You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-10-29 21:50:42 UTC
HMDB IDHMDB00517
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Arginine
DescriptionArginine 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 . 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.
Structure
Thumb
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 FormulaC6H14N4O2
Average Molecular Weight174.201
Monoisotopic Molecular Weight174.111675712
IUPAC Name(2S)-2-amino-5-[(diaminomethylidene)amino]pentanoic acid
Traditional NameL-arginine
CAS Registry Number74-79-3
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 KeyODKSFYDXXFIFQN-BYPYZUCNSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha 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 ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected 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
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point222 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility182 mg/mL at 25 °CHuman Metabolome Project
LogP-4.20HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility7.59ALOGPS
logP-3.9ALOGPS
logP-3.2ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.41ChemAxon
pKa (Strongest Basic)11.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area127.72 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity43.63 m3·mol-1ChemAxon
Polarizability17.92 Å3ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Adipose Tissue
  • Adrenal Cortex
  • Bladder
  • Epidermis
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Myelin
  • Nerve Cells
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Stratum Corneum
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Arginine and Proline MetabolismSMP00020map00330
Glycine and Serine MetabolismSMP00004map00260
Transcription/TranslationSMP00019Not Available
Urea CycleSMP00059map00330
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified129.5 +/- 30 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified73.0 (6.0-140.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified99.00 +/- 22.8 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified80 (60.0 - 100) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified50.0 +/- 20.0 uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified92.0 +/- 19.0 uMChildren (1-13 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified84.0 +/- 20.0 uMChildren (1-13 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified89.0 +/- 26.0 uMAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified75.0 +/- 24.0 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified111.6 (82.2-140.9) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified113.6 +/- 14.6 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified218.0 +/- 6.0 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified63.45 (40.0 - 86.9) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified9.33 +/- 0.81 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified20.2 +/- 6.3 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified24.2 +/- 5.1 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified18.3 +/- 3.2 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified6000-29000 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified20.5 (15.7 - 25.3) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified17.9 +/- 5.7 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified24.7 (18.3-31.1) uMAdult (>18 years old)BothNormal details
SalivaDetected and Quantified24.89 +/- 6.78 uMAdult (>18 years old)FemaleNormal details
SalivaDetected and Quantified9.00 +/- 2.75 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified6.5 +/- 1.6 uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified5.2 +/- 1.7 uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified7.5 +/- 2.3 uMAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified28.9 +/- 20.1 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified35.73 +/- 17.33 uMAdult (>18 years old)BothNormal
    • Dame, ZT. et al. ...
details
SalivaDetected and Quantified5.9 +/- 1.4 uMAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified2.37 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBothNormal details
UrineDetected and Quantified6.6 (2.5-10.8) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified<4.02-22.97 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified16.69 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified0.83 +/- 0.43 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified2.0 +/- 1.15 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified1.35 +/- 0.89 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified3.5 (2.0-6.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.96 +/- 1.77 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified7.4 (3.2-14.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified8.6 (3.8-18.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified8.0 (2.3-14.0) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified2.0 (1.5-2.5) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.515 (0.395 - 2.632) umol/mmol creatinineAdult (>18 years old)BothNormal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified101.6 +/- 39.2 uMAdult (>18 years old)BothChronic renal failure details
    BloodDetected and Quantified45 (23.0 - 67.0) uMAdult (>18 years old)BothPermanent Intestinal Failure details
    BloodDetected and Quantified91.34 +/- 13.1 uMElderly (>65 years old)BothAlzheimer's disease details
    BloodDetected and Quantified1250.0 (1000.0-1500.0) uMChildren (1-13 years old)BothArgininemia details
    BloodDetected and Quantified218.0 +/- 7.0 uMAdult (>18 years old)Both
    Heart failure
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified88000 uMChildren (1-13 years old)Femaleargininemia details
    Cerebrospinal Fluid (CSF)Detected and Quantified21.5 +/- 4.8 uMChildren (1-13 years old)Not SpecifiedLeukemia details
    Cerebrospinal Fluid (CSF)Detected and Quantified 0.00000964 +/- 0.000001244 uMAdult (>18 years old)BothSchizophrenia details
    Cerebrospinal Fluid (CSF)Detected and Quantified16.6 +/- 6.3 uMChildren (1-13 years old)Not Specified
