ChemicalBook > CAS DataBase List > enniatin A

enniatin A

Product Name
enniatin A
CAS No.
2503-13-1
Chemical Name
enniatin A
Synonyms
enniatin A;Lateritin I;N-Methylcyclo(L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-);(3S,6R,9S,12R,15S,18R)-3,9,15-tris[(2S)-butan-2-yl]-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone;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]
CBNumber
CB02079105
Molecular Formula
C36H63N3O9
Formula Weight
681.906
MOL File
2503-13-1.mol
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enniatin A Property

Melting point:
122-124 °C
Boiling point:
847.4±65.0 °C(Predicted)
Density 
1.022±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO: soluble10mg/mL
form 
White to off-white crystalline solid.
pka
-0.96±0.70(Predicted)
biological source
Gnomonia errabunda
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Safety

Hazard Codes 
T
Risk Statements 
23/24/25
Safety Statements 
45
RIDADR 
2811
WGK Germany 
3
HazardClass 
6.1(a)
PackingGroup 
I
HS Code 
2934999090
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
E9661
Product name
Enniatin A
Purity
from Gnomonia errabunda, ≥95% (HPLC)
Packaging
1mg
Price
$225
Updated
2025/07/31
Cayman Chemical
Product number
17456
Product name
Enniatin A
Purity
≥99%
Packaging
500μg
Price
$193
Updated
2024/03/01
Cayman Chemical
Product number
17456
Product name
Enniatin A
Purity
≥99%
Packaging
2.5mg
Price
$816
Updated
2024/03/01
Usbiological
Product number
E3222-26
Product name
Enniatin A
Packaging
500ug
Price
$426
Updated
2021/12/16
TRC
Product number
E555990
Product name
EnnlatinA
Packaging
25mg
Price
$11815
Updated
2021/12/16
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enniatin A Chemical Properties,Usage,Production

Description

Enniatins are cyclohexadepsipeptides commonly isolated from fungi that are known to have antibiotic properties and to induce apoptosis in several cancer lines. Many function as ionophores, forming pores in cellular membranes to allow selective ion transport. Enniatin A is one of four major analogs in the enniatin complex . It has been shown to moderately inhibit acyl-CoA:cholesterol acyltranferase activity in rat liver microsomes with an IC50 value of 22 μM. Enniatin A also demonstrates anthelmintic properties against N. brasiliensis, T. spiralis, and H. spumosa.

Uses

Enniatins are a family of depsipeptide ionophores, produced by several Fusarium species. More recently, the effects of the enniatins on acyl-CoA cholesterol transferase, transporters and the selectivity of their antitumour action have received more focus. Enniatin A is one of four major analogues of the enniatin complex and has not previously been available for investigation.

Uses

Enniatins are a family of depsipeptide ionophores, produced by several Fusarium species. Recently, the effects of the enniatins on acyl-CoA cholesterol transferase, transporters and the selectivity of their antitumor action have received more focus. Enniatin A is one of four major analogues of the enniatin complex.

Uses

Enniatins are cyclohexadepsipeptides commonly isolated from fungi that are known to have antibiotic properties and to induce apoptosis in several cancer lines. Many function as ionophores, forming pores in cellular membranes to allow selective ion transport. Enniatin A is one of four major analogs in the enniatin complex . It has been shown to moderately inhibit acyl-CoA:cholesterol acyltranferase activity in rat liver microsomes with an IC50 value of 22 μM. Enniatin A also demonstrates anthelmintic properties against N. brasiliensis, T. spiralis, and H. spumosa.[Cayman Chemical]

Definition

ChEBI: An enniatin obtained from formal cyclocondensation of three N-[(2R)-2-hydroxy-3-methylbutanoyl]-N-methyl-L-isoleucine units.

Biochem/physiol Actions

Enniatins are a group of cyclohexadepsipeptide mycotoxins produced by Gnomonia errabuda and several Fusaria species, with phytotoxic, antibiotic, and insecticidal activities. Enniatins function as ionophors by their incorporation into the cellular membrane to form dimeric structures that transport monovalent ions across the membrane (especially the mitochondrial membranes) affecting oxidative phosphorylation uncoupling. It has been demonstrated that enniatins have a cytotoxic effect on human cancer cells. Furthermore, incubation of H4IIE hepatoma cells with enniatins strongly diminished phosphorylation of the ERK (p44/p42).

IC 50

ACAT

References

[1] H TOMODA. Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics.[J]. Journal of Antibiotics, 1992, 45 10: 1626-1632. DOI: 10.7164/antibiotics.45.1626
[2] ARLENE A SY-CORDERO  Nicholas H O  Cedric J Pearce. Revisiting the enniatins: a review of their isolation, biosynthesis, structure determination and biological activities[J]. Journal of Antibiotics, 2012, 65 11: 541-549. DOI: 10.1038/ja.2012.71

enniatin A Preparation Products And Raw materials

Raw materials

Preparation Products

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2503-13-1, enniatin ARelated Search:


  • enniatin A
  • N-Methylcyclo(L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-N-methyl-L-Ile-D-Hmb-)
  • Lateritin I
  • 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]
  • (3S,6R,9S,12R,15S,18R)-3,9,15-tris[(2S)-butan-2-yl]-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
  • 2503-13-1
  • C36H63N3O9