Basic Info

Common NameL-Lysine(F05301)
2D Structure
Description

L-Lysine (abbreviated as Lys or K) is an alpha-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2. This amino acid is an essential amino acid, which means that humans cannot synthesize it. Its codons are AAA and AAG.

L-Lysine is a base, as are arginine and histidine. The epsilon-amino group often participates in hydrogen bonding and as a general base in catalysis. Common posttranslational modifications include methylation of the epsilon-amino group, giving methyl-, dimethyl-, and trimethyllysine. The latter occurs in calmodulin. Other posttranslational modifications include acetylation. Collagen contains hydroxylysine which is derived from lysine by lysyl hydroxylase. O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell.L-lysine is an essential amino acid. Normal requirements for lysine have been found to be about 8 g per day or 12 mg/kg in adults. 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. Lysine is high in foods such as wheat germ, cottage cheese and chicken. Of meat products, wild game and pork have the highest concentration of lysine. Fruits and vegetables contain little lysine, except avocados. Normal lysine metabolism is dependent upon many nutrients including niacin, vitamin B6, riboflavin, vitamin C, glutamic acid and iron. Excess arginine antagonizes lysine. Several inborn errors of lysine metabolism are known. 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. Lysine also may be a useful adjunct in the treatment of osteoporosis. Although high protein diets result in loss of large amounts of calcium in urine, so does lysine deficiency. Lysine may be an adjunct therapy because it reduces calcium losses in urine. Lysine deficiency also may result in immunodeficiency. Requirements for this amino acid are probably increased by stress. Lysine toxicity has not occurred with oral doses in humans. Lysine dosages are presently too small and may fail to reach the concentrations necessary to prove potential therapeutic applications. Lysine metabolites, amino caproic acid and carnitine have already shown their therapeutic potential. Thirty grams daily of amino caproic acid has been used as an initial daily dose in treating blood clotting disorders, indicating that the proper doses of lysine, its precursor, have yet to be used in medicine. 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 the level 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. Dosing has not been adequately studied, but beneficial clinical effects occur in 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. Some researchers think herpes simplex virus is involved in many other diseases related to cranial nerves such as migraines, Bell's palsy and Meniere's disease. Herpes blister fluid will produce fatal encephalitis in the rabbit.

FRCD IDF05301
CAS Number56-87-1
PubChem CID5962
FormulaC6H14N2O2
IUPAC Name

(2S)-2,6-diaminohexanoic acid

InChI Key

KDXKERNSBIXSRK-YFKPBYRVSA-N

InChI

InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1

Canonical SMILES

C(CCN)CC(C(=O)O)N

Isomeric SMILES

C(CCN)C[C@@H](C(=O)O)N

WikipediaL-Lysine
Synonyms
        
            L-lysine
        
            lysine
        
            56-87-1
        
            h-Lys-oh
        
            lysine acid
        
            (S)-Lysine
        
            Aminutrin
        
            (2S)-2,6-diaminohexanoic acid
        
            L-(+)-Lysine
        
            alpha-Lysine
        
Classifies
                

                  
                    Animal Toxin
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids
Direct ParentL-alpha-amino acids
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsL-alpha-amino acid - Medium-chain fatty acid - Amino fatty acid - Fatty acid - Fatty acyl - Amino acid - Monocarboxylic acid or derivatives - Carboxylic acid - Organic oxide - Organopnictogen compound - Organic oxygen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Carbonyl group - Organic nitrogen compound - Amine - Hydrocarbon derivative - Aliphatic acyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight146.19
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Complexity106
Monoisotopic Mass146.106
Exact Mass146.106
XLogP-3
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.7107
Human Intestinal AbsorptionHIA+0.8514
Caco-2 PermeabilityCaco2-0.7663
P-glycoprotein SubstrateNon-substrate0.5949
P-glycoprotein InhibitorNon-inhibitor0.9863
Non-inhibitor0.9625
Renal Organic Cation TransporterNon-inhibitor0.8878
Distribution
Subcellular localizationLysosome0.5313
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8500
CYP450 2D6 SubstrateNon-substrate0.7525
CYP450 3A4 SubstrateNon-substrate0.8287
CYP450 1A2 InhibitorNon-inhibitor0.9379
CYP450 2C9 InhibitorNon-inhibitor0.9643
CYP450 2D6 InhibitorNon-inhibitor0.9749
CYP450 2C19 InhibitorNon-inhibitor0.9653
CYP450 3A4 InhibitorNon-inhibitor0.9338
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9912
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9694
Non-inhibitor0.9525
AMES ToxicityAMES toxic0.8612
CarcinogensNon-carcinogens0.8476
Fish ToxicityLow FHMT0.7653
Tetrahymena Pyriformis ToxicityLow TPT0.9838
Honey Bee ToxicityLow HBT0.7166
BiodegradationReady biodegradable0.8163
Acute Oral ToxicityIV0.4919
Carcinogenicity (Three-class)Non-required0.6531

Model Value Unit
Absorption
Aqueous solubility-0.8567LogS
Caco-2 Permeability0.5261LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.3190LD50, mol/kg
Fish Toxicity3.3127pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.9810pIGC50, ug/L

