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Berbamine

AlkaPlorer ID: AK001119

Synonym: None

IUPAC Name: (1S,14R)-20,21,25-trimethoxy-15,30-dimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.23,6.18,12.114,18.027,31.022,33]hexatriaconta-3(36),4,6(35),8,10,12(34),18,20,22(33),24,26,31-dodecaen-9-ol

Structure

SMILES: COC1=CC2=C3C=C1OC1=C4C(=CC(OC)=C1OC)CCN(C)[C@@H]4CC1=CC=C(O)C(=C1)OC1=CC=C(C=C1)C[C@@H]3N(C)CC2

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InChI: InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(41-3)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-31-18-23(8-11-30(31)40)17-29-35-25(13-15-39(29)2)20-34(42-4)36(43-5)37(35)45-33/h6-11,18-21,28-29,40H,12-17H2,1-5H3/t28-,29+/m0/s1

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InChIKey: DFOCUWZXJBAUSQ-URLMMPGGSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Photinus marginellus Photinus Lampyridae Coleoptera Insecta Arthropoda Metazoa Eukaryota
Sargassum fulvellum Sargassum Sargassaceae Fucales Phaeophyceae None None Eukaryota
Sideritis ferrensis Sideritis Lamiaceae Lamiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Garcinia paucinervis Garcinia Clusiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cetraria australiensis Cetraria Parmeliaceae Lecanorales Lecanoromycetes Ascomycota Fungi Eukaryota
Pilosocereus chrysacanthus Pilosocereus Cactaceae Caryophyllales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Doronicum grandiflorum Doronicum Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dictyodendrilla cavernosa Dictyodendrilla Dictyodendrillidae Dendroceratida Demospongiae Porifera Metazoa Eukaryota
Piper retrofractum Piper Piperaceae Piperales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Bohadschia marmorata Bohadschia Holothuriidae Aspidochirotida Holothuroidea Echinodermata Metazoa Eukaryota
Conus gladiator Conus Conidae Neogastropoda Gastropoda Mollusca Metazoa Eukaryota
Radula voluta Radula Radulaceae Porellales Jungermanniopsida Streptophyta Viridiplantae Eukaryota
Grifola frondosa Grifola Grifolaceae Polyporales Agaricomycetes Basidiomycota Fungi Eukaryota
Acnistus arborescens Acnistus Solanaceae Solanales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Hylomecon japonica Hylomecon Papaveraceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Dunaliella salina Dunaliella Dunaliellaceae Chlamydomonadales Chlorophyceae Chlorophyta Viridiplantae Eukaryota
Lithocarpus haipinii Lithocarpus Fagaceae Fagales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Haplophyllum latifolium Haplophyllum Rutaceae Sapindales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Frullania dilatata Frullania Frullaniaceae Porellales Jungermanniopsida Streptophyta Viridiplantae Eukaryota
Thalictrum foliolosum Thalictrum Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Trifolium stellatum Trifolium Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Microstrobos niphophilus Microstrobos Podocarpaceae Araucariales Pinopsida Streptophyta Viridiplantae Eukaryota
Cryptantha leiocarpa Cryptantha Boraginaceae Boraginales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Berberis oblonga Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Berberis fortunei Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Cyclea barbata Cyclea Menispermaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Sphaerophysa salsula Sphaerophysa Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Panax quinquefolius Panax Araliaceae Apiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Oxytropis lanata Oxytropis Fabaceae Fabales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Populus balsamifera Populus Salicaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Berberis vulgaris Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Euphorbia characias Euphorbia Euphorbiaceae Malpighiales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Ligularia nelumbifolia Ligularia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Leibnitzia anandria Leibnitzia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Berberis thunbergii Berberis Berberidaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota
Moesziomyces antarcticus Moesziomyces Ustilaginaceae Ustilaginales Ustilaginomycetes Basidiomycota Fungi Eukaryota
Chrysactinia mexicana Chrysactinia Asteraceae Asterales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 608.735

