1.0 2011-09-21 00:15:49 UTC 2015-07-21 06:57:15 UTC FDB022556 N6,N6,N6-Trimethyl-L-lysine N6,N6,N6-Trimethyl-L-lysine is a methylated derivative of the amino acid lysine. It is a component of histone proteins, a precursor of carnitine and a coenzyme of fatty acid oxidation. N6,N6,N6-Trimethyl-L-lysine residues are found in a number of proteins and are generated by the action of S-adenosyl-L-methionine on exposed lysine residues. When trimethyllysine is released from cognate proteins via proteolysis, it serves as a precursor for carnitine biosynthesis. Mitochondrial 6-N-trimethyllysine dioxygenase converts 6-N-trimethyllysine to 3-hydroxy-6-N-trimethyllysine as the first step for carnitine biosynthesis. Because the subsequent carnitine biosynthesis enzymes are cytosolic, 3-hydroxy-6-N-trimethyllysine must be transported out of the mitochondria by a putative mitochondrial 6-N-trimethyllysine/3-hydroxy-6-N-trimethyllysine transporter system. Plasma -N-trimethyllysine concentrations are significantly lower in systemic carnitine deficiency patients compared to normal individuals, but no significant difference in urinary -N-trimethyllysine excretion is seen between the two groups. [HMDB] (S)-2-amino-6-(trimethylammonio)hexanoate (S)-2-amino-6-(trimethylammonio)hexanoic acid delta-trimethyllysine epsilon-N-trimethyl-L-lysine epsilon-trimethyl-L-lysine N(6),N(6),N(6)-trimethyl-L-lysine N6,N6,N6-trimethyl-L-lysine S)-5-amino-5-carboxy-N,N,N-trimethyl-1-pentanaminium trimethyllysine C9H20N2O2 188.2673 188.152477894 (2S)-2-amino-6-(trimethylazaniumyl)hexanoate n-trimethyllysine 19253-88-4 C[N+](C)(C)CCCC[C@H](N)C([O-])=O InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/t8-/m0/s1 MXNRLFUSFKVQSK-QMMMGPOBSA-N belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-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 acid salts Carboxylic acids Hydrocarbon derivatives Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives Organic oxides Organic salts Organic zwitterions Organopnictogen compounds Tetraalkylammonium salts Aliphatic acyclic compound Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid Carboxylic acid salt Fatty acid Fatty acyl Hydrocarbon derivative L-alpha-amino acid Medium-chain fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organic salt Organic zwitterion Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine Quaternary ammonium salt Tetraalkylammonium salt Solid logp -3.18 ALOGPS logs -3.31 ALOGPS solubility 1.19e-01 g/l ALOGPS logp -6.2 ChemAxon pka_strongest_acidic 2.41 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac (2S)-2-amino-6-(trimethylazaniumyl)hexanoate ChemAxon average_mass 188.2673 ChemAxon mono_mass 188.152477894 ChemAxon smiles C[N+](C)(C)CCCC[C@H](N)C([O-])=O ChemAxon formula C9H20N2O2 ChemAxon inchi InChI=1S/C9H20N2O2/c1-11(2,3)7-5-4-6-8(10)9(12)13/h8H,4-7,10H2,1-3H3/t8-/m0/s1 ChemAxon inchikey MXNRLFUSFKVQSK-QMMMGPOBSA-N ChemAxon polar_surface_area 66.15 ChemAxon refractivity 74.63 ChemAxon polarizability 21.55 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Carnitine Synthesis SMP00465 Specdb::CMs 18619 Specdb::CMs 156069 Specdb::MsIr 1203 Specdb::MsIr 1204 Specdb::MsIr 1205 Specdb::NmrOneD 147390 Specdb::NmrOneD 147391 Specdb::NmrOneD 147392 Specdb::NmrOneD 147393 Specdb::NmrOneD 147394 Specdb::NmrOneD 147395 Specdb::NmrOneD 147396 Specdb::NmrOneD 147397 Specdb::NmrOneD 147398 Specdb::NmrOneD 147399 Specdb::NmrOneD 147400 Specdb::NmrOneD 147401 Specdb::NmrOneD 147402 Specdb::NmrOneD 147403 Specdb::NmrOneD 147404 Specdb::NmrOneD 147405 Specdb::NmrOneD 147406 Specdb::NmrOneD 147407 Specdb::NmrOneD 147408 Specdb::NmrOneD 147409 Specdb::MsMs 307318 Specdb::MsMs 307319 Specdb::MsMs 307320 Specdb::MsMs 351238 Specdb::MsMs 351239 Specdb::MsMs 351240 Specdb::MsMs 2226705 Specdb::MsMs 2228037 Specdb::MsMs 2229104 Specdb::MsMs 2230329 Specdb::MsMs 2231427 Specdb::MsMs 2232790 Specdb::MsMs 2233759 Specdb::MsMs 2235170 Specdb::MsMs 2244460 Specdb::MsMs 2245636 Specdb::MsMs 2246626 Specdb::MsMs 2247675 Specdb::MsMs 2248609 Specdb::MsMs 2249762 Specdb::MsMs 2250616 Specdb::MsMs 2251790 Specdb::MsMs 2258759 Specdb::MsMs 2259827 Specdb::MsMs 2339130 HMDB01325 17311 #<Reference:0x000055ce31fcf3f0> #<Reference:0x000055ce31fcf238> #<Reference:0x000055ce31fcf080> #<Reference:0x000055ce31fceec8> #<Reference:0x000055ce31fced10> #<Reference:0x000055ce31fceb58> 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 Signal peptidase complex subunit 1 Q9Y6A9 SPCS1