| Identification | Back Directory | [Name]
enniatin A | [CAS]
2503-13-1 | [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] | [Molecular Formula]
C36H63N3O9 | [MDL Number]
MFCD19442801 | [MOL File]
2503-13-1.mol | [Molecular Weight]
681.906 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. | [Biological Activity]
Ionophore antibiotic. Potential anticancer compound. | [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 | [storage]
Store at -20°C | [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 |
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