bullatacin
 
Notes:
None found
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CAS Number: 123123-32-0Picture of molecule3D/inchi
Other: 121917-13-3
Nikkaji Web: J674.622E
XlogP3-AA: 9.70 (est)
Molecular Weight: 622.92742000
Formula: C37 H66 O7
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Category: natural substances and extractives
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 7.216e-006 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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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
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for bullatacin usage levels up to:
 not for fragrance use.
 
Recommendation for bullatacin flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 11124994
National Institute of Allergy and Infectious Diseases: Data
 (2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
Chemidplus: 0123123320
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References:
 (2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 11124994
Pubchem (cas): 123123-32-0
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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
CHEBI: View
CHEMBL: View
HMDB (The Human Metabolome Database): HMDB31369
FooDB: FDB018176
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
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 annona reticulata
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 annona squamosa
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 rollinia mucosa
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Synonyms:
 annonareticin
(2S)-4-[(2R,13R)-2,13-dihydroxy-13-[(2R,5R)-5-[(2R,5R)-5-[(1S)-1-hydroxyundecyl]oxolan-2-yl]oxolan-2-yl]tridecyl]-2-methyl-2H-furan-5-one
2(5H)-furanone, 3-(2,13-dihydroxy-13-(octahydro-5'-(1-hydroxyundecyl)(2,2'-bifuran)-5-yl)tridecyl)-5-methyl-, (2R-(2alpha(2'R*,5'R*(S*)),5beta(1(S*),2R*,13R*)))-
 rolliniastatin 2
 squamocin G
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Articles:
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: [Structure activity relationship of annonaceous acetogenins against multidrug resistant human lung cancer cell line A549/Taxol in vitro].
PubMed: Reduction of Synthetic Ubiquinone QT Catalyzed by Bovine Mitochondrial Complex I Is Decoupled from Proton Translocation.
PubMed: Acetogenins as Potential Anticancer Agents.
PubMed: Amilorides bind to the quinone binding pocket of bovine mitochondrial complex I.
PubMed: Pinpoint chemical modification of Asp160 in the 49 kDa subunit of bovine mitochondrial complex I via a combination of ligand-directed tosyl chemistry and click chemistry.
PubMed: Site-specific chemical labeling of mitochondrial respiratory complex I through ligand-directed tosylate chemistry.
PubMed: Synthesis and tumor cell growth inhibitory activity of biotinylated annonaceous acetogenins.
PubMed: Antitumor activity and toxicity relationship of annonaceous acetogenins.
PubMed: Anti-tumor activity of Annona squamosa seeds extract containing annonaceous acetogenin compounds.
PubMed: Determination of bullatacin in rat plasma by liquid chromatography-mass spectrometry.
PubMed: Forskolin and derivatives as tools for studying the role of cAMP.
PubMed: Cytotoxic bistetrahydrofuran annonaceous acetogenins from the seeds of Annona squamosa.
PubMed: Bis-THF motif of acetogenin binds to the third matrix-side loop of ND1 subunit in mitochondrial NADH-ubiquinone oxidoreductase.
PubMed: In vitro trematocidal effects of crude alcoholic extracts of Artemisia annua, A. absinthium, Asimina triloba, and Fumaria officinalis: trematocidal plant alcoholic extracts.
PubMed: The membrane subunit NuoL(ND5) is involved in the indirect proton pumping mechanism of Escherichia coli complex I.
PubMed: Susceptibility of complete bacteria and spheroplasts of Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi to rolliniastatin-2.
PubMed: Exploring the binding site of delta(lac)-acetogenin in bovine heart mitochondrial NADH-ubiquinone oxidoreductase.
PubMed: The ND2 subunit is labeled by a photoaffinity analogue of asimicin, a potent complex I inhibitor.
PubMed: Identification of annonaceous acetogenins in the ripe fruit of the North American pawpaw ( Asimina triloba ).
PubMed: Bullatacin triggered ABCB1-overexpressing cell apoptosis via the mitochondrial-dependent pathway.
PubMed: Differential effects of mitochondrial Complex I inhibitors on production of reactive oxygen species.
PubMed: Two new adjacent bis-tetrahydrofuran annonaceous acetogenins from seeds of Annona cornifolia.
PubMed: Alteration of the bis-tetrahydrofuran core stereochemistries in asimicin can affect the cytotoxicity.
PubMed: Synthesis, determination of the absolute configuration of tonkinelin, and inhibitory action with bovine heart mitochondrial complex I.
PubMed: Advances in Lewis acid controlled carbon-carbon bond-forming reactions enable a concise and convergent total synthesis of bullatacin.
PubMed: An outside-in approach to adjacent bistetrahydrofuran annonaceous acetogenins with C2 core symmetry. Total synthesis of asimicin and a C32 analogue.
PubMed: Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I.
PubMed: Synthesis of (+)-bullatacin via the highly diastereoselective [3+2] annulation reaction of a racemic aldehyde and a nonracemic allylsilane.
PubMed: Total synthesis of asimicin via highly stereoselective [3 + 2] annulation reactions of substituted allylsilanes.
PubMed: Stereoselective syntheses of rolliniastatin 1, rollimembrin, and membranacin.
PubMed: Synthesis and inhibition mechanism of Delta lac-acetogenins, a novel type of inhibitor of bovine heart mitochondrial complex I.
PubMed: Synthesis and inhibitory action of novel acetogenin mimics with bovine heart mitochondrial complex I.
