Annonacin

Annonacin
Names
Preferred IUPAC name
(5S)-5-Methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13-{(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl}tridecyl]furan-2(5H)-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1 checkY
    Key: XNODZYPOIPVPRF-CGWDHHCXSA-N checkY
  • InChI=1/C35H64O7/c1-3-4-5-6-7-8-9-10-11-15-21-31(38)33-23-24-34(42-33)32(39)22-17-16-19-29(36)18-13-12-14-20-30(37)26-28-25-27(2)41-35(28)40/h25,27,29-34,36-39H,3-24,26H2,1-2H3/t27-,29+,30+,31+,32+,33+,34+/m0/s1
    Key: XNODZYPOIPVPRF-CGWDHHCXBQ
  • CCCCCCCCCCCCC(C1CCC(O1)C(CCCCC(CCCCCC(CC2=CC(OC2=O)C)O)O)O)O
  • O=C\1O[C@H](/C=C/1C[C@H](O)CCCCC[C@@H](O)CCCC[C@@H](O)[C@@H]2O[C@@H]([C@H](O)CCCCCCCCCCCC)CC2)C
Properties
C35H64O7
Molar mass 596.890 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Annonacin is a chemical compound with toxic effects, especially in the nervous system, found in some fruits such as the paw paw, custard apples, soursop, and others from the family Annonaceae. It is a member of the class of compounds known as acetogenins. Annonacin-containing fruit products are regularly consumed throughout the West Indies for their traditional medicine uses.