Human Metabolome Database Version 3.5

Showing metabocard for L-Arginine (HMDB00517)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:27:16 -0600
HMDB ID HMDB00517
Secondary Accession Numbers None
Metabolite Identification
Common Name L-Arginine
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 PMID: 20841502 Link_out. 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 Link_outArginine 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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (S)-2-amino-5-[(aminoiminomethyl)amino]-Pentanoate
  2. (S)-2-amino-5-[(aminoiminomethyl)amino]-Pentanoic acid
  3. (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoate
  4. (S)-2-Amino-5-[(aminoiminomethyl)amino]pentanoic acid
  5. 2-Amino-5-guanidinovalerate
  6. 2-Amino-5-guanidinovaleric acid
  7. 5-[(Aminoiminomethyl)amino]-L-Norvaline
  8. Arginine
  9. L-(+)-Arginine
  10. L-a-Amino-D-guanidinovalerate
  11. L-a-Amino-D-guanidinovaleric acid
  12. L-alpha-Amino-delta-guanidinovalerate
  13. L-alpha-Amino-delta-guanidinovaleric acid
  14. N5-(aminoiminomethyl)-L-Ornithine
Chemical Formula C6H14N4O2
Average Molecular Weight 174.201
Monoisotopic Molecular Weight 174.111675712
IUPAC Name (2S)-2-amino-5-[(diaminomethylidene)amino]pentanoic acid
Traditional IUPAC Name L-arginine
CAS Registry Number 74-79-3
SMILES N[C@@H](CCCN=C(N)N)C(O)=O
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
InChI Key ODKSFYDXXFIFQN-BYPYZUCNSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Common amino acids(KEGG)
  • L-alpha-amino acid(ChEBI)
  • arginine(ChEBI)
Substituents
  • Carboxylic Acid
  • Guanidine
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Drug
  • Drug metabolite
  • Food
Biofunction
  • Component of Alanine and aspartate metabolism
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Arginine and proline metabolism
  • Component of Glycine, serine and threonine metabolism
  • Essential amino acid
  • Essential amino acids
  • Waste products
  • semi-essential amino acids
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 222 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 182 mg/mL at 25 °C Human Metabolome Project
LogP -4.20 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 7.59 g/L ALOGPS
LogP -3.87 ALOGPS
LogP -3.2 ChemAxon
LogS -1.36 ALOGPS
pKa (strongest acidic) 2.41 ChemAxon
pKa (strongest basic) 11.94 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 127.72 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 43.63 ChemAxon
Polarizability 17.92 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
13C NMR Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
MS/MS Spectrum LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic)
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Muscle
  • Skeletal Muscle
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Pancreas
  • Placenta
  • Testes
  • Kidney
  • Liver
  • Epidermis
  • Myelin
  • Prostate
  • Adipose Tissue
  • Adrenal Cortex
  • Nerve Cells
  • Platelet
  • Gonads
  • Spleen
  • Stratum Corneum
Pathways
Name SMPDB Link KEGG Link
Urea Cycle SMP00059 map00330 Link_out
Transcription/Translation SMP00019 Not Available
Arginine and Proline Metabolism SMP00020 map00330 Link_out
Glycine and Serine Metabolism SMP00004 map00260 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
129.5 +/- 30 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
73.0 (6.0-140.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
99.00 +/- 22.8 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
80 (60.0 - 100) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
50.0 +/- 20.0 uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
92.0 +/- 19.0 uM Children (1-13 year old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
84.0 +/- 20.0 uM Children (1-13 year old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
89.0 +/- 26.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
75.0 +/- 24.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
111.6 (82.2-140.9) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
113.6 +/- 14.6 uM Adult (>18 years old) Not Specified Normal
Blood Detected and Quantified
218.0 +/- 6.0 uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
63.45 (40.0 - 86.9) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
9.33 +/- 0.81 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
20.2 +/- 6.3 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
24.2 +/- 5.1 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
18.3 +/- 3.2 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
6000-29000 uM Not Specified Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
20.5 (15.7 - 25.3) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
17.9 +/- 5.7 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
24.7 (18.3-31.1) uM Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.37 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected but not Quantified
Not Applicable Not Available Both Normal
Urine Detected and Quantified
6.6 (2.5-10.8) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
<4.02-22.97 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
16.69 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Shaykhutdino...
