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Oxyberberine

AlkaPlorer ID: AK006193

Synonym: None

IUPAC Name: 16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(21),2,4(8),9,15(20),16,18-heptaen-14-one

Structure

SMILES: COC1=CC=C2C=C3C4=CC5=C(C=C4CCN3C(=O)C2=C1OC)OCO5

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InChI: InChI=1S/C20H17NO5/c1-23-15-4-3-12-7-14-13-9-17-16(25-10-26-17)8-11(13)5-6-21(14)20(22)18(12)19(15)24-2/h3-4,7-9H,5-6,10H2,1-2H3

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InChIKey: ZHYQCBCBTQWPLC-UHFFFAOYSA-N

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Reference

Family Berberidaceae

PubChem CID: 11066

CAS: 549-21-3

LOTUS: LTS0237537

SuperNatural Ⅲ: SN0470882

COCONUT: CNP0284218

data_source: manually

Source

Species Genus Family Order Class Phylum Kingdom Domain
Coptis japonica Coptis Ranunculaceae Ranunculales Magnoliopsida Streptophyta Viridiplantae Eukaryota

Properties Information

Molecule Weight: 351.3580000000001

TPSA？: 58.92

MolLogP？: 2.9705000000000013

Number of H-Donors: 0

Number of H-Acceptors: 6

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Acetylcholinesterase IC50 100000.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens Amyloid-beta A4 protein Inhibition -79.0 % 10.1016/j.ejmech.2021.113289
Homo sapiens Butyrylcholinesterase IC50 68000.0 nM 10.1021/acs.jnatprod.8b00592
Homo sapiens Glycogen synthase kinase-3 beta Inhibition nan % 10.1021/acs.jnatprod.8b00592
Homo sapiens Prolyl endopeptidase IC50 200000.0 nM 10.1021/acs.jnatprod.8b00592
Mus musculus Mus musculus T-C 0.1 day 10.1021/jm00401a006
Mus musculus Mus musculus T-C 0.3 day 10.1021/jm00401a006
Mus musculus Mus musculus T-C 0.5 day 10.1021/jm00401a006
Plasmodium falciparum Plasmodium falciparum IC50 0.557 ug.mL-1 10.1021/jm00401a006
Plasmodium falciparum Plasmodium falciparum IC50 2.008 ug.mL-1 10.1021/jm00401a006
Rattus norvegicus PC-12 CC50 137000.0 nM 10.1016/j.ejmech.2021.113289
Toxoplasma gondii Toxoplasma gondii ID50 12.0 uM 10.1016/j.bmcl.2012.02.038
None ADMET TD50 97.0 uM 10.1016/j.bmcl.2012.02.038
None ADMET TI 8.0 None 10.1016/j.bmcl.2012.02.038
None No relevant target permeability nan None 10.1021/acs.jnatprod.8b00592
None Unchecked Ratio IC50 1.1 None 10.1021/acs.jnatprod.8b00592

Metabolism Information