1.0 2011-09-21 01:52:21 UTC 2015-07-21 06:59:40 UTC FDB029239 Lipoyllysine lipollysine is an important lipoic acid derivative. Most alpha-lipoic acid in food is derived from lipoamide-containing enzymes and is bound to the amino acid, lysine (lipoyllysine). Animal tissues that are rich in lipoyllysine include kidney, heart, and liver, while plant sources that are rich in lipoyllysine include spinach, broccoli, and tomatoes. Somewhat lower amounts of lipoyllysine have been measured in peas, brussel sprouts, and rice bran. Lipoic acid can be found in many common foods such as potatoes, carrots, broccoli, yeasts, beets, yams, and red meat. Dietary sources of ALA include flaxseeds, flaxseed oil, canola (rapeseed) oil, soybeans and soybean oil, pumpkin seeds and pumpkin seed oil, purslane, perilla seed oil, walnuts and walnut oil. The best food sources of lipoic acid are believed to be those foods rich in mitochondria - red meat (skeletal muscle, heart, liver, kidney). Other sources are yeast, spinach, and broccoli. lypoyllysine is involved in Lipoate metabolism pathway where lipoyllysine is undergo hydrolysis to produce liporate and l-lysine [HMDB] DL-Lipoyl-L-lysine Lipoyl-N-epsilon-lysine mono-1,2-dithiolane-3-pentanoate mono-1,2-dithiolane-3-pentanoate-L-Lysine mono-1,2-dithiolane-3-pentanoic acid C14H26N2O3S2 334.498 334.138484088 (2R)-2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid (2R)-2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid 20902-53-8 N[C@H](CCCCNC(=O)CCCCC1CCSS1)C(O)=O InChI=1S/C14H26N2O3S2/c15-12(14(18)19)6-3-4-9-16-13(17)7-2-1-5-11-8-10-20-21-11/h11-12H,1-10,15H2,(H,16,17)(H,18,19)/t11?,12-/m1/s1 COTIXRRJLCSLLS-PIJUOVFKSA-N belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring. Lipoamides Organic compounds Organoheterocyclic compounds Dithiolanes Lipoamides Aliphatic heteromonocyclic compounds 1,2-dithiolanes Amino acids Carbonyl compounds Carboxylic acids D-alpha-amino acids Heterocyclic fatty acids Hydrocarbon derivatives Medium-chain fatty acids Monoalkylamines Monocarboxylic acids and derivatives N-acyl amines Organic disulfides Organic oxides Organopnictogen compounds Secondary carboxylic acid amides 1,2-dithiolane Aliphatic heteromonocyclic compound Alpha-amino acid Alpha-amino acid or derivatives Amine Amino acid Amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Carboxylic acid derivative D-alpha-amino acid Fatty acid Fatty acyl Fatty amide Heterocyclic fatty acid Hydrocarbon derivative Lipoamide Medium-chain fatty acid Monocarboxylic acid or derivatives N-acyl-amine Organic disulfide 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 -0.02 ALOGPS logs -3.55 ALOGPS solubility 9.49e-02 g/l ALOGPS logp -0.82 ChemAxon pka_strongest_acidic 2.24 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac (2R)-2-amino-6-[5-(1,2-dithiolan-3-yl)pentanamido]hexanoic acid ChemAxon average_mass 334.498 ChemAxon mono_mass 334.138484088 ChemAxon smiles N[C@H](CCCCNC(=O)CCCCC1CCSS1)C(O)=O ChemAxon formula C14H26N2O3S2 ChemAxon inchi InChI=1S/C14H26N2O3S2/c15-12(14(18)19)6-3-4-9-16-13(17)7-2-1-5-11-8-10-20-21-11/h11-12H,1-10,15H2,(H,16,17)(H,18,19)/t11?,12-/m1/s1 ChemAxon inchikey COTIXRRJLCSLLS-PIJUOVFKSA-N ChemAxon polar_surface_area 92.42 ChemAxon refractivity 88.98 ChemAxon polarizability 36.78 ChemAxon rotatable_bond_count 11 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 9929 Specdb::CMs 40029 Specdb::CMs 175326 Specdb::MsMs 287962 Specdb::MsMs 287963 Specdb::MsMs 287964 Specdb::MsMs 326935 Specdb::MsMs 326936 Specdb::MsMs 326937 Specdb::MsMs 2388692 Specdb::MsMs 2388693 Specdb::MsMs 2388694 Specdb::MsMs 2574544 Specdb::MsMs 2574545 Specdb::MsMs 2574546 Specdb::NmrOneD 98378 Specdb::NmrOneD 98379 Specdb::NmrOneD 98380 Specdb::NmrOneD 98381 Specdb::NmrOneD 98382 Specdb::NmrOneD 98383 Specdb::NmrOneD 98384 Specdb::NmrOneD 98385 Specdb::NmrOneD 98386 Specdb::NmrOneD 98387 Specdb::NmrOneD 98388 Specdb::NmrOneD 98389 Specdb::NmrOneD 98390 Specdb::NmrOneD 98391 Specdb::NmrOneD 98392 Specdb::NmrOneD 98393 Specdb::NmrOneD 98394 Specdb::NmrOneD 98395 Specdb::NmrOneD 98396 Specdb::NmrOneD 98397 HMDB12996