5355

Canonical SMILES:  COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2

Standard 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

Standard InChI Key:  YBHILYKTIRIUTE-UHFFFAOYSA-N

Alternative Forms

  1. Alternative Forms:

  2. Parent:

    ALA295124

    BERBERINE

Associated Targets(Human)

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMN1 Tchem Survival motor neuron protein (34246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPT Tclin Microtubule-associated protein tau (95507 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HIF1A Tchem Hypoxia-inducible factor 1 alpha (6027 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KCNH2 Tclin HERG (29587 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA2 Tchem AMP-activated protein kinase, AMPK (12273 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TERT Tchem Telomerase reverse transcriptase (2428 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO2B1 Tchem Solute carrier organic anion transporter family member 2B1 (580 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DDC Tclin DOPA decarboxylase (27 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Tclin Butyrylcholinesterase (7174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MT-CO2 Tchem Cytochrome c oxidase subunit 2 (250 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTGES Tchem Prostaglandin E synthase (3082 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKAA2 Tchem AMPK alpha2/beta1/gamma1 (210 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PTPN1 Tchem Protein-tyrosine phosphatase 1B (8528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AKR1C2 Tchem Aldo-keto reductase family 1 member C2 (639 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AKR1C3 Tchem Aldo-keto-reductase family 1 member C3 (1414 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PREP Tchem Prolyl endopeptidase (1176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HeLa 229 (50 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HepG2 (196354 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW1990 (722 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMMC-7721 (5516 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HUVEC (11049 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HaCaT (4069 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
quadruplex DNA (2700 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM1A Tchem Lysine-specific histone demethylase 1 (3916 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CXCL8 Tchem Interleukin-8 (642 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP (8286 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CWR22R (2180 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LNCaP C4-2B (271 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARA Tclin Peroxisome proliferator-activated receptor alpha (9197 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PPARD Tchem Peroxisome proliferator-activated receptor delta (6293 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-HEP1 (1155 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Huh-7 (12904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hep 3B2 (2332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Impa1 Inositol monophosphatase 1 (16203 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus aureus (210822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ache Acetylcholinesterase (12221 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Cholinesterase (8742 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAW264.7 (28094 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pmp22 Peripheral myelin protein 22 (1279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Toxoplasma gondii (4585 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecalis (29875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ftsZ Cell division protein ftsZ (380 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Entamoeba histolytica (2676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CEL Cholesterol esterase (67 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Proteus vulgaris (5823 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pseudomonas aeruginosa (123386 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Shigella dysenteriae (933 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Escherichia coli (133304 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Micrococcus luteus (7463 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus subtilis (32866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DNA (1199 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida albicans (78123 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Candida (1648 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cyberlindnera jadinii (900 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus spizizenii (1898 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NA Neuraminidase (159 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Clostridium perfringens (1165 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
C2C12 (756 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
3T3-L1 (3664 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Salmonella typhi (4293 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pichia norvegensis (331 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Aspergillus flavus (8875 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hamster (598 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Klebsiella pneumoniae (43867 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Acinetobacter baumannii (41033 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chikungunya virus (1339 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BHK-21 (725 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDCK (10148 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Influenza A virus (11224 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NA Neuraminidase (1107 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DNA (609 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterococcus faecium (13803 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Staphylococcus epidermidis (22802 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
oprM MexXY/OprM (76 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Zika virus (1028 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero C1008 (1716 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei brucei (13300 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SARS-CoV-2 (38078 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Bacillus pumilus (984 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Streptococcus pyogenes (16140 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Enterobacter cloacae (7976 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hepatitis C virus (23859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Lung (1108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
H22 (575 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: YesOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: YesAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 336.37Molecular Weight (Monoisotopic): 336.1230AlogP: 3.10#Rotatable Bonds: 2
Polar Surface Area: 40.80Molecular Species: NEUTRALHBA: 4HBD:
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: -1.28CX LogD: -1.28
Aromatic Rings: 3Heavy Atoms: 25QED Weighted: 0.67Np Likeness Score: 1.30

