Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:04:35 UTC |
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Update date | 2019-11-26 02:54:54 UTC |
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Primary ID | FDB000505 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Canavanine |
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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. |
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CAS Number | 543-38-4 |
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Structure | |
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Synonyms | Synonym | Source |
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(2S)-2-Ammonio-4-(carbamimidamidooxy)butanoate | ChEBI | (2S)-2-Ammonio-4-(carbamimidamidooxy)butanoic acid | Generator | (l)-canavanine | biospider | 2-Amino-4-(guanidinooxy)butyric acid | biospider | 543-38-4 (FREE BASE) | biospider | Butyric acid, 2-amino-4-(guanidinooxy)-, L | biospider | Butyric acid, 2-amino-4-(guanidinooxy)-, L- | biospider | Canavanin | biospider | Canavanine | biospider | Canavanine; L-form | db_source | GGB | biospider | L-2-AMINO-4-(GUANIDINOOXY)BUTYRIC ACID | biospider | L-canavanine | biospider | L-canavanine sulfate | biospider | L-homoserine, o-((aminoiminomethyl)amino)- | biospider | L-Homoserine, O-((aminoiminomethyl)amino)- (9CI) | biospider | L(+)-canavanine | biospider | NSC8921 (SULFATE) | biospider | O-((aminoiminomethyl)amino)-l-homoserine | biospider | O-((aminoiminomethyl)amino)homoserine | biospider |
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Predicted Properties | |
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Chemical Formula | C5H12N4O3 |
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IUPAC name | 2-amino-4-{[(diaminomethylidene)amino]oxy}butanoic acid |
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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) |
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InChI Key | FSBIGDSBMBYOPN-UHFFFAOYSA-N |
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Isomeric SMILES | NC(CCON=C(N)N)C(O)=O |
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Average Molecular Weight | 176.1738 |
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Monoisotopic Molecular Weight | 176.09094027 |
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Classification |
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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). |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Alpha amino acids |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 34.09%; H 6.87%; N 31.80%; O 27.24% | DFC |
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Melting Point | Mp 184° | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | -3.324 | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]20D +7.9 (H2O) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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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 |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 388342 |
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ChEMBL ID | CHEMBL443732 |
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KEGG Compound ID | C00308 |
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Pubchem Compound ID | 439202 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB01833 |
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HMDB ID | HMDB02706 |
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CRC / DFC (Dictionary of Food Compounds) ID | HDB91-Y:BCZ27-E |
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EAFUS ID | Not Available |
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Dr. Duke ID | CANAVANINE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001347 |
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HET ID | GGB |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Canavanine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Not Available |
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Pathways | Not Available |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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