Marvin  03200909332D          

 23 27  0  0  0  0            999 V2000
   -0.2357    1.7973    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9502    1.3848    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9502    0.5598    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2357    0.1473    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4788    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4788    1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6646    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6646   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357   -0.6777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3791    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0936   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3791   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -0.9326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3631   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    0.4022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6647    1.7973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357    2.6223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357    0.9723    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9502   -0.2652    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622   -0.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5893   -0.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  5  6  2  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 14  8  2  0  0  0  0
  8  7  1  0  0  0  0
 11  7  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 12 17  1  0  0  0  0
 12 13  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 18  1  6  0  0  0
  1 19  1  1  0  0  0
  4 20  1  6  0  0  0
  3 21  1  1  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 22  1  0  0  0  0
M  END
> <ID>
CHEBI:6601

> <NAME>
lycorine

> <DEFINITION>
An  indolizidine alkaloid that is 3,12-didehydrogalanthan substituted by hydroxy groups at positions and 2 and a methylenedioxy group across positions 9 and 10. Isolated from Crinum asiaticum, it  has been shown to exhibit antimalarial activity.

> <STAR>
3

> <SYNONYM>
Narcissine; Lycorine; Licorine; Galanthidine; Amarylline; (-)-lycorine

> <IUPAC_NAME>
9,10-(methylenedioxy)-3,12-didehydrogalanthan-1alpha,2beta-diol

> <FORMULA>
C16H17NO4

> <MASS>
287.31050

> <MONOISOTOPIC_MASS>
287.11576

> <CHARGE>
0

> <SMILES>
[H][C@]12[C@H](O)[C@@H](O)C=C3CCN(Cc4cc5OCOc5cc14)[C@@]23[H]

> <INCHI>
InChI=1S/C16H17NO4/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19/h3-5,11,14-16,18-19H,1-2,6-7H2/t11-,14-,15+,16+/m0/s1

> <INCHIKEY>
XGVJWXAYKUHDOO-DANNLKNASA-N

> <BEILSTEIN_REGISTRY_NUMBER>
93605

> <CAS_REGISTRY_NUMBER>
476-28-8

> <REAXYS_REGISTRY_NUMBER>
93605

> <CHEMIDPLUS>
476-28-8

> <KEGG_COMPOUND_ACCESSION>
C08532

> <KNAPSACK_ACCESSION>
C00001576

> <PDBECHEM_ACCESSION>
3KD

> <PUBMED_CITATION>
12232602; 14669261; 15386196; 19788245

$$$$