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2503-13-1,MFCD19442801
Catalog No.:AA002Q5I

2503-13-1 | Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl]

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2.5mg
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  • Technical Information
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Technical Information
Catalog Number:
AA002Q5I
Chemical Name:
Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl]
CAS Number:
2503-13-1
Molecular Formula:
C36H63N3O9
Molecular Weight:
681.9001
MDL Number:
MFCD19442801
SMILES:
CC[C@@H]([C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H]([C@H](CC)C)C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)[C@H](CC)C)C)C(C)C)C
Properties
Computed Properties
 
Complexity:
1000  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
48  
Hydrogen Bond Acceptor Count:
9  
Rotatable Bond Count:
9  
XLogP3:
7.6  

Literature

Title: 'Emerging' mycotoxins in cereals processing chains: changes of enniatins during beer and bread making.

Journal: Food chemistry 20130115

Title: Effect of polyphenols on enniatins-induced cytotoxic effects in mammalian cells.

Journal: Toxicology mechanisms and methods 20121101

Title: Co-exposure of Fusarium mycotoxins: in vitro myelotoxicity assessment on human hematopoietic progenitors.

Journal: Toxicon : official journal of the International Society on Toxinology 20121101

Title: Lysosomes as a possible target of enniatin B-induced toxicity in Caco-2 cells.

Journal: Chemical research in toxicology 20120820

Title: The soluble dietary fiber inulin can influence the bioaccessibility of enniatins.

Journal: Food & function 20120801

Title: Biosynthesis of 15N3-labeled enniatins and beauvericin and their application to stable isotope dilution assays.

Journal: Journal of agricultural and food chemistry 20120725

Title: Enniatin B-induced cell death and inflammatory responses in RAW 267.4 murine macrophages.

Journal: Toxicology and applied pharmacology 20120515

Title: Polymorphism of mycotoxin biosynthetic genes among Fusarium equiseti isolates from Italy and Poland.

Journal: Journal of applied genetics 20120501

Title: Study of the potential toxicity of commercial crispy breads by evaluation of bioaccessibility and bioavailability of minor Fusarium mycotoxins.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120201

Title: Study of the potential toxicity of enniatins A, A(1), B, B(1) by evaluation of duodenal and colonic bioavailability applying an in vitro method by Caco-2 cells.

Journal: Toxicon : official journal of the International Society on Toxinology 20120101

Title: Effects of ¹⁴C-labelled precursor feeding on production of beauvericin, enniatins H, I, and MK1688 by Fusarium oxysporum KFCC11363P.

Journal: Journal of bioscience and bioengineering 20120101

Title: In vitro myelotoxicity assessment of the emerging mycotoxins Beauvericin, Enniatin b and Moniliformin on human hematopoietic progenitors.

Journal: Toxicon : official journal of the International Society on Toxinology 20120101

Title: Evaluation of enniatins A, A1, B, B1 and beauvericin in Portuguese cereal-based foods.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20120101

Title: Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market.

Journal: Journal of agricultural and food chemistry 20111228

Title: Pathogenicity, symptom development, and mycotoxin formation in wheat by Fusarium species frequently isolated from sugar beet.

Journal: Phytopathology 20111101

Title: Characterization and mycotoxigenic potential of Fusarium species in freshly harvested and stored sugar beet in Europe.

Journal: Phytopathology 20111101

Title: Antibacterial effects of enniatins J(1) and J(3) on pathogenic and lactic acid bacteria.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20111001

Title: Antibacterial activity of the enniatin B, produced by Fusarium tricinctum in liquid culture, and cytotoxic effects on Caco-2 cells.

Journal: Toxicology mechanisms and methods 20110901

Title: In vitro metabolism of the mycotoxin enniatin B in different species and cytochrome p450 enzyme phenotyping by chemical inhibitors.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20110901

Title: Stimulation of erythrocyte phospholipid scrambling by enniatin A.

Journal: Molecular nutrition & food research 20110901

Title: Toxigenicity of enniatins from Western Australian Fusarium species to brine shrimp (Artemia franciscana).

Journal: Toxicon : official journal of the International Society on Toxinology 20110401

Title: The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis.

Journal: Toxicology 20100930

Title: Isolation and purification of enniatins A, A(1), B, B(1), produced by Fusarium tricinctum in solid culture, and cytotoxicity effects on Caco-2 cells.

Journal: Toxicon : official journal of the International Society on Toxinology 20100901

Title: Further data on the presence of Fusarium emerging mycotoxins enniatins, fusaproliferin and beauvericin in cereals available on the Spanish markets.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100501

Title: Contamination by moulds of grape berries in Slovakia.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20100501

Title: Beauvericin and enniatins H, I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase.

Journal: The Journal of antibiotics 20091201

Title: Oxidative stress and DNA interactions are not involved in Enniatin- and Beauvericin-mediated apoptosis induction.

Journal: Molecular nutrition & food research 20090901

Title: Interactions between ABC-transport proteins and the secondary Fusarium metabolites enniatin and beauvericin.

Journal: Molecular nutrition & food research 20090701

Title: Structural studies on minor enniatins from Fusarium sp. VI 03441: novel N-methyl-threonine containing enniatins.

Journal: Toxicon : official journal of the International Society on Toxinology 20090601

Title: Quantification of Fusarium poae DNA and associated mycotoxins in asymptomatically contaminated wheat.

