L-canaline (CHEBI:41401)

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ChEBI Name	L-canaline

ChEBI ID	CHEBI:41401

ChEBI ASCII Name	L-canaline

Definition	A non-proteinogenic L-α-amino acid that is L-homoserine in which the hydroxy group at position 4 is substituted by an aminooxy group. It has been isolated from legumes and plays an essential role in lugume chemical defense against insects.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:6200

Supplier Information

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Formula

C4H10N2O3

Net Charge

Average Mass

134.135

Monoisotopic Mass

134.06914

InChI

InChI=1S/C4H10N2O3/c5-3(4(7)8)1-2-9-6/h3H,1-2,5-6H2,(H,7,8)/t3-/m0/s1

InChIKey

FQPGMQABJNQLLF-VKHMYHEASA-N

SMILES

C(C[C@@H](C(O)=O)N)ON

Metabolite of Species	Details
Canavalia ensiformis (NCBI:txid3823)	See: DOI

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. antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. phytogenic insecticide An insecticide compound naturally occurring in plants.

ChEBI Ontology
Outgoing	L-canaline (CHEBI:41401) has functional parent L-homoserine (CHEBI:15699) L-canaline (CHEBI:41401) has role antimetabolite (CHEBI:35221) L-canaline (CHEBI:41401) has role antineoplastic agent (CHEBI:35610) L-canaline (CHEBI:41401) has role phytogenic insecticide (CHEBI:22917) L-canaline (CHEBI:41401) has role plant metabolite (CHEBI:76924) L-canaline (CHEBI:41401) is a non-proteinogenic L-α-amino acid (CHEBI:83822) L-canaline (CHEBI:41401) is tautomer of L-canaline zwitterion (CHEBI:145769)

Incoming	L-canaline zwitterion (CHEBI:145769) is tautomer of L-canaline (CHEBI:41401)

IUPAC Name

O-amino-L-homoserine

Synonyms	Sources
(2S)-2-amino-4-(aminooxy)butanoic acid	IUPAC
(2S)-2-amino-4-(aminooxy)butyric acid	HMDB
canaline	ChemIDplus
L-2-amino-4-(aminooxy)butyric acid	MetaCyc
L-canaline	ChemIDplus

Registry Number	Type	Source
496-93-5	CAS Registry Number	ChemIDplus

Last Modified

25 February 2020