    Leukemia
    details
    Cerebrospinal Fluid (CSF)Detected and Quantified6.0 +/- 1.4 uMAdult (>18 years old)BothAlzheimer's disease details
    Cerebrospinal Fluid (CSF)Detected and Quantified58.78 (0.0-117.56) uMAdult (>18 years old)BothHyperargininemia details
    SalivaDetected and Quantified15.58 +/- 5.74 uMAdult (>18 years old)MaleAlzheimer's disease details
    SalivaDetected and Quantified18.89 +/- 1.07 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
    SalivaDetected and Quantified14.27 +/- 1.60 uMAdult (>18 years old)BothLewy body disease details
    UrineDetected and Quantified500.0 (200.0-800.0) umol/mmol creatinineChildren (1-13 years old)BothCystinuria details
    UrineDetected and Quantified1941.3 +/- 122.5 umol/mmol creatinineAdult (>18 years old)BothArgininosuccinic aciduria (ASL) details
    UrineDetected and Quantified39.3 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
    UrineDetected and Quantified33.8 +/- 3.2 umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I details
    UrineDetected and Quantified50.3 +/- 10.6 umol/mmol creatinineAdult (>18 years old)BothMaple syrup urine disease details
    UrineDetected and Quantified31.5 +/- 6.7 umol/mmol creatinineAdult (>18 years old)BothAminoaciduria details
    UrineDetected and Quantified2.0 +/- 0.21 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease details
    UrineDetected and Quantified2.0-10.0 umol/mmol creatinineChildren (1-13 years old)BothHyperdibasic aminoaciduria I details
    UrineDetected and Quantified6 (2-10) umol/mmol creatinineChildren (1-13 years old)BothLysinuric protein intolerance details
    Associated Disorders and Diseases
    Disease References
    Alzheimer's disease
    1. 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
    Argininemia
    1. MetaGene
    Chronic renal failure
    1. 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
    Cystinuria
    1. MetaGene
    Schizophrenia
    1. 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
    Heart failure
    1. 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
    Hyperargininemia
    1. 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
    Leukemia
    1. 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
    Lysinuric protein intolerance
    1. MetaGene
    Intestinal failure
    1. 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
    Hyperdibasic aminoaciduria I
    1. MetaGene
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDDBMET00502
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB002257
    KNApSAcK IDC00001340
    Chemspider ID6082
    KEGG Compound IDC00062
    BioCyc IDARG
    BiGG ID33707
    Wikipedia LinkL-Arginine
    NuGOwiki LinkHMDB00517
    Metagene LinkHMDB00517
    METLIN ID5502
    PubChem Compound6322
    PDB ID1FOL
    ChEBI ID16467
    References
    Synthesis ReferenceMeyer, 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. 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
    2. 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
    3. 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
    4. 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
    5. 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
    6. 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
    7. 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
    8. 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
    9. 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
    10. 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
    11. 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
    12. 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
    13. 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
    14. 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
    15. 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
    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
    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

    Enzymes

    General function:
    Involved in arginase activity
    Specific function:
    Not Available
    Gene Name:
    ARG1
    Uniprot ID:
    P05089
    Molecular weight:
    34734.655
    Reactions
    L-Arginine + Water → Ornithine + Ureadetails
    General function:
    Amino acid transport and metabolism
    Specific function:
    Catalyzes the biosynthesis of guanidinoacetate, the immediate precursor of creatine. Creatine plays a vital role in energy metabolism in muscle tissues. May play a role in embryonic and central nervous system development. May be involved in the response to heart failure by elevating local creatine synthesis.
    Gene Name:
    GATM
    Uniprot ID:
    P50440
    Molecular weight:
    48455.01
    Reactions
    L-Arginine + Glycine → Ornithine + Guanidoacetic aciddetails
    L-Arginine + Gamma-Aminobutyric acid → Ornithine + 4-Guanidinobutanoic aciddetails
    General function:
    Involved in nucleotide binding
    Specific function:
    Forms part of a macromolecular complex that catalyzes the attachment of specific amino acids to cognate tRNAs during protein synthesis. Modulates the secretion of AIMP1 and may be involved in generation of the inflammatory cytokine EMAP2 from AIMP1.
    Gene Name:
    RARS
    Uniprot ID:
    P54136
    Molecular weight:
    75378.295
    Reactions
    Adenosine triphosphate + L-Arginine + tRNA(Arg) → Adenosine monophosphate + Pyrophosphate + L-arginyl-tRNA(Arg)details
    Adenosine triphosphate + L-Arginine + tRNA(Arg) → Adenosine monophosphate + Pyrophosphate + L-Arginyl-tRNA(Arg)details
    General function:
    Involved in argininosuccinate synthase activity
    Specific function:
    Not Available
    Gene Name:
    ASS1
    Uniprot ID:
    P00966
    Molecular weight:
    46530.055
    General function:
    Involved in protein-arginine deiminase activity
    Specific function:
    Catalyzes the citrullination/deimination of arginine residues of proteins. Citrullinates histone H3 at 'Arg-8' and/or 'Arg-17' and histone H4 at 'Arg-3', which prevents their methylation by CARM1 and HRMT1L2/PRMT1 and represses transcription. Citrullinates EP300/P300 at 'Arg-2142', which favors its interaction with NCOA2/GRIP1.
