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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:20:27 UTC |
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Update Date | 2020-06-04 20:48:06 UTC |
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BMDB ID | BMDB0000168 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Asparagine |
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Description | L-Asparagine, also known as Asn or aspartamic acid, belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. L-Asparagine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. L-Asparagine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Asparagine exists in all living species, ranging from bacteria to humans. L-Asparagine is a potentially toxic compound. L-Asparagine has been found to be associated with several diseases known as pregnancy, cystic fibrosis, gout, and leukemia; also l-asparagine has been linked to the inborn metabolic disorders including celiac disease. |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2,4-Diamino-4-oxobutanoic acid | ChEBI | (2S)-2-Amino-3-carbamoylpropanoic acid | ChEBI | (S)-2-Amino-3-carbamoylpropanoic acid | ChEBI | (S)-Asparagine | ChEBI | 2-Aminosuccinamic acid | ChEBI | alpha-Aminosuccinamic acid | ChEBI | Asn | ChEBI | ASPARAGINE | ChEBI | Aspartamic acid | ChEBI | L-2-Aminosuccinamic acid | ChEBI | L-Asparagin | ChEBI | L-Aspartic acid beta-amide | ChEBI | N | ChEBI | (2S)-2,4-Diamino-4-oxobutanoate | Generator | (2S)-2-Amino-3-carbamoylpropanoate | Generator | (S)-2-Amino-3-carbamoylpropanoate | Generator | 2-Aminosuccinamate | Generator | a-Aminosuccinamate | Generator | a-Aminosuccinamic acid | Generator | alpha-Aminosuccinamate | Generator | Α-aminosuccinamate | Generator | Α-aminosuccinamic acid | Generator | Aspartamate | Generator | L-2-Aminosuccinamate | Generator | L-Aspartate b-amide | Generator | L-Aspartate beta-amide | Generator | L-Aspartate β-amide | Generator | L-Aspartic acid b-amide | Generator | L-Aspartic acid β-amide | Generator | (-)-Asparagine | HMDB | (S)-2,4-Diamino-4-oxobutanoate | HMDB | (S)-2,4-Diamino-4-oxobutanoic acid | HMDB | Agedoite | HMDB | alpha Amminosuccinamate | HMDB | alpha Amminosuccinamic acid | HMDB | Altheine | HMDB | Asparagine acid | HMDB | Asparamide | HMDB | Aspartic acid amide | HMDB | Aspartic acid b-amide | HMDB | Aspartic acid beta amide | HMDB | b2,4-(S)-Diamino-4-oxo-utanoate | HMDB | b2,4-(S)-Diamino-4-oxo-utanoic acid | HMDB | Crystal VI | HMDB | L-2,4-Diamino-4-oxobutanoate | HMDB | L-2,4-Diamino-4-oxobutanoic acid | HMDB | L-Aspartamine | HMDB | L-b-Asparagine | HMDB | L-beta-Asparagine | HMDB |
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Chemical Formula | C4H8N2O3 |
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Average Molecular Weight | 132.1179 |
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Monoisotopic Molecular Weight | 132.053492132 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 70-47-3 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1 |
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InChI Key | DCXYFEDJOCDNAF-REOHCLBHSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as asparagine and derivatives. Asparagine and derivatives are compounds containing asparagine or a derivative thereof resulting from reaction of asparagine 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 | Asparagine and derivatives |
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Alternative Parents | |
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Substituents | - Asparagine or derivatives
- Alpha-amino acid
- L-alpha-amino acid
- Fatty amide
- Fatty acyl
- Fatty acid
- Carboxamide group
- Amino acid
- Primary carboxylic acid amide
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organic nitrogen compound
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Hydrocarbon derivative
- Primary aliphatic amine
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Amine
- 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 | |
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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 | 234 - 235 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 29.4 mg/mL | Not Available | LogP | -3.82 | CHMELIK,J ET AL. (1991) |
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Predicted Properties | Not Available |
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Spectra |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semimembranosus Muscle
- Testis
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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 | 27.4 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 22-27 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 25.6 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 20-33 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 34-40 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 25 +/- 4 uM | 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 but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 169 +/- 37 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 40 +/- 12 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 | 6.6 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6.5 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 7 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6.5 +/- 0.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 8 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 5.3 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 6 +/- 2 uM | 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 | 106-225 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 | 1 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 46 +/- 17 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 48 +/- 11 nmol/g of tissue | 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 | 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 | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Mycobacterium avium subsp. paratuberculosis infection | | details | Blood | Detected and Quantified | 23.6 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | details | Blood | Detected and Quantified | 24 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | 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 |
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External Links |
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HMDB ID | HMDB0000168 |
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DrugBank ID | DB00174 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB000787 |
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KNApSAcK ID | C00001341 |
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Chemspider ID | 6031 |
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KEGG Compound ID | C00152 |
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BioCyc ID | ASN |
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BiGG ID | 34055 |
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Wikipedia Link | Asparagine |
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METLIN ID | 14 |
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PubChem Compound | 6267 |
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PDB ID | Not Available |
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ChEBI ID | 17196 |
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References |
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Synthesis Reference | Wang, Fangda. Preparation of L-b-asparagine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 8 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - 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 ]
- 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.
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