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CHEBI:609827 - L-canavanine

ChEBI IDCHEBI:609827
ChEBI NameL-canavanine
Stars
ASCII NameL-canavanine
DefinitionA non-proteinogenic L-α-amino acid that is L-homoserine substituted at oxygen with a guanidino (carbamimidamido) group. Although structurally related to L-arginine, it is non-proteinogenic.
Secondary ChEBI IDsCHEBI:3345, CHEBI:42902, CHEBI:616834
Last Modified25 February 2020
DownloadsMolfile
FormulaC5H12N4O3
Net Charge0
Average Mass176.176
Monoisotopic Mass176.09094
SMILESN=C(N)NOCC[C@H](N)C(=O)O
InChIInChI=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
InChIKeyFSBIGDSBMBYOPN-VKHMYHEASA-N
Wikipedia
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Role:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
Application:
phytogenic insecticide  An insecticide compound naturally occurring in plants.
ChEBI Ontology
Outgoing Relation(s)
L-canavanine (CHEBI:609827) has functional parent L-homoserine (CHEBI:15699)
L-canavanine (CHEBI:609827) has role phytogenic insecticide (CHEBI:22917)
L-canavanine (CHEBI:609827) has role plant metabolite (CHEBI:76924)
L-canavanine (CHEBI:609827) is a non-proteinogenic L-α-amino acid (CHEBI:83822)
L-canavanine (CHEBI:609827) is conjugate base of L-canavanine(1+) (CHEBI:78902)
L-canavanine (CHEBI:609827) is tautomer of L-canavanine zwitterion (CHEBI:405237)
Incoming Relation(s)
L-canavanine(1+) (CHEBI:78902) is conjugate acid of L-canavanine (CHEBI:609827)
L-canavanine zwitterion (CHEBI:405237) is tautomer of L-canavanine (CHEBI:609827)
IUPAC Name 
O-carbamimidamido-L-homoserine
Synonyms  Source
2-Amino-4-(guanidinooxy)butyric acidChemIDplus
CanavanineKEGG COMPOUND
L-CanavanineKEGG COMPOUND
L-CANAVANINEPDBeChem
O-((Aminoiminomethyl)amino)-L-homoserineChemIDplus
Manual XrefsDatabases
C00001347KNApSAcK
C00308KEGG COMPOUND
CanavanineWikipedia
CANAVANINEMetaCyc
GGBPDBeChem
HMDB0002706HMDB
Registry NumbersSources
Reaxys:1726113Reaxys
CAS:543-38-4KEGG COMPOUND
CAS:543-38-4ChemIDplus
Citations