Record Information |
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Version | 1.0 |
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Creation date | 2015-10-09 22:29:16 UTC |
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Update date | 2017-01-19 02:36:17 UTC |
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FoodComEx ID | PC000215 |
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FoodDB Record | FDB002257 |
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Chemical Information |
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Name | Arginine |
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Description | Arginine or l-arginine, abbreviated Arg or R, is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Pre-term infants are unable to effectively synthesize arginine, making it nutritionally essential for them. Adults, however, synthesize arginine from glutamate via citrulline. Arginine is a basic amino acid as its side chain contains a positively charged guanidinium group, which is highly polar, at the end of a hydrophobic aliphatic hydrocarbon chain. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is a precursor of nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of the hormones, growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. While many studies suggested that plant based protein-rich foods like soy protein, which contain less arginine, reduced cardiovascular risk compared to arginine rich foods like animal proteins, other studies have found little or null effects (PMID: 20042191). |
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CAS Number | 74-79-3 |
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Structure | |
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Synonyms | Synonym | Source |
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(2S)-2-amino-5-(Carbamimidamido)pentanoate | Generator | (2S)-2-Amino-5-(carbamimidamido)pentanoic acid | biospider | (2S)-2-Amino-5-(diaminomethylideneamino)pentanoic acid | biospider | (2S)-2-amino-5-Guanidinopentanoate | Generator | (2S)-2-Amino-5-guanidinopentanoic acid | biospider | (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoate | biospider | (S)-2-Amino-5-[(aminoiminomethyl)amino]-pentanoic acid | biospider | (S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoate | HMDB | (S)-2-amino-5-[(Aminoiminomethyl)amino]pentanoic acid | HMDB | (S)-2-amino-5-Guanidinopentanoate | Generator | (S)-2-Amino-5-guanidinopentanoic acid | biospider | (S)-2-amino-5-Guanidinovalerate | Generator | (S)-2-Amino-5-guanidinovaleric acid | biospider | 2-amino-5-Guanidinovalerate | HMDB | 2-amino-5-Guanidinovaleric acid | HMDB | 5-[(Aminoiminomethyl)amino]-L-Norvaline | biospider | Arg | biospider | Arginine, INN, USAN; L-form | db_source | FEMA 3819 | db_source | L-(+)-Arginine | biospider | L-a-Amino-d-guanidinovalerate | biospider | L-a-Amino-d-guanidinovaleric acid | biospider | L-alpha-Amino-delta-guanidinovalerate | biospider | L-alpha-Amino-delta-guanidinovaleric acid | biospider | L-Arg | ChEBI | L-Arginin | ChEBI | L-Arginine | ChEBI | L-Arginine (9CI) | biospider | N5-(Aminoiminomethyl)-L-ornithine | biospider | Pentanoic acid, 2-amino-5-((aminoiminomethyl)amino)-, (S)- | biospider | R | ChEBI | S-(+)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid | biospider | S-Arginine | manual |
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Chemical Formula | C6H14N4O2 |
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IUPAC name | (2S)-2-amino-5-carbamimidamidopentanoic acid |
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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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Isomeric SMILES | N[C@@H](CCCNC(N)=N)C(O)=O |
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Average Molecular Weight | 174.201 |
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Monoisotopic Molecular Weight | 174.111675712 |
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Chemical Taxonomy |
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Classification | Not classified |
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Physico-Chemical Properties - Experimental |
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Property | Value | Reference |
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Experimental logP | -4.20 | HANSCH,C ET AL. (1995) |
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Experimental Water Solubility | 182 mg/mL at 25 oC | YALKOWSKY,SH & DANNENFELSER,RM (1992) |
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Melting Point | Mp 244 dec. (anhyd. 105°) | DFC |
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Foods of Origin |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Production Data |
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Production Method | commercial |
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Production Method Reference | Not Available |
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Production Method Reference File | Not Available |
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Quantity Available | Production upon request, up to 2 g |
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Delivery Time | Not Available |
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Storage Form | solid |
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Storage Conditions | -80°C |
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Stability | Not Available |
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Purity | Not Available |
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Spectra |
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Spectral Data Upon Request | Not Available |
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Provider Information |
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Commercial Vendors |
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AKSci | K277 |
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Glentham | GM7438 |
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Glentham | GM1092 |
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MetaSci | HMDB0000517 |
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Sigma-Aldrich | HMDB0000517 |
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Toronto Research Chemicals | A769505 |
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