1.0 2011-09-21 00:25:39 UTC 2025-11-19 02:43:23 UTC FDB023167 D-Arginine Arginine 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. 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, 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. The ratio of L-arginine to lysine is also important: soy and other plant proteins have more L-arginine than animal sources of protein. (2R)-2-amino-5-(Carbamimidamido)pentanoate (2R)-2-amino-5-(Carbamimidamido)pentanoic acid (2R)-2-amino-5-Guanidinopentanoate (2R)-2-amino-5-Guanidinopentanoic acid (R)-2-amino-5-Guanidinopentanoate (R)-2-amino-5-Guanidinopentanoic acid D-2-Amino-5-guanidinovalerate D-2-Amino-5-guanidinovaleric acid D-Arginin C6H14N4O2 174.201 174.111675712 (2R)-2-amino-5-carbamimidamidopentanoic acid D-arginine 157-06-2 N[C@H](CCCNC(N)=N)C(O)=O 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-/m1/s1 ODKSFYDXXFIFQN-SCSAIBSYSA-N belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-alpha-amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboximidamides Carboxylic acids Fatty acids and conjugates Guanidines Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Amine Amino acid Carbonyl group Carboximidamide Carboxylic acid D-alpha-amino acid Fatty acid Guanidine Hydrocarbon derivative Monocarboxylic acid or derivatives Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound D-alpha-amino acid Other amino acids arginine Solid logp -3.49 ALOGPS logs -1.88 ALOGPS solubility 2.28e+00 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 2.41 ChemAxon pka_strongest_basic 12.41 ChemAxon iupac (2R)-2-amino-5-carbamimidamidopentanoic acid ChemAxon average_mass 174.201 ChemAxon mono_mass 174.111675712 ChemAxon smiles N[C@H](CCCNC(N)=N)C(O)=O ChemAxon formula C6H14N4O2 ChemAxon 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-/m1/s1 ChemAxon inchikey ODKSFYDXXFIFQN-SCSAIBSYSA-N ChemAxon polar_surface_area 125.22 ChemAxon refractivity 53.92 ChemAxon polarizability 18.04 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 6 ChemAxon donor_count 5 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon D-Arginine and D-Ornithine Metabolism SMP00036 map00472 Specdb::NmrTwoD 1900 Specdb::CMs 8120 Specdb::CMs 38594 Specdb::CMs 156909 Specdb::NmrOneD 1965 Specdb::NmrOneD 21742 Specdb::NmrOneD 21743 Specdb::NmrOneD 21744 Specdb::NmrOneD 21745 Specdb::NmrOneD 21746 Specdb::NmrOneD 21747 Specdb::NmrOneD 21748 Specdb::NmrOneD 21749 Specdb::NmrOneD 21750 Specdb::NmrOneD 21751 Specdb::NmrOneD 21752 Specdb::NmrOneD 21753 Specdb::NmrOneD 21754 Specdb::NmrOneD 21755 Specdb::NmrOneD 21756 Specdb::NmrOneD 21757 Specdb::NmrOneD 21758 Specdb::NmrOneD 21759 Specdb::NmrOneD 21760 Specdb::NmrOneD 21761 Specdb::MsMs 2292 Specdb::MsMs 2293 Specdb::MsMs 2294 Specdb::MsMs 257889 Specdb::MsMs 257890 Specdb::MsMs 257891 Specdb::MsMs 277827 Specdb::MsMs 277828 Specdb::MsMs 277829 Specdb::MsMs 2377690 Specdb::MsMs 2377691 Specdb::MsMs 2377692 Specdb::MsMs 2561850 Specdb::MsMs 2561851 Specdb::MsMs 2561852 HMDB03416 15816 #<Reference:0x000055ce32f5e168> #<Reference:0x000055ce32f5df88> #<Reference:0x000055ce32f5dd80> #<Reference:0x000055ce32f5db78> #<Reference:0x000055ce32f5d9c0> #<Reference:0x000055ce32f5d6f0> #<Reference:0x000055ce32f5d470> #<Reference:0x000055ce32f5d1a0> #<Reference:0x000055ce32f5cef8> #<Reference:0x000055ce32f5cbd8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823