Ketcher 01071916122D 1   1.00000     0.00000     0

 28 32  0     1  0            999 V2000
   18.6174   -8.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3083   -7.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3301   -7.5441    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6610   -8.2872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9701   -9.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9482   -9.4462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7266   -6.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4175   -7.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0867   -8.2873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7047   -6.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3738   -7.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0649   -8.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8738   -8.6672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3738   -7.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6829   -8.0794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0211   -6.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0429   -6.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2572  -10.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2354  -10.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5954   -8.9109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9046   -9.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2646   -8.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5881  -11.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2791  -10.1894    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2865   -7.9599    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6100  -10.9325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8972  -12.0914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2281  -12.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 20  1  1  0     0  0
  1 25  1  1     0  0
  1  2  1  0     0  0
  2  3  1  0     0  0
  3 16  2  0     0  0
  3  4  1  0     0  0
 15  4  2  0     0  0
  4  5  1  0     0  0
  1  6  1  0     0  0
  5  6  1  0     0  0
  6 18  1  0     0  0
  6 24  1  6     0  0
 10  7  1  0     0  0
  7  8  2  0     0  0
  8  9  1  0     0  0
  9 12  2  0     0  0
 11 10  2  0     0  0
 11 12  1  0     0  0
 14 11  1  0     0  0
 12 13  1  0     0  0
 13 15  1  0     0  0
 14 15  1  0     0  0
 17 14  2  0     0  0
 16 17  1  0     0  0
 18 19  2  0     0  0
 18 23  1  0     0  0
 19 21  1  0     0  0
 20 21  1  0     0  0
 20 22  1  6     0  0
 23 26  2  0     0  0
 23 27  1  0     0  0
 27 28  1  0     0  0
M  CHG  2   3   1  13  -1
M  END
> <ID>
CHEBI:9119

> <NAME>
serpentine

> <DEFINITION>
An indole alkaloid that is 18-oxayohimban dehydrogenated at positions 3, 4, 5, 6, 16 and 17 and substituted by a methyl group at the 19α position and by a methoxycarbonyl group at position 16.

> <STAR>
3

> <SYNONYM>
Serpentine (alkaloid); Serpentine; methyl (19alpha)-19-methyl-3,4,5,6,16,17-hexadehydrooxayohimban-4-ium-1-ide-16-carboxylate; (4S,4aR,14aS)-4-methyl-1-[(methyloxy)carbonyl]-4a,5,14,14a-tetrahydro-4H-indolo[2,3-a]pyrano[3,4-g]quinolizin-6-ium-13-ide; (19alpha)-3,4,5,6,16,17-hexadehydro-16-(methoxycarbonyl)-19-methyloxayohimbanium

> <IUPAC_NAME>
methyl (19alpha)-19-methyl-3,4,5,6,16,17-hexadehydro-18-oxayohimban-4-ium-1-ide-16-carboxylate

> <FORMULA>
C21H20N2O3; C21H20N2O3

> <MASS>
348.396

> <MONOISOTOPIC_MASS>
348.14739

> <CHARGE>
0

> <SMILES>
[C@]12([C@@H](OC=C([C@]1(CC=3[N+](C2)=CC=C4C5=CC=CC=C5[N-]C34)[H])C(=O)OC)C)[H]

> <INCHI>
InChI=1S/C21H20N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-8,11-12,15-16H,9-10H2,1-2H3/t12-,15-,16+/m0/s1

> <INCHIKEY>
WYTGDNHDOZPMIW-VBNZEHGJSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
5421116

> <CAS_REGISTRY_NUMBER>
18786-24-8

> <CHEMIDPLUS>
18786-24-8

> <KEGG_COMPOUND_ACCESSION>
C09241

> <KNAPSACK_ACCESSION>
C00001769

$$$$