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MetaCyc Compound: L-citrulline

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

Superclasses: an acid all carboxy acids a carboxylate an amino acid an alpha amino acid
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

L-citrulline compound structure

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:57743 , DrugBank:DB00155 , HMDB:HMDB00904 , IAF1260:34627 , KEGG:C00327 , MetaboLights:MTBLC16349 , PubChem:6992098

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

Reactions known to consume the compound:

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

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

3-hydroxy-L-homotyrosine biosynthesis :
4-(4-hydroxyphenyl)-2-oxobutanoate + an amino acidL-homotyrosine + a 2-oxo acid

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

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

L-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 Nω-hydroxy-L-arginine + NAD(P)H + 2 oxygen → 2 L-citrulline + 2 nitric oxide + NAD(P)+ + 2 H2O + H+
2 L-arginine + 3 NAD(P)H + H+ + 4 oxygen → 2 L-citrulline + 2 nitric oxide + 3 NAD(P)+ + 4 H2O
2 Nω-hydroxy-L-arginine + NADPH + 2 oxygen → 2 L-citrulline + 2 nitric oxide + NADP+ + 2 H2O + H+

Not in pathways:
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

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a β-monogalactosyldiacylglycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

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

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

L-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]

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
N6,N6-dimethyl-L-arginine + H2O = dimethylamine + L-citrulline

Not in pathways:
a 5-L-glutamyl-[peptide] + an amino acid = a 5-L-glutamyl-amino acid + a peptide

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

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]

This compound has been characterized as an alternative substrate of the following enzymes: canavaninosuccinate synthetase , arginine-α-ketoglutarate transaminase , arginine racemase


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


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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 19.0 on Tue Jul 7, 2015, biocyc12.