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annonacin

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CAS Number: 111035-65-5Picture of molecule3D/inchi
FDA UNII: 40372ET6TM
Nikkaji Web:J246.239G
XlogP3-AA:8.40 (est)
Molecular Weight:596.88948000
Formula:C35 H64 O7
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 7.712e-005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Annonacin >97%
Odor: characteristic
Use: Annonacin is a natural lipophilic mitochondrial complex I inhibitor found in the herbs of Annona glabra. Annonacin has cytotoxicity and may have anti-cancer activity. anti-cancer
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for annonacin usage levels up to:
 not for fragrance use.
 
Recommendation for annonacin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :354398
National Institute of Allergy and Infectious Diseases:Data
(2S)-2-methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
Chemidplus:0111035655
 
References:
 (2S)-2-methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):354398
Pubchem (cas):111035-65-5
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
KEGG (GenomeNet):C20213
HMDB (The Human Metabolome Database):Search
FooDB:FDB011354
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 guanabana fruit
Search Trop Picture
 
Synonyms:
(2S)-2-methyl-4-[(2R,8R,13R)-2,8,13-trihydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-one
 

Articles:

PubMed:Annonacin Exerts Antitumor Activity through Induction of Apoptosis and Extracellular Signal-regulated Kinase Inhibition.
PubMed:Characterization of interactions of eggPC lipid structures with different biomolecules.
PubMed:Acetogenins and alkaloids during the initial development of Annona muricata L. (Annonaceae).
PubMed:Annona muricata leaves extracts prevent DMBA/TPA-induced skin tumorigenesis via modulating antioxidants enzymes system in ICR mice.
PubMed:Structural Characterisation of Acetogenins from Annona muricata by Supercritical Fluid Chromatography Coupled to High-Resolution Tandem Mass Spectrometry.
PubMed:The Value of Caspase-3 after the Application ofAnnona muricataLeaf Extract in COLO-205 Colorectal Cancer Cell Line.
PubMed:The fruit of Annona squamosa L. as a source of environmental neurotoxins: From quantification of squamocin to annotation of Annonaceous acetogenins by LC-MS/MS analysis.
PubMed:PERK activation mitigates tau pathologyin vitroandin vivo.
PubMed:Chronic consumption of Annona muricata juice triggers and aggravates cerebral tau phosphorylation in wild-type and MAPT transgenic mice.
PubMed:Validation data for the quantification of the Annonaceous acetogenin annonacin in Rat brain by UPLC-MS/MS.
PubMed:Quantification of the environmental neurotoxin annonacin in Rat brain by UPLC-MS/MS.
PubMed:Method development for quantification of the environmental neurotoxin annonacin in Rat plasma by UPLC-MS/MS and application to a pharmacokinetic study.
PubMed:Acetogenins as Potential Anticancer Agents.
PubMed:Determination of Neurotoxic Acetogenins in Pawpaw (Asimina triloba) Fruit by LC-HRMS.
PubMed:Mitochondrial complex 1 inhibition increases 4-repeat isoform tau by SRSF2 upregulation.
PubMed:Styryllactones and acetogenins from the fruits of Goniothalamus macrocalyx.
PubMed:Annonacin, a natural lipophilic mitochondrial complex I inhibitor, increases phosphorylation of tau in the brain of FTDP-17 transgenic mice.
PubMed:Natural toxins implicated in the development of Parkinson's disease.
PubMed:Annonacin in Asimina triloba fruit: implication for neurotoxicity.
PubMed:Annonacin induces cell cycle-dependent growth arrest and apoptosis in estrogen receptor-α-related pathways in MCF-7 cells.
PubMed:Cytotoxic activity of acetogenins and styryl lactones isolated from Goniothalamus undulatus Ridl. root extracts against a lung cancer cell line (COR-L23).
PubMed:Synthesis of annonacin isolated from Annona densicoma.
PubMed:The alternative medicine pawpaw and its acetogenin constituents suppress tumor angiogenesis via the HIF-1/VEGF pathway.
PubMed:Complex I: inhibitors, inhibition and neurodegeneration.
PubMed:Natural lipophilic inhibitors of mitochondrial complex I are candidate toxins for sporadic neurodegenerative tau pathologies.
PubMed:Tucupentol, a novel mono-tetrahydrofuranic acetogenin from Annona montana, as a potent inhibitor of mitochondrial complex I.
PubMed:Atypical parkinsonism in the Caribbean island of Guadeloupe: etiological role of the mitochondrial complex I inhibitor annonacin.
PubMed:Annonacin, a natural mitochondrial complex I inhibitor, causes tau pathology in cultured neurons.
