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Enniatin B1

CAT: 0804-HY-N3807-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N3807-01Size:1 mg
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Description
Enniatin B1 is a Fusarium mycotoxin. Enniatin B1 inhibits acyl-CoA: cholesterol acyltransferase (ACAT) activity with an IC50 of 73 μM in an enzyme assay using rat liver microsomes[1]. Enniatin B1 crosss the blood-brain barrier[2]. Enniatin B1 decreases the activation of ERK (p44/p42) . Enniatin B1 inhibits moderately TNF-α-induced NF-κB activation[3].
CAS Number
19914-20-6
UNSPSC
12352005
Hazard Statement
H301+H311+H331
Target
Acyltransferase; ERK; NF-κB
Type
Natural Products
Related Pathways
MAPK/ERK Pathway; Metabolic Enzyme/Protease; NF-κB; Stem Cell/Wnt
Applications
COVID-19-immunoregulation
Field of Research
Cancer; Infection; Cardiovascular Disease
Assay Protocol
https://www.medchemexpress.com/enniatin-b1.html
Purity
99.34
Solubility
DMSO : ≥ 10 mg/mL
Smiles
CC[C@@H]([C@]1([H])N(C([C@H](OC([C@](N(C([C@@H](C(C)C)OC([C@H](C(C)C)N(C)C([C@](C(C)C)([H])OC1=O)=O)=O)=O)C)([H])C(C)C)=O)C(C)C)=O)C)C
Molecular Formula
C34H59N3O9
Molecular Weight
653.85
Precautions
H301+H311+H331
References & Citations
[1]Tomoda H, et al. Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J Antibiot (Tokyo) . 1992 Oct;45 (10) :1626-32.|[2]Krug I, et al. Transport of enniatin B and enniatin B1 across the blood-brain barrier and hints for neurotoxic effects in cerebral cells. PLoS One. 2018 May 16;13 (5) :e0197406.|[3]Wätjen W, et al. 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. Mol Nutr Food Res. 2009 Apr;53 (4) :431-40.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture and light)
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
ACAT; ERK; NF-κB

Chemical Information

Enniatin B1

UQCSETXJXJTMKO-UMURLBKASA-N has been reported in Fusarium, Pinus sylvestris, and other organisms with data available.

CAS Number19914-20-6
PubChem CID11262300
IUPAC Name(3S,6R,9S,12R,15S,18R)-3-[(2S)-butan-2-yl]-4,10,16-trimethyl-6,9,12,15,18-penta(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Molecular FormulaC34H59N3O9
Molecular Weight653.8
XLogP6.9
Topological Polar Surface Area140
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count9
Rotatable Bond Count7
Heavy Atom Count46
Formal Charge0
Complexity1100
SMILES
CC[C@H](C)[C@H]1C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)C(C)C)C)C(C)C)C(C)C)C)C(C)C
InChI
InChI=1S/C34H59N3O9/c1-16-22(12)25-34(43)46-27(20(8)9)30(39)36(14)23(17(2)3)32(41)44-26(19(6)7)29(38)35(13)24(18(4)5)33(42)45-28(21(10)11)31(40)37(25)15/h17-28H,16H2,1-15H3/t22-,23-,24-,25-,26+,27+,28+/m0/s1
InChIKey
UQCSETXJXJTMKO-UMURLBKASA-N
Chemical Structure
2D Structure
2D structure of Enniatin B1
CAS: 19914-20-6
CID: 11262300
Formula: C34H59N3O9
MW: 653.8
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight653.8
XLogP36.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count9
Rotatable Bond Count7
Exact Mass653.42513047
Monoisotopic Mass653.42513047
Topological Polar Surface Area140 Ų
Heavy Atom Count46
Formal Charge0
Complexity1100
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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