1.0 2011-09-21 01:38:44 UTC 2015-07-21 06:59:23 UTC FDB028371 N(6)-(Octanoyl)lysine N(6)-(Octanoyl)lysine is a modified lysine amino acid that is normally found in acyl carrier protein. The enzyme lipoyl(octanoyl) transferase (EC 2.3.1.181) catalyzes this amino acid residue modification with the following reaction: octanoyl-[acyl-carrier-protein] + protein <-> protein N6-(octanoyl)lysine + acyl carrier protein. In other words, it catalyzes the transfer of endogenously produced octanoic acid from octanoyl-acyl-carrier-protein onto the lipoyl domains of lipoate-dependent enzymes. Another enzyme called lipoyl synthase (EC 2.8.1.8) catalyzes the chemical reaction: protein N6-(octanoyl)lysine + 2 sulfur + 2 S-adenosyl-L-methionine <-> protein N6-(lipoyl)lysine + 2 L-methionine + 2 5'-deoxyadenosine. In other words, this enzyme catalyzes the radical-mediated insertion of two sulfur atoms into the C-6 and C-8 positions of the octanoyl moiety bound to the lipoyl domains of lipoate-dependent enzymes, thereby converting the octanoylated domains into lipoylated derivatives. Degradation of acyl carrier protein or of lipoate derivatized proteins will lead to free N(6)-(Octanoyl)lysine. [HMDB] C14H28N2O3 272.3837 272.209992772 2-amino-6-octanamidohexanoic acid 2-amino-6-octanamidohexanoic acid CCCCCCCC(=O)NCCCCC(N)C(O)=O InChI=1S/C14H28N2O3/c1-2-3-4-5-6-10-13(17)16-11-8-7-9-12(15)14(18)19/h12H,2-11,15H2,1H3,(H,16,17)(H,18,19) DUZODDYGMSCYMJ-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 Amino fatty acids Carbonyl compounds Carboxylic acids Hydrocarbon derivatives Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives N-acyl amines Organic oxides Organopnictogen compounds Secondary carboxylic acid amides Aliphatic acyclic compound Alpha-amino acid Amine Amino acid Amino fatty acid Carbonyl group Carboxamide group Carboxylic acid Fatty acid Fatty acyl Fatty amide Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives N-acyl-amine Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Secondary carboxylic acid amide Solid logp -0.35 ALOGPS logs -3.27 ALOGPS solubility 1.48e-01 g/l ALOGPS logp -0.23 ChemAxon pka_strongest_acidic 2.24 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac 2-amino-6-octanamidohexanoic acid ChemAxon average_mass 272.3837 ChemAxon mono_mass 272.209992772 ChemAxon smiles CCCCCCCC(=O)NCCCCC(N)C(O)=O ChemAxon formula C14H28N2O3 ChemAxon inchi InChI=1S/C14H28N2O3/c1-2-3-4-5-6-10-13(17)16-11-8-7-9-12(15)14(18)19/h12H,2-11,15H2,1H3,(H,16,17)(H,18,19) ChemAxon inchikey DUZODDYGMSCYMJ-UHFFFAOYSA-N ChemAxon polar_surface_area 92.42 ChemAxon refractivity 74.89 ChemAxon polarizability 32.49 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 10390 Specdb::CMs 39764 Specdb::CMs 164760 Specdb::NmrOneD 93992 Specdb::NmrOneD 93993 Specdb::NmrOneD 93994 Specdb::NmrOneD 93995 Specdb::NmrOneD 93996 Specdb::NmrOneD 93997 Specdb::NmrOneD 93998 Specdb::NmrOneD 93999 Specdb::NmrOneD 94000 Specdb::NmrOneD 94001 Specdb::NmrOneD 94002 Specdb::NmrOneD 94003 Specdb::NmrOneD 94004 Specdb::NmrOneD 94005 Specdb::NmrOneD 94006 Specdb::NmrOneD 94007 Specdb::NmrOneD 94008 Specdb::NmrOneD 94009 Specdb::NmrOneD 94010 Specdb::NmrOneD 94011 Specdb::MsMs 288928 Specdb::MsMs 288929 Specdb::MsMs 288930 Specdb::MsMs 328198 Specdb::MsMs 328199 Specdb::MsMs 328200 Specdb::MsMs 2270446 Specdb::MsMs 2270447 Specdb::MsMs 2270448 Specdb::MsMs 3067892 Specdb::MsMs 3067893 Specdb::MsMs 3067894 HMDB11684 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Putative lipoyltransferase 2, mitochondrial A6NK58 LIPT2