Canavanine

Canavanine
Names
	Preferred IUPAC name Canavanine
	Systematic IUPAC name (2S)-2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid
Identifiers
CAS Number	543-38-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:609827;
ChemSpider	388342;
DrugBank	DB01833;
ECHA InfoCard	100.153.281
EC Number	624-714-2;
KEGG	C00308;
MeSH	Canavanine
PubChem CID	275;
UNII	3HZV514J4B ;
CompTox Dashboard (EPA)	DTXSID5045041 ;
	InChI InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-12-9-5(7)8/h3H,1-2,6H2,(H,10,11)(H4,7,8,9)/t3-/m0/s1;
	SMILES N[C@@H](CCON=C(N)N)C(O)=O;
Properties
Chemical formula	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)
Solubility in water	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:
Pictograms
Signal word	Warning
Hazard statements	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). Infobox references

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.