1.0 2011-09-21 00:28:18 UTC 2018-05-28 18:36:27 UTC FDB023337 N-(o)-Hydroxyarginine N(omega)-hydroxyarginine is a product of the arginine-Nitric Oxide pathway, and is the first intermediate in the process catalyzed by nitric oxide synthase (EC 1.14.13.99, NOS, a heme protein that catalyzes the oxygenation of L-arginine in the presence of NADPH to form nitric oxide + citrulline). N(omega)-hydroxyarginine appears to interfere with cell proliferation/cell growth by inhibiting arginase (EC 3.5.3.1, a binuclear Mn (2+) metalloenzyme that catalyzes the hydrolysis of L-arginine to L-ornithine and urea), and that has 6R-tetrahydrobiopterin (H4B) as an enzyme-bound cofactor. (PMID: 11259671, 11258880, 14504282, 9735327) [HMDB] N-(G)-Hydroxyarginine N-(omega)-Hydroxyarginine C6H14N4O3 190.2004 190.106590334 2-amino-5-(N'-hydroxycarbamimidamido)pentanoic acid N-(G)-hydroxyarginine 53054-07-2 NC(CCC\N=C(/N)NO)C(O)=O InChI=1S/C6H14N4O3/c7-4(5(11)12)2-1-3-9-6(8)10-13/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10) FQWRAVYMZULPNK-UHFFFAOYSA-N belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Alpha amino acids Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic acyclic compounds Amino acids Carbonyl compounds Carboximidamides Carboxylic acids Fatty acids and conjugates Hydrocarbon derivatives Monoalkylamines Monocarboxylic acids and derivatives N-hydroxyguanidines Organic oxides Organopnictogen compounds Propargyl-type 1,3-dipolar organic compounds Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Carbonyl group Carboximidamide Carboxylic acid Fatty acid Guanidine Hydrocarbon derivative Monocarboxylic acid or derivatives N-hydroxyguanidine Organic 1,3-dipolar compound Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Propargyl-type 1,3-dipolar organic compound N(omega)-hydroxyarginine Solid logp -3.57 ALOGPS logs -2.10 ALOGPS solubility 1.49e+00 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 2.2 ChemAxon pka_strongest_basic 10.48 ChemAxon iupac 2-amino-5-(N'-hydroxycarbamimidamido)pentanoic acid ChemAxon average_mass 190.2004 ChemAxon mono_mass 190.106590334 ChemAxon smiles NC(CCC\N=C(/N)NO)C(O)=O ChemAxon formula C6H14N4O3 ChemAxon inchi InChI=1S/C6H14N4O3/c7-4(5(11)12)2-1-3-9-6(8)10-13/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10) ChemAxon inchikey FQWRAVYMZULPNK-UHFFFAOYSA-N ChemAxon polar_surface_area 131.46 ChemAxon refractivity 66.18 ChemAxon polarizability 18.91 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 6 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Arginine and Proline Metabolism SMP00020 map00330 Specdb::CMs 16617 Specdb::CMs 38733 Specdb::MsMs 302704 Specdb::MsMs 302705 Specdb::MsMs 302706 Specdb::MsMs 345490 Specdb::MsMs 345491 Specdb::MsMs 345492 HMDB04224 #<Reference:0x000055ce318c84f8> #<Reference:0x000055ce318c8318> #<Reference:0x000055ce318c8160> #<Reference:0x000055ce318c7f80> NOS1 mutant B3VK56 NOS1