Record Information |
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Version | 5.0 |
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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 | 2023-07-07 20:53:57 UTC |
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HMDB ID | HMDB0000182 |
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Secondary Accession Numbers | - HMDB00182
- HMDB0062809
- HMDB62809
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Metabolite Identification |
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Common Name | Lysine |
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Description | Lysine (Lys), also known as L-lysine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (-NH2) and carboxyl (-COOH) functional groups, along with a side chain (R group) specific to each amino acid. Lysine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Lysine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, positively charged or basic amino acid. In humans, lysine is an essential amino acid, meaning the body cannot synthesize it, and it must be obtained from the diet. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. Children and infants need more, 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. In organisms that synthesise lysine, it has two main biosynthetic pathways, the diaminopimelate and alpha-aminoadipate pathways, which employ distinct enzymes and substrates and are found in diverse organisms. Lysine catabolism occurs through one of several pathways, the most common of which is the saccharopine pathway. Lysine plays several roles in humans, most importantly proteinogenesis, but also in the crosslinking of collagen polypeptides, uptake of essential mineral nutrients, and in the production of carnitine, which is key in fatty acid metabolism. Lysine is also often involved in histone modifications, and thus, impacts the epigenome. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for lysine are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize the level and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and those treated with coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) (http://www.dcnutrition.com). Lysine has also been shown to play a role in anaemia, as lysine is suspected to have an effect on the uptake of iron and, subsequently, the concentration of ferritin in blood plasma. |
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Structure | InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1 |
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Synonyms | Value | Source |
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(S)-2,6-Diaminohexanoic acid | ChEBI | (S)-alpha,epsilon-Diaminocaproic acid | ChEBI | (S)-Lysine | ChEBI | 6-Ammonio-L-norleucine | ChEBI | K | ChEBI | L-2,6-Diaminocaproic acid | ChEBI | L-Lysin | ChEBI | Lys | ChEBI | Lysina | ChEBI | Lysine | ChEBI | Lysine acid | ChEBI | Lysinum | ChEBI | 2,6-Diaminohexanoic acid | Kegg | (S)-2,6-Diaminohexanoate | Generator | (S)-a,epsilon-Diaminocaproate | Generator | (S)-a,epsilon-Diaminocaproic acid | Generator | (S)-alpha,epsilon-Diaminocaproate | Generator | (S)-Α,epsilon-diaminocaproate | Generator | (S)-Α,epsilon-diaminocaproic acid | Generator | L-2,6-Diaminocaproate | Generator | 2,6-Diaminohexanoate | Generator | (+)-S-Lysine | HMDB | (S)-2,6-Diamino-hexanoate | HMDB | (S)-2,6-Diamino-hexanoic acid | HMDB | (S)-a,e-Diaminocaproate | HMDB | (S)-a,e-Diaminocaproic acid | HMDB | 6-Amino-aminutrin | HMDB | 6-Amino-L-norleucine | HMDB | a-Lysine | HMDB | alpha-Lysine | HMDB | Aminutrin | HMDB | H-Lys-OH | HMDB | L-(+)-Lysine | HMDB | L-2,6-Diainohexanoate | HMDB | L-2,6-Diainohexanoic acid | HMDB | L-Lys | HMDB | Acetate, lysine | HMDB | Enisyl | HMDB | Lysine hydrochloride | HMDB | L Lysine | HMDB | Lysine acetate | HMDB |
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Chemical Formula | C6H14N2O2 |
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Average Molecular Weight | 146.1876 |
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Monoisotopic Molecular Weight | 146.105527702 |
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IUPAC Name | (2S)-2,6-diaminohexanoic acid |
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Traditional Name | L-lysine |
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CAS Registry Number | 56-87-1 |
