ContaminantDB: Enniatin A1

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (30)XML

Record Information

Version

1.0

Creation Date

2010-05-18 15:31:20 UTC

Update Date

2026-04-06 02:25:40 UTC

Accession Number

CHEM002725

Identification

Common Name

Enniatin A1

Class

Small Molecule

Description

Enniatin A1 is an exogenous solid with the chemical formula C35H61N3O9. Enniatin A1 belongs to the depsipeptides, a subclass of peptidomimetics within the organic compounds. With an average molecular weight of 667.87 g/mol, Enniatin A1 is a heavy molecule. This compound is found in or released from 13 recorded sources across several sectors. These include Electrical & Electronic Equipment, such as batteries, cell phones, capacitors, wires and cables, and printed circuit boards; Textiles, leather & furnishings, including carpets, rugs, and synthetic textiles; Food, food processing & cookware via food packaging; Healthcare, pharmaceuticals & veterinary products through medical devices; and Lubricants within the Energy, oil & gas and Industrial manufacturing & chemical processing sectors. Recorded exposure routes include touch, oral, and inhalation. Enniatin A1 interacts with four recorded protein targets. It inhibits acyl coenzyme A:cholesterol acyltransferase, specifically targeting Sterol O-acyltransferase 1 (SOAT1) and Sterol O-acyltransferase 2 (SOAT2). Additionally, it inhibits the activity of membrane-located ATP-binding cassette (ABC) transporters, including the ATP-dependent translocase ABCB1 and the broad substrate specificity ATP-binding cassette transporter ABCG2; these multidrug pumps affect the bioavailability of pharmaceuticals and xenobiotics. Enniatin A1 is also cytotoxic and can cause DNA fragmentation through an unnamed protein.

Contaminant Sources

T3DB toxins

Contaminant Type

Amide
Amine
Ester
Ether
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound
PFAS

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₅H₆₁N₃O₉

Average Molecular Mass

667.874 g/mol

Monoisotopic Mass

667.441 g/mol

CAS Registry Number

4530-21-6

IUPAC Name

Not Available

Traditional Name

3-butyl-6,12,15,18-tetraisopropyl-4,10,16-trimethyl-9-(sec-butyl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone

SMILES

CCCCC1N(C)C(=O)C(OC(=O)C(C(C)CC)N(C)C(=O)C(OC(=O)C(C(C)C)N(C)C(=O)C(OC1=O)C(C)C)C(C)C)C(C)C

InChI Identifier

InChI=1S/C35H61N3O9/c1-15-17-18-24-33(42)45-28(21(7)8)31(40)37(13)25(19(3)4)34(43)46-29(22(9)10)32(41)38(14)26(23(11)16-2)35(44)47-27(20(5)6)30(39)36(24)12/h19-29H,15-18H2,1-14H3

InChI Key

VGOLHAPJYMAXRH-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Peptidomimetics

Sub Class

Depsipeptides

Direct Parent

Cyclic depsipeptides

Alternative Parents

Substituents

Cyclic depsipeptide
Macrolide lactam
Alpha-amino acid ester
Macrolactam
Macrolide
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Lactone
Oxacycle
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	4.39	ALOGPS
logP	5.93	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	18.8	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	139.83 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	175.93 m³·mol⁻¹	ChemAxon
Polarizability	73.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-02vi-3056069000-0815609c021399cab329	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zi9-5791300000-f696ce9a8b569c74728c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01t9-3492100000-bc890d382cfefb59eac7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0un9-4190500000-bad7aeeb3fe61ad79a8e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03l0-2950401000-876840ba65797ae4be06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06sj-4922010000-68c6bf84c1cf4ea80fb4	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (4)

Mechanism of Toxicity

Enniatins are toxic due to their ability to act as ionophores, changing ion transport across membranes and disrupting the ionic selectivity of cell walls. In the membrane, enniatins form a dimeric structure and are able to transport monovalent ions (especially K+, Mg2+,Ca2+ and Na+) across the membranes. This effect is particularly harmful in mitochondrial membranes, resulting in the uncoupling of oxidative phosphorylation. They are also know to inhibit several enzymes, including acyl coenzyme A:cholesterol acyltransferase and cyclic nucleotide phosphodiesterase. Enniatins are cytotoxic and can cause DNA fragmentation, induce apoptosis, and disrupt the ERK signalling pathway. They can also inhibit the activity of membrane-located ATP-binding cassette (ABC) transporters, multidrug pumps which affect the bioavailability of xenobiotics and pharmaceuticals. (1, 2, 3)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Enniatins are mycotoxins that appear in nature as a mixture of cyclohexadepsipeptides produced by bacteria, fungi, and plants. They may be found in contaminated cereal crops. (5, 1)

Minimum Risk Level

Not Available

Health Effects

Enniatins are cytotoxic. They may also act as antifungal and antibacterial agents, and immunomodulatory substances. (1)

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

57369704

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Enniatin A1 (CHEM002725)

Structure for CHEM002725: Enniatin A1