Hypoglycin

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Hypoglycin
Hypoglycin
Identifiers
CAS number 156-56-9 YesY
PubChem 11768666
ChemSpider 9943349 YesY
ChEMBL CHEMBL1615355 N
Jmol-3D images Image 1
Properties
Molecular formula C7H11NO2
Molar mass 141.17 g mol−1
Melting point 282 °C (540 °F; 555 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Hypoglycin is a naturally occurring organic compound in the species Blighia sapida. It is particularly concentrated in the fruit of the plant. Hypoglycin is toxic if ingested and is the causative agent of Jamaican vomiting sickness.[1] It is an amino acid and chemically related to lysine. It competitively binds to enzymes used in the catabolism of lysine and is the reason why it and its metabolite methylene cyclopropyl acetic acid (MCPA) are toxic.

The metabolite MCPA also is a potent inhibitor of acyl CoA dehydrogenase, preventing the metabolism of fatty acids. The symptoms of hypoglycin ingestion are intolerance to prolonged fasting (due to inability to switch from glucose to fatty acid oxidation), impaired ketogensis, vomiting, lethargy, unconsciousness, coma, death, and increased urinary excretion of dicarboxylic acids, due to omega oxidation that occurs in the ER.[disambiguation needed]

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