PubMed: In vitro antitumor SAR of threo/cis/threo/cis/erythro bis-THF acetogenins: correlations with their inhibition of mitochondrial Complex I.
PubMed: New adjacent Bis-tetrahydrofuran Annonaceous acetogenins from Annona muricata.
PubMed: A modular synthesis of annonaceous acetogenins.
PubMed: [Inhibition of oxygen consumption by annonaceous acetogenins in liver cell respiration and their structure-activity relationship].
PubMed: Selective action of acetogenin mitochondrial complex I inhibitors.
PubMed: Bullatacin, a potent antitumor Annonaceous acetogenin, induces apoptosis through a reduction of intracellular cAMP and cGMP levels in human hepatoma 2.2.15 cells.
PubMed: [Antitumor effect of anuoning].
PubMed: [Classification and NMR characteristics of the gamma-lactone and THF rings of antitumor bioactive Annonaceous acetogenins].
PubMed: Mimicry of annonaceous acetogenins: enantioselective synthesis of a (4R)-hydroxy analogue having potent antitumor activity.
PubMed: Bullatacin, a potent antitumor annonaceous acetogenin, inhibits proliferation of human hepatocarcinoma cell line 2.2.15 by apoptosis induction.
PubMed: Gamma-lactone-Functionalized antitumoral acetogenins are the most potent inhibitors of mitochondrial complex I.
PubMed: Definition of crucial structural factors of acetogenins, potent inhibitors of mitochondrial complex I.
PubMed: Total synthesis of asimicin and bullatacin.
PubMed: Circumvention of tumor multidrug resistance by a new annonaceous acetogenin: atemoyacin-B.
PubMed: Design syntheses and mitochondrial complex I inhibitory activity of novel acetogenin mimics.
PubMed: New annonaceous acetogenins from Rollinia mucosa.
PubMed: Tryptamine derived amides and acetogenins from the seeds of Rollinia mucosa.
PubMed: Kinetic characterization of mitochondrial complex I inhibitors using annonaceous acetogenins.
PubMed: Inhibition of mitochondrial oxidative phosphorylation induces hyper-expression of glutamic acid decarboxylase in pancreatic islet cells.
PubMed: NADH-quinone oxidoreductase: PSST subunit couples electron transfer from iron-sulfur cluster N2 to quinone.
PubMed: Biochemical features of mtDNA 14484 (ND6/M64V) point mutation associated with Leber's hereditary optic neuropathy.
PubMed: Three classes of inhibitors share a common binding domain in mitochondrial complex I (NADH:ubiquinone oxidoreductase).
PubMed: Annonaceous acetogenins as natural pesticides: potent toxicity against insecticide-susceptible and -resistant German cockroaches (Dictyoptera: Blattellidae).
PubMed: Purpurediolin and purpurenin, two new cytotoxic adjacent bis-tetrahydrofuran annonaceous acetogenins from the seeds of Annona purpurea.
PubMed: Acetogenins from seeds of Annona reticulata.
PubMed: Membrane conformations and their relation to cytotoxicity of asimicin and its analogues.
PubMed: Cherimolin-1, new selective inhibitor of the first energy-coupling site of the NADH: ubiquinone oxidoreductase (complex I).
PubMed: Regulation of ornithine decarboxylase induction by deguelin, a natural product cancer chemopreventive agent.
PubMed: Structure-activity relationships of diverse Annonaceous acetogenins against multidrug resistant human mammary adenocarcinoma (MCF-7/Adr) cells.
PubMed: Leber's hereditary optic neuropathy: biochemical effect of 11778/ND4 and 3460/ND1 mutations and correlation with the mitochondrial genotype.
PubMed: The Annonaceous acetogenin bullatacin is cytotoxic against multidrug-resistant human mammary adenocarcinoma cells.
PubMed: Measurement of the membrane potential generated by complex I in submitochondrial particles.
PubMed: Genetic evidence for the existence of two quinone related inhibitor binding sites in NADH-CoQ reductase.
PubMed: Longimicins A-D: novel bioactive acetogenins from Asimina longifolia (annonaceae) and structure-activity relationships of asimicin type of annonaceous acetogenins.
PubMed: Squamotacin: an annonaceous acetogenin with cytotoxic selectivity for the human prostate tumor cell line (PC-3).
PubMed: SARs of annonaceous acetogenins in rat liver mitochondria.
PubMed: The absolute configuration of adjacent bis-THF acetogenins and asiminocin, a novel highly potent asimicin isomer from Asimina triloba.
PubMed: Mode of action of bullatacin, a potent antitumor acetogenin: inhibition of NADH oxidase activity of HeLa and HL-60, but not liver, plasma membranes.
PubMed: Natural substances (acetogenins) from the family Annonaceae are powerful inhibitors of mitochondrial NADH dehydrogenase (Complex I).
PubMed: Asimin, asiminacin, and asiminecin: novel highly cytotoxic asimicin isomers from Asimina triloba.
PubMed: Bullatacin--in vivo and in vitro experience in an ovarian cancer model.
PubMed: Mode of action of bullatacin: a potent antitumor and pesticidal annonaceous acetogenin.
PubMed: Additional bioactive compounds and trilobacin, a novel highly cytotoxic acetogenin, from the bark of Asimina triloba.
PubMed: Bullatacin, bullatacinone, and squamone, a new bioactive acetogenin, from the bark of Annona squamosa.
PubMed: Bullatacin and bullatacinone: two highly potent bioactive acetogenins from Annona bullata.
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