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Human Metabolome Database Version 3.5

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Showing metabocard for L-Arginine (HMDB00517)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:44 -0700
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 | 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
  • Food
  • Drug
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
  • 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
  • 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 Comments
Blood Detected and Quantified
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129.5 +/- 30 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
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99.00 +/- 22.8 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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80 (60.0 - 100) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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50.0 +/- 20.0 uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
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92.0 +/- 19.0 uM Children (1-13 year old) Male Normal Not Available
Blood Detected and Quantified
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84.0 +/- 20.0 uM Children (1-13 year old) Female Normal Not Available
Blood Detected and Quantified
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89.0 +/- 26.0 uM Adult (>18 years old) Male Normal Not Available
Blood Detected and Quantified
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75.0 +/- 24.0 uM Adult (>18 years old) Female Normal Not Available
Blood Detected and Quantified
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111.6 (82.2-140.9) uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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113.6 +/- 14.6 uM Adult (>18 years old) Not Specified Normal Not Available
Blood Detected and Quantified
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218.0 +/- 6.0 uM Adult (>18 years old) Both Normal Not Available
Blood Detected and Quantified
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63.45 (40.0 - 86.9) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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9.33 +/- 0.81 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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20.2 +/- 6.3 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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24.2 +/- 5.1 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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18.3 +/- 3.2 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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6000-29000 uM Not Specified Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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20.5 (15.7 - 25.3) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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17.9 +/- 5.7 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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24.7 (18.3-31.1) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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2.37 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Not Available Both Normal Not Available
Urine Detected and Quantified
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<4.02-22.97 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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16.69 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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0.83 +/- 0.43 umol/mmol creatinine Children (1-13 year old) Both Normal Not Available
Urine Detected and Quantified
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2.0 +/- 1.15 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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1.35 +/- 0.89 umol/mmol creatinine Adult (>18 years old) Female Normal Not Available
Urine Detected and Quantified
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3.5 (2.0-6.0) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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1.96 +/- 1.77 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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7.4 (3.2-14.6) umol/mmol creatinine Adult (>18 years old) Both Normal by LC-MS/MS (Biocrates kit)
Urine Detected and Quantified
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8.6 (3.8-18.6) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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2.0 (1.5-2.5) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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1.515 (0.395 - 2.632) umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
73.0 (6.0-140.0) uM Adult (>18 years old) Both Argininemia. Hyperargininemia, arginase deficiency Not Available
Blood Detected and Quantified
Article_icon
101.6 +/- 39.2 uM Adult (>18 years old) Both Chronic renal failure Not Available
Blood Detected and Quantified
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45 (23.0 - 67.0) uM Adult (>18 years old) Both Permanent Intestinal Failure Not Available
Blood Detected and Quantified
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91.34 +/- 13.1 uM Elderly (>65 years old) Both Alzheimer's disease Not Available
Blood Detected and Quantified
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1250.0 (1000.0-1500.0) uM Adult (>18 years old) Both Argininemia Not Available
Blood Detected and Quantified
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218.0 +/- 7.0 uM Adult (>18 years old) Both Heart failure Non-diabetic patients with chronic heart failure
Cerebrospinal Fluid (CSF) Detected and Quantified
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88000 uM Children (1-13 year old) Female argininemia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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21.5 +/- 4.8 uM Children (1-13 year old) Not Specified Leukemia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
9.64 +/- 1.24 Not Specified Adult (>18 years old) Both Schizophrenia Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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16.6 +/- 6.3 uM Children (1-13 year old) Not Specified Leukemia Acute Lymphoblastic Leukemia (ALL) with Central...
Cerebrospinal Fluid (CSF) Detected and Quantified
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6.0 +/- 1.4 uM Adult (>18 years old) Both Alzheimer's disease Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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58.78 (0.0-117.56) uM Adult (>18 years old) Both Hyperargininemia Not Available
Urine Detected and Quantified
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6.6 (2.5-10.8) umol/mmol creatinine Adult (>18 years old) Both Cystinuria Not Available
Urine Detected and Quantified
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500.0 (200.0-800.0) umol/mmol creatinine Adult (>18 years old) Both Cystinuria Not Available
Urine Detected and Quantified
Article_icon
1941.3 +/- 122.5 umol/mmol creatinine Adult (>18 years old) Both Arginosuccinic aciduria Not Available
Urine Detected and Quantified
Article_icon
39.3 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia Not Available
Urine Detected and Quantified
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33.8 +/- 3.2 umol/mmol creatinine Adult (>18 years old) Both Tyrosinemia I Not Available
Urine Detected and Quantified
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50.3 +/- 10.6 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease Not Available
Urine Detected and Quantified
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31.5 +/- 6.7 umol/mmol creatinine Adult (>18 years old) Both Aminoaciduria Not Available
Urine Detected and Quantified
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2.0 +/- 0.21 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease Not Available
Urine Detected and Quantified
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8.0 (2.3-14.0) umol/mmol creatinine Adult (>18 years old) Both Hyperdibasic aminoaciduria I Not Available
Urine Detected and Quantified