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SMILES | NCCCC[C@H](N)C(O)=O |
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InChI Identifier | InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1 |
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InChI Key | KDXKERNSBIXSRK-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 acid
- Fatty acyl
- Amino acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Organic nitrogen compound
- Amine
- Hydrocarbon derivative
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 224.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1000 mg/mL | Not Available | LogP | -3.05 | HANSCH,C ET AL. (1995) |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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L-Lysine,1TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@@H](N)CCCCN | 1465.0 | Semi standard non polar | 33892256 | L-Lysine,1TMS,isomer #2 | C[Si](C)(C)NCCCC[C@H](N)C(=O)O | 1618.2 | Semi standard non polar | 33892256 | L-Lysine,1TMS,isomer #3 | C[Si](C)(C)N[C@@H](CCCCN)C(=O)O | 1589.5 | Semi standard non polar | 33892256 | L-Lysine,2TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C | 1579.6 | Semi standard non polar | 33892256 | L-Lysine,2TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C | 1678.3 | Standard non polar | 33892256 | L-Lysine,2TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C | 2345.0 | Standard polar | 33892256 | L-Lysine,2TMS,isomer #2 | C[Si](C)(C)NCCCC[C@H](N)C(=O)O[Si](C)(C)C | 1618.5 | Semi standard non polar | 33892256 | L-Lysine,2TMS,isomer #2 | C[Si](C)(C)NCCCC[C@H](N)C(=O)O[Si](C)(C)C | 1735.8 | Standard non polar | 33892256 | L-Lysine,2TMS,isomer #2 | C[Si](C)(C)NCCCC[C@H](N)C(=O)O[Si](C)(C)C | 2354.6 | Standard polar | 33892256 | L-Lysine,2TMS,isomer #3 | C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)O | 1722.9 | Semi standard non polar | 33892256 | L-Lysine,2TMS,isomer #3 | C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)O | 1737.3 | Standard non polar | 33892256 | L-Lysine,2TMS,isomer #3 | C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)O | 2247.7 | Standard polar | 33892256 | L-Lysine,2TMS,isomer #4 | C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C | 1854.0 | Semi standard non polar | 33892256 | L-Lysine,2TMS,isomer #4 | C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C | 1770.1 | Standard non polar | 33892256 | L-Lysine,2TMS,isomer #4 | C[Si](C)(C)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C | 2773.3 | Standard polar | 33892256 | L-Lysine,2TMS,isomer #5 | C[Si](C)(C)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C | 1731.7 | Semi standard non polar | 33892256 | L-Lysine,2TMS,isomer #5 | C[Si](C)(C)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C | 1705.9 | Standard non polar | 33892256 | L-Lysine,2TMS,isomer #5 | C[Si](C)(C)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C | 2500.2 | Standard polar | 33892256 | L-Lysine,3TMS,isomer #1 | C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1715.3 | Semi standard non polar | 33892256 | L-Lysine,3TMS,isomer #1 | C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1842.6 | Standard non polar | 33892256 | L-Lysine,3TMS,isomer #1 | C[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1896.4 | Standard polar | 33892256 | L-Lysine,3TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C | 1783.0 | Semi standard non polar | 33892256 | L-Lysine,3TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C | 1800.7 | Standard non polar | 33892256 | L-Lysine,3TMS,isomer #2 | C[Si](C)(C)OC(=O)[C@H](CCCCN)N([Si](C)(C)C)[Si](C)(C)C | 2231.6 | Standard polar | 33892256 | L-Lysine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C | 1823.3 | Semi standard non polar | 33892256 | L-Lysine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C | 1887.9 | Standard non polar | 33892256 | L-Lysine,3TMS,isomer #3 | C[Si](C)(C)OC(=O)[C@@H](N)CCCCN([Si](C)(C)C)[Si](C)(C)C | 2276.5 | Standard polar | 33892256 | L-Lysine,3TMS,isomer #4 | C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 1915.8 | Semi standard non polar | 33892256 | L-Lysine,3TMS,isomer #4 | C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 1873.0 | Standard non polar | 33892256 | L-Lysine,3TMS,isomer #4 | C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O | 2136.6 | Standard polar | 33892256 | L-Lysine,3TMS,isomer #5 | C[Si](C)(C)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1875.1 | Semi standard non polar | 33892256 | L-Lysine,3TMS,isomer #5 | C[Si](C)(C)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 1866.5 | Standard non polar | 33892256 | L-Lysine,3TMS,isomer #5 | C[Si](C)(C)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C | 2048.9 | Standard polar | 33892256 | L-Lysine,4TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1907.7 | Semi standard non polar | 33892256 | L-Lysine,4TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1947.7 | Standard non polar | 33892256 | L-Lysine,4TMS,isomer #1 | C[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)C(=O)O[Si](C)(C)C | 1874.9 | Standard polar | 33892256 | L-Lysine,4TMS,isomer #2 | C[Si](C)(C)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1891.0 | Semi standard non polar | 33892256 | L-Lysine,4TMS,isomer #2 | C[Si](C)(C)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1955.3 | Standard non polar | 33892256 | L-Lysine,4TMS,isomer #2 | C[Si](C)(C)NCCCC[C@@H](C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1836.3 | Standard polar | 33892256 | L-Lysine,4TMS,isomer #3 | C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2051.7 | Semi standard non polar | 33892256 | L-Lysine,4TMS,isomer #3 | C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 1993.4 | Standard non polar | 33892256 | L-Lysine,4TMS,isomer #3 | C[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2008.6 | Standard polar | 33892256 | L-Lysine,5TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2136.7 | Semi standard non polar | 33892256 | L-Lysine,5TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 2055.8 | Standard non polar | 33892256 | L-Lysine,5TMS,isomer #1 | C[Si](C)(C)OC(=O)[C@H](CCCCN([Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C | 1835.1 | Standard polar | 33892256 | L-Lysine,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN | 1694.5 | Semi standard non polar | 33892256 | L-Lysine,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N)C(=O)O | 1876.9 | Semi standard non polar | 33892256 | L-Lysine,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN)C(=O)O | 1836.8 | Semi standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C(C)(C)C | 2059.4 | Semi standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C(C)(C)C | 2069.3 | Standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN)C(=O)O[Si](C)(C)C(C)(C)C | 2390.4 | Standard polar | 33892256 | L-Lysine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C | 2071.1 | Semi standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C | 2136.4 | Standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N)C(=O)O[Si](C)(C)C(C)(C)C | 2421.6 | Standard polar | 33892256 | L-Lysine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O | 2226.0 | Semi standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O | 2125.0 | Standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O | 2324.4 | Standard polar | 33892256 | L-Lysine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 2263.6 | Semi standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 2173.1 | Standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N(CCCC[C@H](N)C(=O)O)[Si](C)(C)C(C)(C)C | 2691.0 | Standard polar | 33892256 | L-Lysine,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C(C)(C)C | 2175.1 | Semi standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C(C)(C)C | 2105.7 | Standard non polar | 33892256 | L-Lysine,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)N([C@@H](CCCCN)C(=O)O)[Si](C)(C)C(C)(C)C | 2462.8 | Standard polar | 33892256 | L-Lysine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2385.1 | Semi standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2384.0 | Standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NCCCC[C@H](N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2244.2 | Standard polar | 33892256 | L-Lysine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2448.9 | Semi standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2371.2 | Standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2395.3 | Standard polar | 33892256 | L-Lysine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2490.5 | Semi standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2462.7 | Standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2452.0 | Standard polar | 33892256 | L-Lysine,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2597.7 | Semi standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2430.6 | Standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O | 2376.8 | Standard polar | 33892256 | L-Lysine,3TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2564.3 | Semi standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2419.3 | Standard non polar | 33892256 | L-Lysine,3TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2317.5 | Standard polar | 33892256 | L-Lysine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2795.5 | Semi standard non polar | 33892256 | L-Lysine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2656.7 | Standard non polar | 33892256 | L-Lysine,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N[C@@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C | 2331.5 | Standard polar | 33892256 | L-Lysine,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2800.7 | Semi standard non polar | 33892256 | L-Lysine,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2646.6 | Standard non polar | 33892256 | L-Lysine,4TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)NCCCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2305.6 | Standard polar | 33892256 | L-Lysine,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2889.3 | Semi standard non polar | 33892256 | L-Lysine,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2706.0 | Standard non polar | 33892256 | L-Lysine,4TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)N(CCCC[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2377.6 | Standard polar | 33892256 | L-Lysine,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 3160.5 | Semi standard non polar | 33892256 | L-Lysine,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2898.8 | Standard non polar | 33892256 | L-Lysine,5TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC(=O)[C@H](CCCCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2379.1 | Standard polar | 33892256 |
|
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-00di-3910000000-98c565675de67aa87900 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0ab9-1910000000-87ef8534f592041f50f2 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS) | splash10-0a4i-1921000000-84f7815b0f650fa17444 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-MS (3 TMS) | splash10-001i-9600000000-823408dba509cb204acf | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-MS (3 TMS) | splash10-00di-3910000000-4f5578af5e7d8b6c49f7 | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-MS (4 TMS) | splash10-0adi-1921000000-4e56d95e623e792f9e6b | 2014-06-16 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine EI-B (Non-derivatized) | splash10-00di-0921000000-eeb49e57bc1a75193058 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine EI-B (Non-derivatized) | splash10-0ab9-0921000000-ebb902be0f3754225b2f | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-TOF (Non-derivatized) | splash10-00di-3910000000-98c565675de67aa87900 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-TOF (Non-derivatized) | splash10-0ab9-1910000000-87ef8534f592041f50f2 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-QQ (Non-derivatized) | splash10-0fdk-3923000000-15b84c2649c1b0455de1 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-TOF (Non-derivatized) | splash10-0a4i-1921000000-84f7815b0f650fa17444 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-MS (Non-derivatized) | splash10-001i-9600000000-823408dba509cb204acf | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-MS (Non-derivatized) | splash10-00di-3910000000-4f5578af5e7d8b6c49f7 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-MS (Non-derivatized) | splash10-0adi-1921000000-4e56d95e623e792f9e6b | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Lysine GC-EI-TOF (Non-derivatized) | splash10-0abi-1900000000-9ad174122e4d6e003eb8 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (Non-derivatized) - 70eV, Positive | splash10-0089-9100000000-974cc55c9130ed5213eb | 2016-09-22 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (1 TMS) - 70eV, Positive | splash10-0ue9-9700000000-57b24ae819b6ec26bfd2 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Lysine GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-003r-8900000000-470a0beb4f338ed89bca | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-001i-9000000000-74e9193d9d33c2509bfa | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-0a59-9000000000-822c4e78250fffa56e39 | 2012-07-24 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0002-0900000000-04f9a62a77fb5a37ca22 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-001i-9000000000-035035ecfa084671479b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-001i-0900000000-5bb15839f86f4fca0d0b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-001i-0900000000-6c8ef03aa83eb1cab35b | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-01ot-0910000000-c182a7dcdbc260666978 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-0a4j-0900000000-6c5f378cef2f14204e15 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-001i-0900000000-41e1a6499097748934b0 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive-QTOF | splash10-03di-0390000000-7270a0b85b9e3f9f6373 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF | splash10-0002-0900000000-a997e809874357908880 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF | splash10-0002-2900000000-f64110414f82c93e1fe8 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF | splash10-014m-9200000000-33a38e6370811c5ddc82 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF | splash10-0006-9000000000-3a8b0b6e62f5c66d3720 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF | splash10-0006-9000000000-d5167570d11d77fd541e | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF | splash10-0002-0900000000-a46231bd529176101129 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF | splash10-001i-9200000000-f8b9f01b2a9886c51df9 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF | splash10-001i-9000000000-ace0361476d939043e98 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF | splash10-001i-9000000000-5b06b6e9dcf9faf8e89c | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF | splash10-053r-9000000000-2894ef6d7f72ea71688e | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive-QTOF | splash10-0002-0900000000-290902f43cf851e8ef5e | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-001i-9300000000-f81193f6b50235ec8147 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF | splash10-001i-9300000000-8931d2193adab166d5e4 | 2012-08-31 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Lysine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF | splash10-0002-0900000000-b4825cc64fcb830c6967 | 2012-08-31 | HMDB team, MONA | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-29 | Wishart Lab | View Spectrum | Experimental 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, experimental) | 2021-10-10 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+) | 2022-02-11 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
|
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Disease References | Refractory localization-related epilepsy |
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- Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [PubMed:14992292 ]
| Alzheimer's disease |
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- Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. [PubMed:17031479 ]
- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Schizophrenia |
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- Bjerkenstedt L, Edman G, Hagenfeldt L, Sedvall G, Wiesel FA: Plasma amino acids in relation to cerebrospinal fluid monoamine metabolites in schizophrenic patients and healthy controls. Br J Psychiatry. 1985 Sep;147:276-82. [PubMed:2415198 ]
| Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
| Lysinuric protein intolerance |
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- Kurko J, Tringham M, Tanner L, Nanto-Salonen K, Vaha-Makila M, Nygren H, Poho P, Lietzen N, Mattila I, Olkku A, Hyotylainen T, Oresic M, Simell O, Niinikoski H, Mykkanen J: Imbalance of plasma amino acids, metabolites and lipids in patients with lysinuric protein intolerance (LPI). Metabolism. 2016 Sep;65(9):1361-75. doi: 10.1016/j.metabol.2016.05.012. Epub 2016 May 27. [PubMed:27506743 ]
- Habib A, Azize NA, Yakob Y, Md Yunus Z, Wee TK: Biochemical and molecular characteristics of Malaysian patients with lysinuric protein intolerance. Malays J Pathol. 2016 Dec;38(3):305-310. [PubMed:28028301 ]
- Olli Simell (1995). Lysinuric Protein Intolerance and Other Cationic Aminoacidurias. The metabolic and molecular bases of inherited disease, 7/e; Editors: C.R.Scriver, A.L.Beaudet, W.S.Sly, D.Valle; McGraw-Hill Inc. (1995) DOI: 10.1036/ommbid.225. McGraw-Hill Inc..
| Fumarase deficiency |
