L-Lysine
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Basic Info
Common Name | L-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 ID | F05301 |
CAS Number | 56-87-1 |
PubChem CID | 5962 |
Formula | C6H14N2O2 |
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 |
Wikipedia | L-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 Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
Kingdom | Organic compounds |
Superclass | Organic acids and derivatives |
Class | Carboxylic acids and derivatives |
Subclass | Amino acids, peptides, and analogues |
Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids |
Direct Parent | L-alpha-amino acids |
Alternative Parents | |
Molecular Framework | Aliphatic acyclic compounds |
Substituents | L-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 |
Description | This 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 Name | Property Value |
---|---|
Molecular Weight | 146.19 |
Hydrogen Bond Donor Count | 3 |
Hydrogen Bond Acceptor Count | 4 |
Rotatable Bond Count | 5 |
Complexity | 106 |
Monoisotopic Mass | 146.106 |
Exact Mass | 146.106 |
XLogP | -3 |
Formal Charge | 0 |
Heavy Atom Count | 10 |
Defined Atom Stereocenter Count | 1 |
Undefined Atom Stereocenter Count | 0 |
Defined Bond Stereocenter Count | 0 |
Undefined Bond Stereocenter Count | 0 |
Isotope Atom Count | 0 |
Covalently-Bonded Unit Count | 1 |
ADMET
Model | Result | Probability |
---|---|---|
Absorption | ||
Blood-Brain Barrier | BBB+ | 0.7107 |
Human Intestinal Absorption | HIA+ | 0.8514 |
Caco-2 Permeability | Caco2- | 0.7663 |
P-glycoprotein Substrate | Non-substrate | 0.5949 |
P-glycoprotein Inhibitor | Non-inhibitor | 0.9863 |
Non-inhibitor | 0.9625 | |
Renal Organic Cation Transporter | Non-inhibitor | 0.8878 |
Distribution | ||
Subcellular localization | Lysosome | 0.5313 |
Metabolism | ||
CYP450 2C9 Substrate | Non-substrate | 0.8500 |
CYP450 2D6 Substrate | Non-substrate | 0.7525 |
CYP450 3A4 Substrate | Non-substrate | 0.8287 |
CYP450 1A2 Inhibitor | Non-inhibitor | 0.9379 |
CYP450 2C9 Inhibitor | Non-inhibitor | 0.9643 |
CYP450 2D6 Inhibitor | Non-inhibitor | 0.9749 |
CYP450 2C19 Inhibitor | Non-inhibitor | 0.9653 |
CYP450 3A4 Inhibitor | Non-inhibitor | 0.9338 |
CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9912 |
Excretion | ||
Toxicity | ||
Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9694 |
Non-inhibitor | 0.9525 | |
AMES Toxicity | AMES toxic | 0.8612 |
Carcinogens | Non-carcinogens | 0.8476 |
Fish Toxicity | Low FHMT | 0.7653 |
Tetrahymena Pyriformis Toxicity | Low TPT | 0.9838 |
Honey Bee Toxicity | Low HBT | 0.7166 |
Biodegradation | Ready biodegradable | 0.8163 |
Acute Oral Toxicity | IV | 0.4919 |
Carcinogenicity (Three-class) | Non-required | 0.6531 |
Model | Value | Unit |
---|---|---|
Absorption | ||
Aqueous solubility | -0.8567 | LogS |
Caco-2 Permeability | 0.5261 | LogPapp, cm/s |
Distribution | ||
Metabolism | ||
Excretion | ||
Toxicity | ||
Rat Acute Toxicity | 1.3190 | LD50, mol/kg |
Fish Toxicity | 3.3127 | pLC50, mg/L |
Tetrahymena Pyriformis Toxicity | -0.9810 | pIGC50, ug/L |
References
Title | Journal | Date | Pubmed ID |
---|---|---|---|
Low level aflatoxin exposure associated with greater linear growth in southernMexico: A longitudinal study. | Matern Child Nutr | 2018 May 21:e12619 | 29781250 |
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 Chem | 2018 Mar 28 | 29526104 |
Deciphering physio-biochemical, yield, and nutritional quality attributes ofwater-stressed radish (Raphanus sativus L.) plants grown from Zn-Lys primedseeds. | Chemosphere | 2018 Mar | 29268176 |
Lactation response to soybean meal and rumen-protected methionine supplementationof corn silage-based diets. | J Dairy Sci | 2018 Mar | 29290449 |
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 Prot | 2018 Jun | 29749766 |
Screening and Identification of Lassa Virus Entry Inhibitors from an FDA-ApprovedDrug Library. | J Virol | 2018 Jul 31 | 29899092 |
Evaluation of different saccharides and chitin as eco-friendly additive toimprove the magnetic cross-linked enzyme aggregates (CLEAs) activities. | Int J Biol Macromol | 2018 Jul 20 | 30009910 |
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 Med | 2018 Jul | 29496986 |
Crustacean amphipods from marsh ponds: a nutritious feed resource with potential for application in Integrated Multi-Trophic Aquaculture. | PeerJ | 2018 Jan 12 | 29340233 |
Investigating the effect of dietary calcium levels on ileal endogenous amino acidlosses and standardized ileal amino acid digestibility in broilers and layinghens. | Poult Sci | 2018 Jan 1 | 29077891 |
The protective role of low-concentration alcohol in high-fructose induced adversecardiovascular events in mice. | Biochem Biophys Res Commun | 2018 Jan 1 | 29175209 |
Interactions of dietary protein and threonine on growth performance in Pekinducklings from 1 to 14 days of age. | Poult Sci | 2018 Jan 1 | 29136220 |
Aflatoxin exposure in Nigerian children with severe acute malnutrition. | Food Chem Toxicol | 2018 Jan | 29175577 |
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 Sci | 2018 Jan | 29103714 |
Contribution of Histidine and Lysine to the Generation of Volatile Compounds inJinhua Ham Exposed to Ripening Conditions Via Maillard Reaction. | J Food Sci | 2018 Jan | 29194607 |
Effects of maltose and lysine treatment on coffee aroma by flash gaschromatography electronic nose and gas chromatography-mass spectrometry. | J Sci Food Agric | 2018 Jan | 28547803 |
Effects of Highland Barley Bran Extract Rich in Phenolic Acids on the Formationof Nε-Carboxymethyllysine in a Biscuit Model. | J Agric Food Chem | 2018 Feb 28 | 29414239 |
Characterization of the Lytic Capability of a LysK-Like Endolysin, Lys-phiSA012, Derived from a Polyvalent Staphylococcus aureus Bacteriophage. | Pharmaceuticals (Basel) | 2018 Feb 24 | 29495305 |
Fluorescent Carbon Dots Derived from Maillard Reaction Products: TheirProperties, Biodistribution, Cytotoxicity, and Antioxidant Activity. | J Agric Food Chem | 2018 Feb 14 | 29360356 |
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 Sci | 2018 Feb | 29248224 |
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
- 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
- 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
- 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
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]