ENNIATIN A

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C36H63N3O9
Molecular Weight	681.9001
Optical Activity	UNSPECIFIED
Defined Stereocenters	9 / 9
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1([C@@H](C)CC)N(C)C(=O)[C@H](OC(=O)[C@]([H])([C@@H](C)CC)N(C)C(=O)[C@H](OC(=O)[C@]([H])([C@@H](C)CC)N(C)C(=O)[C@H](OC1=O)C(C)C)C(C)C)C(C)C

InChI

InChIKey=TWHBYJSVDCWICV-BHZTXFQCSA-N

InChI=1S/C36H63N3O9/c1-16-22(10)25-34(43)46-29(20(6)7)32(41)38(14)27(24(12)18-3)36(45)48-30(21(8)9)33(42)39(15)26(23(11)17-2)35(44)47-28(19(4)5)31(40)37(25)13/h19-30H,16-18H2,1-15H3/t22-,23-,24-,25-,26-,27-,28+,29+,30+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C36H63N3O9
Molecular Weight	681.9001
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	9 / 9
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22990381

Enniatin A was reported from the fungus Fusarium orthoceras var. enniatinum by Gaumann et al. in 1947, and was shown to be active against several mycobacteria in vitro. In 1974, Audhya and Russel identified that previously reported enniatin A was actually a mixture of threo and erythro optical isomers. At that time, only enniatin B had been observed pure from a natural source. Enniatin A is one of four major analogs in the enniatin complex. It has been shown to moderately inhibit acyl-CoA: cholesterol acyltransferase activity in rat liver microtomes with an IC50 value of 22 µM.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Acetyl-CoA acetyltransferase, mitochondrial 1 Target ID: P17764 Gene ID: 25014.0 Gene Symbol: Acat1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1473990	Inhibitor 8297		22.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics.	1992 Oct	1473990
Revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities.	2012 Nov	22990381

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

There was investigated the in vitro effects of enniatins (ENs) A, A1, B and B1, alone and in combinations, on Caco-2 cells viability by MTT assay after 24h of exposure. Cells were treated with concentrations ranging from 0.9 to 15.0 μM, individually and in combination of two, three and four mycotoxins. IC50 values obtained for all individually tested mycotoxins ranged from 1.3 to >15 μM. In ENs combination tests, synergistic effect in Caco-2 viability are observed for EN B+EN A1, EN B1+EN A1 and EN A+EN A1+EN B (CI=0.33-0.52).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:58:06 GMT 2023` Edited by `admin` on `Fri Dec 15 17:58:06 GMT 2023`
Record UNII	59877B2B5T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ENNIATIN A

Common Name

English

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)

Common Name

English

ENNIATIN A [MI]

Common Name

English

ISOLEUCINE, N-(D-2-HYDROXY-3-METHYLBUTYRYL)-N-METHYL-, TRIMOL. CYCLIC ESTER

Common Name

English

Code System Code Type Description

CHEBI

64651