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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
Structure of ENNIATIN B

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

HIDE SMILES / InChI

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

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)

Originator

Sources: DOI: 10.1002/hlca.19480310248
Curator's Comment: Gäumann, E. et al. DOI: 10.1007/BF02163993 natural Enniatin (A&B) Shemyakin, M.M. et al. DOI: 10.1016/S0040-4039(01)90736-1 synthesis of enniatin B

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Isolation and characterization of new anti-HIV and cytotoxic leads from plants, marine, and microbial organisms.
1997 May
Natural antimycobacterial metabolites: current status.
2004 Apr
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
An investigation of the endocrine disrupting potential of enniatin B using in vitro bioassays.
2015 Mar 4
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
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
Occurrence of 26 Mycotoxins in the Grain of Cereals Cultivated in Poland.
2016 May 25
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
Comparative Oral Bioavailability, Toxicokinetics, and Biotransformation of Enniatin B1 and Enniatin B in Broiler Chickens.
2016 Sep 28
Multi-mycotoxin contamination of couscous semolina commercialized in Morocco.
2017 Jan 1
Multi-mycotoxin stable isotope dilution LC-MS/MS method for Fusarium toxins in beer.
2017 Mar 1
Enniatin B and beauvericin are common in Danish cereals and show high hepatotoxicity on a high-content imaging platform.
2017 May
Differences in the arrangement of the Pdr5p multidrug transporter binding pocket of Saccharomyces cerevisiae and Kluyveromyces lactis.
2017 Nov 1
Patents

Sample Use Guides

Mice: 5 mg/kg body weight
Route of Administration: Intraperitoneal
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 Fri Dec 15 19:50:28 UTC 2023
Edited
by admin
on Fri Dec 15 19:50:28 UTC 2023
Record UNII
H02S2TZR95
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ENNIATIN B
MI  
Common Name English
ENNIATIN B [MI]
Common Name English
CYCLO((2R)-2-HYDROXY-3-METHYLBUTANOYL-N-METHYL-L-VALYL-(2R)-2-HYDROXY-3-METHYLBUTANOYL-N-METHYL-L-VALYL-(2R)-2-HYDROXY-3-METHYLBUTANOYL-N-METHYL-L-VALYL)
Common Name English
Code System Code Type Description
CAS
917-13-5
Created by admin on Fri Dec 15 19:50:28 UTC 2023 , Edited by admin on Fri Dec 15 19:50:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID30891862
Created by admin on Fri Dec 15 19:50:28 UTC 2023 , Edited by admin on Fri Dec 15 19:50:28 UTC 2023
PRIMARY
FDA UNII
H02S2TZR95
Created by admin on Fri Dec 15 19:50:28 UTC 2023 , Edited by admin on Fri Dec 15 19:50:28 UTC 2023
PRIMARY
MESH
C100264
Created by admin on Fri Dec 15 19:50:28 UTC 2023 , Edited by admin on Fri Dec 15 19:50:28 UTC 2023
PRIMARY
PUBCHEM
164754
Created by admin on Fri Dec 15 19:50:28 UTC 2023 , Edited by admin on Fri Dec 15 19:50:28 UTC 2023
PRIMARY
MERCK INDEX
m4909
Created by admin on Fri Dec 15 19:50:28 UTC 2023 , Edited by admin on Fri Dec 15 19:50:28 UTC 2023
PRIMARY Merck Index