L-Arginine
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Basic Info
Common Name | L-Arginine(F05324) |
2D Structure | |
Description | Arginine is an essential amino acid that is physiologically active in the L-form. In mammals, arginine is formally classified as a semiessential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. Arginine can be considered to be a basic amino acid as the part of the side chain nearest to the backbone is long, carbon-containing and hydrophobic, whereas the end of the side chain is a complex guanidinium group. 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 used to make compounds such as nitric oxide, creatine, L-glutamate, L-proline, and it can be converted to glucose and glycogen if needed. In large doses, L-arginine also stimulates the release of 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 (A13142). 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 (A13143). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. The ratio of L-arginine to lysine is also important - soy and other plant proteins have more L-arginine than animal sources of protein. |
FRCD ID | F05324 |
CAS Number | 74-79-3 |
PubChem CID | 6322 |
Formula | C6H14N4O2 |
IUPAC Name | (2S)-2-amino-5-(diaminomethylideneamino)pentanoic acid |
InChI Key | ODKSFYDXXFIFQN-BYPYZUCNSA-N |
InChI | 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 |
Canonical SMILES | C(CC(C(=O)O)N)CN=C(N)N |
Isomeric SMILES | C(C[C@@H](C(=O)O)N)CN=C(N)N |
Wikipedia | L-Arginine |
Synonyms | L-(+)-Arginine L-Arg L(+)-Arginine L-arginine arginine 74-79-3 H-Arg-OH (S)-2-Amino-5-guanidinopentanoic acid (L)-Arginine Arginina |
Classifies | Animal Toxin |
Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic acids and derivatives |
Class | Carboxylic acids and derivatives |
Subclass | Amino acids, peptides, and analogues |
Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids |
Direct Parent | L-alpha-amino acids |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
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 |
Description | This compound 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. |
Properties
Property Name | Property Value |
---|---|
Molecular Weight | 174.204 |
Hydrogen Bond Donor Count | 4 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 5 |
Complexity | 176 |
Monoisotopic Mass | 174.112 |
Exact Mass | 174.112 |
XLogP | -4.2 |
Formal Charge | 0 |
Heavy Atom Count | 12 |
Defined Atom Stereocenter Count | 1 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.6926 |
Human Intestinal Absorption | HIA+ | 0.7537 |
Caco-2 Permeability | Caco2- | 0.7315 |
P-glycoprotein Substrate | Non-substrate | 0.5352 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9846 |
Non-inhibitor | 0.9156 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.7389 |
Distribution | ||
Subcellular localization | Mitochondria | 0.6201 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.7939 |
CYP450 2D6 Substrate | Non-substrate | 0.6806 |
CYP450 3A4 Substrate | Non-substrate | 0.7967 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.8006 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9251 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9270 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9025 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.8813 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9954 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9590 |
Non-inhibitor | 0.9709 | |
AMES Toxicity | AMES toxic | 0.6882 |
Carcinogens | Non-carcinogens | 0.9304 |
Fish Toxicity | Low FHMT | 0.8565 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.7700 |
Honey Bee Toxicity | Low HBT | 0.7135 |
Biodegradation | Ready biodegradable | 0.7386 |
Acute Oral Toxicity | IV | 0.6176 |
Carcinogenicity (Three-class) | Non-required | 0.6495 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -1.4289 | LogS |
Caco-2 Permeability | -0.0394 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.5310 | LD50, mol/kg |
Fish Toxicity | 2.6933 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.3374 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
l-arginine protects against oxidative damage induced by T-2 toxin in mouse Leydig cells. | J Biochem Mol Toxicol | 2018 Oct | 30091165 |
