Hypoglycin A

Hypoglycin A is a naturally occurring amino acid derivative found in the unripened fruit of the Ackee tree (Blighia sapida) and in the seeds of the box elder tree (Acer negundo). It is toxic if ingested, and is the causative agent of Jamaican vomiting sickness. A 2017 Lancet report established a link between the consumption of unripened lychees (containing hypoglycin A or methylenecyclopropylglycine (MCPG)) resulting in hypoglycaemia and death from acute toxic encephalopathy.

Hypoglycin
Names
IUPAC name
3-[(1R-2-Methylidenecyclopropyl]-L-alanine
Systematic IUPAC name
(2S)-2-Amino-3-[(1R)-2-methylidenecyclopropyl]propanoic acid
Other names
Hypoglycin A; Hypoglycine; 2-Methylenecyclopropanylalanine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.189.936
PubChem CID
UNII
  • 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
SMILES
  • O=C(O)[C@@H](N)C[C@@H]1C(=C)C1
Properties
C7H11NO2
Molar mass 141.170 g·mol−1
Melting point 282 °C (540 °F; 555 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references
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