AFCDB: L-Canavanine (FDB000505)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:35 UTC

Update date

2019-11-26 02:54:54 UTC

Primary ID

FDB000505

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Canavanine

Description

Stored 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 Number

543-38-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	11.1 g/L	ALOGPS
logP	-3.8	ALOGPS
logP	-4.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	2.1	ChemAxon
pKa (Strongest Basic)	9.16	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.95 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.34 m³·mol⁻¹	ChemAxon
Polarizability	17.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H12N4O3

IUPAC name

2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid

InChI Identifier

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)

InChI Key

FSBIGDSBMBYOPN-UHFFFAOYSA-N

Isomeric SMILES

NC(CCON=C(N)N)C(O)=O

Average Molecular Weight

176.1738

Monoisotopic Molecular Weight

176.09094027

Classification

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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 34.09%; H 6.87%; N 31.80%; O 27.24%	DFC
Melting Point	Mp 184°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	-3.324
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +7.9 (H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0569-2900000000-6018918223cd95093d45	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-06zi-9700000000-c7ea219fb6909c4603dd	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fr-9000000000-383c77609becf6055895	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-4900000000-f69af7725371043afbed	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9400000000-a77fd65e4ff93ac42c57	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-4bc013713f2338a457af	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB01833

HMDB ID

HMDB02706

CRC / DFC (Dictionary of Food Compounds) ID

HDB91-Y:BCZ27-E

EAFUS ID

Not Available

Dr. Duke ID

CANAVANINE

BIGG ID

Not Available

KNApSAcK ID

C00001347

HET ID

GGB

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Canavanine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allelochemic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti feedant			DUKE
anti flu	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti metabolic			DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
juvabional			DUKE
lupus generating	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
mitogenic			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

L-Canavanine (FDB000505)

Structure for FDB000505 (L-Canavanine)