Record Information |
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Version | 2.0 |
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Creation Date | 2014-08-29 06:21:59 UTC |
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Update Date | 2014-12-24 20:26:46 UTC |
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Accession Number | T3D4320 |
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Identification |
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Common Name | L-Alanine |
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Class | Small Molecule |
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Description | Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system. |
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Compound Type | - Amine
- Animal Toxin
- Dietary Supplement
- Drug
- Food Toxin
- Household Toxin
- Metabolite
- Micronutrient
- Natural Compound
- Non-Essential Amino Acid
- Nutraceutical
- Organic Compound
- Supplement
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Chemical Structure | |
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Synonyms | Synonym | (2S)-2-Aminopropanoate | (2S)-2-Aminopropanoic acid | (S)-(+)-Alanine | (S)-2-amino-Propanoate | (S)-2-amino-Propanoic acid | (S)-2-Aminopropanoate | (S)-2-Aminopropanoic acid | (S)-Alanine | 2-Aminopropanoate | 2-Aminopropanoic acid | 2-Aminopropionate | 2-Aminopropionic acid | 2-Ammoniopropanoate | 2-Ammoniopropanoic acid | a-Alanine | a-Aminopropionate | a-Aminopropionic acid | Ala | Alanine | alpha-Alanine | alpha-Aminopropanoate | alpha-Aminopropanoic acid | alpha-Aminopropionate | alpha-Aminopropionic acid | L-(+)-Alanine | L-2-Aminopropanoate | L-2-Aminopropanoic acid | L-2-Aminopropionate | L-2-Aminopropionic acid | L-a-Alanine | L-a-Aminopropionate | L-a-Aminopropionic acid | L-alpha-Alanine | L-alpha-Aminopropionate | L-alpha-Aminopropionic acid | L-α-alanine |
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Chemical Formula | C3H7NO2 |
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Average Molecular Mass | 89.093 g/mol |
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Monoisotopic Mass | 89.048 g/mol |
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CAS Registry Number | 56-41-7 |
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IUPAC Name | (2S)-2-aminopropanoic acid |
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Traditional Name | L-alanine |
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SMILES | [H][C@@](C)(N)C(O)=O |
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InChI Identifier | InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1 |
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InChI Key | InChIKey=QNAYBMKLOCPYGJ-REOHCLBHSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as alanine and derivatives. Alanine and derivatives are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
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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 | Alanine and derivatives |
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Alternative Parents | |
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Substituents | - Alanine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Hydrocarbon derivative
- Organic oxygen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Primary aliphatic amine
- Carbonyl group
- Amine
- Organopnictogen compound
- Organic oxide
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Endogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Lysosome
- Membrane
- Mitochondria
- Peroxisome
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Biofluid Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Applications | Not Available |
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Biological Roles | |
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Chemical Roles | |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 300 dec°C | Boiling Point | Not Available | Solubility | 1.64E+005 mg/L (at 25°C) | LogP | -2.85 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-014i-0900000000-c7f6dbace291e8305a4e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-014i-0900000000-381ddf4d9ea77be0b8a5 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS) | splash10-01b9-6900000000-6a7c1bb2915e5dd0791f | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (2 TMS) | splash10-014i-1900000000-84b389f82562c29a8148 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-00kf-9000000000-b2f7507be509a85d821b | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-014i-0900000000-941672891ab94cf5015d | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-0f79-0910000000-47bd3e3aa274a653a64e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-0900000000-c7f6dbace291e8305a4e | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-014i-0900000000-381ddf4d9ea77be0b8a5 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-QQ (Non-derivatized) | splash10-0a4i-1940000000-5def9f7c902aaf1ef607 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-01b9-6900000000-6a7c1bb2915e5dd0791f | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-014i-1900000000-84b389f82562c29a8148 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9000000000-d31f7a2ed8284a740b59 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0006-9100000000-ab365202f52df8e6d401 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-9000000000-96b54b269c91ab21be08 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0006-9000000000-a8008305399aa1097e1a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-7253c912562200edc231 