Moniliformin is an unusual mycotoxin, a feed contaminant that is lethal to fowl, especially ducklings.

Moniliformin

Names
IUPAC name Sodium 3,4-dioxo-1-cyclobuten-1-olate
Other names 3-Hydroxycyclobut-3-ene-1,2-dione sodium salt Moniliformin Semisquaric acid sodium salt Sodium semisquarate
Identifiers
CAS Number	31876-38-7 Y
3D model (JSmol)	Interactive image
ChemSpider	36957 Y
PubChem CID	40452
UNII	G5JMQ8SDF8 Y
CompTox Dashboard (EPA)	DTXSID10185731
InChI InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H Y Key: KGPQKNJSZNXOPV-UHFFFAOYSA-N Y InChI=1/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H Key: KGPQKNJSZNXOPV-UHFFFAOYAJ
SMILES O=C1C(\O)=C/C1=O
Properties
Chemical formula	NaC4HO3
Molar mass	120.039 g·mol−1
Appearance	Yellow crystalline solid
Melting point	Decomposes at 345-355 °C without melting
Solubility in water	very good
Related compounds
Related compounds	Squaric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Moniliformin is formed in many cereals by a number of Fusarium species that include Fusarium moniliforme, Fusarium avenaceum, Fusarium subglutinans, Fusarium proliferatum, Fusarium fujikuroi and others. It is mainly cardiotoxic and causes ventricular hypertrophy. Moniliformin actually causes competitive inhibition of the activity of pyruvate dehydrogenase complex of respiratory reaction, which prevents pyruvic acid, product of glycolysis, to convert to acetyl-CoA.^[1][2][3] Ultrastructural examination of right ventricular wall of 9 month old female mink (Mustela vison) fed acute doses of moniliformin (2.2 and 2.8 mg/kg diet) and sub-acute doses (1.5 to 3.2 mg/kg diet) reveals significant damage to myofiber, mitochondria, Z and M lines and sarcoplasmic reticulum as well as increased extracellular collagen deposition.^{[clarification needed]} Minks are considered most sensitive mammals to the toxicity of moniliformin.^[4] Chemically speaking, it is the sodium salt of deoxysquaric acid (the other name of that acid is semisquaric acid).