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- Allegri G, Fernandes MJ, Scalco FB, Correia P, Simoni RE, Llerena JC Jr, de Oliveira ML: Fumaric aciduria: an overview and the first Brazilian case report. J Inherit Metab Dis. 2010 Aug;33(4):411-9. doi: 10.1007/s10545-010-9134-2. Epub 2010 Jun 15. [PubMed:20549362 ]
| Histidinemia |
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- Nyhan WL, Hilton S: Histidinuria: defective transport of histidine. Am J Med Genet. 1992 Nov 15;44(5):558-61. [PubMed:1481808 ]
| Citrullinemia type II, neonatal-onset |
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- Ohura T, Kobayashi K, Tazawa Y, Nishi I, Abukawa D, Sakamoto O, Iinuma K, Saheki T: Neonatal presentation of adult-onset type II citrullinemia. Hum Genet. 2001 Feb;108(2):87-90. [PubMed:11281457 ]
| Pyruvate carboxylase deficiency |
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- Habarou F, Brassier A, Rio M, Chretien D, Monnot S, Barbier V, Barouki R, Bonnefont JP, Boddaert N, Chadefaux-Vekemans B, Le Moyec L, Bastin J, Ottolenghi C, de Lonlay P: Pyruvate carboxylase deficiency: An underestimated cause of lactic acidosis. Mol Genet Metab Rep. 2014 Nov 28;2:25-31. doi: 10.1016/j.ymgmr.2014.11.001. eCollection 2015 Mar. [PubMed:28649521 ]
| Lipoyltransferase 1 Deficiency |
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- Soreze Y, Boutron A, Habarou F, Barnerias C, Nonnenmacher L, Delpech H, Mamoune A, Chretien D, Hubert L, Bole-Feysot C, Nitschke P, Correia I, Sardet C, Boddaert N, Hamel Y, Delahodde A, Ottolenghi C, de Lonlay P: Mutations in human lipoyltransferase gene LIPT1 cause a Leigh disease with secondary deficiency for pyruvate and alpha-ketoglutarate dehydrogenase. Orphanet J Rare Dis. 2013 Dec 17;8:192. doi: 10.1186/1750-1172-8-192. [PubMed:24341803 ]
| Leukemia |
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- Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [PubMed:15911239 ]
| L-2-Hydroxyglutaric aciduria |
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- Barbot C, Fineza I, Diogo L, Maia M, Melo J, Guimaraes A, Pires MM, Cardoso ML, Vilarinho L: L-2-Hydroxyglutaric aciduria: clinical, biochemical and magnetic resonance imaging in six Portuguese pediatric patients. Brain Dev. 1997 Jun;19(4):268-73. [PubMed:9187477 ]
| Crohn's disease |
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- Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Ulcerative colitis |
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- Marchesi JR, Holmes E, Khan F, Kochhar S, Scanlan P, Shanahan F, Wilson ID, Wang Y: Rapid and noninvasive metabonomic characterization of inflammatory bowel disease. J Proteome Res. 2007 Feb;6(2):546-51. [PubMed:17269711 ]
- Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
- Kolho KL, Pessia A, Jaakkola T, de Vos WM, Velagapudi V: Faecal and Serum Metabolomics in Paediatric Inflammatory Bowel Disease. J Crohns Colitis. 2017 Mar 1;11(3):321-334. doi: 10.1093/ecco-jcc/jjw158. [PubMed:27609529 ]
| Irritable bowel syndrome |
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- Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
- Hong YS, Hong KS, Park MH, Ahn YT, Lee JH, Huh CS, Lee J, Kim IK, Hwang GS, Kim JS: Metabonomic understanding of probiotic effects in humans with irritable bowel syndrome. J Clin Gastroenterol. 2011 May-Jun;45(5):415-25. doi: 10.1097/MCG.0b013e318207f76c. [PubMed:21494186 ]
| Colorectal cancer |
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- Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ]
- Ritchie SA, Ahiahonu PW, Jayasinghe D, Heath D, Liu J, Lu Y, Jin W, Kavianpour A, Yamazaki Y, Khan AM, Hossain M, Su-Myat KK, Wood PL, Krenitsky K, Takemasa I, Miyake M, Sekimoto M, Monden M, Matsubara H, Nomura F, Goodenowe DB: Reduced levels of hydroxylated, polyunsaturated ultra long-chain fatty acids in the serum of colorectal cancer patients: implications for early screening and detection. BMC Med. 2010 Feb 15;8:13. doi: 10.1186/1741-7015-8-13. [PubMed:20156336 ]
- Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
- Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
| Autism |
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- De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
| Perillyl alcohol administration for cancer treatment |
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- Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