    Gene Name:
    PADI4
    Uniprot ID:
    Q9UM07
    Molecular weight:
    74078.65
    General function:
    Involved in protein-arginine deiminase activity
    Specific function:
    Catalyzes the deimination of arginine residues of proteins.
    Gene Name:
    PADI3
    Uniprot ID:
    Q9ULW8
    Molecular weight:
    74742.705
    General function:
    Involved in argininosuccinate lyase activity
    Specific function:
    Not Available
    Gene Name:
    ASL
    Uniprot ID:
    P04424
    Molecular weight:
    51657.505
    Reactions
    Argininosuccinic acid → Fumaric acid + L-Argininedetails
    General function:
    Involved in zinc ion binding
    Specific function:
    NAD-dependent protein deacetylase. Has deacetylase activity towards histone H3K9Ac and H3K56Ac. Modulates acetylation of histone H3 in telomeric chromatin during the S-phase of the cell cycle. Deacetylates histone H3K9Ac at NF-kappa-B target promoters and may down-regulate the expression of a subset of NF-kappa-B target genes. Acts as a corepressor of the transcription factor HIF1A to control the expression of multiple glycolytic genes to regulate glucose homeostasis. Required for genomic stability. Regulates the production of TNF protein. Has a role in the regulation of life span (By similarity). Deacetylation of nucleosomes interferes with RELA binding to target DNA. May be required for the association of WRN with telomeres during S-phase and for normal telomere maintenance. Required for genomic stability. Required for normal IGF1 serum levels and normal glucose homeostasis. Modulates cellular senescence and apoptosis. On DNA damage, promotes DNA end resection via deacetylation of RBBP8. Has very weak deacetylase activity and can bind NAD(+) in the absence of acetylated substrate.
    Gene Name:
    SIRT6
    Uniprot ID:
    Q8N6T7
    Molecular weight:
    36064.295
    General function:
    Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    ART3
    Uniprot ID:
    Q13508
    Molecular weight:
    43922.97
    General function:
    Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    ART5
    Uniprot ID:
    Q96L15
    Molecular weight:
    32053.48
    General function:
    Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
    Specific function:
    Has ADP-ribosyltransferase activity toward GLP1R.
    Gene Name:
    ART1
    Uniprot ID:
    P52961
    Molecular weight:
    36334.32
    General function:
    Involved in NAD(P)+-protein-arginine ADP-ribosyltransferase activity
    Specific function:
    Not Available
    Gene Name:
    ART4
    Uniprot ID:
    Q93070
    Molecular weight:
    35878.285
    General function:
    Involved in oxidoreductase activity
    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.
    Gene Name:
    NOS2
    Uniprot ID:
    P35228
    Molecular weight:
    131116.3
    Reactions
    L-Arginine + NADPH + Oxygen → Citrulline + Nitric oxide + NADP + Waterdetails
    L-Arginine + Oxygen + NADPH + Hydrogen Ion → Nitric oxide + Citrulline + NADP + Waterdetails
    L-Arginine + Oxygen + NADPH + Hydrogen Ion → N-(o)-Hydroxyarginine + NADP + Waterdetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR.
    Gene Name:
    NOS1
    Uniprot ID:
    P29475
    Molecular weight:
    160969.095
    Reactions
    L-Arginine + NADPH + Oxygen → Citrulline + Nitric oxide + NADP + Waterdetails
    L-Arginine + Oxygen + NADPH + Hydrogen Ion → Nitric oxide + Citrulline + NADP + Waterdetails
    L-Arginine + Oxygen + NADPH + Hydrogen Ion → N-(o)-Hydroxyarginine + NADP + Waterdetails
    General function:
    Involved in oxidoreductase activity
    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:
    133273.59
    Reactions
    L-Arginine + NADPH + Oxygen → Citrulline + Nitric oxide + NADP + Waterdetails
    L-Arginine + Oxygen + NADPH + Hydrogen Ion → Nitric oxide + Citrulline + NADP + Waterdetails
    L-Arginine + Oxygen + NADPH + Hydrogen Ion → N-(o)-Hydroxyarginine + NADP + Waterdetails
    General function:
    Involved in arginase activity
    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
    Reactions
    L-Arginine + Water → Ornithine + Ureadetails
    General function:
    Involved in catalytic activity
    Specific function:
    Decarboxylates L-arginine to agmatine. Truncated splice isoforms probably lack activity.
