Ketcher 02081815022D 1   1.00000     0.00000     0

 27 29  0     1  0            999 V2000
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    6.3402  -12.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7634  -14.0550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8951  -14.5333    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   10.2681  -11.2107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  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:136455

> <NAME>
jaconine

> <DEFINITION>
A pyrrolizine alkaloid that is jacoline in which the secondary hydroxy group has been replaced by a chlorine.

> <STAR>
3

> <SYNONYM>
(15alpha,20R)-20-Chloro-15,20-dihydro-12,15-dihydroxysenecionan-11,16-dione

> <IUPAC_NAME>
(3R,5R,6R,14aR,14bR)-3,6-dihydroxy-3-[(1R)-1-chloroethyl]-3,6-dihydroxy-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>
C18H26ClNO6

> <MASS>
387.856

> <MONOISOTOPIC_MASS>
387.14487

> <CHARGE>
0

> <SMILES>
[C@@]1([C@@H](C)Cl)(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/C18H26ClNO6/c1-10-8-18(24,11(2)19)16(22)26-13-5-7-20-6-4-12(14(13)20)9-25-15(21)17(10,3)23/h4,10-11,13-14,23-24H,5-9H2,1-3H3/t10-,11-,13-,14-,17-,18+/m1/s1

> <INCHIKEY>
CKPJPJSVQMEGBC-YLFNNMARSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
56049

> <CAS_REGISTRY_NUMBER>
480-75-1

> <REAXYS_REGISTRY_NUMBER>
56049

> <CHEMIDPLUS>
480-75-1

> <NIST_CHEMISTRY_WEBBOOK>
480-75-1

> <AGRICOLA_CITATION>
IND44598050

> <PUBMED_CITATION>
16826978; 17913058; 19169751; 21159354; 21506416; 21969251; 22516740; 835011; 9328525

$$$$