| Pancreatic cancer |
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- Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
- Zhang L, Jin H, Guo X, Yang Z, Zhao L, Tang S, Mo P, Wu K, Nie Y, Pan Y, Fan D: Distinguishing pancreatic cancer from chronic pancreatitis and healthy individuals by (1)H nuclear magnetic resonance-based metabonomic profiles. Clin Biochem. 2012 Sep;45(13-14):1064-9. doi: 10.1016/j.clinbiochem.2012.05.012. Epub 2012 May 19. [PubMed:22613268 ]
| Periodontal disease |
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- Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
| Frontotemporal dementia |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Lewy body disease |
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- Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
| Attachment loss |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Missing teeth |
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- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Periodontal Probing Depth |
---|
- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Supragingival Calculus |
---|
- Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
| Carbamoyl Phosphate Synthetase Deficiency |
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- Freeman JM, Nicholson JF, Schimke RT, Rowland LP, Carter S: Congenital hyperammonemia. Association with hyperglycinemia and decreased levels of carbamyl phosphate synthetase. Arch Neurol. 1970 Nov;23(5):430-7. [PubMed:5471650 ]
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| Autosomal dominant polycystic kidney disease |
---|
- Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
| Propionic acidemia |
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- Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
| Tyrosinemia I |
---|
- Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
| Eosinophilic esophagitis |
---|
- Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
| Hyperdibasic aminoaciduria I |
---|
- Whelan DT, Scriver CR: Hyperdibasicaminoaciduria: an inherited disorder of amino acid transport. Pediatr Res. 1968 Nov;2(6):525-34. [PubMed:5727921 ]
| Cystinuria |
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- Fjellstedt E, Harnevik L, Jeppsson JO, Tiselius HG, Soderkvist P, Denneberg T: Urinary excretion of total cystine and the dibasic amino acids arginine, lysine and ornithine in relation to genetic findings in patients with cystinuria treated with sulfhydryl compounds. Urol Res. 2003 Dec;31(6):417-25. Epub 2003 Oct 25. [PubMed:14586528 ]
| Alpha-aminoadipic and alpha-ketoadipic aciduria |
---|
- Takechi T, Okada T, Wakiguchi H, Morita H, Kurashige T, Sugahara K, Kodama H: Identification of N-acetyl-alpha-aminoadipic acid in the urine of a patient with alpha-aminoadipic and alpha-ketoadipic aciduria. J Inherit Metab Dis. 1993;16(1):119-26. [PubMed:8487492 ]
| 2,4-dienoyl-CoA reductase deficiency |
---|
- Houten SM, Denis S, Te Brinke H, Jongejan A, van Kampen AH, Bradley EJ, Baas F, Hennekam RC, Millington DS, Young SP, Frazier DM, Gucsavas-Calikoglu M, Wanders RJ: Mitochondrial NADP(H) deficiency due to a mutation in NADK2 causes dienoyl-CoA reductase deficiency with hyperlysinemia. Hum Mol Genet. 2014 Sep 15;23(18):5009-16. doi: 10.1093/hmg/ddu218. Epub 2014 May 8. [PubMed:24847004 ]
| Hyperlysinuria |
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- Omura K, Yamanaka N, Higami S, Matsuoka O, Fujimoto A: Lysine malabsorption syndrome: a new type of transport defect. Pediatrics. 1976 Jan;57(1):102-5. [PubMed:1246485 ]
- Fjellstedt E, Harnevik L, Jeppsson JO, Tiselius HG, Soderkvist P, Denneberg T: Urinary excretion of total cystine and the dibasic amino acids arginine, lysine and ornithine in relation to genetic findings in patients with cystinuria treated with sulfhydryl compounds. Urol Res. 2003 Dec;31(6):417-25. Epub 2003 Oct 25. [PubMed:14586528 ]
| Hyperlysinemia I, familial |
---|
- Tondo M, Calpena E, Arriola G, Sanz P, Martorell L, Ormazabal A, Castejon E, Palacin M, Ugarte M, Espinos C, Perez B, Perez-Duenas B, Perez-Cerda C, Artuch R: Clinical, biochemical, molecular and therapeutic aspects of 2 new cases of 2-aminoadipic semialdehyde synthase deficiency. Mol Genet Metab. 2013 Nov;110(3):231-6. doi: 10.1016/j.ymgme.2013.06.021. Epub 2013 Jul 6. [PubMed:23890588 ]
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