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Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:32:00 UTC |
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Update Date | 2020-06-04 21:47:35 UTC |
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BMDB ID | BMDB0000517 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | L-Arginine |
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Description | L-Arginine, also known as Arg, 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. L-Arginine is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalance. L-Arginine is a very strong basic compound (based on its pKa). L-Arginine exists in all living species, ranging from bacteria to humans. Within cattle, L-arginine participates in a number of enzymatic reactions. In particular, fumaric acid and L-arginine can be biosynthesized from argininosuccinic acid; which is catalyzed by the enzyme argininosuccinate lyase. In addition, L-arginine and glycine can be converted into ornithine and guanidoacetic acid; which is mediated by the enzyme glycine amidinotransferase, mitochondrial. In cattle, L-arginine is involved in the metabolic pathway called the arginine and proline metabolism pathway. L-Arginine is a potentially toxic compound. L-Arginine, with regard to humans, has been found to be associated with several diseases such as frontotemporal dementia, periodontal probing depth, and autism; L-arginine has also been linked to several inborn metabolic disorders including cystinuria and argininemia. |
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Structure | |
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Synonyms | Value | Source |
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(2S)-2-Amino-5-(carbamimidamido)pentanoic acid | ChEBI | (2S)-2-Amino-5-guanidinopentanoic acid | ChEBI | (S)-2-Amino-5-guanidinopentanoic acid | ChEBI | (S)-2-Amino-5-guanidinovaleric acid | ChEBI | Arg | ChEBI | Arginine | ChEBI | L-(+)-Arginine | ChEBI | L-Arg | ChEBI | L-Arginin | ChEBI | R | ChEBI | (2S)-2-Amino-5-(carbamimidamido)pentanoate | Generator | (2S)-2-Amino-5-guanidinopentanoate | Generator | (S)-2-Amino-5-guanidinopentanoate | Generator | (S)-2-Amino-5-guanidinovalerate | Generator | (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoate | HMDB | (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acid | HMDB | (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoate | HMDB | (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid | HMDB | 2-Amino-5-guanidinovalerate | HMDB | 2-Amino-5-guanidinovaleric acid | HMDB | 5-[(Aminoiminomethyl)amino]-L-norvaline | HMDB | L-a-Amino-D-guanidinovalerate | HMDB | L-a-Amino-D-guanidinovaleric acid | HMDB | L-alpha-Amino-delta-guanidinovalerate | HMDB | L-alpha-Amino-delta-guanidinovaleric acid | HMDB | N5-(Aminoiminomethyl)-L-ornithine | HMDB | DL-Arginine acetate, monohydrate | HMDB | L-Isomer arginine | HMDB | Monohydrate DL-arginine acetate | HMDB | L Arginine | HMDB | Arginine, L isomer | HMDB | Arginine, L-isomer | HMDB | Hydrochloride, arginine | HMDB | Arginine hydrochloride | HMDB | DL Arginine acetate, monohydrate | HMDB |
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Chemical Formula | C6H14N4O2 |
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Average Molecular Weight | 174.201 |
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Monoisotopic Molecular Weight | 174.111675712 |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | 74-79-3 |
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SMILES | Not Available |
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InChI Identifier | InChI=1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m0/s1 |
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InChI Key | ODKSFYDXXFIFQN-BYPYZUCNSA-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
- Fatty acid
- Guanidine
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Carboximidamide
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Amine
- Hydrocarbon derivative
- Organic oxide
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Primary aliphatic amine
- Organic oxygen compound
- Organic nitrogen compound
- Carbonyl group
- 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
- Mitochondria
- Myelin sheath
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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 | 222 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 182 mg/mL at 25 °C | Human Metabolome Project | LogP | -4.2 | HANSCH,C ET AL. (1995) |
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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 | - Cytoplasm
- Mitochondria
- Myelin sheath
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Biospecimen Locations | - Adipose Tissue
- Adrenal Cortex
- Bladder
- Blood
- Colostrum
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Liver
- Longissimus Thoracis Muscle
- Milk
- Muscle
- Neuron
- Ovary
- Pancreas
- Placenta
- Platelet
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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Adipose Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Adrenal Cortex | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Bladder | 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 | 218 +/- 33 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 73-98 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 57.2 uM | Not Specified | Both | Normal | | details | Blood | Detected and Quantified | 59 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 135-182 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 54.7-60.4 uM | Not Specified | Not Specified | Normal | | details | Blood | Detected and Quantified | 93.3 +/- 21.7 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 | Epidermis | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Intestine | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Kidney | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 9 +/- 5 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 | 61 +/- 14 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 27.5 +/- 7.2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 27 +/- 12 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 30 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 31.4 +/- 10.3 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21 +/- 1 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 19 +/- 2 uM | Not Specified | Not Specified | Normal | | details | Milk | Detected and Quantified | 21 +/- 3 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 | 299-686 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Neuron | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Ovary | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Pancreas | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Platelet | 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 | 18.84 +/- 14.13 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 17 +/- 11 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 14.2 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 19.9 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 44.5 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 18.8 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 14 +/- 7 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 20 +/- 10 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 44.5 +/- 35.6 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 19 +/- 14 uM | Not Specified | Not Specified | Normal | | details | Ruminal Fluid | Detected and Quantified | 19 +/- 14 uM | Not Specified | Not Specified | Normal | | details | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 70 +/- 16 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Spleen | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 200-460 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 51 +/- 12 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | 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 | Heat stress | | 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 | Ruminal Fluid | Detected and Quantified | 44.51 +/- 34.49 uM | Not Specified | Not Specified | Rumen acidosis | | details |
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External Links |
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HMDB ID | HMDB0000517 |
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DrugBank ID | DB00125 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB002257 |
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KNApSAcK ID | C00001340 |
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Chemspider ID | 6082 |
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KEGG Compound ID | C00062 |
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BioCyc ID | ARG |
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BiGG ID | 33707 |
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Wikipedia Link | L-arginine |
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METLIN ID | 5502 |
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PubChem Compound | 6322 |
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PDB ID | Not Available |
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ChEBI ID | 16467 |
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References |
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Synthesis Reference | Meyer, Helmut E.; Swiderek, Kristine; Hoffmann-Posorske, Edeltraut; Korte, Horst; Heilmeyer, Ludwig M. G., Jr. Quantitative determination of phosphoserine by high-performance liquid chromatography as the phenylthiocarbamyl-S-ethylcysteine. Application to |
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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 ]
- 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 ]
- 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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