Urine Detected and Quantified
0.83 +/- 0.43 umol/mmol creatinine Children (1-13 year old) Both Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
2.0 +/- 1.15 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
1.35 +/- 0.89 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
3.5 (2.0-6.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.96 +/- 1.77 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
7.4 (3.2-14.6) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
8.6 (3.8-18.6) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
8.0 (2.3-14.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
2.0 (1.5-2.5) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.515 (0.395 - 2.632) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 101.6 +/- 39.2 uM Adult (>18 years old) Both Chronic renal failure
Blood Detected and Quantified 45 (23.0 - 67.0) uM Adult (>18 years old) Both Permanent Intestinal Failure
Blood Detected and Quantified 91.34 +/- 13.1 uM Elderly (>65 years old) Both Alzheimer's disease
Blood Detected and Quantified 1250.0 (1000.0-1500.0) uM Children (1-13 year old) Both Argininemia
Blood Detected and Quantified 218.0 +/- 7.0 uM Adult (>18 years old) Both Comment Heart failure
Cerebrospinal Fluid (CSF) Detected and Quantified 88000 uM Children (1-13 year old) Female argininemia
Cerebrospinal Fluid (CSF) Detected and Quantified 21.5 +/- 4.8 uM Children (1-13 year old) Not Specified Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 9.64 +/- 1.24 Not Specified Adult (>18 years old) Both Schizophrenia
Cerebrospinal Fluid (CSF) Detected and Quantified 16.6 +/- 6.3 uM Children (1-13 year old) Not Specified Comment Leukemia
Cerebrospinal Fluid (CSF) Detected and Quantified 6.0 +/- 1.4 uM Adult (>18 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 58.78 (0.0-117.56) uM Adult (>18 years old) Both Hyperargininemia
Urine Detected and Quantified 500.0 (200.0-800.0) umol/mmol creatinine Children (1-13 year old) Both Cystinuria
Urine Detected and Quantified 1941.3 +/- 122.5 umol/mmol creatinine Adult (>18 years old) Both Arginosuccinic aciduria
Urine Detected and Quantified 39.3 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia
Urine Detected and Quantified 33.8 +/- 3.2 umol/mmol creatinine Adult (>18 years old) Both Tyrosinemia I
Urine Detected and Quantified 50.3 +/- 10.6 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease
Urine Detected and Quantified 31.5 +/- 6.7 umol/mmol creatinine Adult (>18 years old) Both Aminoaciduria
Urine Detected and Quantified 2.0 +/- 0.21 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
Urine Detected and Quantified 2.0-10.0 umol/mmol creatinine Children (1-13 year old) Both Hyperdibasic aminoaciduria I
Urine Detected and Quantified 6 (2-10) umol/mmol creatinine Children (1-13 year old) Both Lysinuric protein intolerance
Associated Disorders and Diseases
Disease References
Intestinal failure
  • Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. Pubmed: 11113071 Link_out
      Hyperargininemia
      • Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. Pubmed: 3433275 Link_out
          Leukemia
          • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
              Alzheimer's disease
              • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479 Link_out
                  Heart failure
                  • Norrelund H, Wiggers H, Halbirk M, Frystyk J, Flyvbjerg A, Botker HE, Schmitz O, Jorgensen JO, Christiansen JS, Moller N: Abnormalities of whole body protein turnover, muscle metabolism and levels of metabolic hormones in patients with chronic heart failure. J Intern Med. 2006 Jul;260(1):11-21. Pubmed: 16789974 Link_out
                      Argininemia
                          Cystinuria
                              Hyperdibasic aminoaciduria I
                                  Lysinuric protein intolerance
                                      Chronic renal failure
                                      • Kikuchi T, Orita Y, Ando A, Mikami H, Fujii M, Okada A, Abe H: Liquid-chromatographic determination of guanidino compounds in plasma and erythrocyte of normal persons and uremic patients. Clin Chem. 1981 Nov;27(11):1899-902. Pubmed: 7296840 Link_out
                                          Schizophrenia
                                          • Do KQ, Lauer CJ, Schreiber W, Zollinger M, Gutteck-Amsler U, Cuenod M, Holsboer F: gamma-Glutamylglutamine and taurine concentrations are decreased in the cerebrospinal fluid of drug-naive patients with schizophrenic disorders. J Neurochem. 1995 Dec;65(6):2652-62. Pubmed: 7595563 Link_out
                                              Associated OMIM IDs
                                              DrugBank ID Not Available
                                              DrugBank Metabolite ID DBMET00502 Link_out
                                              Phenol Explorer Compound ID Not Available
                                              Phenol Explorer Metabolite ID Not Available
                                              FoodDB ID FDB002257
