4078 L-Hypoglycin A Hypoglycin is toxic if ingested and is the causative agent of Jamaican vomiting sickness. It is an amino acid and chemically related to lysine. 156-56-9 441451 C7H11NO2 White powder. Generally, hypoglycin 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 metabolitemethylene cyclopropyl acetic acid (MCPA) are toxic. The metabolite MCPA also is a potent inhibitor of acyl CoA dehydrogenase, preventing the metabolism of fatty acids. It has been shown that oxidation of leucine is inhibited by hypoglycin A. In contrast, oxidation of valine and isoleucine are not significantly inhibited by this compound. However, the specific step in the pathway of leucine metabolism that is inhibited by hypoglycin A has not been precisely identified. Hypoglycemia and depletion of glycogen were due to the decreased gluconeogenesis resulting from impairment of long chain fatty acid metabolism after injection of hypoglycin A. Hypoglycin A or its metabolite, methylenecyclopropylacetic acid, and also 4-pentenoic acid (4-PE) were shown to inhibit long-chain fatty acid oxidation; whereas oxidation of straight short chain fatty acids including butyrate, hexanoate, and octanoate was not inhibited. Hypolglycin A inhibits dehydrogenation of isovaleryl-CoA and alpha-methylbutyryl-CoA by liver slices in vitro, and that it induces isovaleric and alpha-methylbutyric acidemias in experimental animals in vivo. (PMID: 4636318; PMID:5276292) No indication of carcinogenicity to humans (not listed by IARC). 2014-08-29T04:49:23Z 2014-12-24T20:26:36Z Hypoglycin C08287 true [H][C@](N)(C[C@]1([H])CC1=C)C(O)=O C7H11NO2 InChI=1S/C7H11NO2/c1-4-2-5(4)3-6(8)7(9)10/h5-6H,1-3,8H2,(H,9,10)/t5-,6-/m0/s1 InChIKey=OOJZCXFXPZGUBJ-WDSKDSINSA-N 141.1677 141.078978601 Exogenous Solid 390184