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive | splash10-00kf-9000000000-72694f3a1a5de3b49790 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-000i-9000000000-55d0139f513946f76461 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-000i-9000000000-5b0dff13a98daf782205 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-000i-9000000000-37db595fcf7364600bc9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0006-9000000000-5129e160acf979ac549e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-0006-9000000000-11c20eba8c5ad41d806c | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-0006-9000000000-df7c7d6a6ae2d6bccefe | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-0006-9000000000-32477244247613182214 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-000f-9002000000-4873ce0cdcac54d68186 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positive | splash10-0006-9000000000-8193842b36c819ca3ec6 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-55d0139f513946f76461 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-5b0dff13a98daf782205 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-000i-9000000000-37db595fcf7364600bc9 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-fefc31c264a2f0fcf6d0 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-ba42bcd60aa9182a780e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-0006-9000000000-df7c7d6a6ae2d6bccefe | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-9000000000-080ffbbf05d95b7bcfe6 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-0dfcc5cb0b7d9f01e04a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-002f-9000000000-130c999fe6b63419cfa1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-9000000000-2ddc0bb04bae8f928a23 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-9000000000-98c403c9cd494594babf | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-9000000000-38a12affa4e4f4e91626 | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | L-Alanine is a non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and the central nervous system. BCAAs are used as a source of energy for muscle cells. During prolonged exercise, BCAAs are released from skeletal muscles and their carbon backbones are used as fuel, while their nitrogen portion is used to form another amino acid, Alanine. Alanine is then converted to Glucose by the liver. This form of energy production is called the Alanine-Glucose cycle, and it plays a major role in maintaining the body's blood sugar balance. |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | Used for protein synthesis. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00160 |
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HMDB ID | HMDB00161 |
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PubChem Compound ID | 5950 |
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ChEMBL ID | CHEMBL12198 |
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ChemSpider ID | 5735 |
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KEGG ID | C01401 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 16977 |
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BioCyc ID | L-ALPHA-ALANINE |
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CTD ID | Not Available |
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Stitch ID | Not Available |
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PDB ID | ALA |
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ACToR ID | Not Available |
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Wikipedia Link | 2-Aminopropanoic acid |
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References |
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Synthesis Reference | Daniel T. Belmont, Valerie Hendrickson, Mark J. Hoekman, “Process for the preparation of an L-alanine compound.” U.S. Patent US5268483, issued October, 1953. |
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MSDS | Link |
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General References | - Iioka H, Hisanaga H, Moriyama IS, Akada S, Shimamoto T, Yamada Y, Ichijo M: Characterization of human placental activity for transport of L-alanine, using brush border (microvillous) membrane vesicles. Placenta. 1992 Mar-Apr;13(2):179-90. [1631030 ]
- 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. [15911239 ]
- Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [12297216 ]
- 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. [14992292 ]
- Bairaktari E, Katopodis K, Siamopoulos KC, Tsolas O: Paraquat-induced renal injury studied by 1H nuclear magnetic resonance spectroscopy of urine. Clin Chem. 1998 Jun;44(6 Pt 1):1256-61. [9625050 ]
- Saklatvala J: Hydrolysis of the elastase substrate succinyltrialanine nitroanilide by a metal-dependent enzyme in rheumatoid synovial fluid. J Clin Invest. 1977 May;59(5):794-801. [16038 ]
- Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. [7729054 ]
- Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [12097436 ]
- Klassen P, Furst P, Schulz C, Mazariegos M, Solomons NW: Plasma free amino acid concentrations in healthy Guatemalan adults and in patients with classic dengue. Am J Clin Nutr. 2001 Mar;73(3):647-52. [11237944 ]
- Stahl A, Frick A, Imler M, Schlienger JL: Semiautomated enzymic microassay for plasma L-alanine. Enzyme. 1979;24(5):294-301. [41707 ]
- Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. [6696735 ]
- Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [6198473 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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