Human Metabolome Database Version 3.5

Showing metabocard for Citrulline (HMDB00904)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:33 -0700
HMDB ID HMDB00904
Secondary Accession Numbers None
Metabolite Identification
Common Name Citrulline
Description Citrulline is an amino acid made from ornithine and carbamoyl phosphate in one of the central reactions in the urea cycle. It is also produced from arginine as a by-product of the reaction catalyzed by NOS family (NOS; EC 1.14.13.39). In this reaction arginine is first oxidized into N-hydroxyl-arginine, which is then further oxidized to citrulline concomitant with the release of nitric oxide. EC 1.14.13.39). Citrulline's name is derived from citrullus, the Latin word for watermelon, from which it was first isolated.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2S)-2-amino-5-(carbamoylamino)pentanoate
  2. (2S)-2-amino-5-(carbamoylamino)pentanoic acid
  3. (S)-2-amino-5-(aminocarbonyl)aminopentanoate
  4. (S)-2-amino-5-(aminocarbonyl)aminopentanoic acid
  5. (S)-2-Amino-5-ureidopentanoate
  6. (S)-2-Amino-5-ureidopentanoic acid
  7. 2-Amino-5-uredovalerate
  8. 2-Amino-5-uredovaleric acid
  9. 2-Amino-5-ureidovalerate
  10. 2-Amino-5-ureidovaleric acid
  11. A-Amino-D-ureidovalerate
  12. A-Amino-D-ureidovaleric acid
  13. alpha-Amino-delta-ureidovalerate
  14. alpha-Amino-delta-ureidovaleric acid
  15. alpha-Amino-gamma-ureidovalerate
  16. alpha-Amino-gamma-ureidovaleric acid
  17. Amino-ureidovalerate
  18. Amino-ureidovaleric acid
  19. CIR
  20. CIT
  21. Cytrulline
  22. D-Ureidonorvaline
  23. delta-Ureidonorvaline
  24. DL-citrulline
  25. Gammaureidonorvaline
  26. H-Cit-oh
  27. L(+)-2-Amino-5-ureidovalerate
  28. L(+)-2-Amino-5-ureidovaleric acid
  29. L(+)-Citrulline
  30. L-2-Amino-5-ureido-valerate
  31. L-2-Amino-5-ureido-valeric acid
  32. L-2-Amino-5-ureidovalerate
  33. L-2-Amino-5-ureidovaleric acid
  34. L-Citrulline
  35. L-Cytrulline
  36. L-N5-carbamoyl-Ornithine
  37. N()-Carbamylornithine
  38. N(5)-(Aminocarbonyl)-DL-Ornithine
  39. N(delta)-Carbamylornithine
  40. N-Carbamylornithine
  41. N5-(Aminocarbonyl)-L-ornithine
  42. N5-(aminocarbonyl)-Ornithine
  43. N5-(Aminocarbonyl)ornithine
  44. N5-Carbamoyl-L-ornithine
  45. N5-carbamoylornithine
  46. N5-carbamylornithine
  47. N<SUP>5</SUP>-(aminocarbonyl)ornithine
  48. ND-carbamylornithine
  49. Ndelta-carbamy-ornithine
  50. Ndelta-carbamylornithine
  51. Ngamma-carbamylornithine
  52. Sitrulline
  53. Ureidonorvaline
  54. Ureidovalerate
  55. Ureidovaleric acid
Chemical Formula C6H13N3O3
Average Molecular Weight 175.1857
Monoisotopic Molecular Weight 175.095691297
IUPAC Name (2S)-2-amino-5-(carbamoylamino)pentanoic acid
Traditional IUPAC Name L-citrulline
CAS Registry Number 372-75-8
SMILES N[C@@H](CCCNC(N)=O)C(O)=O
InChI Identifier InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
InChI Key RHGKLRLOHDJJDR-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
  • citrullines(ChEBI)
Substituents
  • Carboxylic Acid
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
  • Urea
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Alanine and aspartate metabolism
  • Component of Arginine and proline metabolism
Application Not Available
Cellular locations
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 235.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 212 mg/mL Not Available
LogP -3.19 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 21.8 g/L ALOGPS
LogP -3.27 ALOGPS
LogP -3.9 ChemAxon
LogS -0.90 ALOGPS
pKa (strongest acidic) 2.27 ChemAxon
pKa (strongest basic) 9.23 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 118.44 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 41.33 ChemAxon
Polarizability 17.35 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 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
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Intestine
  • Neuron
  • Placenta
  • Kidney
  • Liver
  • Epidermis
  • Myelin
  • Prostate
  • Nerve Cells
  • Platelet
Pathways
Name SMPDB Link KEGG Link
Arginine and Proline Metabolism SMP00020 map00330 Link_out
Aspartate Metabolism SMP00067 map00250 Link_out
Urea Cycle SMP00059 map00330 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
27.5 (10.0-45.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
38.0 (30.0-46.0) uM Adult (>18 years old) Both Normal
Blood Detected and Quantified
36.0 +/- 8.0 uM Children (1-13 year old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
37.0 +/- 9.0 uM Adult (>18 years old) Male Normal
  • Geigy Scient...
