Hypoglycin

Hypoglycin

IUPAC name L(S)-2-amino-3-(2-methylidenecyclopropyl)- propanoic acid
Other names Hypoglycin A, Hypoglycine, 2-Methylenecyclopropanylalanine
Identifiers
CAS number	156-56-9^Y
PubChem	11768666
ChemSpider	9943349^Y
Jmol-3D images	Image 1
SMILES O=C(O)[C@@H](N)C[C@@H]1C(=C)C1
InChI InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)/t5-,6+/m1/s1^Y Key: OOJZCXFXPZGUBJ-RITPCOANSA-N^Y InChI=1/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)/t5-,6+/m1/s1 Key: OOJZCXFXPZGUBJ-RITPCOANBH
Properties
Molecular formula	C₇H₁₁NO₂
Molar mass	141.17 g/mol
Melting point	282°C (555.15 K)
Boiling point	(? K)
Solubility in water	? g/100 ml (?°C)
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. 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 MCPA (methylene cyclopropyl acetic acid) are toxic.

The metabolite MCPA also is a potent inhibitor of Acyl-CoA dehydrogenase, preventing the metabolism of fatty acids. The symptoms of Hypoglycin-A 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 acid, due to omega oxidation that occurs in the ER.