TPSA？: 72.86

MolLogP？: 6.859400000000009

Number of H-Donors: 1

Number of H-Acceptors: 8

RingCount: 8

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Anthrax lethal factor Potency 3162.3 nM None
Chlorocebus sabaeus Vero CC50 50000.0 nM 10.1101/2020.03.20.999730
Entamoeba histolytica Entamoeba histolytica IC50 22.37 ug.mL-1 10.1007/s00044-011-9767-1
Homo sapiens Acetylcholinesterase IC50 100000.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens Arachidonate 15-lipoxygenase, type II Potency 15848.9 nM None
Homo sapiens Butyrylcholinesterase IC50 100000.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens Cytochrome P450 3A4 Potency 19952.6 nM None
Homo sapiens Endoplasmic reticulum-associated amyloid beta-peptide-binding protein Potency 31622.8 nM None
Homo sapiens Glycogen synthase kinase-3 beta Inhibition nan % 10.1021/acs.jnatprod.8b00592
Homo sapiens HepG2 Activity nan None 10.1016/j.ejmech.2020.112810
Homo sapiens K562 Activity nan None 10.1016/j.ejmech.2009.02.018
Homo sapiens K562 IC50 8930.0 nM 10.1016/j.ejmech.2009.02.018
Homo sapiens K562 IC50 11100.0 nM 10.1016/j.ejmech.2022.114442
Homo sapiens K562 IC50 17100.0 nM 10.1016/j.ejmech.2022.114442
Homo sapiens K562 Inhibition nan % 10.1016/j.ejmech.2009.02.018
Homo sapiens KB ED50 9210.0 nM 10.1021/np980144f
Homo sapiens P-glycoprotein 1 Inhibition nan % 10.1016/j.bmc.2020.115553
Homo sapiens Phosphodiesterase 1A IC50 22000.0 nM 10.1021/np50075a001
Homo sapiens Prolyl endopeptidase IC50 200000.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens Telomerase reverse transcriptase Activity 5.0 % 10.1039/C0MD00241K
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 9441.1 nM None
Homo sapiens U-937 Activity 70.0 % 10.1016/j.bmc.2012.06.017
Homo sapiens U-937 FC 1.2 None 10.1016/j.bmc.2012.06.017
Homo sapiens U-937 IC50 50000.0 nM 10.1016/j.bmc.2012.06.017
Homo sapiens U-937 MED 25.0 uM 10.1016/j.bmc.2012.06.017
Plasmodium falciparum Plasmodium falciparum IC50 128.0 nM 10.1021/np980144f
Plasmodium falciparum Plasmodium falciparum IC50 313.0 nM 10.1021/np980144f
Rattus norvegicus Muscarinic acetylcholine receptor Ki 190.0 nM 10.1021/np50075a001
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 7870.0 nM 10.1101/2020.03.20.999730
None ADMET Selectivity index 6.35 None 10.1101/2020.03.20.999730
None No relevant target permeability nan None 10.1021/acs.jnatprod.8b00592
None Unchecked IC50 3.84 ug.mL-1 10.1016/j.ejmech.2022.114442
None Unchecked IC50 5.09 ug.mL-1 10.1016/j.ejmech.2022.114442
None Unchecked IC50 8.17 ug.mL-1 10.1016/j.ejmech.2022.114442
None Unchecked IC50 185.2 ug.mL-1 10.1016/j.ejmech.2022.114442
None Unchecked IC50 60000.0 nM 10.1021/np50075a001
None Unchecked Inhibition 56.4 % 10.1021/np50075a001
None Unchecked Potency 2818.4 nM None
None Unchecked Potency 11220.2 nM None
None Unchecked Ratio IC50 0.4 None 10.1021/acs.jnatprod.8b00592
None Unchecked Selectivity Index 29.0 None 10.1021/np980144f
None Unchecked Selectivity Index 72.0 None 10.1021/np980144f

Metabolism Information