Blood Detected and Quantified
35.0 +/- 10.0 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
38.0 (30.0-46.0) uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.8 +/- 1.0 uM Adult (>18 years old) Male Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.8 +/- 1.8 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.62 (1.35-3.89) uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
5.81+/- 1.23 uM Adult (>18 years old) Both Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
1.5 +/- 0.5 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
1.08 (0.065-2.1) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.19 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.00-74.25 umol/mmol creatinine Adult (>18 years old) Both Normal
  • David F. Put...
Urine Detected and Quantified
0.50 +/- 0.54 umol/mmol creatinine Children (1-13 year old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
1.1 +/- 0.84 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
0.99 +/- 0.69 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Urine Detected and Quantified
0.24 +/- 0.23 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.8 (0.2-1.7) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 10.00 (5.00-15.00) uM Children (1-13 year old) Both N-Acetylglutamate synthetase deficiency
Blood Detected and Quantified 200.0 (100.0-300.0) uM Children (1-13 year old) Both Argininosuccinic aciduria (ASL)
Blood Detected and Quantified 13.0 (6.0-20.0) uM Adult (>18 years old) Both Permanent intestinal failure
Blood Detected and Quantified 25.4 (23.4-27.4) uM Adult (>18 years old) Both Comment Seizures
Blood Detected and Quantified 26.8 (25.4-28.2) uM Adult (>18 years old) Both Comment Epilepsy
Blood Detected and Quantified 26.9 (25.2-28.6) uM Children (1-13 year old) Both Comment Epilepsy
Blood Detected and Quantified 94.97 +/- 11.18 uM Elderly (>65 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 27.0 +/- 2.6 uM Adult (>18 years old) Both Alzheimer's disease
Cerebrospinal Fluid (CSF) Detected and Quantified 5.38 +/- 0.94 uM Adult (>18 years old) Both Schizophrenia
Urine Detected and Quantified 21.0 +/- 2.8 umol/mmol creatinine Adult (>18 years old) Both Alzheimer's disease
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
      Epilepsy
      • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292 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
              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
                  Argininosuccinic aciduria
                      N-acetylglutamate synthetase deficiency
                          Associated OMIM IDs
                          DrugBank ID DB00155 Link_out
                          DrugBank Metabolite ID Not Available
                          Phenol Explorer Compound ID Not Available
                          Phenol Explorer Metabolite ID Not Available
                          FoodDB ID FDB011841
                          KNApSAcK ID C00001348 Link_out
                          Chemspider ID 9367 Link_out
                          KEGG Compound ID C00327 Link_out
                          BioCyc ID L-CITRULLINE Link_out
                          BiGG ID 34627 Link_out
                          Wikipedia Link Citrulline Link_out
                          NuGOwiki Link HMDB00904 Link_out
                          Metagene Link HMDB00904 Link_out
                          METLIN ID 16 Link_out
                          PubChem Compound 9750 Link_out
                          PDB ID CIR Link_out
                          ChEBI ID 16349 Link_out
                          References
                          Synthesis Reference Kakimoto, Toshio; Shibatani, Takeji; Nishimura, Noriyuki; Chibata, Ichiro. Enzymic production of L-citrulline by Pseudomonas putida. Applied Microbiology (1971), 22(6), 992-9.
                          Material Safety Data Sheet (MSDS) Download (PDF)
                          General References
                          1. DeLong GR, Glick TH: Ammonia metabolism in Reye syndrome and the effect of citrulline. Ann Neurol. 1982 Jan;11(1):53-8. Pubmed: 7059128 Link_out
                          2. Jianfeng G, Weiming Z, Ning L, Fangnan L, Li T, Nan L, Jieshou L: Serum citrulline is a simple quantitative marker for small intestinal enterocytes mass and absorption function in short bowel patients. J Surg Res. 2005 Aug;127(2):177-82. Pubmed: 15921697 Link_out
                          3. 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
                          4. Liappis N, Pohl B, Weber HP, el-Karkani H: [Free amino acids in the saliva of children with phenylketonuria] Klin Padiatr. 1986 Jan-Feb;198(1):25-8. Pubmed: 3959486 Link_out
                          5. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292 Link_out
                          6. Fleisher LD, Harris CJ, Mitchell DA, Nadler HL: Citrullinemia: prenatal diagnosis of an affected fetus. Am J Hum Genet. 1983 Jan;35(1):85-90. Pubmed: 6823975 Link_out
                          7. Potter MA, Zeesman S, Brennan B, Kobayashi K, Gao HZ, Tabata A, Saheki T, Whelan DT: Pregnancy in a healthy woman with untreated citrullinemia. Am J Med Genet A. 2004 Aug 15;129(1):77-82. Pubmed: 15266621 Link_out
                          8. Wheatley DN, Kilfeather R, Stitt A, Campbell E: Integrity and stability of the citrulline-arginine pathway in normal and tumour cell lines. Cancer Lett. 2005 Sep 28;227(2):141-52. Pubmed: 16112417 Link_out
                          9. Melis GC, Boelens PG, van der Sijp JR, Popovici T, De Bandt JP, Cynober L, van Leeuwen PA: The feeding route (enteral or parenteral) affects the plasma response of the dipetide Ala-Gln and the amino acids glutamine, citrulline and arginine, with the administration of Ala-Gln in preoperative patients. Br J Nutr. 2005 Jul;94(1):19-26. Pubmed: 16115328 Link_out
