1.02011-09-21 00:25:35 UTC2020-09-17 15:30:47 UTCFDB023163D-LysineLysine 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 acidD-2,6-DiaminohexanoateD-2,6-Diaminohexanoic acidD-LysinC6H14N2O2146.19146.105527699(2R)-2,6-diaminohexanoic acidD-lysine923-27-3NCCCC[C@@H](N)C(O)=OInChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1KDXKERNSBIXSRK-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 acidsOrganic compoundsOrganic acids and derivativesCarboxylic acids and derivativesAmino acids, peptides, and analoguesAliphatic acyclic compoundsAmino acidsAmino fatty acidsCarbonyl compoundsCarboxylic acidsHydrocarbon derivativesMedium-chain fatty acidsMonoalkylaminesMonocarboxylic acids and derivativesOrganic oxidesOrganopnictogen compoundsAliphatic acyclic compoundAmineAmino acidAmino fatty acidCarbonyl groupCarboxylic acidD-alpha-amino acidFatty acidFatty acylHydrocarbon derivativeMedium-chain fatty acidMonocarboxylic acid or derivativesOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPrimary aliphatic aminePrimary amineD-alpha-amino acidOther amino acidslysineSolidlogp-3.76logs-0.14solubility1.05e+02 g/llogp-3.2pka_strongest_acidic2.74pka_strongest_basic10.29iupac(2R)-2,6-diaminohexanoic acidaverage_mass146.19mono_mass146.105527699smilesNCCCC[C@@H](N)C(O)=OformulaC6H14N2O2inchiInChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1inchikeyKDXKERNSBIXSRK-RXMQYKEDSA-Npolar_surface_area89.34refractivity37.81polarizability15.91rotatable_bond_count5acceptor_count4donor_count3physiological_charge1formal_charge0Specdb::CMs166724Specdb::NmrTwoD1897Specdb::MsMs87384Specdb::MsMs87385Specdb::MsMs87386Specdb::MsMs149877Specdb::MsMs149878Specdb::MsMs149879Specdb::MsMs2310435Specdb::MsMs2310436Specdb::MsMs2310437Specdb::MsMs2655959Specdb::MsMs2655960Specdb::MsMs2655961Specdb::NmrOneD1962Specdb::NmrOneD21662Specdb::NmrOneD21663Specdb::NmrOneD21664Specdb::NmrOneD21665Specdb::NmrOneD21666Specdb::NmrOneD21667Specdb::NmrOneD21668Specdb::NmrOneD21669Specdb::NmrOneD21670Specdb::NmrOneD21671Specdb::NmrOneD21672Specdb::NmrOneD21673Specdb::NmrOneD21674Specdb::NmrOneD21675Specdb::NmrOneD21676Specdb::NmrOneD21677Specdb::NmrOneD21678Specdb::NmrOneD21679Specdb::NmrOneD21680Specdb::NmrOneD21681HMDB0340516855DLY#<Reference:0x0000555675ad39e8>#<Reference:0x0000555675ad3790>#<Reference:0x0000555675ad3588>#<Reference:0x0000555675ad3290>AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823