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<compound>
  <id type="integer">3811</id>
  <title>T3D3757</title>
  <common-name>Enniatin A1</common-name>
  <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 &amp; Electronic Equipment, such as batteries, cell phones, capacitors, wires and cables, and printed circuit boards; Textiles, leather &amp; furnishings, including carpets, rugs, and synthetic textiles; Food, food processing &amp; cookware via food packaging; Healthcare, pharmaceuticals &amp; veterinary products through medical devices; and Lubricants within the Energy, oil &amp; gas and Industrial manufacturing &amp; 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.</description>
  <cas>4530-21-6</cas>
  <pubchem-id>16727692</pubchem-id>
  <chemical-formula>C35H61N3O9</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point nil="true"/>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility nil="true"/>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)</route-of-exposure>
  <target nil="true"/>
  <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. (A3055, A3056, A3057)</mechanism-of-toxicity>
  <metabolism nil="true"/>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>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. (L1965, A3055)</use-source>
  <min-risk-level nil="true"/>
  <health-effects>Enniatins are cytotoxic. They may also act as antifungal and antibacterial agents, and immunomodulatory substances. (A3055)</health-effects>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2010-05-18T15:31:20Z</created-at>
  <updated-at type="dateTime">2026-04-06T02:25:40Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>http://en.wikipedia.org/wiki/Enniatin</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id nil="true"/>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id nil="true"/>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-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</moldb-smiles>
  <moldb-formula>C35H61N3O9</moldb-formula>
  <moldb-inchi>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</moldb-inchi>
  <moldb-inchikey>VGOLHAPJYMAXRH-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">667.8735</moldb-average-mass>
  <moldb-mono-mass type="decimal">667.440780565</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp nil="true"/>
  <hmdb-id nil="true"/>
  <chembl-id nil="true"/>
  <chemspider-id>28184660</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002725</chemdb-id>
  <dsstox-id>DTXSID50891864</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00094903</susdat-id>
  <iupac nil="true"/>
  <moldb-polar-surface-area>139.83000000000004</moldb-polar-surface-area>
  <moldb-refractivity>175.9301000000001</moldb-refractivity>
  <moldb-polarizability>73.22435589071054</moldb-polarizability>
  <moldb-rotatable-bond-count>9</moldb-rotatable-bond-count>
  <moldb-acceptor-count>6</moldb-acceptor-count>
  <moldb-donor-count>0</moldb-donor-count>
  <moldb-pka-strongest-acidic>18.802691322391123</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-5.478968687941619</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>1</moldb-number-of-rings>
  <moldb-alogps-logp>4.39</moldb-alogps-logp>
  <moldb-alogps-logs>-4.73</moldb-alogps-logs>
  <moldb-alogps-solubility>1.24e-02 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organic acids and derivatives</superklass>
  <klass>Peptidomimetics</klass>
  <subklass>Depsipeptides</subklass>
  <paper-count type="integer">582</paper-count>
  <sync-id>CED0010499</sync-id>
  <structure-inchikey>VGOLHAPJYMAXRH-UHFFFAOYSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:54Z</structure-indexed-at>
</compound>