Article_icon
2.0-10.0 umol/mmol creatinine Adult (>18 years old) Both Hyperdibasic aminoaciduria I Not Available
Urine Detected and Quantified
Article_icon
3.9 (1.3-6.5) umol/mmol creatinine Adult (>18 years old) Both Lysinuric protein intolerance Not Available
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
              • http://www.metagene.de/program/d.prg?mp=ARGININEMIA.%20HYPERARGININEMIA,%20ARGINASE%20DEFICIENCY
              Cystinuria
                • http://www.metagene.de/program/d.prg?mp=CYSTINURIA
                Hyperdibasic aminoaciduria I
                  • http://www.metagene.de/program/d.prg?mp=HYPERDIBASIC%20AMINOACIDURIA%20I
                  Lysinuric protein intolerance
                    • http://www.metagene.de/program/d.prg?mp=LYSINURIC%20PROTEIN%20INTOLERANCE%20(LPI)
                    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
                        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
                        Enzymes
                        Name: Arginase-1
                        Reactions:
                        • L-arginine + H2O = L-ornithine + urea [RN:R00551]
                        Gene Name: ARG1
                        Uniprot ID: P05089 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Glycine amidinotransferase, mitochondrial
                        Reactions:
                        • L-arginine + glycine = L-ornithine + guanidinoacetate [RN:R00565]
                        Gene Name: GATM
                        Uniprot ID: P50440 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Arginyl-tRNA synthetase, cytoplasmic
                        Reactions:
                        • ATP + L-arginine + tRNAArg = AMP + diphosphate + L-arginyl-tRNAArg [RN:R03646]
                        Gene Name: RARS
                        Uniprot ID: P54136 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Argininosuccinate synthase
                        Reactions:
                        • ATP + L-citrulline + L-aspartate = AMP + diphosphate + 2-(Nomega-L-arginino)succinate [RN:R01954]
                        Gene Name: ASS1
                        Uniprot ID: P00966 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Protein-arginine deiminase type-4
                        Reactions:
                        • protein L-arginine + H2O = protein L-citrulline + NH3 [RN:R02621]
                        Gene Name: PADI4
                        Uniprot ID: Q9UM07 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Protein-arginine deiminase type-3
                        Reactions:
                        • protein L-arginine + H2O = protein L-citrulline + NH3 [RN:R02621]
                        Gene Name: PADI3
                        Uniprot ID: Q9ULW8 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: Argininosuccinate lyase
                        Reactions:
                        • 2-(Nomega-L-arginino)succinate = fumarate + L-arginine [RN:R01086]
                        Gene Name: ASL
                        Uniprot ID: P04424 Link_out
                        Protein Sequence: FASTA
                        Gene Sequence: FASTA
                        Name: NAD-dependent deacetylase sirtuin-6
                        Reactions:
                          Gene Name: SIRT6
                          Uniprot ID: Q8N6T7 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Ecto-ADP-ribosyltransferase 3
                          Reactions:
                          • NAD+ + protein L-arginine = nicotinamide + Nomega-(ADP-D-ribosyl)-protein-L-arginine [RN:R00555]
                          Gene Name: ART3
                          Uniprot ID: Q13508 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Ecto-ADP-ribosyltransferase 5
                          Reactions:
                          • NAD+ + protein L-arginine = nicotinamide + Nomega-(ADP-D-ribosyl)-protein-L-arginine [RN:R00555]
                          Gene Name: ART5
                          Uniprot ID: Q96L15 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: GPI-linked NAD(P)(+)--arginine ADP-ribosyltransferase 1
                          Reactions:
                          • NAD+ + protein L-arginine = nicotinamide + Nomega-(ADP-D-ribosyl)-protein-L-arginine [RN:R00555]
                          Gene Name: ART1
                          Uniprot ID: P52961 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Ecto-ADP-ribosyltransferase 4
                          Reactions:
                          • NAD+ + protein L-arginine = nicotinamide + Nomega-(ADP-D-ribosyl)-protein-L-arginine [RN:R00555]
                          Gene Name: ART4
                          Uniprot ID: Q93070 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Nitric oxide synthase, inducible
                          Reactions:
                          • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
                          Gene Name: NOS2
                          Uniprot ID: P35228 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Nitric oxide synthase, brain
                          Reactions:
                          • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
                          Gene Name: NOS1
                          Uniprot ID: P29475 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Nitric oxide synthase, endothelial
                          Reactions:
                          • L-arginine + n NADPH + n H+ + m O2 = citrulline + nitric oxide + n NADP+ [RN:R00557]
                          Gene Name: NOS3
                          Uniprot ID: P29474 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Arginase-2, mitochondrial
                          Reactions:
                          • L-arginine + H2O = L-ornithine + urea [RN:R00551]
                          Gene Name: ARG2
                          Uniprot ID: P78540 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Arginine decarboxylase
                          Reactions:
                          • L-arginine = agmatine + CO2 [RN:R00566]
                          Gene Name: ADC
                          Uniprot ID: Q96A70 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Y+L amino acid transporter 1
                          Reactions:
                            Gene Name: SLC7A7
                            Uniprot ID: Q9UM01 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: 4F2 cell-surface antigen heavy chain
                            Reactions:
                              Gene Name: SLC3A2
                              Uniprot ID: P08195 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: High affinity cationic amino acid transporter 1
                              Reactions:
                              • --- []
                              Gene Name: SLC7A1
                              Uniprot ID: P30825 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: Probable arginyl-tRNA synthetase, mitochondrial
                              Reactions:
                              • ATP + L-arginine + tRNAArg = AMP + diphosphate + L-arginyl-tRNAArg [RN:R03646]
                              Gene Name: RARS2
                              Uniprot ID: Q5T160 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: Y+L amino acid transporter 2
                              Reactions:
                                Gene Name: SLC7A6
                                Uniprot ID: Q92536 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA
                                Name: NOS1 mutant
                                Reactions:
                                  Gene Name: NOS1
                                  Uniprot ID: B3VK56 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA
                                  Name: [Protein ADP-ribosylarginine] hydrolase
                                  Reactions:
                                  • (1) protein-Nomega-(ADP-D-ribosyl)-L-arginine + H2O = ADP-ribose + protein-L-arginine [RN:R07626]
                                  • (2) Nomega-(ADP-D-ribosyl)-L-arginine + H2O = ADP-ribose + L-arginine [RN:R01886]
                                  Gene Name: ADPRH
                                  Uniprot ID: P54922 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA