Enniatin A1 (CHEM002725)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2010-05-18 15:31:20 UTC
Update Date2026-04-06 02:25:40 UTC
Accession NumberCHEM002725
Identification
Common NameEnniatin A1
ClassSmall Molecule
DescriptionEnniatins 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. Enniatins have various biological activities and can act as enzyme inhibitors, antifungal and antibacterial agents, and immunomodulatory substances. (5, 1)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC35H61N3O9
Average Molecular Mass667.874 g/mol
Monoisotopic Mass667.441 g/mol
CAS Registry Number4530-21-6
IUPAC Name3-(butan-2-yl)-15-butyl-4,10,16-trimethyl-6,9,12,18-tetrakis(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Traditional Name3-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
SMILESCCCCC1N(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 IdentifierInChI=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 KeyVGOLHAPJYMAXRH-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic 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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.012 g/LALOGPS
logP4.39ALOGPS
logP5.93ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)18.8ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area139.83 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity175.93 m³·mol⁻¹ChemAxon
Polarizability73.22 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02vi-3056069000-0815609c021399cab329Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi9-5791300000-f696ce9a8b569c74728cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-3492100000-bc890d382cfefb59eac7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0un9-4190500000-bad7aeeb3fe61ad79a8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03l0-2950401000-876840ba65797ae4be06Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06sj-4922010000-68c6bf84c1cf4ea80fb4Spectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (4)
Mechanism of ToxicityEnniatins 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)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesEnniatins 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 LevelNot Available
Health EffectsEnniatins are cytotoxic. They may also act as antifungal and antibacterial agents, and immunomodulatory substances. (1)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID57369704
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available