References

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4. Junio HA, Sy-Cordero AA, Ettefagh KA, Burns JT, Micko KT, Graf TN, Richter SJ, Cannon RE, Oberlies NH, Cech NB..  (2011)  Synergy-directed fractionation of botanical medicines: a case study with goldenseal (Hydrastis canadensis).,  74  (7): [PMID:21661731] [10.1021/np200336g]
5. Chen XB, Zhuang JJ, Liu JH, Lei M, Ma L, Chen J, Shen X, Hu LH..  (2011)  Potential AMPK activators of cucurbitane triterpenoids from Siraitia grosvenorii Swingle.,  19  (19): [PMID:21893415] [10.1016/j.bmc.2011.08.030]
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7. Shan WJ, Huang L, Zhou Q, Meng FC, Li XS..  (2011)  Synthesis, biological evaluation of 9-N-substituted berberine derivatives as multi-functional agents of antioxidant, inhibitors of acetylcholinesterase, butyrylcholinesterase and amyloid-β aggregation.,  46  (12): [PMID:22019228] [10.1016/j.ejmech.2011.09.051]
8. Park JE, Cuong TD, Hung TM, Lee I, Na M, Kim JC, Ryoo S, Lee JH, Choi JS, Woo MH, Min BS..  (2011)  Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells.,  21  (23): [PMID:22024033] [10.1016/j.bmcl.2011.09.128]
9. He H, Bai LP, Jiang ZH..  (2012)  Synthesis and human telomeric G-quadruplex DNA-binding activity of glucosaminosides of shikonin/alkannin.,  22  (4): [PMID:22281188] [10.1016/j.bmcl.2011.12.143]
10. Maiti M, Nauwelaerts K, Herdewijn P..  (2012)  Pre-microRNA binding aminoglycosides and antitumor drugs as inhibitors of Dicer catalyzed microRNA processing.,  22  (4): [PMID:22257890] [10.1016/j.bmcl.2011.12.103]
11. Kong D, Yamori T..  (2012)  JFCR39, a panel of 39 human cancer cell lines, and its application in the discovery and development of anticancer drugs.,  20  (6): [PMID:22336246] [10.1016/j.bmc.2012.01.017]
12. Krivogorsky B, Pernat JA, Douglas KA, Czerniecki NJ, Grundt P..  (2012)  Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.,  22  (8): [PMID:22425568] [10.1016/j.bmcl.2012.02.038]
13. Huang L, Su T, Shan W, Luo Z, Sun Y, He F, Li X..  (2012)  Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenyl-benzoheterocyclic hybrids.,  20  (9): [PMID:22472046] [10.1016/j.bmc.2012.02.059]
14. Tran TD, Do TH, Tran NC, Ngo TD, Huynh TN, Tran CD, Thai KM..  (2012)  Synthesis and anti Methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics.,  22  (14): [PMID:22727643] [10.1016/j.bmcl.2012.05.112]
15. Parhi A, Lu S, Kelley C, Kaul M, Pilch DS, LaVoie EJ..  (2012)  Antibacterial activity of substituted dibenzo[a,g]quinolizin-7-ium derivatives.,  22  (22): [PMID:23058886] [10.1016/j.bmcl.2012.08.123]
16. Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P..  (2012)  Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions.,  55  (10): [PMID:22541068] [10.1021/jm300212s]
17. Kelley C, Zhang Y, Parhi A, Kaul M, Pilch DS, LaVoie EJ..  (2012)  3-Phenyl substituted 6,7-dimethoxyisoquinoline derivatives as FtsZ-targeting antibacterial agents.,  20  (24): [PMID:23127490] [10.1016/j.bmc.2012.10.009]
18. Chen Z, Ye X, Yi J, Chen X, Li X.  (2012)  Synthesis of 9-O-glycosyl-berberine derivatives and bioavailability evaluation,  21  (8): [10.1007/s00044-011-9678-1]
19. Ramirez-Galicia G, Martinez-Pacheco H, Garduno-Juarez R, Deeb O.  (2012)  Exploring QSAR of antiamoebic agents of isolated natural products by MLR, ANN, and RTO,  21  (9): [10.1007/s00044-011-9767-1]
20. Mohammad M, Al-masri IM, Issa A, Khdair A, Bustanji Y.  (2013)  Inhibition of pancreatic lipase by berberine and dihydroberberine: an investigation by docking simulation and experimental validation,  22  (5): [10.1007/s00044-012-0221-9]
21. Zhang SL, Chang JJ, Damu GL, Fang B, Zhou XD, Geng RX, Zhou CH..  (2013)  Novel berberine triazoles: synthesis, antimicrobial evaluation and competitive interactions with metal ions to human serum albumin.,  23  (4): [PMID:23312473] [10.1016/j.bmcl.2012.12.036]