                                              KNApSAcK ID C00001340 Link_out
                                              Chemspider ID 6082 Link_out
                                              KEGG Compound ID C00062 Link_out
                                              BioCyc ID ARG Link_out
                                              BiGG ID 33707 Link_out
                                              Wikipedia Link L-Arginine Link_out
                                              NuGOwiki Link HMDB00517 Link_out
                                              Metagene Link HMDB00517 Link_out
                                              METLIN ID 5502 Link_out
                                              PubChem Compound 6322 Link_out
                                              PDB ID 1FOL Link_out
                                              ChEBI ID 16467 Link_out
                                              References
                                              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
                                              Material Safety Data Sheet (MSDS) Download (PDF)
                                              General References
                                              1. Mori A, Watanabe Y, Fujimoto N: Fluorometrical analysis of guanidino compounds in human cerebrospinal fluid. J Neurochem. 1982 Feb;38(2):448-50. Pubmed: 7108550 Link_out
                                              2. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239 Link_out
                                              3. Haas W, Grabe K, Geis C, Pach T, Stoll K, Fuchs M, Haberl B, Loy C: Recognition and invasion of human skin by Schistosoma mansoni cercariae: the key-role of L-arginine. Parasitology. 2002 Feb;124(Pt 2):153-67. Pubmed: 11860033 Link_out
                                              4. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216 Link_out
                                              5. Martens-Lobenhoffer J, Bode-Boger SM: Measurement of asymmetric dimethylarginine (ADMA) in human plasma: from liquid chromatography estimation to liquid chromatography-mass spectrometry quantification. Eur J Clin Pharmacol. 2006 Feb;62(Supplement 13):61-68. Pubmed: 16217682 Link_out
                                              6. Stothers L, Laher I, Christ GT: A review of the L-arginine - nitric oxide - guanylate cyclase pathway as a mediator of lower urinary tract physiology and symptoms. Can J Urol. 2003 Oct;10(5):1971-80. Pubmed: 14633324 Link_out
                                              7. Avogaro A, Toffolo G, Kiwanuka E, de Kreutzenberg SV, Tessari P, Cobelli C: L-arginine-nitric oxide kinetics in normal and type 2 diabetic subjects: a stable-labelled 15N arginine approach. Diabetes. 2003 Mar;52(3):795-802. Pubmed: 12606522 Link_out
                                              8. Kotikoski H, Moilanen E, Vapaatalo H, Aine E: Biochemical markers of the L-arginine-nitric oxide pathway in the aqueous humour in glaucoma patients. Acta Ophthalmol Scand. 2002 Apr;80(2):191-5. Pubmed: 11952488 Link_out
                                              9. Noris M, Todeschini M, Cassis P, Pasta F, Cappellini A, Bonazzola S, Macconi D, Maucci R, Porrati F, Benigni A, Picciolo C, Remuzzi G: L-arginine depletion in preeclampsia orients nitric oxide synthase toward oxidant species. Hypertension. 2004 Mar;43(3):614-22. Epub 2004 Jan 26. Pubmed: 14744923 Link_out
                                              10. Kirkeby HJ, Svane D, Poulsen J, Tottrup A, Forman A, Andersson KE: Role of the L-arginine/nitric oxide pathway in relaxation of isolated human penile cavernous tissue and circumflex veins. Acta Physiol Scand. 1993 Nov;149(3):385-92. Pubmed: 8310843 Link_out
                                              11. Mizutani N, Hayakawa C, Ohya Y, Watanabe K, Watanabe Y, Mori A: Guanidino compounds in hyperargininemia. Tohoku J Exp Med. 1987 Nov;153(3):197-205. Pubmed: 3433275 Link_out
                                              12. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252 Link_out
                                              13. Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. Pubmed: 11113071 Link_out
                                              14. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473 Link_out
                                              15. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411 Link_out
                                              16. Bauchart-Thevret C, Cui L, Wu G, Burrin DG: Arginine-induced stimulation of protein synthesis and survival in IPEC-J2 cells is mediated by mTOR but not nitric oxide. Am J Physiol Endocrinol Metab. 2010 Dec;299(6):E899-909. doi: 10.1152/ajpendo.00068.2010. Epub 2010 Sep 14. Pubmed: 20841502 Link_out
                                              17. Linden KC, Wadley GD, Garnham AP, McConell GK: Effect of l-arginine infusion on glucose disposal during exercise in humans. Med Sci Sports Exerc. 2011 Sep;43(9):1626-34. doi: 10.1249/MSS.0b013e318212a317. Pubmed: 21311355 Link_out

