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L-Canavanine (PC000843)

Record Information
Version1.0
Creation date2015-10-09 22:33:02 UTC
Update date2017-01-19 02:36:38 UTC
FoodComEx IDPC000843
FoodDB RecordFDB000505
Chemical Information
NameL-Canavanine
DescriptionStored in large quantities in the seeds of leguminous plants in three subfamilies. Isol. originally from Jackbean (Canavalia ensiformis) L-(+)-(S)-Canavanine is a non-proteinogenic amino acid of certain leguminous plants. It is structurally related to the proteinogenic amino acid, L-arginine. Canavanine is accumulated primarily in the seeds where it serves both as a defensive compound against herbivores and a vital source of nitrogen for the growing embryo. Organisms that consume it can mistakenly incorporate it into their own proteins in the place of arginine, thereby producing structurally aberrant proteins that may not function properly. Some specialized herbivores tolerate L-canavanine either because they metabolize it efficiently or avoid its incorporation into their own nascent proteins.; L-Canavanine, a non-protein amino acid of certain leguminous plants, is related structurally to the protein amino acid, L-arginine. Canavanine is accumulated primarily in the seeds where it serves both as a defensive compound against herbivores and a vital source of nitrogen for the growing embryo. Organisms that consume it can mistakenly incorporate it into their own proteins, in the place of arginine thereby producing structurally aberrant proteins that may not function properly or not at all. Some specialized herbivores tolerate L-canavanine either because they metabolize it efficiently or avoid its incorporation into their own nascent proteins. -- Wikipedia (unverified). L-Canavanine is found in many foods, some of which are mamey sapote, purslane, hard wheat, and cabbage.
CAS Number543-38-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoateChEBI
(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoic acidGenerator
(l)-canavaninebiospider
2-Amino-4-(guanidinooxy)butyric acidbiospider
543-38-4 (FREE BASE)biospider
Butyric acid, 2-amino-4-(guanidinooxy)-, Lbiospider
Butyric acid, 2-amino-4-(guanidinooxy)-, L-biospider
Canavaninbiospider
Canavaninebiospider
Canavanine; L-formdb_source
GGBbiospider
L-2-AMINO-4-(GUANIDINOOXY)BUTYRIC ACIDbiospider
L-canavaninebiospider
L-canavanine sulfatebiospider
L-homoserine, o-((aminoiminomethyl)amino)-biospider
L-Homoserine, O-((aminoiminomethyl)amino)- (9CI)biospider
L(+)-canavaninebiospider
NSC8921 (SULFATE)biospider
O-((aminoiminomethyl)amino)-l-homoserinebiospider
O-((aminoiminomethyl)amino)homoserinebiospider
Chemical FormulaC5H12N4O3
IUPAC name2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid
InChI IdentifierInChI=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)
InChI KeyFSBIGDSBMBYOPN-UHFFFAOYSA-N
Isomeric SMILESNC(CCON=C(N)N)C(O)=O
Average Molecular Weight176.1738
Monoisotopic Molecular Weight176.09094027
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Fatty acid
  • Guanidine
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP-3.324
Experimental Water SolubilityNot Available
Melting PointMp 184°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 40 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci X6876