Summary

IMPPAT Phytochemical identifier: IMPPAT3_PHYID002558

Phytochemical name: Berberine

Synonymous chemical names:
berberine, berbericine, umbellatine, Umbellatine

External chemical identifiers:
CID:CID_2353, ChEMBL:CHEMBL295124, ChEBI:CHEBI:16118, ZINC:ZINC000003779067, FDASRS:0I8Y3P32UF, SureChEMBL:SCHEMBL25632, MolPort-002-507-191

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Chemical structure information

SMILES:
COc1c(OC)ccc2c1c[n+]1CCc3c(-c1c2)cc1c(c3)OCO1

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

DeepSMILES:
COccOC))cccc6c[n+]CCcc-c6c%10))cccc6)OCO5

Functional groups:
cOC, c[n+](c)C, c1cOCO1

Link to spectral information:
MSBNK-Univ_Toyama-TY000105, MSBNK-Univ_Toyama-TY000043, MSBNK-RIKEN_NPDepo-CB000105, MSBNK-MPI_for_Chemical_Ecology-CE000115, MSBNK-MPI_for_Chemical_Ecology-CE000114, MSBNK-MPI_for_Chemical_Ecology-CE000113, MSBNK-Keio_Univ-KO008888, MSBNK-Keio_Univ-KO008887, MSBNK-Keio_Univ-KO008886, MSBNK-Keio_Univ-KO002477, MSBNK-Keio_Univ-KO002474, MSBNK-Keio_Univ-KO002475, MSBNK-Keio_Univ-KO002473, MSBNK-IPB_Halle-PB005922, MSBNK-IPB_Halle-PB005921, MSBNK-IPB_Halle-PB005914, MSBNK-IPB_Halle-PB005913, MSBNK-IPB_Halle-PB001482, MSBNK-IPB_Halle-PB001481, MSBNK-Keio_Univ-KO002476

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Molecular scaffolds

Scaffold Graph/Node/Bond level:
c1ccc2c[n+]3c(cc2c1)-c1cc2c(cc1CC3)OCO2

Scaffold Graph/Node level:
C1CCC2CN3CCC4CC5OCOC5CC4C3CC2C1

Scaffold Graph level:
C1CCC2CC3C(CCC4CC5CCCC5CC43)CC2C1

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Chemical classification

ClassyFire Kingdom: Organic compounds

ClassyFire Superclass: Alkaloids and derivatives

ClassyFire Class: Protoberberine alkaloids and derivatives

NP-Likeness score: 1.302

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Chemical structure download