Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: L-citrulline

Synonyms: Nγ-carbamylornithine, α-amino-γ-ureidovaleric acid, γureidonorvaline, N5-(Aminocarbonyl)-L-ornithine

Superclasses: an amino acid or its derivative an amino acid an alpha amino acid

Chemical Formula: C6H13N3O3

Molecular Weight: 175.19 Daltons

Monoisotopic Molecular Weight: 175.0956912992 Daltons

SMILES: C(NC(N)=O)CCC([N+])C(=O)[O-]

InChI: 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

InChIKey: InChIKey=RHGKLRLOHDJJDR-BYPYZUCNSA-N

Unification Links: CAS:372-75-8 , ChEBI:16349 , DrugBank:DB00155 , HMDB:HMDB00904 , IAF1260:34627 , KEGG:C00327 , MetaboLights:MTBLC16349 , PubChem:25244873

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 9.65456 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

arginine biosynthesis I (via L-ornithine) , arginine biosynthesis II (acetyl cycle) , arginine biosynthesis III (via N-acetyl-L-citrulline) , arginine biosynthesis IV (archaebacteria) , citrulline-nitric oxide cycle , urea cycle :
L-aspartate + L-citrulline + ATP → L-arginino-succinate + AMP + diphosphate + H+

proline biosynthesis II (from arginine) :
L-citrulline + 2 H+ + H2O → L-ornithine + CO2 + ammonium

Reactions known to produce the compound:

arginine biosynthesis III (via N-acetyl-L-citrulline) :
N-acetyl-L-citrulline + H2O → L-citrulline + acetate

citrulline-nitric oxide cycle , nitric oxide biosynthesis (plants) :
2 L-arginine + 3 NADPH + H+ + 4 oxygen → 2 L-citrulline + 2 nitric oxide + 3 NADP+ + 4 H2O

Not in pathways:
2 L-arginine + 3 NAD(P)H + H+ + 4 oxygen → 2 L-citrulline + 2 nitric oxide + 3 NAD(P)+ + 4 H2O


amino acids(n) + H2O → amino acids(n-1) + an α amino acid
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a protein + H2O → a protein + an α amino acid

Reactions known to both consume and produce the compound:

arginine biosynthesis I (via L-ornithine) , arginine biosynthesis II (acetyl cycle) , arginine biosynthesis IV (archaebacteria) , citrulline biosynthesis , citrulline degradation , urea cycle :
L-ornithine + carbamoyl-phosphate ↔ L-citrulline + phosphate + H+

arginine degradation V (arginine deiminase pathway) :
L-arginine + H2O ↔ ammonium + L-citrulline

proline biosynthesis II (from arginine) :
L-ornithine + carbamoyl-phosphate ↔ L-citrulline + phosphate + H+
L-arginine + H2O ↔ ammonium + L-citrulline

Not in pathways:
L-ornithine[chloroplast stroma] + carbamoyl-phosphate[chloroplast stroma]L-citrulline[chloroplast stroma] + phosphate[chloroplast stroma] + H+[chloroplast stroma]

In Reactions of unknown directionality:

Not in pathways:
N6,N6-dimethyl-L-arginine + H2O = dimethylamine + L-citrulline
2 Nω-hydroxy-L-arginine + NADPH + 2 oxygen = 2 L-citrulline + 2 nitric oxide + NADP+ + 2 H2O + H+
2 Nω-hydroxy-L-arginine + NAD(P)H + 2 oxygen = 2 L-citrulline + 2 nitric oxide + NAD(P)+ + 2 H2O + H+


a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

In Transport reactions:
L-citrulline[mitochondrial lumen]L-citrulline[cytosol]

Enzymes inhibited by L-citrulline, sorted by the type of inhibition, are:

Inhibitor (Noncompetitive) of: arginase [Colleluori01]

Inhibitor (Mechanism unknown) of: N-acetylglutamate synthase [Marvil77]


References

Colleluori01: Colleluori DM, Morris SM, Ash DE (2001). "Expression, purification, and characterization of human type II arginase." Arch Biochem Biophys 389(1);135-43. PMID: 11370664

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Marvil77: Marvil DK, Leisinger T (1977). "N-acetylglutamate synthase of Escherichia coli: purification, characterization, and molecular properties." J Biol Chem 1977;252(10);3295-303. PMID: 16890


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Wed Dec 17, 2014, biocyc13.