                          10. Reparon-Schuijt CC, van Esch WJ, van Kooten C, Schellekens GA, de Jong BA, van Venrooij WJ, Breedveld FC, Verweij CL: Secretion of anti-citrulline-containing peptide antibody by B lymphocytes in rheumatoid arthritis. Arthritis Rheum. 2001 Jan;44(1):41-7. Pubmed: 11212174 Link_out
                          11. Maruyama H, Ogawa M, Nishio T, Kobayashi K, Saheki T, Sunohara N: Citrullinemia type II in a 64-year-old man with fluctuating serum citrulline levels. J Neurol Sci. 2001 Jan 1;182(2):167-70. Pubmed: 11137523 Link_out
                          12. McLaurin J, Moscarello MA: The preparation of antibodies reactive against citrulline-containing charge isomers of myelin basic protein but not against the arginine-containing charge isomers. Anal Biochem. 1990 Dec;191(2):272-7. Pubmed: 1707596 Link_out
                          13. Facchinetti F, Longo M, Piccinini F, Neri I, Volpe A: L-arginine infusion reduces blood pressure in preeclamptic women through nitric oxide release. J Soc Gynecol Investig. 1999 Jul-Aug;6(4):202-7. Pubmed: 10486782 Link_out
                          14. Origuchi Y, Ushijima T, Sakaguchi M, Akaboshi I, Matsuda I: Citrullinemia presenting as uncontrollable epilepsy. Brain Dev. 1984;6(3):328-31. Pubmed: 6486381 Link_out
                          15. Booth FA, Haworth JC, Dilling LA, Perry TL, Greenberg CR, Seargeant LE, Penn AM, Rhead WJ: Mitochondrial encephalomyopathy with associated aminoacidopathy in a male sibship. J Pediatr. 1989 Jul;115(1):81-8. Pubmed: 2738799 Link_out
                          16. 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
                          17. Le Boucher J, Charret C, Coudray-Lucas C, Giboudeau J, Cynober L: Amino acid determination in biological fluids by automated ion-exchange chromatography: performance of Hitachi L-8500A. Clin Chem. 1997 Aug;43(8 Pt 1):1421-8. Pubmed: 9267323 Link_out
                          18. 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
                          19. 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
                          20. 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: Argininosuccinate synthase
                          Reactions:
                          Adenosine triphosphate + Citrulline + L-Aspartic acid unknown Adenosine monophosphate + Pyrophosphate + Argininosuccinic acid details
                          Adenosine triphosphate + Citrulline + L-Aspartic acid unknown Adenosine monophosphate + Pyrophosphate + Argininosuccinic acid details
                          Gene Name: ASS1
                          Uniprot ID: P00966 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Protein-arginine deiminase type-6
                          Reactions: Not Available
                          Gene Name: PADI6
                          Uniprot ID: Q6TGC4 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: Protein-arginine deiminase type-2
                          Reactions: Not Available
                          Gene Name: PADI2
                          Uniprot ID: Q9Y2J8 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Protein-arginine deiminase type-1
                          Reactions: Not Available
                          Gene Name: PADI1
                          Uniprot ID: Q9ULC6 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: N(G),N(G)-dimethylarginine dimethylaminohydrolase 1
                          Reactions:
                          Asymmetric dimethylarginine + Water unknown Dimethylamine + Citrulline details
                          Gene Name: DDAH1
                          Uniprot ID: O94760 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: N(G),N(G)-dimethylarginine dimethylaminohydrolase 2
                          Reactions:
                          Asymmetric dimethylarginine + Water unknown Dimethylamine + Citrulline details
                          Gene Name: DDAH2
                          Uniprot ID: O95865 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
                          NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Water details
                          L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown Nitric oxide + Citrulline + NADP + Water details
                          Gene Name: NOS2
                          Uniprot ID: P35228 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Ornithine carbamoyltransferase, mitochondrial
                          Reactions:
                          Carbamoyl phosphate + Ornithine unknown Phosphoric acid + Citrulline details
                          Gene Name: OTC
                          Uniprot ID: P00480 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
                          NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Water details
                          L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown Nitric oxide + Citrulline + 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
                          NADPH + N-(o)-Hydroxyarginine + Oxygen + Hydrogen Ion unknown NADP + Nitric oxide + Citrulline + Water details
                          L-Arginine + Oxygen + NADPH + Hydrogen Ion unknown Nitric oxide + Citrulline + NADP + Water details
                          Gene Name: NOS3
                          Uniprot ID: P29474 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Argininosuccinate synthase
                          Reactions: Not Available
                          Gene Name: ASS1
                          Uniprot ID: Q5T6L4 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