| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:20:21 UTC |
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| Update Date | 2020-06-04 22:07:36 UTC |
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| BMDB ID | BMDB0000161 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | L-Alanine |
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| Description | L-Alanine, also known as (S)-alanine or L-alpha-alanine, 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. L-Alanine is a drug which is used for protein synthesis. L-Alanine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Alanine exists in all living species, ranging from bacteria to humans. L-Alanine is a potentially toxic compound. L-Alanine has been found to be associated with several diseases known as eosinophilic esophagitis, late-onset preeclampsia, autism, and perillyl alcohol administration for cancer treatment; also l-alanine has been linked to the inborn metabolic disorders including glucagon deficiency. |
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| Structure | |
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| Synonyms | | Value | Source |
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| (2S)-2-Aminopropanoic acid | ChEBI | | (S)-2-Aminopropanoic acid | ChEBI | | (S)-Alanine | ChEBI | | A | ChEBI | | Ala | ChEBI | | ALANINE | ChEBI | | L-2-Aminopropionic acid | ChEBI | | L-Alanin | ChEBI | | L-alpha-Alanine | ChEBI | | (2S)-2-Aminopropanoate | Generator | | (S)-2-Aminopropanoate | Generator | | L-2-Aminopropionate | Generator | | L-a-Alanine | Generator | | L-Α-alanine | Generator | | (S)-(+)-Alanine | HMDB | | (S)-2-Amino-propanoate | HMDB | | (S)-2-Amino-propanoic acid | HMDB | | 2-Aminopropanoate | HMDB | | 2-Aminopropanoic acid | HMDB | | 2-Aminopropionate | HMDB | | 2-Aminopropionic acid | HMDB | | 2-Ammoniopropanoate | HMDB | | 2-Ammoniopropanoic acid | HMDB | | a-Alanine | HMDB | | a-Aminopropionate | HMDB | | a-Aminopropionic acid | HMDB | | alpha-Alanine | HMDB | | alpha-Aminopropanoate | HMDB | | alpha-Aminopropanoic acid | HMDB | | alpha-Aminopropionate | HMDB | | alpha-Aminopropionic acid | HMDB | | L-(+)-Alanine | HMDB | | L-2-Aminopropanoate | HMDB | | L-2-Aminopropanoic acid | HMDB | | L-a-Aminopropionate | HMDB | | L-a-Aminopropionic acid | HMDB | | L-alpha-Aminopropionate | HMDB | | L-alpha-Aminopropionic acid | HMDB | | Abufène | HMDB | | Alanine doms-adrian brand | HMDB | | Alanine, L-isomer | HMDB | | Doms-adrian brand OF alanine | HMDB | | Doms adrian brand OF alanine | HMDB | | L-Isomer alanine | HMDB | | Alanine, L isomer | HMDB | | L Alanine | HMDB |
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| Chemical Formula | C3H7NO2 |
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| Average Molecular Weight | 89.0932 |
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| Monoisotopic Molecular Weight | 89.047678473 |
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| IUPAC Name | (2S)-2-aminopropanoic acid |
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| Traditional Name | L-alanine |
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| CAS Registry Number | 56-41-7 |
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| SMILES | C[C@H](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 | 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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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cytoplasm
- Lysosome
- Mitochondria
- Peroxisome
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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 | 300 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 204 mg/mL | Human Metabolome Project | | LogP | -2.85 | SANGSTER (1994) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Lysosome
- Mitochondria
- Peroxisome
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| Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
- Urine
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| Pathways | |
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| Normal Concentrations |
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| All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 188.9 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 1343 +/- 402 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 162-179 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 160.5 uM | Not Specified | Both | Normal | | details | | Blood | Detected and Quantified | 151-222 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 162-212 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 187-206 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 240 +/- 30 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 2366-3515 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 1388 +/- 276 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 1465 +/- 272 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 29.20 +/- 5.91 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 29 - 78 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 9 - 91 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13469.0414 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13469.0414 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13469.0414 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 13469.0414 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12346.621 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12346.621 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 12346.621 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 29 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 33 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 31 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 32 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 31 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 33 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 32 +/- 1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 34 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 27.45 +/- 5.67 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 23.82 +/- 5.36 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1087.79 +/- 32.71 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1147.17 +/- 64.08 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1163.71 +/- 86.55 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1237.91 +/- 72.51 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1055-1310 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 22790 +/- 1780 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 26340 +/- 2260 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 16280 +/- 2200 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 18950 +/- 1630 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 2300 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 167-239 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 1916-3173 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 244 +/- 40 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 314 +/- 84 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 441 +/- 74 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 220 +/- 51 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 220 +/- 51 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 83-799 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 135-315 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 212 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 397 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 415 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 197 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 234.9 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 323.4 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 1060 +/- 484 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 480.1 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 212.1 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 212.13 +/- 47.03 uM | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 1472 +/- 278 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 880-1200 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 1400 +/- 294 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | | Blood | Detected and Quantified | 174.7 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | | Blood | Detected and Quantified | 253.3 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | details | | Blood | Detected and Quantified | 1149 +/- 192 uM | Not Specified | Not Specified | Left displaced abomasum (LDA) | | details | | Blood | Detected and Quantified | 903 +/- 238 uM | Not Specified | Not Specified | Right displaced abomasum (RDA) | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Ruminal Fluid | Detected and Quantified | 480.07 +/- 70.1 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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| External Links |
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| HMDB ID | HMDB0000161 |
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| DrugBank ID | DB00160 |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB000556 |
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| KNApSAcK ID | C00001332 |
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| Chemspider ID | 5735 |
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| KEGG Compound ID | C00041 |
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| BioCyc ID | L-ALPHA-ALANINE |
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| BiGG ID | 33629 |
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| Wikipedia Link | Alanine |
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| METLIN ID | Not Available |
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| PubChem Compound | 5950 |
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| PDB ID | Not Available |
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| ChEBI ID | 16977 |
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| References |
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| Synthesis Reference | Chibata I; Kakimoto T; Kato J Enzymatic production of L-alanine by Pseudomonas dacunhae. Applied microbiology (1965), 13(5), 638-45. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Klein MS, Buttchereit N, Miemczyk SP, Immervoll AK, Louis C, Wiedemann S, Junge W, Thaller G, Oefner PJ, Gronwald W: NMR metabolomic analysis of dairy cows reveals milk glycerophosphocholine to phosphocholine ratio as prognostic biomarker for risk of ketosis. J Proteome Res. 2012 Feb 3;11(2):1373-81. doi: 10.1021/pr201017n. Epub 2011 Dec 9. [PubMed:22098372 ]
- Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
- Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6. [PubMed:25108860 ]
- Lu J, Antunes Fernandes E, Paez Cano AE, Vinitwatanakhun J, Boeren S, van Hooijdonk T, van Knegsel A, Vervoort J, Hettinga KA: Changes in milk proteome and metabolome associated with dry period length, energy balance, and lactation stage in postparturient dairy cows. J Proteome Res. 2013 Jul 5;12(7):3288-96. doi: 10.1021/pr4001306. Epub 2013 Jun 5. [PubMed:23738862 ]
- Sun HZ, Wang DM, Wang B, Wang JK, Liu HY, Guan le L, Liu JX: Metabolomics of four biofluids from dairy cows: potential biomarkers for milk production and quality. J Proteome Res. 2015 Feb 6;14(2):1287-98. doi: 10.1021/pr501305g. Epub 2015 Jan 28. [PubMed:25599412 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
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