ContaminantDB: Moniliformin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (7)XML

Record Information

Version

1.0

Creation Date

2010-05-25 14:32:14 UTC

Update Date

2026-04-06 13:27:20 UTC

Accession Number

CHEM002737

Identification

Common Name

Moniliformin

Class

Small Molecule

Description

Moniliformin is a mycotoxin produced by a number of fungi of the Fusarium species. It can by found in contaminated cereal crops and is known to be a lethal food contaminant to fowl as well as a cause of Kashin-Beck disease in humans. (8, 2)

Contaminant Sources

T3DB toxins

Contaminant Type

Carbamate
Food Toxin
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Moniliformin, sodium salt	MeSH
Moniliformin, potassium salt	MeSH

Chemical Formula

C₄H₂O₃

Average Molecular Mass

98.057 g/mol

Monoisotopic Mass

98.000 g/mol

CAS Registry Number

71376-34-6

IUPAC Name

3-hydroxycyclobut-3-ene-1,2-dione

Traditional Name

moniliformin

SMILES

OC1=CC(=O)C1=O

InChI Identifier

InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H

InChI Key

KGPQKNJSZNXOPV-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Vinylogous acids

Sub Class

Not Available

Direct Parent

Vinylogous acids

Alternative Parents

Substituents

Vinylogous acid
Cyclic ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

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	158°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	150 g/L	ALOGPS
logP	-0.21	ALOGPS
logP	0.28	ChemAxon
logS	0.19	ALOGPS
pKa (Strongest Acidic)	6.32	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	22.83 m³·mol⁻¹	ChemAxon
Polarizability	8.09 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9000000000-bee8fab3a03c257d35ba	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-0006-9000000000-74527f2fd30ebf4007ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9000000000-815d20e946ab89d060fb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-9000000000-d658971bcdfc4832f2b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-1a20f0ba8a130bdd7756	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-0b4c42c4195ca5523e92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0005-9000000000-90d030c8ccc394671fd6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9000000000-4a5123231f3b3564f568	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-9000000000-ad152969e2985e58d200	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-3166a519aff91bfd5c6e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-6ffb9541e24882de3fac	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (5)

Mechanism of Toxicity

Moniliformin reversibly inhibits the enzymes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase by competing for the binding site of pyruvate. This interferes with the tricarboxylic acid cycle by preventing the necessary incorporation of pyruvate and oxidation of the alpha-ketoglutarate intermediate. Moniliformin has also been shown to interfere with carbohydrate metabolism by inhibiting transketolase and aldose reductase. Moniliformin causes the necrosis of human chondrocytes in cartilage. It does so by increasing the expression of matrix catabolic enzymes, such as MMP-1 and MMP-13, and decreasing the syntheses of extracellular matrix components such as aggrecan and type II collage. This accelerates the catabolism of the extracellular matrix in articular cartilages, inducing a loss of cartilage function and eventually leading to cartilage degradation. Moniliformin is also known to cause DNA damage, inducing chromatid breaks, chromosome breaks, and chromatid exchanges. (2, 3, 4)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

LD50: 20.9 mg/kg (Mouse, Intraperitoneal) (4)

Carcinogenicity (IARC Classification)

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

Uses/Sources

Moniliformin is a mycotoxin produced by a number of fungi of the Fusarium species. It can by found in contaminated cereal crops. (8, 2)

Minimum Risk Level

Not Available

Health Effects

Moniliformin is believed to be a cause of Kashin-Beck disease, which causes joint destruction and deformity. It may also have immunosuppressive properties and can cause fungal infections such as mycotic keratitis. (1, 2, 3, 9)

Symptoms

The main symptoms of acute moniliformin toxication in animals are muscular weakness, respiratory stress, myocardial degeneration, as well as some histopathological changes in organs such as the kidneys, the lungs and the pancreas, followed by coma and death. Kashin-Beck disease is characterized by joint pain, with restriction of movement and joint enlargement. (4)

Treatment

Kashin-Beck disease cannot be cured but can be treated with physical therapy and corrective surgery. Natamycin ophthalmic suspension is the drug of choice for filamentous fungal infections such as mycotic keratitis. (7, 6)

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

Moniliformin

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

Not Available

Kegg Compound ID

C20592

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Moniliformin (CHEM002737)

Structure for CHEM002737: Moniliformin