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Annonacin information


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
CAS Number
  • 111035-65-5 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChEMBL
  • ChEMBL476498 ☒N
ChemSpider
  • 314587 checkY
PubChem CID
  • 354398
UNII
  • 40372ET6TM checkY
CompTox Dashboard (EPA)
  • DTXSID20892989 Edit this at Wikidata
InChI
  • 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
SMILES
  • 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
Chemical formula
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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Infobox references

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.

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Annonacin

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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...

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Soursop

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no other micronutrients in appreciable amounts (table). The compound annonacin is contained in the fruit, seeds, and leaves of soursop. The leaves of...

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Annona

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attract small beetles such as Nitidulidae or Staphylinidae. The compound annonacin and dozens of other acetogenins contained in the seeds and fruit of some...

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Asimina triloba

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However, the bark, leaves, fruit, and seeds contain the potent neurotoxin annonacin. This plant's scientific name is Asimina triloba. The genus name Asimina...

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Acetogenin

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Many acetogenins are characterized by neurotoxicity. Examples include: Annonacin Annonins Bullatacin Uvaricin Structurally, acetogenins are a series of...

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Annonaceae

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associated as a causal agent in "atypical Parkinsonism". The causative agent, annonacin, is present in the seeds and leaves of many of the Annonaceae, though...

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Progressive supranuclear palsy

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from PSP. Lytico-bodig disease (Parkinsonism-Dementia Complex of Guam) Annonacin Shukla R, Sinha M, Kumar R, Singh D (April 2009). "'Hummingbird' sign...

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Tetrahydrofuran

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Chemical structure of annonacin, an acetogenin....

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Polyketide

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agent doxycycline Acetogenins bullatacin squamocin molvizarin uvaricin annonacin Others The immunosuppressants tacrolimus (FK506) (a calcineurin inhibitor)...

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Cherimoya

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entire plant contains small amounts of neurotoxic acetogenins, such as annonacin, which appear to be linked to atypical parkinsonism in Guadeloupe. Moreover...

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Talponia plummeriana

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is one of the few species capable of surviving the elevated level of annonacin found in pawpaws. Feeding takes place when larvae bore into the peduncle...

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