References

TitleJournalDatePubmed ID
Low level aflatoxin exposure associated with greater linear growth in southernMexico: A longitudinal study.Matern Child Nutr2018 May 21:e1261929781250
Valine Supplementation in a Reduced Protein Diet Regulates Growth PerformancePartially through Modulation of Plasma Amino Acids Profile, Metabolic Responses, Endocrine, and Neural Factors in Piglets.J Agric Food Chem2018 Mar 2829526104
Deciphering physio-biochemical, yield, and nutritional quality attributes ofwater-stressed radish (Raphanus sativus L.) plants grown from Zn-Lys primedseeds.Chemosphere2018 Mar29268176
Lactation response to soybean meal and rumen-protected methionine supplementationof corn silage-based diets.J Dairy Sci2018 Mar29290449
Evaluation of the Impact of Varied Carvacrol Concentrations on SalmonellaRecovery in Oregano and How Corn Oil Can Minimize the Effect of Carvacrol during Preenrichment.J Food Prot2018 Jun29749766
Screening and Identification of Lassa Virus Entry Inhibitors from an FDA-ApprovedDrug Library.J Virol2018 Jul 3129899092
Evaluation of different saccharides and chitin as eco-friendly additive toimprove the magnetic cross-linked enzyme aggregates (CLEAs) activities.Int J Biol Macromol2018 Jul 2030009910
In Vivo Characterization of Platinum(II)-Based Linker Technology for theDevelopment of Antibody-Drug Conjugates: Taking Advantage of Dual Labeling with195mPt and 89Zr.J Nucl Med2018 Jul29496986
Crustacean amphipods from marsh ponds: a nutritious feed resource with potential for application in Integrated Multi-Trophic Aquaculture.PeerJ2018 Jan 1229340233
Investigating the effect of dietary calcium levels on ileal endogenous amino acidlosses and standardized ileal amino acid digestibility in broilers and layinghens.Poult Sci2018 Jan 129077891
The protective role of low-concentration alcohol in high-fructose induced adversecardiovascular events in mice.Biochem Biophys Res Commun2018 Jan 129175209
Interactions of dietary protein and threonine on growth performance in Pekinducklings from 1 to 14 days of age.Poult Sci2018 Jan 129136220
Aflatoxin exposure in Nigerian children with severe acute malnutrition.Food Chem Toxicol2018 Jan29175577
Ethyl-cellulose rumen-protected methionine alleviates inflammation and oxidative stress and improves neutrophil function during the periparturient period andearly lactation in Holstein dairy cows.J Dairy Sci2018 Jan29103714
Contribution of Histidine and Lysine to the Generation of Volatile Compounds inJinhua Ham Exposed to Ripening Conditions Via Maillard Reaction.J Food Sci2018 Jan29194607
Effects of maltose and lysine treatment on coffee aroma by flash gaschromatography electronic nose and gas chromatography-mass spectrometry.J Sci Food Agric2018 Jan28547803
Effects of Highland Barley Bran Extract Rich in Phenolic Acids on the Formationof Nε-Carboxymethyllysine in a Biscuit Model.J Agric Food Chem2018 Feb 2829414239
Characterization of the Lytic Capability of a LysK-Like Endolysin, Lys-phiSA012, Derived from a Polyvalent Staphylococcus aureus Bacteriophage.Pharmaceuticals (Basel)2018 Feb 2429495305
Fluorescent Carbon Dots Derived from Maillard Reaction Products: TheirProperties, Biodistribution, Cytotoxicity, and Antioxidant Activity.J Agric Food Chem2018 Feb 1429360356
Varying the ratio of Lys:Met while maintaining the ratios of Thr:Phe, Lys:Thr,Lys:His, and Lys:Val alters mammary cellular metabolites, mammalian target ofrapamycin signaling, and gene transcription.J Dairy Sci2018 Feb29248224

Targets

General Function:
L-ornithine transmembrane transporter activity
Specific Function:
Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
Gene Name:
SLC7A3
Uniprot ID:
Q8WY07
Molecular Weight:
67168.31 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
General Function:
Trna binding
Specific Function:
Catalyzes the specific attachment of an amino acid to its cognate tRNA in a 2 step reaction: the amino acid (AA) is first activated by ATP to form AA-AMP and then transferred to the acceptor end of the tRNA. When secreted, acts as a signaling molecule that induces immune response through the activation of monocyte/macrophages. Catalyzes the synthesis of diadenosine oligophosphate (Ap4A), a signaling molecule involved in the activation of MITF transcriptional activity. Interacts with HIV-1 virus GAG protein, facilitating the selective packaging of tRNA(3)(Lys), the primer for reverse transcription initiation.
Gene Name:
KARS
Uniprot ID:
Q15046
Molecular Weight:
68047.54 Da
References
  1. Wu XR, Kenzior A, Willmot D, Scanlon S, Chen Z, Topin A, He SH, Acevedo A, Folk WR: Altered expression of plant lysyl tRNA synthetase promotes tRNA misacylation and translational recoding of lysine. Plant J. 2007 May;50(4):627-36. Epub 2007 Apr 8. [17425721 ]
General Function:
L-ornithine transmembrane transporter activity
Specific Function:
Involved in the transport of the cationic amino acids (arginine, lysine and ornithine).
Gene Name:
SLC7A4
Uniprot ID:
O43246
Molecular Weight:
68267.17 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
General Function:
L-ornithine transmembrane transporter activity
Specific Function:
High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor.
Gene Name:
SLC7A1
Uniprot ID:
P30825
Molecular Weight:
67637.62 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
General Function:
Low-affinity l-arginine transmembrane transporter activity
Specific Function:
Functions as permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine); the affinity for its substrates differs between isoforms created by alternative splicing. Isoform 1 functions as permease that mediates the transport of the cationic amino acids (arginine, lysine and ornithine), and it has much higher affinity for arginine than isoform 2. Isoform 2 functions as low-affinity, high capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) (PubMed:9174363). May play a role in classical or alternative activation of macrophages via its role in arginine transport.
Gene Name:
SLC7A2
Uniprot ID:
P52569
Molecular Weight:
71672.175 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]