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Moniliformin

HCID 40452
NotesReactions

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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
31876-38-7
Standard SMILES
O=c1cc(O)c1=O
InChIKey
KGPQKNJSZNXOPV-UHFFFAOYSA-N
Molecular formula
C4H2O3
Average molar mass
98.06 g/mol
Monoisotopic mass
98.00039392

Names & identifiers

Preferred name
Moniliformin
IUPAC
3-hydroxycyclobut-3-ene-1,2-dione
English name
moniliformin
Molecular formula
C4H2O3
Molecular weight
98.06

Names & synonyms

Moniliformin31876-38-73-hydroxycyclobut-3-ene-1,2-dioneSemisquaric acid3-Cyclobutene-1,2-dione, 3-hydroxy-1-Hydroxycyclobut-1-ene-3,4-dioneHydroxycyclobutenedione3-Hydroxy-3-cyclobutene-1,2-dione3-Hydroxy-3-cyclobutenedioneG5JMQ8SDF81-Hydroxy-cyclobut-1-ene-3,4-dioneDTXSID10185731
Show more names
RefChem:159498DTXCID50108222636-113-2981-476-51-hydroxycyclobutene-3,4-dioneNSC2928961345994-72-039284-13-4

Database identifiers

CAS
31876-38-7、71376-34-6
PubChem CID
40452
DTXSID
DTXSID10185731
ChEMBL
CHEMBL1977616
ChEBI
CHEBI:222613
UNII
G5JMQ8SDF8
EC Number
636-113-2、981-476-5
Nikkaji
J20.107C

Properties

Computed structural propertiesFilling in

XLogP
-0.6
Topological polar surface area
54.4 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
0
Heavy atoms
7
Formal charge
0
Complexity
166

Physicochemical properties

Melting point
163 °C · 163°C (rough estimate)
Boiling point
123.51 °C · 123.51°C (rough estimate)
Density
1.3154 · 1.3154 (rough estimate)
refractive index
1.454 · 1.4540 (estimate)
pka
-0.21 · -0.21±0.25(Predicted)
FDA UNII
5 JMQ8SDF8 · G5JMQ8SDF8

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and Categories · 2 items

Acute Tox. 3 (100%)

Acute Tox. 2 (100%);Skin Irrit. 2 (100%);Eye Irrit. 2A (100%);STOT SE 3 (100%)

Toxicology

TreatmentKashin-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. (L1964, L1828)
Health Effects · 1 item

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. (A3021, A3075, A3076, L1970)

Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

Chemistry & industry

Uses & manufacturing

UsesMoniliformin is a mycotoxin produced by a number of fungi of the Fusarium species. It can by found in contaminated cereal crops. (L1969, A3075)

Applications

UsesMoniliformin is a toxic secondary metabolite ofFusarium spp..

Upstream & downstream products

Upstream raw materials

dichloroketene3-Cyclobutene-1,2-dione, 3-chloro-4-hydroxy-2-Cyclobuten-1-one, 2,3,4-tris(1,1-dimethylethoxy)-Cyclobutanone, 2,2,3,3-tetraethoxy-Cyclobutene, 1,4-dichloro-3,3,4-trifluoro-2,3-di-tert-butoxy-4-hydroxy-2-cyclobuten-1-oneTetramethoxyethyleneketeneEthyl vinyl ether

Related reactions

1 records
New reaction record
HRID 372627 reaction equation
HRID 372627As reactantuspto-grants-1978_05

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Toxicity Summary · 1 item

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. (A3075, A3076, A3077)

Signs and Symptoms · 1 item

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. (A3077)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Regulatory information

Regulatory InformationRegulation (EC) No 178/2002 (amended)