Ketcher 11101616272D 1   1.00000     0.00000     0

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  4  1  1  0     0  0
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  3  2  2  0     0  0
 21  2  1  0     0  0
  6  2  1  0     0  0
  5  3  1  0     0  0
  7  3  1  0     0  0
 21 13  1  0     0  0
  5  4  1  0     0  0
  9  6  2  0     0  0
  8  7  2  0     0  0
  9  8  1  0     0  0
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 12 10  1  0     0  0
 14 10  1  0     0  0
 13 11  1  0     0  0
 15 11  1  0     0  0
 17 14  2  0     0  0
 18 14  1  0     0  0
 16 15  2  0     0  0
 17 16  1  0     0  0
 19 17  1  0     0  0
 20 19  1  0     0  0
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 23  9  1  0     0  0
 25  8  1  0     0  0
M  END
> <ID>
CHEBI:132749

> <NAME>
(S)-nandinine

> <DEFINITION>
A berberine alkaloid that is 5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline carrying hydroxy and methoxy substituents at positions 9 and 10 respectively.

> <STAR>
3

> <SYNONYM>
S-Tetrahydroberberrubine; Nandinine; 10-Methoxy-2,3-(methylenedioxy)berbin-9-ol; (S)-nandinine; (+)-Tetrahydroberberrubine; (+)-nandinine; (+)-Nandinin

> <IUPAC_NAME>
(13aS)-10-methoxy-5,8,13,13a-tetrahydro-2H,6H-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-9-ol

> <FORMULA>
C19H19NO4

> <MASS>
325.359

> <MONOISOTOPIC_MASS>
325.13141

> <CHARGE>
0

> <SMILES>
N12[C@](C3=C(CC1)C=C4C(=C3)OCO4)(CC5=C(C2)C(=C(C=C5)OC)O)[H]

> <INCHI>
InChI=1S/C19H19NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1

> <INCHIKEY>
PQECCKIOFCWGRJ-HNNXBMFYSA-N

> <CAS_REGISTRY_NUMBER>
572-76-9

> <REAXYS_REGISTRY_NUMBER>
21963851

> <CHEMIDPLUS>
572-76-9

> <KEGG_COMPOUND_ACCESSION>
C21370

> <METACYC_ACCESSION>
CPD-16783

> <CHINESE_ABSTRACTS_CITATION>
618457

> <PUBMED_CITATION>
17250743; 21094631; 27462872; 28085967

$$$$