Moniliformin 分子结构式
HCID40452

Moniliformin

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

C4H2O398.06 g/molCAS 31876-38-7

IDENTITY

结构与身份

标准SMILES
O=c1cc(O)c1=O
InChIKey
KGPQKNJSZNXOPV-UHFFFAOYSA-N
分子式
C4H2O3
平均分子量
98.06 g/mol
单同位素质量
98.00039392

COMPUTED

结构计算性质

已同步
XLogP
-0.6
极性表面积
54.4 Ų
氢键供体
1
氢键受体
3
可旋转键
0
重原子
7
形式电荷
0
复杂度
166

GHS

GHS分类

来源:PubChem
GHS Classification

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.

HAZARDS

危害信息

来源:PubChem
Regulatory Information

Regulation (EC) No 178/2002 (amended)

Hazard Classes and Categories

Acute Tox. 3 (100%)

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

TOXICITY

毒理信息

来源:PubChem
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. (L1964, L1828)

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. (A3021, A3075, A3076, L1970)

Exposure Routes

Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)

Toxicity Summary

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

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 Classification

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

REGULATORY

法规信息

来源:PubChem
Regulatory Information

Regulation (EC) No 178/2002 (amended)

USES

用途与制造

来源:PubChem
Uses

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

ALIASES

名称与别名

共 44 条
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-dioneDTXSID10185731RefChem:159498DTXCID50108222636-113-2981-476-51-hydroxycyclobutene-3,4-dioneNSC2928961345994-72-039284-13-4

REACTIONS

参与反应

1
HRID 372627 反应方程式

uspto-grants-1978_05 · 10.6084/m9.figshare.5104873.v1 · US04092146

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