Hypoglycin B

Hypoglycin B is a naturally occurring organic compound in the species Blighia sapida. It is particularly concentrated in the fruit of the plant especially in the seeds. Hypoglycin B is toxic if ingested and is one of the causative agents of Jamaican vomiting sickness.[1] It is a dipeptide of glutamic acid and hypoglycin A.

Hypoglycin B
Hypoglycin B
Names
IUPAC name
γ-Glutamyl-3-[(1R-2-methylidenecyclopropyl]alanine
Systematic IUPAC name
(2S)-5-({(1S)-1-Carboxy-2-[(1S)-2-methylidenecyclopropyl]ethyl}amino)-5-oxopentanoic acid
Other names
L-γ-Glutamyl-L-hypoglycin; L-γ-Glutamyl-3-[(1S)-2-methylenecyclopropyl]-L-alanine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
UNII
  • InChI=1S/C12H18N2O5/c1-6-4-7(6)5-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h7-9H,1-5,13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-,9-/m0/s1 checkY
    Key: UYDZYCPIQSRXKU-CIUDSAMLSA-N checkY
  • InChI=1/C12H18N2O5/c1-6-4-7(6)5-9(12(18)19)14-10(15)3-2-8(13)11(16)17/h7-9H,1-5,13H2,(H,14,15)(H,16,17)(H,18,19)/t7-,8-,9-/m0/s1
    Key: UYDZYCPIQSRXKU-CIUDSAMLBD
  • O=C(N[C@H](C(=O)O)C[C@H]1C(=C)C1)CC[C@@H](C(=O)O)N
Properties
C12H18N2O5
Molar mass 270.285 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. "Ackee Fruit Toxicity". Medscape. 28 March 2022.


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