    Gene Name:
    ADC
    Uniprot ID:
    Q96A70
    Molecular weight:
    49979.185
    Reactions
    L-Arginine → Agmatine + CO(2)details
    L-Arginine → Agmatine + Carbon dioxidedetails
    General function:
    Involved in transport
    Specific function:
    Involved in the sodium-independent uptake of dibasic amino acids and sodium-dependent uptake of some neutral amino acids. Requires co-expression with SLC3A2/4F2hc to mediate the uptake of arginine, leucine and glutamine. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Involved in the transport of L- arginine in monocytes
    Gene Name:
    SLC7A7
    Uniprot ID:
    Q9UM01
    Molecular weight:
    55990.0
    General function:
    Involved in catalytic activity
    Specific function:
    Required for the function of light chain amino-acid transporters. Involved in sodium-independent, high-affinity transport of large neutral amino acids such as phenylalanine, tyrosine, leucine, arginine and tryptophan. Involved in guiding and targeting of LAT1 and LAT2 to the plasma membrane. When associated with SLC7A6 or SLC7A7 acts as an arginine/glutamine exchanger, following an antiport mechanism for amino acid transport, influencing arginine release in exchange for extracellular amino acids. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Required for normal and neoplastic cell growth. When associated with SLC7A5/LAT1, is also involved in the transport of L-DOPA across the blood-brain barrier, and that of thyroid hormones triiodothyronine (T3) and thyroxine (T4) across the cell membrane in tissues such as placenta. Involved in the uptake of methylmercury (MeHg) when administered as the L-cysteine or D,L-homocysteine complexes, and hence plays a role in metal ion homeostasis and toxicity. When associated with SLC7A5 or SLC7A8, involved in the cellular activity of small molecular weight nitrosothiols, via the stereoselective transport of L- nitrosocysteine (L-CNSO) across the transmembrane. Together with ICAM1, regulates the transport activity LAT2 in polarized intestinal cells, by generating and delivering intracellular signals. When associated with SLC7A5, plays an important role in transporting L-leucine from the circulating blood to the retina across the inner blood-retinal barrier
    Gene Name:
    SLC3A2
    Uniprot ID:
    P08195
    Molecular weight:
    67993.3
    General function:
    Involved in transport
    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:
    67637.6
    General function:
    Involved in nucleotide binding
    Specific function:
    Not Available
    Gene Name:
    RARS2
    Uniprot ID:
    Q5T160
    Molecular weight:
    65504.855
    Reactions
    Adenosine triphosphate + L-Arginine + tRNA(Arg) → Adenosine monophosphate + Pyrophosphate + L-arginyl-tRNA(Arg)details
    Adenosine triphosphate + L-Arginine + tRNA(Arg) → Adenosine monophosphate + Pyrophosphate + L-Arginyl-tRNA(Arg)details
    General function:
    Involved in catalytic activity
    Specific function:
    Catalyzes the synthesis of carnosine and homocarnosine. Carnosine is synthesized more efficiently than homocarnosine.
    Gene Name:
    CARNS1
    Uniprot ID:
    A5YM72
    Molecular weight:
    101318.725
    Reactions
    Adenosine triphosphate + L-Arginine + Beta-Alanine → Adenosine monophosphate + Pyrophosphate + beta-Alanyl-L-argininedetails
    General function:
    Involved in transport
    Specific function:
    Involved in the sodium-independent uptake of dibasic amino acids and sodium-dependent uptake of some neutral amino acids. Requires co-expression with SLC3A2/4F2hc to mediate the uptake of arginine, leucine and glutamine. Also acts as an arginine/glutamine exchanger, following an antiport mechanism for amino acid transport, influencing arginine release in exchange for extracellular amino acids. Plays a role in nitric oxide synthesis in human umbilical vein endothelial cells (HUVECs) via transport of L-arginine. Involved in the transport of L-arginine in monocytes. Reduces uptake of ornithine in retinal pigment epithelial (RPE) cells
    Gene Name:
    SLC7A6
    Uniprot ID:
    Q92536
    Molecular weight:
    56826.9
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    NOS1
    Uniprot ID:
    B3VK56
    Molecular weight:
    160969.1
    General function:
    Involved in magnesium ion binding
    Specific function:
    Catalyzes the reverse reaction of mono-ADP-ribosylation.
    Gene Name:
    ADPRH
    Uniprot ID:
    P54922
    Molecular weight:
    39506.34
    Reactions
    ADP-Ribosyl-L-arginine + Water → Adenosine diphosphate ribose + L-Argininedetails