Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C33H57N3O9 |
Molecular Weight | 639.8204 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](C(C)C)N(C)C(=O)[C@H](OC(=O)[C@H](C(C)C)N(C)C1=O)C(C)C)C(C)C
InChI
InChIKey=MIZMDSVSLSIMSC-VYLWARHZSA-N
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/t22-,23-,24-,25+,26+,27+/m0/s1
Molecular Formula | C33H57N3O9 |
Molecular Weight | 639.8204 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Enniatin B is a cyclic hexadepsipeptide it contains three N-methyl-Lvaline and three a-hydroxy-D-isovaleric molecules. It is generated by multiple Fusarium strains. It has ionophoric, antibiotic and insecticidal activity. A mixture of Enniatins A, A1, B and B1 (called fusafungine) was originally patented as local antibiotic for the topically treatment of nose and throat infections. Enniatin B is a mycotoxin contaminant found in vegetables, cereals and coffee. Enniatin B did not show genotoxic activity but demonstrated cytotoxicity at low micromolar concentrations. The observed activities included the specific inhibition of acyl-CoA cholesterol acyltransferase, depolarization of mitochondria, inhibition of osteoclastic bone resorption, and induction of apoptosis in cancer cells as well as the interaction with ATP-binding cassette transporters such as P-glycoprotein. Enniatin B demonstrated synergistic activity against cervical cancer in vitro and in vivo.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26892719
Curator's Comment: although the brain consists of nearly 60% fat, relatively low levels of the
ENNIATIN B was found in this organ (0.1 mg Enn B/kg)
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: WP400 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25557295 |
|||
Target ID: WP402 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25557295 |
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Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21622627 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Isolation and characterization of new anti-HIV and cytotoxic leads from plants, marine, and microbial organisms. | 1997 May |
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Natural antimycobacterial metabolites: current status. | 2004 Apr |
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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. | 2009 Apr |
|
In vitro phase I metabolism of the depsipeptide enniatin B. | 2011 Jul |
|
In vitro metabolism of the mycotoxin enniatin B in different species and cytochrome p450 enzyme phenotyping by chemical inhibitors. | 2011 Sep |
|
Lysosomes as a possible target of enniatin B-induced toxicity in Caco-2 cells. | 2012 Aug 20 |
|
The naturally born fusariotoxin enniatin B and sorafenib exert synergistic activity against cervical cancer in vitro and in vivo. | 2015 Feb 1 |
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An investigation of the endocrine disrupting potential of enniatin B using in vitro bioassays. | 2015 Mar 4 |
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Mouse tissue distribution and persistence of the food-born fusariotoxins Enniatin B and Beauvericin. | 2016 Apr 15 |
|
Fusarium mycotoxin enniatin B: Cytotoxic effects and changes in gene expression profile. | 2016 Aug |
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Interaction effects of enniatin B, deoxinivalenol and alternariol in Caco-2 cells. | 2016 Jan 22 |
|
Presence of Fusarium Species and Other Toxigenic Fungi in Malting Barley and Multi-Mycotoxin Analysis by Liquid Chromatography-High-Resolution Mass Spectrometry. | 2016 Jun 1 |
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Occurrence of 26 Mycotoxins in the Grain of Cereals Cultivated in Poland. | 2016 May 25 |
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Occurrence of beauvericin and enniatins in wheat flour and corn grits on the Japanese market, and their co-contamination with type B trichothecene mycotoxins. | 2016 Oct |
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Comparative Oral Bioavailability, Toxicokinetics, and Biotransformation of Enniatin B1 and Enniatin B in Broiler Chickens. | 2016 Sep 28 |
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Multi-mycotoxin contamination of couscous semolina commercialized in Morocco. | 2017 Jan 1 |
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Multi-mycotoxin stable isotope dilution LC-MS/MS method for Fusarium toxins in beer. | 2017 Mar 1 |
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Enniatin B and beauvericin are common in Danish cereals and show high hepatotoxicity on a high-content imaging platform. | 2017 May |
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Differences in the arrangement of the Pdr5p multidrug transporter binding pocket of Saccharomyces cerevisiae and Kluyveromyces lactis. | 2017 Nov 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25557295
Mice: 5 mg/kg body weight
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19065580
3 h incubation time revealed low toxicity in hepatoma H4IIE cells for Enniatin B -
EC50-value approximately 10 uM.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:50:28 UTC 2023
by
admin
on
Fri Dec 15 19:50:28 UTC 2023
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Record UNII |
H02S2TZR95
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Record Status |
Validated (UNII)
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Record Version |
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