Production of Antigen-Binding Fragment against O,O-Diethyl OrganophosphorusPesticides and Molecular Dynamics Simulations of Antibody Recognition. | Int J Mol Sci | 2018 May 6 | 29734787 |
Effectiveness of Sofosbuvir, Ribavirin and PEG-IFNα-2a in the Treatment of Naïve Egyptian Patients With Chronic Hepatitis C Virus Genotype 4. | Am J Med Sci | 2018 May | 29753376 |
Highly selective apo-arginase based method for sensitive enzymatic assay ofmanganese (II) and cobalt (II) ions. | Spectrochim Acta A Mol Biomol Spectrosc | 2018 Mar 15 | 29268235 |
A novel calcium-binding peptide from Antarctic krill protein hydrolysates andidentification of binding sites of calcium-peptide complex. | Food Chem | 2018 Mar 15 | 29146354 |
Monosodium glutamate impairs the contraction of uterine visceral smooth muscle ex vivo of rat through augmentation of acetylcholine and nitric oxide signaling pathways. | Reprod Biol | 2018 Mar | 29402603 |
Novel photoluminescence enzyme immunoassay based on supramolecular host-guest recognition using L-arginine/6-aza-2-thiothymine-stabilized gold nanocluster. | Biosens Bioelectron | 2018 Jun 30 | 29529510 |
Exploring the Probiotic and Compound Feed Fermentative Applications ofLactobacillus plantarum SK1305 Isolated from Korean Green Chili Pickled Pepper. | Probiotics Antimicrob Proteins | 2018 Jul 20 | 30030782 |
Investigating the effect of dietary calcium levels on ileal endogenous amino acidlosses and standardized ileal amino acid digestibility in broilers and layinghens. | Poult Sci | 2018 Jan 1 | 29077891 |
Milk replacers supplemented with either L-arginine or L-carnitine potentiallyimprove muscle maturation of early reared low birth weight piglets fromhyperprolific sows. | Animal | 2018 Jan | 28641602 |
Protein engineering of CYP105s for their industrial uses. | Biochim Biophys Acta | 2018 Jan | 28583351 |
Genetic Markers Are Associated with the Ruminal Microbiome and Metabolome inGrain and Sugar Challenged Dairy Heifers. | Front Genet | 2018 Feb 27 | 29535763 |
Mechanism of co-aggregation in a protein mixture with small additives. | Int J Biol Macromol | 2018 Feb | 28988840 |
Marginal deficiencies of dietary arginine and methionine could suppress growthperformance and immunological responses in broiler chickens. | J Anim Physiol Anim Nutr (Berl) | 2018 Feb | 28447340 |
Untargeted metabolomics of fresh and heat treatment Tiger nut (Cyperus esculentusL.) milks reveals further insight into food quality and nutrition. | J Chromatogr A | 2017 Sep 8 | 28768579 |
Contributions of molecular size, charge distribution, and specific amino acids tothe iron-binding capacity of sea cucumber (Stichopus japonicus) ovumhydrolysates. | Food Chem | 2017 Sep 1 | 28407960 |
Effects of multi-carbohydrase and phytase on standardized ileal digestibility of amino acids and apparent metabolizable energy in canola meal fed to broilerchicks. | Poult Sci | 2017 Sep 1 | 28854754 |
Benefits of L-alanine or L-arginine supplementation against adiposity and glucoseintolerance in monosodium glutamate-induced obesity. | Eur J Nutr | 2017 Sep | 27317126 |
Dietary l-arginine inhibits intestinal Clostridium perfringens colonisation andattenuates intestinal mucosal injury in broiler chickens. | Br J Nutr | 2017 Sep | 28901890 |
Collagen Peptides from Crucian Skin Improve Calcium Bioavailability andStructural Characterization by HPLC-ESI-MS/MS. | J Agric Food Chem | 2017 Oct 11 | 28915036 |
Targets
- General Function:
- Tetrahydrobiopterin binding
- Specific Function:
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM.
- Gene Name:
- NOS2
- Uniprot ID:
- P35228
- Molecular Weight:
- 131116.3 Da
References
- Cui YY, Tang CS, Geng B: [Restraint stress down-regulates L-Arg/NOS/NO pathway of platelet and aortic intima in rats]. Beijing Da Xue Xue Bao. 2006 Jun 18;38(3):231-5. [16778961 ]
- General Function:
- Argininosuccinate lyase activity
- Gene Name:
- ASL
- Uniprot ID:
- P04424
- Molecular Weight:
- 51657.505 Da
References
- Moradi H, Kwok V, Vaziri ND: Effect of chronic renal failure on arginase and argininosuccinate synthetase expression. Am J Nephrol. 2006;26(3):310-8. Epub 2006 Jun 29. [16809898 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor.