                                              Enzymes
                                              Name: Arginase-1
                                              Reactions:
                                              L-Arginine + Water unknown Ornithine + Urea details
                                              Gene Name: ARG1
                                              Uniprot ID: P05089 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Glycine amidinotransferase, mitochondrial
                                              Reactions:
                                              L-Arginine + Glycine unknown Ornithine + Guanidoacetic acid details
                                              L-Arginine + Gamma-Aminobutyric acid unknown Ornithine + 4-Guanidinobutanoic acid details
                                              Gene Name: GATM
                                              Uniprot ID: P50440 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Arginine--tRNA ligase, cytoplasmic
                                              Reactions:
                                              Adenosine triphosphate + L-Arginine + tRNA(Arg) unknown Adenosine monophosphate + Pyrophosphate + L-arginyl-tRNA(Arg) details
                                              Adenosine triphosphate + L-Arginine + tRNA(Arg) unknown Adenosine monophosphate + Pyrophosphate + L-Arginyl-tRNA(Arg) details
                                              Gene Name: RARS
                                              Uniprot ID: P54136 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Argininosuccinate synthase
                                              Reactions: Not Available
                                              Gene Name: ASS1
                                              Uniprot ID: P00966 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Protein-arginine deiminase type-4
                                              Reactions: Not Available
                                              Gene Name: PADI4
                                              Uniprot ID: Q9UM07 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Protein-arginine deiminase type-3
                                              Reactions: Not Available
                                              Gene Name: PADI3
                                              Uniprot ID: Q9ULW8 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Argininosuccinate lyase
                                              Reactions:
                                              Argininosuccinic acid unknown Fumaric acid + L-Arginine details
                                              Gene Name: ASL
                                              Uniprot ID: P04424 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: NAD-dependent protein deacetylase sirtuin-6
                                              Reactions: Not Available
                                              Gene Name: SIRT6
                                              Uniprot ID: Q8N6T7 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Ecto-ADP-ribosyltransferase 3
                                              Reactions: Not Available
                                              Gene Name: ART3
                                              Uniprot ID: Q13508 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Ecto-ADP-ribosyltransferase 5
                                              Reactions: Not Available
                                              Gene Name: ART5
                                              Uniprot ID: Q96L15 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: GPI-linked NAD(P)(+)--arginine ADP-ribosyltransferase 1
                                              Reactions: Not Available
                                              Gene Name: ART1
                                              Uniprot ID: P52961 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Ecto-ADP-ribosyltransferase 4
                                              Reactions: Not Available
                                              Gene Name: ART4
                                              Uniprot ID: Q93070 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Nitric oxide synthase, inducible
                                              Reactions:
                                              L-Arginine + NADPH + Oxygen unknown Citrulline + Nitric oxide + NADP + Water details
                                              L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown Nitric oxide + Citrulline + NADP + Water details
                                              L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Water details
                                              Gene Name: NOS2
                                              Uniprot ID: P35228 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Nitric oxide synthase, brain
                                              Reactions:
