Details of the Drug

General Information of Drug (ID: DMC5Q8X)

Drug Name
Berberine
Synonyms
berberine; 2086-83-1; Berberin; Umbellatine; UNII-0I8Y3P32UF; 0I8Y3P32UF; CHEBI:16118; EINECS 218-229-1; Berberal; BRN 3570374; ST055798; 9,10-Dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetrahydroberbinium; Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-; 9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium; Berbamine sulphate acid; CHEMBL12089; 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)berbinium; BERBINIUM, 7,8,13,13a-TETRAHYDRO-9,10-DIMETHOXY-2,3-(METHYLE
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 336.4
Logarithm of the Partition Coefficient (xlogp) 3.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
Chemical Identifiers
Formula
C20H18NO4+
IUPAC Name
16,17-dimethoxy-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-octaene
Canonical SMILES
COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC
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
InChIKey
YBHILYKTIRIUTE-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
2353
ChEBI ID
CHEBI:16118
CAS Number
2086-83-1
DrugBank ID
DB04115
TTD ID
D0W8WB
VARIDT ID
DR00307
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Telomerase reverse transcriptase (TERT) TTUJFD0 TERT_HUMAN Inhibitor [1]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Organic cation transporter 1 (SLC22A1) DTT79CX S22A1_HUMAN Substrate [2]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
72 kDa type IV collagenase (MMP2) OT5NIWA2 MMP2_HUMAN Gene/Protein Processing [4]
Acetylcholinesterase (ACHE) OT2H8HG6 ACES_HUMAN Gene/Protein Processing [5]
Actin-histidine N-methyltransferase (SETD3) OTO5RAU2 SETD3_HUMAN Gene/Protein Processing [6]
Aggrecan core protein (ACAN) OTUOCW8K PGCA_HUMAN Gene/Protein Processing [7]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [8]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [8]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Gene/Protein Processing [9]
Aurora kinase B (AURKB) OTIY4VHU AURKB_HUMAN Gene/Protein Processing [6]
Aurora kinase C (AURKC) OTJMOW9V AURKC_HUMAN Gene/Protein Processing [6]
Baculoviral IAP repeat-containing protein 5 (BIRC5) OTILXZYL BIRC5_HUMAN Protein Interaction/Cellular Processes [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Telomerase reverse transcriptase (TERT) DTT TERT 8.59E-10 -0.08 -0.33
P-glycoprotein 1 (ABCB1) DTP P-GP 3.39E-11 -2.93E-01 -6.11E-01
Organic cation transporter 1 (SLC22A1) DTP SLC22A1 6.12E-03 -2.40E-02 -7.73E-02
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Stage specificity of Plasmodium falciparum telomerase and its inhibition by berberine. Parasitol Int. 2002 Mar;51(1):99-103.
2 Vectorial transport of the plant alkaloid berberine by double-transfected cells expressing the human organic cation transporter 1 (OCT1, SLC22A1) and the efflux pump MDR1 P-glycoprotein (ABCB1). Naunyn Schmiedebergs Arch Pharmacol. 2008 Feb;376(6):449-61.
3 P-glycoprotein-mediated transport of berberine across Caco-2 cell monolayers. J Pharm Sci. 2002 Dec;91(12):2614-21.
4 Berberine enhances inhibition of glioma tumor cell migration and invasiveness mediated by arsenic trioxide. BMC Cancer. 2008 Feb 25;8:58. doi: 10.1186/1471-2407-8-58.
5 Profiling the Tox21 Chemical Collection for Acetylcholinesterase Inhibition. Environ Health Perspect. 2021 Apr;129(4):47008. doi: 10.1289/EHP6993. Epub 2021 Apr 12.
6 Berberine acts as a putative epigenetic modulator by affecting the histone code. Toxicol In Vitro. 2016 Oct;36:10-17. doi: 10.1016/j.tiv.2016.06.004. Epub 2016 Jun 13.
7 Berberine promotes bone marrow-derived mesenchymal stem cells osteogenic differentiation via canonical Wnt/-catenin signaling pathway. Toxicol Lett. 2016 Jan 5;240(1):68-80. doi: 10.1016/j.toxlet.2015.10.007. Epub 2015 Oct 22.
8 Cytotoxicity of berberine on human cervical carcinoma HeLa cells through mitochondria, death receptor and MAPK pathways, and in-silico drug-target prediction. Toxicol In Vitro. 2010 Sep;24(6):1482-90. doi: 10.1016/j.tiv.2010.07.017. Epub 2010 Jul 23.
9 Activation of the aryl hydrocarbon receptor by berberine in HepG2 and H4IIE cells: biphasic effect on CYP1A1. Biochem Pharmacol. 2005 Sep 15;70(6):925-36.
10 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. doi: 10.1002/jms.1320.