1.0 2011-09-21 00:25:35 UTC 2020-09-17 15:30:47 UTC FDB023163 D-Lysine Lysine and its bioactive form L-lysine, abbreviated Lys or L, is an essential amino acid. Normal requirements for adults are between 8 g per day or 12 mg/kg. Children and infants need more: 44 mg/kg per day for an eleven to-twelve-year old, and 97 mg/kg per day for three-to six-month old. Lysine is highly concentrated in muscle compared to most other amino acids. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Several inborn errors of lysine metabolism are known, such as cystinuria, hyperdibasic aminoaciduria I, lysinuric protein intolerance, propionic acidemia, and tyrosinemia I. Most are marked by mental retardation with occasional diverse symptoms such as absence of secondary sex characteristics, undescended testes, abnormal facial structure, anemia, obesity, enlarged liver and spleen, and eye muscle imbalance. Low lysine levels have been found in patients with Parkinson's, hypothyroidism, kidney disease, asthma and depression. The exact significance of these levels is unclear, yet lysine therapy can normalize these levels and has been associated with improvement of some patients with these conditions. Abnormally elevated hydroxylysines have been found in virtually all chronic degenerative diseases and coumadin therapy. The levels of this stress marker may be improved by high doses of vitamin C. Lysine is particularly useful in therapy for marasmus (wasting) and herpes simplex. It stops the growth of herpes simplex in culture and has helped to reduce the number and occurrence of cold sores in clinical studies. Beneficial clinical effects occurred with lysine doses ranging from 100 mg to 4 g a day. Higher doses may also be useful, and toxicity has not been reported in doses as high as 8 g per day. Diets high in lysine and low in arginine can be useful in the prevention and treatment of herpes as excess arginine antagonizes lysine. Lysine also may be a useful adjunct in the treatment of osteoporosis because it reduces calcium losses in urine. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine is high in foods such as wheat germ, cottage cheese, chicken, wild game and pork. Less lysine is found in apple, apricot, bananas, avocados, guava, lime, brazil nuts, cashews, mung bean, fava bean and black bean as well as other seeds, nuts and fruits. (R)-2,6-Diaminohexanoate (R)-2,6-Diaminohexanoic acid D-2,6-Diaminohexanoate D-2,6-Diaminohexanoic acid D-Lysin C6H14N2O2 146.19 146.105527699 (2R)-2,6-diaminohexanoic acid D-lysine 923-27-3 NCCCC[C@@H](N)C(O)=O InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1 KDXKERNSBIXSRK-RXMQYKEDSA-N belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. D-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 Organic oxides Organopnictogen compounds Aliphatic acyclic compound Amine Amino acid Amino fatty acid Carbonyl group Carboxylic acid D-alpha-amino acid Fatty acid Fatty acyl Hydrocarbon derivative Medium-chain fatty acid Monocarboxylic acid or derivatives Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Primary aliphatic amine Primary amine D-alpha-amino acid Other amino acids lysine Solid logp -3.76 ALOGPS logs -0.14 ALOGPS solubility 1.05e+02 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 2.74 ChemAxon pka_strongest_basic 10.29 ChemAxon iupac (2R)-2,6-diaminohexanoic acid ChemAxon average_mass 146.19 ChemAxon mono_mass 146.105527699 ChemAxon smiles NCCCC[C@@H](N)C(O)=O ChemAxon formula C6H14N2O2 ChemAxon inchi InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1 ChemAxon inchikey KDXKERNSBIXSRK-RXMQYKEDSA-N ChemAxon polar_surface_area 89.34 ChemAxon refractivity 37.81 ChemAxon polarizability 15.91 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 166724 Specdb::MsMs 87384 Specdb::MsMs 87385 Specdb::MsMs 87386 Specdb::MsMs 149877 Specdb::MsMs 149878 Specdb::MsMs 149879 Specdb::MsMs 2310435 Specdb::MsMs 2310436 Specdb::MsMs 2310437 Specdb::MsMs 2655959 Specdb::MsMs 2655960 Specdb::MsMs 2655961 Specdb::NmrOneD 1962 Specdb::NmrOneD 21662 Specdb::NmrOneD 21663 Specdb::NmrOneD 21664 Specdb::NmrOneD 21665 Specdb::NmrOneD 21666 Specdb::NmrOneD 21667 Specdb::NmrOneD 21668 Specdb::NmrOneD 21669 Specdb::NmrOneD 21670 Specdb::NmrOneD 21671 Specdb::NmrOneD 21672 Specdb::NmrOneD 21673 Specdb::NmrOneD 21674 Specdb::NmrOneD 21675 Specdb::NmrOneD 21676 Specdb::NmrOneD 21677 Specdb::NmrOneD 21678 Specdb::NmrOneD 21679 Specdb::NmrOneD 21680 Specdb::NmrOneD 21681 Specdb::NmrTwoD 1897 HMDB03405 16855 DLY #<Reference:0x000055ce32f7b330> #<Reference:0x000055ce32f7b178> #<Reference:0x000055ce32f7afc0> #<Reference:0x000055ce32f7ae08> 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