22. Keffer JL, Huecas S, Hammill JT, Wipf P, Andreu JM, Bewley CA..  (2013)  Chrysophaentins are competitive inhibitors of FtsZ and inhibit Z-ring formation in live bacteria.,  21  (18): [PMID:23932448] [10.1016/j.bmc.2013.07.033]
23. Wang Y, Zhou C, Chen J, Lin Y, Zeng W, Kuang B, Fu W, Chen W.  (2013)  Facile synthesis of a polyether-tethered dimeric berberine as a highly effective DNA-cleaving agent in the presence of Cu(ii) ion,  (10): [10.1039/C3MD00136A]
24. PubChem BioAssay data set, 
25. Islam MM, Basu A, Suresh Kumar G.  (2011)  Binding of 9-O-(-amino) alkyl ether analogues of the plant alkaloid berberine to poly(A): insights into self-structure induction,  (7): [10.1039/C0MD00209G]
26. Zhang S, Chang J, Damu GLV, Geng R, Zhou C.  (2013)  Berberine azoles as antimicrobial agents: synthesis, biological evaluation and their interactions with human serum albumin,  (5): [10.1039/C3MD00032J]
27. Le Gresley A, Abdullah A, Chawla D, Desai P, Ghosh U, Gollapalli U, Kiran M, Lafon S, Sinclair A.  (2011)  Diacrylamides as selective G-quadruplex ligands in in vitro and in vivo assays,  (6): [10.1039/C1MD00020A]
28. Cheng P, Zhou J, Qing Z, Kang W, Liu S, Liu W, Xie H, Zeng J..  (2014)  Synthesis of 5-methyl phenanthridium derivatives: a new class of human DOPA decarboxylase inhibitors.,  24  (12): [PMID:24794108] [10.1016/j.bmcl.2014.04.047]
29. Kim JH, Ryu YB, Lee WS, Kim YH..  (2014)  Neuraminidase inhibitory activities of quaternary isoquinoline alkaloids from Corydalis turtschaninovii rhizome.,  22  (21): [PMID:25277281] [10.1016/j.bmc.2014.09.004]
30. Li X, Ma S..  (2015)  Advances in the discovery of novel antimicrobials targeting the assembly of bacterial cell division protein FtsZ.,  95  [PMID:25791674] [10.1016/j.ejmech.2015.03.026]
31. Nguyen VT, To DC, Tran MH, Oh SH, Kim JA, Ali MY, Woo MH, Choi JS, Min BS..  (2015)  Isolation of cholinesterase and β-secretase 1 inhibiting compounds from Lycopodiella cernua.,  23  (13): [PMID:26003344] [10.1016/j.bmc.2015.04.080]
32. Takeda H, Ishikawa K, Wakana D, Fukuda M, Sato F, Hosoe T..  (2015)  11-Hydroxylation of Protoberberine by the Novel Berberine-Utilizing Aerobic Bacterium Sphingobium sp. Strain BD3100.,  78  (12): [PMID:26654260] [10.1021/acs.jnatprod.5b00408]
33. Son D, Kim CS, Lee KR, Park HJ..  (2016)  Identification of new quinic acid derivatives as histone deacetylase inhibitors by fluorescence-based cellular assay.,  26  (9): [PMID:26996372] [10.1016/j.bmcl.2016.03.010]
34. Kellogg JJ, Todd DA, Egan JM, Raja HA, Oberlies NH, Kvalheim OM, Cech NB..  (2016)  Biochemometrics for Natural Products Research: Comparison of Data Analysis Approaches and Application to Identification of Bioactive Compounds.,  79  (2): [PMID:26841051] [10.1021/acs.jnatprod.5b01014]
35. Duggirala S, Napoleon JV, Nankar RP, Senu Adeeba V, Manheri MK, Doble M..  (2016)  FtsZ inhibition and redox modulation with one chemical scaffold: Potential use of dihydroquinolines against mycobacteria.,  123  [PMID:27517804] [10.1016/j.ejmech.2016.07.058]
36. Wang J, Yang T, Chen H, Xu YN, Yu LF, Liu T, Tang J, Yi Z, Yang CG, Xue W, Yang F..  (2017)  The synthesis and antistaphylococcal activity of 9, 13-disubstituted berberine derivatives.,  127  [PMID:28092858] [10.1016/j.ejmech.2017.01.012]
37. Luo X, Li C, Luo P, Lin X, Ma H, Seeram NP, Song C, Xu J, Gu Q..  (2016)  Pterosin Sesquiterpenoids from Pteris cretica as Hypolipidemic Agents via Activating Liver X Receptors.,  79  (12): [PMID:28006909] [10.1021/acs.jnatprod.6b00558]
38. Lee H, Tuong LT, Jeong JH, Lee SJ, Bae GU, Ryu JH..  (2017)  Isoquinoline alkaloids from Coptis japonica stimulate the myoblast differentiation via p38 MAP-kinase and Akt signaling pathway.,  27  (6): [PMID:28228365] [10.1016/j.bmcl.2017.02.003]
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