PubMed:Atypical parkinsonism in Guadeloupe: a common risk factor for two closely related phenotypes?
PubMed:Is atypical parkinsonism in the Caribbean caused by the consumption of Annonacae?
PubMed:Acetogenins in Annona muricata L. (annonaceae) leaves are potent molluscicides.
PubMed:Quantification of acetogenins in Annona muricata linked to atypical parkinsonism in guadeloupe.
PubMed:Montacin and cis-montacin, two new cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona montana.
PubMed:In vitro antitumor structure-activity relationships of threo/trans/threo mono-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I.
PubMed:Annonacin, a lipophilic inhibitor of mitochondrial complex I, induces nigral and striatal neurodegeneration in rats: possible relevance for atypical parkinsonism in Guadeloupe.
PubMed:Inhibitory effects on mitochondrial complex I of semisynthetic mono-tetrahydrofuran acetogenin derivatives.
PubMed:The mitochondrial complex I inhibitor annonacin is toxic to mesencephalic dopaminergic neurons by impairment of energy metabolism.
PubMed:Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway.
PubMed:Selective action of acetogenin mitochondrial complex I inhibitors.
PubMed:[Classification and NMR characteristics of the gamma-lactone and THF rings of antitumor bioactive Annonaceous acetogenins].
PubMed:New cytotoxic monotetrahydrofuran annonaceous acetogenins from Annona muricata.
PubMed:Cytotoxic compounds from Annonaceus species as DNA topoisomerase I poisons.
PubMed:Annonaceous acetogenins from the leaves of Annona montana.
PubMed:Cytotoxic mono-tetrahydrofuran ring acetogenins from leaves of Annona montana.
PubMed:Murihexol, a linear acetogenin from Annona muricata.
PubMed:Annomocherin, annonacin and annomontacin: a novel and two known bioactive mono-tetrahydrofuran annonaceous acetogenins from Annona cherimolia seeds.
PubMed:Enantioselective syntheses of monotetrahydrofuran Annonaceous acetogenins tonkinecin and annonacin starting from carbohydrates.
PubMed:Three novel monotetrahydrofuran annonaceous acetogenins from Annona montana.
PubMed:Insecticidal and mutagenic evaluation of two annonaceous acetogenins.
PubMed:The first total synthesis of annonacin, the most typical monotetrahydrofuran annonaceous acetogenins.
PubMed:Cytotoxicity and antileishmanial activity of Annona muricata pericarp.
PubMed:cis-Annonacin and (2,4)-cis-and trans-isoannonacins: cytotoxic monotetrahydrofuran annonaceous acetogenins from the seeds of Annona cherimolia.
PubMed:Asitrilobins A and B: cytotoxic mono-THF annonaceous acetogenins from the seeds of Asimina triloba.
PubMed:A new bistetrahydrofuran acetogenin from the roots of Annona salzmanii.
PubMed:The localisations in liposomal membranes of the tetrahydrofuran ring moieties of the annonaceous acetogenins, annonacin and sylvaticin, as determined by 1H NMR spectroscopy.
PubMed:Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea.
PubMed:In vitro antitumor activities of new synthetic bistetrahydrofuran derivatives as analogs of Annonaceous acetogenins.
PubMed:[Studies on the chemical constituents of Annona muricata].
PubMed:Three new adjacent bis-tetrahydrofuran acetogenins with four hydroxyl groups from Asimina triloba.
PubMed:Five novel mono-tetrahydrofuran ring acetogenins from the seeds of Annona muricata.
PubMed:Determination of structure-activity relationships of Annonaceous acetogenins by inhibition of oxygen uptake in rat liver mitochondria.
PubMed:Additional bioactive acetogenins, annomutacin and (2,4-trans and cis)-10R-annonacin-A-ones, from the leaves of Annona muricata.
PubMed:Longicin and goniothalamicinone: novel bioactive monotetrahydrofuran acetogenins from Asimina longifolia.
PubMed:Muricatocins A and B, two new bioactive monotetrahydrofuran Annonaceous acetogenins from the leaves of Annona muricata.
PubMed:Two new cytotoxic monotetrahydrofuran Annonaceous acetogenins, annomuricins A and B, from the leaves of Annona muricata.
PubMed:Bioactive annonaceous acetogenins from the bark of Xylopia aromatica.
PubMed:Biologically active acetogenins from stem bark of Asimina triloba.
PubMed:[Annomonysvin: a new cytotoxic gamma-lactone-monotetrahydrofuranyl acetogenin from Annona montana].
PubMed:[Annonacins and Annonastatin from Annona squamosa].
PubMed:Goniothalamicin and annonacin: bioactive acetogenins from Goniothalamus giganteus (Annonaceae).
PubMed:Annonacin, a novel, biologically active polyketide from Annona densicoma.
 
Notes:
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