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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-06-15 17:04:52 UTC |
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HMDB ID | HMDB0001263 |
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Secondary Accession Numbers | - HMDB0059595
- HMDB01263
- HMDB59595
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Metabolite Identification |
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Common Name | Allysine |
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Description | Allysine (CAS: 1962-83-0), also known as 2-amino-6-oxohexanoic acid or 6-oxonorleucine, 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). Outside of the human body, allysine has been detected, but not quantified in, several different foods, such as winged beans, wasabi, common verbena, arrowhead, and oats. This could make allysine a potential biomarker for the consumption of these foods. Allysine is a derivative of lysine used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin. |
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Structure | |
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Synonyms | Value | Source |
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2-AMINO-6-oxo-hexanoIC ACID | ChEBI | 6-oxo-L-Norleucine | ChEBI | Allysine | ChEBI | L-2-Aminoadipate 6-semialdehyde | ChEBI | L-6-Oxonorleucine | ChEBI | 2-Aminoadipate 6-semialdehyde | Kegg | L-Allysine | Kegg | 2-AMINO-6-oxo-hexanoate | Generator | L-2-Aminoadipic acid 6-semialdehyde | Generator | 2-Aminoadipic acid 6-semialdehyde | Generator | (S)-2-Amino-6-oxohexanoic acid | Generator | 2-Aminoadipate semialdehyde | HMDB | alpha-AASA | HMDB | alpha-Aminoadipate semialdehyde | HMDB | 2-Aminoadipic semialdehyde | HMDB | 2-Amino-5-formylvaleric acid | HMDB | 2-Amino-6-oxohexanoate | HMDB | 6-Oxonorleucine | HMDB | L-Homoglutamic semialdehyde | HMDB | alpha-Aminoadipic acid delta-semialdehyde | HMDB | alpha-Aminoadipic delta-semialdehyde | HMDB | α-Aminoadipic acid δ-semialdehyde | HMDB | α-Aminoadipic δ-semialdehyde | HMDB |
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Chemical Formula | C6H11NO3 |
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Average Molecular Weight | 145.1564 |
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Monoisotopic Molecular Weight | 145.073893223 |
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IUPAC Name | (2S)-2-amino-6-oxohexanoic acid |
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Traditional Name | 2-amino-6-oxo-hexanoic acid |
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CAS Registry Number | 6665-12-9 |
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SMILES | N[C@@H](CCCC=O)C(O)=O |
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InChI Identifier | InChI=1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)/t5-/m0/s1 |
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InChI Key | GFXYTQPNNXGICT-YFKPBYRVSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. |
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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 | L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - L-alpha-amino acid
- Medium-chain fatty acid
- Amino fatty acid
- Fatty acyl
- Fatty acid
- Alpha-hydrogen aldehyde
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Aldehyde
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Primary aliphatic amine
- Organopnictogen compound
- Carbonyl group
- Organic oxygen compound
- Amine
- Organic nitrogen compound
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-00di-9100000000-e7c5c166681ba0316b25 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0udi-7900000000-a87d074458b671b94f65 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0ufs-2900000000-cc3c3ade4cefc6b57880 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ue9-9700000000-1f5f0f3378ed80283ec8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0abc-9000000000-dd87ab890dceec9e01cb | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-5623b839bf292d641b92 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-4900000000-7473bdea5b2f626515f1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-12c42805d877e4f712b6 | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | <0.2 uM | Infant (0-1 year old) | Not Specified | Normal | | details | Urine | Detected and Quantified | <1 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected and Quantified | 1.6-28 umol/mmol creatinine | Infant (0-1 year old) | Not Specified | Pyridoxine dependency with seizures (PDE) | | details |
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Associated Disorders and Diseases |
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Disease References | Pyridoxine-dependent epilepsy |
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- Plecko B, Paul K, Paschke E, Stoeckler-Ipsiroglu S, Struys E, Jakobs C, Hartmann H, Luecke T, di Capua M, Korenke C, Hikel C, Reutershahn E, Freilinger M, Baumeister F, Bosch F, Erwa W: Biochemical and molecular characterization of 18 patients with pyridoxine-dependent epilepsy and mutations of the antiquitin (ALDH7A1) gene. Hum Mutat. 2007 Jan;28(1):19-26. [PubMed:17068770 ]
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Associated OMIM IDs | - 266100 (Pyridoxine-dependent epilepsy)
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External Links |
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DrugBank ID | DB02571 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB010644 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 141126 |
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KEGG Compound ID | C04076 |
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BioCyc ID | ALLYSINE |
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BiGG ID | Not Available |
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Wikipedia Link | Allysine |
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METLIN ID | Not Available |
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PubChem Compound | 160603 |
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PDB ID | Not Available |
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ChEBI ID | 17917 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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