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Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.
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Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi
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{{chembox
{{chembox
| verifiedrevid = 399527858
|ImageFile=Annonacin.png
|ImageFile=Annonacin.png
|ImageSize=200px
|ImageSize=200px
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|OtherNames=
|OtherNames=
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 314587
| ChemSpiderID = 314587
| 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
| 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
| InChIKey = XNODZYPOIPVPRF-CGWDHHCXBQ
| InChIKey = XNODZYPOIPVPRF-CGWDHHCXBQ
| SMILES1 = 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
| SMILES1 = 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = XNODZYPOIPVPRF-CGWDHHCXSA-N
| StdInChIKey = XNODZYPOIPVPRF-CGWDHHCXSA-N
| CASNo=111035-65-5
| CASNo=111035-65-5

Revision as of 15:24, 29 November 2010

Annonacin
Names
IUPAC name
(5S)-5-Methyl-3-[(2R,8R,13R)-2,8,13-trihydroxy-13- [(2R,5R)-5-[(1R)-1- hydroxytridecyl]-2-tetrahydrofuranyl] tridecyl]-5H-furan-2-one
Identifiers
3D model (JSmol)
ChemSpider
  • 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 596.88 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Annonacin is a chemical of the class of acetogenins, found in fruits such as the guanabana (and other from Annonaceae family). It is a member of the class of compounds known as acetogenins. Recent reports have shown that daily consumption in rats caused brain lesions consistent with Parkinson's disease.[1] [2]

Along with other acetogenins, annonacin is reported to block mitochondrial complex I (NADH-dehydrogenase), which is responsible for the conversion of NADH to NAD and the build-up of a proton gradient over the mitochondrial inner membrane. This effectively disables a cell's ability to generate ATP via an oxidative pathway, ultimately forcing a cell into apoptosis or necrosis. [3]

References

  1. ^ Lannuzel, A (6 October 2003). "The mitochondrial complex i inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism". Neuroscience. 121 (2). International Brain Research Organization: 287–296. doi:10.1016/S0306-4522(03)00441-X. PMID 14521988. {{cite journal}}: |access-date= requires |url= (help); Unknown parameter |coauthors= ignored (|author= suggested) (help)
  2. ^ Champy, Pierre; Hoeglinger, Guenter U.; Feger, Jean; Gleye, Christophe; Hocquemiller, Reynald; Laurens, Alain; Guerineau, Vincent; Laprevote, Olivier; Medja, Fadia; Lombes, Anne; Michel, Patrick P.; Lannuzel, Annie; Hirsch, Etienne C.; Ruberg, Merle (2004). "Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: Possible relevance for atypical parkinsonism in Guadeloupe". Journal of Neurochemistry. 88 (1): 63–69. doi:10.1046/j.1471-4159.2003.02138.x. PMID 14675150.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ McLaughlin, J.L. Paw paw and cancer: Annonaceous acetogenins from discovery to commercial products. J. Nat. Prod. 2008, 71, 1311-1321 and references cited


source: https://en.wikipedia.org/w/index.php?diff=399529494&oldid=399527858

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