                                              L-Arginine + NADPH + Oxygen unknown Citrulline + Nitric oxide + NADP + Water details
                                              L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown Nitric oxide + Citrulline + NADP + Water details
                                              L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Water details
                                              Gene Name: NOS1
                                              Uniprot ID: P29475 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Nitric oxide synthase, endothelial
                                              Reactions:
                                              L-Arginine + NADPH + Oxygen unknown Citrulline + Nitric oxide + NADP + Water details
                                              L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown Nitric oxide + Citrulline + NADP + Water details
                                              L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown N-(o)-Hydroxyarginine + NADP + Water details
                                              Gene Name: NOS3
                                              Uniprot ID: P29474 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Arginase-2, mitochondrial
                                              Reactions:
                                              L-Arginine + Water unknown Ornithine + Urea details
                                              Gene Name: ARG2
                                              Uniprot ID: P78540 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Arginine decarboxylase
                                              Reactions:
                                              L-Arginine unknown Agmatine + CO(2) details
                                              L-Arginine unknown Agmatine + Carbon dioxide details
                                              Gene Name: ADC
                                              Uniprot ID: Q96A70 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Y+L amino acid transporter 1
                                              Reactions: Not Available
                                              Gene Name: SLC7A7
                                              Uniprot ID: Q9UM01 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: 4F2 cell-surface antigen heavy chain
                                              Reactions: Not Available
                                              Gene Name: SLC3A2
                                              Uniprot ID: P08195 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: High affinity cationic amino acid transporter 1
                                              Reactions: Not Available
                                              Gene Name: SLC7A1
                                              Uniprot ID: P30825 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Probable arginine--tRNA ligase, mitochondrial
                                              Reactions:
                                              Adenosine triphosphate + L-Arginine + tRNA(Arg) unknown Adenosine monophosphate + Pyrophosphate + L-arginyl-tRNA(Arg) details
                                              Adenosine triphosphate + L-Arginine + tRNA(Arg) unknown Adenosine monophosphate + Pyrophosphate + L-Arginyl-tRNA(Arg) details
                                              Gene Name: RARS2
                                              Uniprot ID: Q5T160 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Carnosine synthase 1
                                              Reactions:
                                              Adenosine triphosphate + L-Arginine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + beta-Alanyl-L-arginine details
                                              Gene Name: CARNS1
                                              Uniprot ID: A5YM72 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: Y+L amino acid transporter 2
                                              Reactions: Not Available
                                              Gene Name: SLC7A6
                                              Uniprot ID: Q92536 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: NOS1 mutant
                                              Reactions: Not Available
                                              Gene Name: NOS1
                                              Uniprot ID: B3VK56 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA
                                              Name: [Protein ADP-ribosylarginine] hydrolase
                                              Reactions:
                                              ADP-Ribosyl-L-arginine + Water unknown Adenosine diphosphate ribose + L-Arginine details
                                              Gene Name: ADPRH
                                              Uniprot ID: P54922 Link_out
                                              Protein Sequence: FASTA
                                              Gene Sequence: FASTA