Basic Info

Common NameL-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 IDF05324
CAS Number74-79-3
PubChem CID6322
FormulaC6H14N4O2
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

WikipediaL-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 DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
Direct ParentL-alpha-amino acids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsL-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
DescriptionThis 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 NameProperty Value
Molecular Weight174.204
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity176
Monoisotopic Mass174.112
Exact Mass174.112
XLogP-4.2
Formal Charge0
Heavy Atom Count12
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.6926
Human Intestinal AbsorptionHIA+0.7537
Caco-2 PermeabilityCaco2-0.7315
P-glycoprotein SubstrateNon-substrate0.5352
P-glycoprotein InhibitorNon-inhibitor0.9846
Non-inhibitor0.9156
Renal Organic Cation TransporterNon-inhibitor0.7389
Distribution
Subcellular localizationMitochondria0.6201
Metabolism
CYP450 2C9 SubstrateNon-substrate0.7939
CYP450 2D6 SubstrateNon-substrate0.6806
CYP450 3A4 SubstrateNon-substrate0.7967
CYP450 1A2 InhibitorNon-inhibitor0.8006
CYP450 2C9 InhibitorNon-inhibitor0.9251
CYP450 2D6 InhibitorNon-inhibitor0.9270
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8813
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9954
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9590
Non-inhibitor0.9709
AMES ToxicityAMES toxic0.6882
CarcinogensNon-carcinogens0.9304
Fish ToxicityLow FHMT0.8565
Tetrahymena Pyriformis ToxicityLow TPT0.7700
Honey Bee ToxicityLow HBT0.7135
BiodegradationReady biodegradable0.7386
Acute Oral ToxicityIV0.6176
Carcinogenicity (Three-class)Non-required0.6495

Model Value Unit
Absorption
Aqueous solubility-1.4289LogS
Caco-2 Permeability-0.0394LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.5310LD50, mol/kg
Fish Toxicity2.6933pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.3374pIGC50, ug/L

References

TitleJournalDatePubmed ID
l-arginine protects against oxidative damage induced by T-2 toxin in mouse Leydig cells.J Biochem Mol Toxicol2018 Oct30091165
Production of Antigen-Binding Fragment against O,O-Diethyl OrganophosphorusPesticides and Molecular Dynamics Simulations of Antibody Recognition.Int J Mol Sci2018 May 629734787
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 Sci2018 May29753376
Highly selective apo-arginase based method for sensitive enzymatic assay ofmanganese (II) and cobalt (II) ions.Spectrochim Acta A Mol Biomol Spectrosc2018 Mar 1529268235
A novel calcium-binding peptide from Antarctic krill protein hydrolysates andidentification of binding sites of calcium-peptide complex.Food Chem2018 Mar 1529146354
Monosodium glutamate impairs the contraction of uterine visceral smooth muscle ex vivo of rat through augmentation of acetylcholine and nitric oxide signaling pathways.Reprod Biol2018 Mar29402603
Novel photoluminescence enzyme immunoassay based on supramolecular host-guest recognition using L-arginine/6-aza-2-thiothymine-stabilized gold nanocluster.Biosens Bioelectron2018 Jun 3029529510
Exploring the Probiotic and Compound Feed Fermentative Applications ofLactobacillus plantarum SK1305 Isolated from Korean Green Chili Pickled Pepper.Probiotics Antimicrob Proteins2018 Jul 2030030782
Investigating the effect of dietary calcium levels on ileal endogenous amino acidlosses and standardized ileal amino acid digestibility in broilers and layinghens.Poult Sci2018 Jan 129077891
Milk replacers supplemented with either L-arginine or L-carnitine potentiallyimprove muscle maturation of early reared low birth weight piglets fromhyperprolific sows.Animal2018 Jan28641602
Protein engineering of CYP105s for their industrial uses.Biochim Biophys Acta2018 Jan28583351
Genetic Markers Are Associated with the Ruminal Microbiome and Metabolome inGrain and Sugar Challenged Dairy Heifers.Front Genet2018 Feb 2729535763
Mechanism of co-aggregation in a protein mixture with small additives.Int J Biol Macromol2018 Feb28988840
Marginal deficiencies of dietary arginine and methionine could suppress growthperformance and immunological responses in broiler chickens.J Anim Physiol Anim Nutr (Berl)2018 Feb28447340
Untargeted metabolomics of fresh and heat treatment Tiger nut (Cyperus esculentusL.) milks reveals further insight into food quality and nutrition.J Chromatogr A2017 Sep 828768579
Contributions of molecular size, charge distribution, and specific amino acids tothe iron-binding capacity of sea cucumber (Stichopus japonicus) ovumhydrolysates.Food Chem2017 Sep 128407960
Effects of multi-carbohydrase and phytase on standardized ileal digestibility of amino acids and apparent metabolizable energy in canola meal fed to broilerchicks.Poult Sci2017 Sep 128854754
Benefits of L-alanine or L-arginine supplementation against adiposity and glucoseintolerance in monosodium glutamate-induced obesity.Eur J Nutr2017 Sep27317126
Dietary l-arginine inhibits intestinal Clostridium perfringens colonisation andattenuates intestinal mucosal injury in broiler chickens.Br J Nutr2017 Sep28901890
Collagen Peptides from Crucian Skin Improve Calcium Bioavailability andStructural Characterization by HPLC-ESI-MS/MS.J Agric Food Chem2017 Oct 1128915036

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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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
  1. 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 ]