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111035-65-5,MFCD27664980
Catalog No.:AA008Y71

111035-65-5 | Annonacin

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  • Technical Information
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Technical Information
Catalog Number:
AA008Y71
Chemical Name:
Annonacin
CAS Number:
111035-65-5
Molecular Formula:
C35H64O7
Molecular Weight:
596.8785
MDL Number:
MFCD27664980
SMILES:
CCCCCCCCCCCC[C@H]([C@H]1CC[C@@H](O1)[C@@H](CCCC[C@@H](CCCCC[C@H](CC1=C[C@@H](OC1=O)C)O)O)O)O
NSC Number:
606194
Properties
Computed Properties
 
Complexity:
726  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Heavy Atom Count:
42  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
26  
XLogP3:
8.4  

Literature

Title: Chronic consumption of Annona muricata juice triggers and aggravates cerebral tau phosphorylation in wild-type and MAPT transgenic mice.

Journal: Journal of neurochemistry 20161101

Title: Annonacin, a natural lipophilic mitochondrial complex I inhibitor, increases phosphorylation of tau in the brain of FTDP-17 transgenic mice.

Journal: Experimental neurology 20140301

Title: Mitochondrial complex 1 inhibition increases 4-repeat isoform tau by SRSF2 upregulation.

Journal: PloS one 20140101

Title: Annonacin in Asimina triloba fruit: implication for neurotoxicity.

Journal: Neurotoxicology 20120101

Title: Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells.

Journal: Journal of ethnopharmacology 20111011

Title: Complex I: inhibitors, inhibition and neurodegeneration.

Journal: Experimental neurology 20100801

Title: The alternative medicine pawpaw and its acetogenin constituents suppress tumor angiogenesis via the HIF-1/VEGF pathway.

Journal: Journal of natural products 20100528

Title: Synthesis of annonacin isolated from Annona densicoma.

Journal: Bioscience, biotechnology, and biochemistry 20100101

Title: Atypical parkinsonism in the Caribbean island of Guadeloupe: etiological role of the mitochondrial complex I inhibitor annonacin.

Journal: Movement disorders : official journal of the Movement Disorder Society 20081115

Title: Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20070718

Title: Is atypical parkinsonism in the Caribbean caused by the consumption of Annonacae?

Journal: Journal of neural transmission. Supplementum 20060101

Title: Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: possible relevance for atypical parkinsonism in Guadeloupe.

Journal: Journal of neurochemistry 20040101

Title: Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway.

Journal: Life sciences 20030509

Title: The mitochondrial complex I inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism.

Journal: Neuroscience 20030101

Title: In vitro antitumor structure-activity relationships of threo/trans/threo mono-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I.

Journal: Oncology research 20030101

Title: Annonaceous acetogenins from the leaves of Annona montana.

Journal: Bioorganic & medicinal chemistry 20020301

Title: Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds.

Journal: Archives of pharmacal research 20010801

Title: Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates.

Journal: The Journal of organic chemistry 20010209

Title: Yiallouris A, et al. Annonacin promotes selective cancer cell death via NKA-dependent and SERCA-dependent pathways. Cell Death Dis. 2018 Jul 9;9(7):764.

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