Ketcher 02081814132D 1   1.00000     0.00000     0

 27 29  0     1  0            999 V2000
   17.3373   -8.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4814   -8.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3288   -7.9617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3373   -9.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1971   -8.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6172   -8.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1971  -10.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4814  -10.4578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0615   -8.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1971  -11.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9132   -8.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0573   -9.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0489  -11.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3918  -12.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7732   -8.9727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0615  -12.6981    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9047  -11.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1386  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7689   -9.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6289   -8.4693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9635  -13.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6516  -12.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9047  -10.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0364  -10.9361    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.4165   -7.6138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4094   -7.6135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4836   -7.4764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0     0  0
  1  3  1  6     0  0
  1  4  1  0     0  0
  1  5  1  0     0  0
  2  6  1  0     0  0
  4  7  1  0     0  0
  4  8  2  0     0  0
  5  9  1  0     0  0
 10  7  1  1     0  0
  9 11  1  0     0  0
  9 12  1  6     0  0
 10 13  1  0     0  0
 10 14  1  0     0  0
 11 15  1  0     0  0
 13 16  1  0     0  0
 13 17  1  0     0  0
 14 18  1  0     0  0
 15 19  1  0     0  0
 15 20  2  0     0  0
 16 21  1  0     0  0
 17 22  2  0     0  0
 17 23  1  0     0  0
 16 18  1  0     0  0
 19 23  1  0     0  0
 21 22  1  0     0  0
 13 24  1  6     0  0
 25 11  1  0     0  0
 11 26  1  1     0  0
  2 27  1  1     0  0
M  END
> <ID>
CHEBI:136452

> <NAME>
jacoline

> <DEFINITION>
A pyrrolizine alkaloid obtained from senecionine by formal addition of hydrogen peroxide across the ethylidene double bond.

> <STAR>
3

> <SYNONYM>
(15alpha,20R)-12,15,20-Trihydroxy-15,20-dihydrosenecionan-11,16-dione

> <IUPAC_NAME>
(3S,5R,6R,14aR,14bR)-3,6-dihydroxy-3-[(1R)-1-hydroxyethyl]-5,6-dimethyl-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione

> <FORMULA>
C18H27NO7

> <MASS>
369.410

> <MONOISOTOPIC_MASS>
369.17875

> <CHARGE>
0

> <SMILES>
[C@@]1([C@@H](C)O)(O)C(O[C@H]2[C@@]3(N(CC=C3COC([C@]([C@@H](C1)C)(C)O)=O)CC2)[H])=O

> <INCHI>
InChI=1S/C18H27NO7/c1-10-8-18(24,11(2)20)16(22)26-13-5-7-19-6-4-12(14(13)19)9-25-15(21)17(10,3)23/h4,10-11,13-14,20,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1

> <INCHIKEY>
FMWJEBGSMAOQNN-YLFNNMARSA-N

> <CAS_REGISTRY_NUMBER>
480-76-2

> <REAXYS_REGISTRY_NUMBER>
56051

> <CHEMIDPLUS>
480-76-2

> <KNAPSACK_ACCESSION>
C00026209

> <NIST_CHEMISTRY_WEBBOOK>
480-76-2

$$$$