CHEBI:609827 - L-canavanine

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ChEBI Name L-canavanine
ChEBI ID CHEBI:609827
ChEBI ASCII Name L-canavanine
Definition A non-proteinogenicL-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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:3345, CHEBI:42902, CHEBI:616834
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Formula C5H12N4O3
Net Charge 0
Average Mass 176.17380
Monoisotopic Mass 176.091
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
InChIKey FSBIGDSBMBYOPN-VKHMYHEASA-N
SMILES N[C@@H](CCONC(N)=N)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
(via L-alpha-amino acid )
Application(s): phytogenic insecticide
An insecticide compound naturally occurring in plants.
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ChEBI Ontology
Outgoing 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 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 Sources
2-Amino-4-(guanidinooxy)butyric acid ChemIDplus
Canavanine KEGG COMPOUND
L-CANAVANINE PDBeChem
L-Canavanine KEGG COMPOUND
O-((Aminoiminomethyl)amino)-L-homoserine ChemIDplus
Manual Xrefs Databases
C00001347 KNApSAcK
C00308 KEGG COMPOUND
Canavanine Wikipedia
CANAVANINE MetaCyc
GGB PDBeChem
HMDB0002706 HMDB
View more database links
Registry Numbers Types Sources
1726113 Reaxys Registry Number Reaxys
543-38-4 CAS Registry Number KEGG COMPOUND
543-38-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
22279227 PubMed citation Europe PMC
23671680 PubMed citation Europe PMC
Last Modified
25 February 2016