Marvin  04250717232D          

 25 29  0  0  0  0            999 V2000
   -1.5877    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5877    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732    0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588    1.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1588   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702    0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702   -0.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2702   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5557    0.5500    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -2.3022    0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3022    1.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9846   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0868    1.6299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0868    0.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5717    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991   -0.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4136   -1.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6991   -2.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4136   -1.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1  3  2  0  0  0  0
 15  2  1  0  0  0  0
  2  4  2  0  0  0  0
  5  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
 14  6  1  0  0  0  0
 14  9  1  0  0  0  0
 14  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8 11  2  0  0  0  0
 10  9  2  0  0  0  0
 10 17  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 18  1  0  0  0  0
 18 17  2  0  0  0  0
 19 21  1  0  0  0  0
 19 16  1  0  0  0  0
 21 20  1  0  0  0  0
 20 15  1  0  0  0  0
 16 15  2  0  0  0  0
 17 22  1  0  0  0  0
 18 24  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
M  CHG  1  14   1
M  END
> <ID>
CHEBI:16118

> <NAME>
berberine

> <STAR>
3

> <SECONDARY_ID>
CHEBI:41098; CHEBI:13893; CHEBI:22753; CHEBI:3066

> <SYNONYM>
Umbellatine; berberine; BERBERINE; Berberine; Berberin; 9,10-dimethoxy-2,3-(methylenedioxy)-7,8,13,13a-tetradehydroberbinium; 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-[methylenebis(oxy)]berbinium; 5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium

> <IUPAC_NAME>
9,10-dimethoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinolin-7-ium

> <FORMULA>
C20H18NO4

> <MASS>
336.36126

> <MONOISOTOPIC_MASS>
336.12303

> <CHARGE>
1

> <SMILES>
COc1ccc2cc3-c4cc5OCOc5cc4CC[n+]3cc2c1OC

> <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

> <BEILSTEIN_REGISTRY_NUMBER>
3570374

> <CAS_REGISTRY_NUMBER>
2086-83-1

> <CHEMIDPLUS>
2086-83-1

> <DRUGBANK_ACCESSION>
DB04115

> <KEGG_COMPOUND_ACCESSION>
C00757

> <KNAPSACK_ACCESSION>
C00001819

> <LINCS_ACCESSION>
LSM-6553

> <METACYC_ACCESSION>
BERBERINE

> <NIST_CHEMISTRY_WEBBOOK>
2086-83-1

> <PDBECHEM_ACCESSION>
BER

> <PESTICIDES_ACCESSION>
berberine

> <WIKIPEDIA_ACCESSION>
Berberine

> <PUBMED_CITATION>
11860742; 12232209; 12428952; 12433089; 12468268; 15040083; 15531889; 15739507; 15768991; 16379555; 16448624; 16505103; 17089049; 17295371; 17531424; 18537696; 19014947; 19336898; 19640223; 19652370; 19704371; 20471843; 20847417; 21401114; 21420512; 21500372; 21661731; 23231038; 26167392; 8730735

$$$$