Journal: International journal of food microbiology 20090415

Title: The Fusarium toxin enniatin B exerts no genotoxic activity, but pronounced cytotoxicity in vitro.

Journal: Molecular nutrition & food research 20090401

Title: Structural analysis of enniatin H, I, and MK1688 and beauvericin by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and their production by Fusarium oxysporum KFCC 11363P.

Journal: Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment 20090401

Title: Analysis of Fusarium avenaceum metabolites produced during wet apple core rot.

Journal: Journal of agricultural and food chemistry 20090225

Title: Development of a LC-MS/MS method for the analysis of enniatins and beauvericin in whole fresh and ensiled maize.

Journal: Journal of agricultural and food chemistry 20081112

Title: Enniatins produced by Fusarium dimerum, an endophytic fungal strain.

Journal: Die Pharmazie 20080701

Title: Cytotoxicities of enniatins H, I, and MK1688 from Fusarium oxysporum KFCC 11363P.

Journal: Toxicon : official journal of the International Society on Toxinology 20080601

Title: Diversity in Beauvericin and Enniatins H, I, and MK1688 by Fusarium oxysporum isolated from potato.

Journal: International journal of food microbiology 20080320

Title: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review.

Journal: Critical reviews in food science and nutrition 20080101

Title: Fusarium avenaceum -- the North European situation.

Journal: International journal of food microbiology 20071020

Title: Further data on the production of beauvericin, enniatins and fusaproliferin and toxicity to Artemia salina by Fusarium species of Gibberella fujikuroi species complex.

Journal: International journal of food microbiology 20070915

Title: Survey of maize from south-western Nigeria for zearalenone, alpha- and beta-zearalenols, fumonisin B1 and enniatins produced by Fusarium species.

Journal: Food additives and contaminants 20070901

Title: Biosynthesis and biological activity of enniatins.

Journal: Die Pharmazie 20070801

Title: PCR approach based on the esyn1 gene for the detection of potential enniatin-producing Fusarium species.

Journal: International journal of food microbiology 20070530

Title: An integrated sample preparation to determine coccidiostats and emerging Fusarium-mycotoxins in various poultry tissues with LC-MS/MS.

Journal: Molecular nutrition & food research 20070501

Title: Enniatin exerts p53-dependent cytostatic and p53-independent cytotoxic activities against human cancer cells.

Journal: Chemical research in toxicology 20070301

Title: Effects of moniliformin in presence of cyclohexadepsipeptides on isolated mammalian tissue and cells.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20061201

Title: Cytotoxicity of enniatins A, A1, B, B1, B2 and B3 from Fusarium avenaceum.

Journal: Toxicon : official journal of the International Society on Toxinology 20060615

Title: Identification of cytotoxic principles from Fusarium avenaceum using bioassay-guided fractionation.

Journal: Toxicon : official journal of the International Society on Toxinology 20050801

Title: A new function of isonitrile as an inhibitor of the Pdr5p multidrug ABC transporter in Saccharomyces cerevisiae.

Journal: Biochemical and biophysical research communications 20050506

Title: Enniatin has a new function as an inhibitor of Pdr5p, one of the ABC transporters in Saccharomyces cerevisiae.

Journal: Biochemical and biophysical research communications 20050325

Title: Enniatin production by the entomopathogenic fungus Verticillium hemipterigenum BCC 1449.

Journal: The Journal of antibiotics 20041101

Title: Determination of beauvericin and four other enniatins in grain by liquid chromatography-mass spectrometry.

Journal: Journal of chromatography. A 20041001

Title: Investigation of the electrophysiological properties of enniatins.

Journal: Archives of biochemistry and biophysics 20040915

Title: Diversity in metabolite production by Fusarium langsethiae, Fusarium poae, and Fusarium sporotrichioides.

Journal: International journal of food microbiology 20040915

Title: Presence and concentrations of the Fusarium-related mycotoxins beauvericin, enniatins and moniliformin in finnish grain samples.

Journal: Food additives and contaminants 20040801

Title: MS(n) characterization of protonated cyclic peptides and metal complexes.

Journal: Journal of the American Society for Mass Spectrometry 20040701

Title: Actions of the antibiotic mycotoxins beauvericin and enniatin on mammalian tissue.

Journal: Forum of nutrition 20030101

Title: Enniatin synthetase is a monomer with extended structure: evidence for an intramolecular reaction mechanism.

Journal: Archives of microbiology 20021001

Title: Mycotoxin production by Fusarium avenaceum strains isolated from Norwegian grain and the cytotoxicity of rice culture extracts to porcine kidney epithelial cells.

Journal: Journal of agricultural and food chemistry 20020508

Title: JM47, a cyclic tetrapeptide HC-toxin analogue from a marine Fusarium species.

Journal: Phytochemistry 20020501

Title: Directed biosynthesis of new enniatins.

Journal: The Journal of antibiotics 20011001

Title: Tomoda H, et al. Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J Antibiot (Tokyo). 1992 Oct;45(10):1626-32.

Title: Mamur S, et al. Assessment of cytotoxic and genotoxic effects of enniatin-A in vitro. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Aug;35(8):1633-1644.

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Tags:2503-13-1 Molecular Formula|2503-13-1 MDL|2503-13-1 SMILES|2503-13-1 Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-isoleucyl]