Record Information |
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Version | 2.0 |
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Creation Date | 2010-05-18 15:40:49 UTC |
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Update Date | 2014-12-24 20:26:30 UTC |
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Accession Number | T3D3758 |
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Identification |
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Common Name | Enniatin B |
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Class | Small Molecule |
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Description | Enniatins are mycotoxins that appear in nature as a mixture of cyclohexadepsipeptides produced by bacteria, fungi, and plants. They may be found in contaminated cereal crops. Enniatins have various biological activities and can act as enzyme inhibitors, antifungal and antibacterial agents, and immunomodulatory substances. (5, 1) |
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Compound Type | - Amide
- Amine
- Ester
- Ether
- Fungal Toxin
- Mycotoxin
- Natural Compound
- Organic Compound
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Chemical Structure | |
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Synonyms | Synonym | 2,8,14-Triaza-3,6,9,12,15,18-hexakis(methylethyl)-2,8,14-trimethyl-5,11,17-trioxacyclooctadecane-1,4,7,10,13,16-hexaone | 3-N-Methylvaline Enniatin | Enniatin b | Enniatins |
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Chemical Formula | C33H57N3O9 |
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Average Molecular Mass | 639.820 g/mol |
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Monoisotopic Mass | 639.409 g/mol |
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CAS Registry Number | 917-13-5 |
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IUPAC Name | 4,10,16-trimethyl-3,6,9,12,15,18-hexakis(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone |
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Traditional Name | fusafungine |
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SMILES | CC(C)C1OC(=O)C(C(C)C)N(C)C(=O)C(OC(=O)C(C(C)C)N(C)C(=O)C(OC(=O)C(C(C)C)N(C)C1=O)C(C)C)C(C)C |
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InChI Identifier | InChI=1S/C33H57N3O9/c1-16(2)22-31(40)43-26(20(9)10)29(38)35(14)24(18(5)6)33(42)45-27(21(11)12)30(39)36(15)23(17(3)4)32(41)44-25(19(7)8)28(37)34(22)13/h16-27H,1-15H3 |
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InChI Key | InChIKey=MIZMDSVSLSIMSC-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Peptidomimetics |
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Sub Class | Depsipeptides |
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Direct Parent | Cyclic depsipeptides |
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Alternative Parents | |
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Substituents | - Cyclic depsipeptide
- Macrolide lactam
- Alpha-amino acid ester
- Macrolactam
- Macrolide
- Alpha-amino acid or derivatives
- Tricarboxylic acid or derivatives
- Tertiary carboxylic acid amide
- Carboxamide group
- Carboxylic acid ester
- Lactam
- Lactone
- Oxacycle
- Carboxylic acid derivative
- Azacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organopnictogen compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-1030029000-106e7d43c382adbece27 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-4923100000-660bec1d14b8f3f7ee31 | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-2491100000-57cc06bc77b70d22027f | 2016-08-01 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00dl-9280500000-332df5d22ac9c4cfcad2 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-06xt-2922300000-bc0b4e1a7a78fa042d04 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0bu9-8932000000-707730a002d53f2b3633 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0000009000-87f3427feabfc67ea2a4 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-0000019000-d87dc9b02063da804845 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dm-5000029000-88278f6b046e6b1282f4 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0000009000-9e42696aa63d5668e160 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0000019000-fe6ac382db41ff20d855 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0000090000-6576404a373fee00413e | 2021-10-12 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (4) |
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Mechanism of Toxicity | Enniatins are toxic due to their ability to act as ionophores, changing ion transport across membranes and disrupting the ionic selectivity of cell walls. In the membrane, enniatins form a dimeric structure and are able to transport monovalent ions (especially K+, Mg2+,Ca2+ and Na+) across the membranes. This effect is particularly harmful in mitochondrial membranes, resulting in the uncoupling of oxidative phosphorylation. They are also know to inhibit several enzymes, including acyl coenzyme A:cholesterol acyltransferase and cyclic nucleotide phosphodiesterase. Enniatins are cytotoxic and can cause DNA fragmentation, induce apoptosis, and disrupt the ERK signalling pathway. They can also inhibit the activity of membrane-located ATP-binding cassette (ABC) transporters, multidrug pumps which affect the bioavailability of xenobiotics and pharmaceuticals. (1, 2, 3) |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Enniatins are mycotoxins that appear in nature as a mixture of cyclohexadepsipeptides produced by bacteria, fungi, and plants. They may be found in contaminated cereal crops. (5, 1) |
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Minimum Risk Level | Not Available |
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Health Effects | Enniatins are cytotoxic. They may also act as antifungal and antibacterial agents, and immunomodulatory substances. (1) |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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PubChem Compound ID | 164754 |
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ChEMBL ID | Not Available |
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ChemSpider ID | Not Available |
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KEGG ID | Not Available |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | Not Available |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Enniatin |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D3758.pdf |
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General References | - Hyun U, Lee DH, Lee C, Shin CG: Apoptosis induced by enniatins H and MK1688 isolated from Fusarium oxysporum FB1501. Toxicon. 2009 Jun;53(7-8):723-8. doi: 10.1016/j.toxicon.2009.02.012. Epub 2009 Feb 25. [19248798 ]
- Watjen W, Debbab A, Hohlfeld A, Chovolou Y, Kampkotter A, Edrada RA, Ebel R, Hakiki A, Mosaddak M, Totzke F, Kubbutat MH, Proksch P: Enniatins A1, B and B1 from an endophytic strain of Fusarium tricinctum induce apoptotic cell death in H4IIE hepatoma cells accompanied by inhibition of ERK phosphorylation. Mol Nutr Food Res. 2009 Apr;53(4):431-40. doi: 10.1002/mnfr.200700428. [19065580 ]
- Dornetshuber R, Heffeter P, Sulyok M, Schumacher R, Chiba P, Kopp S, Koellensperger G, Micksche M, Lemmens-Gruber R, Berger W: Interactions between ABC-transport proteins and the secondary Fusarium metabolites enniatin and beauvericin. Mol Nutr Food Res. 2009 Jul;53(7):904-20. doi: 10.1002/mnfr.200800384. [19517454 ]
- Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
- Wikipedia. Enniatin. Last updated 10 May 2010. [Link]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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