1.0 2011-09-21 00:11:29 UTC 2015-07-21 06:57:07 UTC FDB022282 N-alpha-Acetylcitrulline N-a-Acetylcitrulline is an N-acetylated metabolite of citrulline that is part of the arginine biosynthetic pathway. Arginine biosynthesis is notable for its complexity and variability at the genetic level, and by its connection with several other pathways, such as pyrimidine and polyamine biosynthesis, and certain degradative pathways. The initial steps of the arginine biosynthetic pathways proceed via N-acetylated intermediates. The presumed reason for this is that the acetylation prevents the spontaneous cyclization of glutamate derivatives, which leads to proline biosynthesis. N-acetyl-L-ornithine can be transcarbamylated directly by the enzyme acetylornithine transcarbamylase, resulting in N-acetyl-L-citrulline. The enzyme acetylornithine deacetylase can accept N-acetyl-L-citrulline as a substrate, and can deacetylate it into citrulline. N-a-Acetylcitrulline is found in cases of deficiency of the urea cycle enzyme argininosuccinate synthase (EC 6.3.4.5) that leads to increased concentrations of citrulline and N-acetylcitrulline in the urine. (PMID: 14633929) [HMDB] (2S)-2-(acetylamino)-5-[(aminocarbonyl)amino]pentanoate (2S)-2-(acetylamino)-5-[(aminocarbonyl)amino]pentanoic acid (2S)-2-acetamido-5-(carbamoylamino)pentanoate (2S)-2-acetamido-5-(carbamoylamino)pentanoic acid (S)-2-Acetamido-5-ureidopentanoate (S)-2-Acetamido-5-ureidopentanoic acid 2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoate 2-(acetylamino)-5-[(Aminocarbonyl)amino]pentanoic acid a-N-Acetylcitrulline alpha-N-Acetylcitrulline N-a-acetylcitrulline N-acetyl citrulline N-acetyl-L-citrulline N-alpha-acetylcitrulline N2-acetyl-N5-carbamoyl-L-Ornithine Na-Acetyl-L-citrulline OLN C8H15N3O4 217.2224 217.106255983 5-(carbamoylamino)-2-acetamidopentanoic acid N-acetylcitrulline 33965-42-3 CC(=O)NC(CCCNC(N)=O)C(O)=O InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15) WMQMIOYQXNRROC-UHFFFAOYSA-N belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. N-acyl-alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Acetamides Carbonyl compounds Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organonitrogen compounds Organopnictogen compounds Secondary carboxylic acid amides Ureas Acetamide Aliphatic acyclic compound Carbonic acid derivative Carbonyl group Carboxamide group Carboxylic acid Fatty acid Hydrocarbon derivative Monocarboxylic acid or derivatives N-acyl-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Secondary carboxylic acid amide Urea N-acetyl-amino acid monocarboxylic acid ureas Solid logp -1.96 ALOGPS logs -1.78 ALOGPS solubility 3.57e+00 g/l ALOGPS logp -1.9 ChemAxon pka_strongest_acidic 3.87 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac 5-(carbamoylamino)-2-acetamidopentanoic acid ChemAxon average_mass 217.2224 ChemAxon mono_mass 217.106255983 ChemAxon smiles CC(=O)NC(CCCNC(N)=O)C(O)=O ChemAxon formula C8H15N3O4 ChemAxon inchi InChI=1S/C8H15N3O4/c1-5(12)11-6(7(13)14)3-2-4-10-8(9)15/h6H,2-4H2,1H3,(H,11,12)(H,13,14)(H3,9,10,15) ChemAxon inchikey WMQMIOYQXNRROC-UHFFFAOYSA-N ChemAxon polar_surface_area 121.52 ChemAxon refractivity 50.77 ChemAxon polarizability 21.5 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 4 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19050 Specdb::CMs 37807 Specdb::MsMs 7181 Specdb::MsMs 7182 Specdb::MsMs 7183 Specdb::MsMs 13853 Specdb::MsMs 13854 Specdb::MsMs 13855 HMDB00856 49002 #<Reference:0x000055ce32142840>