Canavanine
Chemical compound / From Wikipedia, the free encyclopedia
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L-(+)-(S)-Canavanine is a non-proteinogenic amino acid found in certain leguminous plants. It is structurally related to the proteinogenic α-amino acid L-arginine, the sole difference being the replacement of a methylene bridge (-CH
2- unit) in arginine with an oxa group (i.e., an oxygen atom) in canavanine. Canavanine is accumulated primarily in the seeds of the organisms which produce it, where it serves both as a highly deleterious defensive compound against herbivores (due to cells mistaking it for arginine) and a vital source of nitrogen for the growing embryo.[citation needed] The related L-canaline is similar to ornithine.
Quick Facts Names, Identifiers ...
Names | |
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Preferred IUPAC name
Canavanine | |
Systematic IUPAC name
(2S)-2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid | |
Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.153.281 |
EC Number |
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KEGG | |
MeSH | Canavanine |
PubChem CID |
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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C5H12N4O3 | |
Molar mass | 176.176 g·mol−1 |
Density | 1.61 g·cm−3 (predicted) |
Melting point | 184 °C (363 °F; 457 K) |
Boiling point | 366 °C (691 °F; 639 K) |
soluble | |
Solubility | insoluble in alcohol, ether, benzene |
log P | -0.91 (predicted) |
Vapor pressure | 1.61 μPa (predicted) |
Acidity (pKa) | 2.35 (carboxylic acid), 7.01 (oxoguanidinium), 9.22 (ammonium) |
Hazards | |
GHS labelling: | |
Warning | |
H302, H312, H332 | |
Flash point | 214.6 °C (418.3 °F; 487.8 K) (predicted) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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