- Gene Name:
- SLC7A1
- Uniprot ID:
- P30825
- Molecular Weight:
- 67637.62 Da
References
- Rotmann A, Simon A, Martine U, Habermeier A, Closs EI: Activation of classical protein kinase C decreases transport via systems y+ and y+L. Am J Physiol Cell Physiol. 2007 Jun;292(6):C2259-68. Epub 2007 Feb 28. [17329401 ]
- General Function:
- Tetrahydrobiopterin binding
- Specific Function:
- Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by forming heterodimers with isoform 1.
- Gene Name:
- NOS3
- Uniprot ID:
- P29474
- Molecular Weight:
- 133287.62 Da
References
- Akamine EH, Kawamoto EM, Scavone C, Nigro D, Carvalho MH, de Cassia A Tostes R, Britto LR, Fortes ZB: Correction of endothelial dysfunction in diabetic female rats by tetrahydrobiopterin and chronic insulin. J Vasc Res. 2006;43(4):309-20. Epub 2006 May 8. [16682803 ]
- General Function:
- Toxic substance binding
- Specific Function:
- Is indirectly involved in the control of blood pressure.
- Gene Name:
- ASS1
- Uniprot ID:
- P00966
- Molecular Weight:
- 46530.055 Da
References
- Moradi H, Kwok V, Vaziri ND: Effect of chronic renal failure on arginase and argininosuccinate synthetase expression. Am J Nephrol. 2006;26(3):310-8. Epub 2006 Jun 29. [16809898 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
- Gene Name:
- SLC7A3
- Uniprot ID:
- Q8WY07
- Molecular Weight:
- 67168.31 Da
References
- Rotmann A, Simon A, Martine U, Habermeier A, Closs EI: Activation of classical protein kinase C decreases transport via systems y+ and y+L. Am J Physiol Cell Physiol. 2007 Jun;292(6):C2259-68. Epub 2007 Feb 28. [17329401 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Involved in the transport of the cationic amino acids (arginine, lysine and ornithine).
- Gene Name:
- SLC7A4
- Uniprot ID:
- O43246
- Molecular Weight:
- 68267.17 Da
References
- Rotmann A, Simon A, Martine U, Habermeier A, Closs EI: Activation of classical protein kinase C decreases transport via systems y+ and y+L. Am J Physiol Cell Physiol. 2007 Jun;292(6):C2259-68. Epub 2007 Feb 28. [17329401 ]
- General Function:
- Putrescine transmembrane transporter activity
- Specific Function:
- Antizyme inhibitor protein that positively regulates ornithine decarboxylase (ODC) activity and polyamine uptake by counteracting the negative effect of antizymes OAZ1, OAZ2 and OAZ3 on ODC1 activity (PubMed:17900240). Inhibits antizyme-dependent ODC1 degradation by binding to antizymes. Releases ODC1 from its inactive complex with antizymes, leading to formation of the catalytically active ODC1. Participates in the morphological integrity of the trans-Golgi network (TGN) and functions as a regulator of intracellular secretory vesicle trafficking (PubMed:20188728).
- Gene Name:
- AZIN2
- Uniprot ID:
- Q96A70
- Molecular Weight:
- 49979.185 Da
References
- Kotil K, Kuscuoglu U, Kirali M, Uzun H, Akcetin M, Bilge T: Investigation of the dose-dependent neuroprotective effects of agmatine in experimental spinal cord injury: a prospective randomized and placebo-control trial. J Neurosurg Spine. 2006 May;4(5):392-9. [16703907 ]
- General Function:
- Metal ion binding
- Specific Function:
- May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to NO synthase. Since NO synthase is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase II plays a role in both male and female sexual arousal. It is therefore a potential target for the treatment of male and female sexual arousal disorders.
- Gene Name:
- ARG2
- Uniprot ID:
- P78540
- Molecular Weight:
- 38577.515 Da
References
- Topal G, Brunet A, Walch L, Boucher JL, David-Dufilho M: Mitochondrial arginase II modulates nitric-oxide synthesis through nonfreely exchangeable L-arginine pools in human endothelial cells. J Pharmacol Exp Ther. 2006 Sep;318(3):1368-74. Epub 2006 Jun 26. [16801455 ]