Hypoglycin A

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
CAS Number	156-56-9 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1615355 ;
ChemSpider	9943349 ;
ECHA InfoCard	100.189.936
PubChem CID	11768666;
UNII	7GB7U7M282 ;
CompTox Dashboard (EPA)	DTXSID70878975 ;
	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 Key: OOJZCXFXPZGUBJ-RITPCOANSA-N ; 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
Chemical formula	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). verify (what is ?) Infobox references

Hypoglycin A is a naturally occurring amino acid derivative found in the unripened fruit of the Ackee tree (Blighia sapida)^[1] and in the seeds of the box elder tree (Acer negundo).^[2] It is toxic if ingested, and is the causative agent of Jamaican vomiting sickness.^[1] 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.^[3]

^ ^a ^b "Ackee Fruit Toxicity". Medscape. 2018-06-13.
^ Valberg, S. J.; Sponseller, B. T.; Hegeman, A. D.; Earing, J.; Bender, J. B.; Martinson, K. L.; Patterson, S. E.; Sweetman, L. (2013-07-01). "Seasonal pasture myopathy/atypical myopathy in North America associated with ingestion of hypoglycin A within seeds of the box elder tree". Equine Veterinary Journal. 45 (4): 419–426. doi:10.1111/j.2042-3306.2012.00684.x. ISSN 2042-3306. PMID 23167695. S2CID 206002430.
^ Shrivastava, Aakash (2017). "Association of acute toxic encephalopathy with litchi consumption in an outbreak in Muzaffarpur, India, 2014: a case-control study". The Lancet Global Health. 5 (4): e458–e466. doi:10.1016/S2214-109X(17)30035-9. PMID 28153514.

[medscape-1] "Ackee Fruit Toxicity". Medscape. 2018-06-13.

[Valberg2013-2] Valberg, S. J.; Sponseller, B. T.; Hegeman, A. D.; Earing, J.; Bender, J. B.; Martinson, K. L.; Patterson, S. E.; Sweetman, L. (2013-07-01). "Seasonal pasture myopathy/atypical myopathy in North America associated with ingestion of hypoglycin A within seeds of the box elder tree". Equine Veterinary Journal. 45 (4): 419–426. doi:10.1111/j.2042-3306.2012.00684.x. ISSN 2042-3306. PMID 23167695. S2CID 206002430.

[3] Shrivastava, Aakash (2017). "Association of acute toxic encephalopathy with litchi consumption in an outbreak in Muzaffarpur, India, 2014: a case-control study". The Lancet Global Health. 5 (4): e458–e466. doi:10.1016/S2214-109X(17)30035-9. PMID 28153514.

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