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Lambertine

AlkaPlorer ID: AK000337

Synonym: Dihydroberberine

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-heptaene

Structure

SMILES: COC1=C(OC)C2=C(C=C3C4=C(C=C5OCOC5=C4)CCN3C2)C=C1

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InChI: InChI=1S/C20H19NO4/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/h3-4,7-9H,5-6,10-11H2,1-2H3

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InChIKey: FZAGOOYMTPGPGF-UHFFFAOYSA-N

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Reference

Berberis vulgaris Linn.

PubChem CID: 10217

CAS: 5956-60-5

LOTUS: LTS0007586

SuperNatural Ⅲ: SN0099336

NPASS: NPC93593

COCONUT: CNP0445601

Properties Information

Molecule Weight: 337.37500000000006

TPSA？: 40.16

MolLogP？: 3.3023000000000016

Number of H-Donors: 0

Number of H-Acceptors: 5

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Cholesterol esterase IC50 8.0 ug.mL-1 10.1007/s00044-012-0221-9
Homo sapiens MRC5 CC50 155000.0 nM 10.1016/j.bmcl.2006.12.085
Human betaherpesvirus 5 Human betaherpesvirus 5 IC50 93000.0 nM 10.1016/j.bmcl.2006.12.085
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 reverse transcriptase IC50 200.0 ug.mL-1 10.1021/np50073a012
Mus musculus Mus musculus Activity 11.0 % 10.1016/j.bmc.2010.06.085
Mus musculus Mus musculus Activity 12.0 % 10.1016/j.bmc.2010.06.085
Mus musculus Mus musculus Activity 14.0 % 10.1016/j.bmc.2010.06.085
Mus musculus Mus musculus Activity 17.0 % 10.1016/j.bmc.2010.06.085
Mus musculus Mus musculus Activity 18.0 % 10.1016/j.bmc.2010.06.085
Mus musculus Mus musculus Activity 25.0 % 10.1016/j.bmc.2010.06.085
Mus musculus Mus musculus Activity nan None 10.1016/j.bmc.2010.06.085
Mus musculus Mus musculus T-C -0.2 day 10.1021/jm00401a006
Mus musculus Mus musculus T-C nan None 10.1021/jm00401a006
Plasmodium falciparum Plasmodium falciparum IC50 0.12 ug.mL-1 10.1021/jm00401a006
Plasmodium falciparum Plasmodium falciparum IC50 0.171 ug.mL-1 10.1021/jm00401a006
Rattus norvegicus Rattus norvegicus F 2.65 % 10.1016/j.bmc.2010.06.085
Toxoplasma gondii Toxoplasma gondii ID50 0.65 uM 10.1016/j.bmcl.2012.02.038
None ADMET TD50 41.0 uM 10.1016/j.bmcl.2012.02.038
None ADMET TI 63.0 None 10.1016/j.bmcl.2012.02.038
None No relevant target Solubility 1000.0 ug.mL-1 10.1016/j.bmc.2010.06.085
None No relevant target Stability 17.0 % 10.1016/j.bmc.2010.06.085
None Unchecked Ratio CC50/IC50 1.7 None 10.1016/j.bmcl.2006.12.085

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT011892 COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1=C2)OCO4>>COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1C2)OCO4 enzymemap_23081
AKRT011893 COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1=C2)OCO4>>COc1ccc2c(c1OC)CN1CCc3cc4c(cc3[C@H]1C2)OCO4 RXN-15641
AKRT011894 COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1C2)OCO4>>COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1=C2)OCO4 enzymemap_23081
AKRT011929 COc1ccc2cc3[n+](cc2c1OC)CCc1cc2c(cc1-3)OCO2>>COc1ccc2c(c1OC)CN1CCc3cc4c(cc3C1=C2)OCO4 RXN-15640