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targets (5) transporters (2)
for drugs
Identification
Name L-Lysine
Accession Number DB00123 (NUTR00037)
Type small molecule
Groups approved, nutraceutical
Description

L-Lysine (abbreviated as Lys or K) is an α-amino acid with the chemical formula HO2CCH(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 ε-amino group often participates in hydrogen bonding and as a general base in catalysis. Common posttranslational modifications include methylation of the ε-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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
(S)-2,6-diaminohexanoic acid
(S)-lysine
(S)-α,ε-diaminocaproic acid
L-lys
LYS
lysine acid
Salts Not Available
Brand names
Name Company
Enisyl
Brand mixtures Not Available
Categories
  • Dietary supplement
  • Micronutrient
  • Essential Amino Acids
CAS number 56-87-1
Weight Average: 146.1876
Monoisotopic: 146.105527702
Chemical Formula C6H14N2O2
InChI Key InChIKey=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
Plain Text
IUPAC Name
(2S)-2,6-diaminohexanoic acid
SMILES
NCCCC[C@H](N)C(O)=O
Plain Text
Mass Spec show (9.31 KB)
Taxonomy
Kingdom Organic
Classes
  • Amino Acids
  • Carboxylic Acids and Derivatives
Substructures
  • Amino Acids
  • Hydroxy Compounds
  • Acetates
  • Aliphatic and Aryl Amines
  • Carboxylic Acids and Derivatives
Pharmacology
Indication Supplemental L-lysine has putative anti-herpes simplex virus activity. There is preliminary research suggesting that it may have some anti-osteoporotic activity.
Pharmacodynamics Insures the adequate absorption of calcium; helps form collagen ( which makes up bone cartilage & connective tissues); aids in the production of antibodies, hormones & enzymes. Recent studies have shown that Lysine may be effective against herpes by improving the balance of nutrients that reduce viral growth. A deficiency may result in tiredness, inability to concentrate, irritability, bloodshot eyes, retarded growth, hair loss, anemia & reproductive problems.
Mechanism of action Proteins of the herpes simplex virus are rich in L-arginine, and tissue culture studies indicate an enhancing effect on viral replication when the amino acid ratio of L-arginine to L-lysine is high in the tissue culture media. When the ratio of L-lysine to L-arginine is high, viral replication and the cytopathogenicity of herpes simplex virus have been found to be inhibited. L-lysine may facilitate the absorption of calcium from the small intestine.
Absorption Absorbed from the lumen of the small intestine into the enterocytes by an active transport process
Volume of distribution Not Available
Protein binding Not Available
Metabolism Hepatic
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms Not Available
Prices
Unit description Cost Unit
Neoprofen 20 mg/2 ml vial 304.5 USD ml
Cayston 75 mg inhal solution 63.24 USD ml
L-lysine ointment 0.16 USD g
Lysine hcl powder 0.16 USD g
Ra l-lysine 1000 mg tablet 0.08 USD tablet
L-lysine hcl 500 mg tablet 0.07 USD tablet
L-lysine 1000 mg tablet 0.04 USD tablet
L-lysine 500 mg tablet 0.04 USD tablet
CVS Pharmacy l-lysine 500 mg tablet 0.03 USD tablet
Lysine 500 mg tablet 0.02 USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 224.5 dec °C PhysProp
water solubility 1E+006 mg/L (at 20 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -3.05 HANSCH,C ET AL. (1995)
pKa 3.12 (at 0 °C) KORTUM,G ET AL (1961)
Predicted Properties
Property Value Source
water solubility 1.05e+02 g/l ALOGPS
logP -3.8 ALOGPS
logP -3.2 ChemAxon
logS -0.14 ALOGPS
pKa (strongest acidic) 2.74 ChemAxon
pKa (strongest basic) 10.29 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 4 ChemAxon
hydrogen donor count 3 ChemAxon
polar surface area 89.34 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 37.81 ChemAxon
polarizability 15.84 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Griffith RS, Norins AL, Kagan C: A multicentered study of lysine therapy in Herpes simplex infection. Dermatologica. 1978;156(5):257-67. Pubmed
External Links
Resource Link
KEGG Drug D02304 Link_out
KEGG Compound C00047 Link_out
PubChem Compound 5962 Link_out
PubChem Substance 46504770 Link_out
ChemSpider 5747 Link_out
ChEBI 18019 Link_out
ChEMBL 18019 Link_out
PharmGKB PA450280 Link_out
HET LYS Link_out
PDRhealth http://www.pdrhealth.com/drug_info/nmdrugprofiles/nutsupdrugs/lly_0166.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/L-Lysine Link_out
ATC Codes
  • B05XB03
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (73.3 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. High-affinity cationic amino acid transporter 1

Pharmacological action: unknown

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

Organism class: human
UniProt ID: P30825 Link_out
Gene: SLC7A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Fernandez J, Lopez AB, Wang C, Mishra R, Zhou L, Yaman I, Snider MD, Hatzoglou M: Transcriptional control of the arginine/lysine transporter, cat-1, by physiological stress. J Biol Chem. 2003 Dec 12;278(50):50000-9. Epub 2003 Sep 30. Pubmed
  4. Lopez AB, Wang C, Huang CC, Yaman I, Li Y, Chakravarty K, Johnson PF, Chiang CM, Snider MD, Wek RC, Hatzoglou M: A feedback transcriptional mechanism controls the level of the arginine/lysine transporter cat-1 during amino acid starvation. Biochem J. 2007 Feb 15;402(1):163-73. Pubmed
  5. Nicholson B, Sawamura T, Masaki T, MacLeod CL: Increased Cat3-mediated cationic amino acid transport functionally compensates in Cat1 knockout cell lines. J Biol Chem. 1998 Jun 12;273(24):14663-6. Pubmed

2. Cationic amino acid transporter 4

Pharmacological action: unknown

Involved in the transport of the cationic amino acids (arginine, lysine and ornithine)

Organism class: human
UniProt ID: O43246 Link_out
Gene: SLC7A4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Rotoli BM, Bussolati O, Sala R, Gazzola GC, Dall’Asta V: The transport of cationic amino acids in human airway cells: expression of system y+L activity and transepithelial delivery of NOS inhibitors. FASEB J. 2005 May;19(7):810-2. Epub 2005 Mar 3. Pubmed

3. Cationic amino acid transporter 3

Pharmacological action: unknown

Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner

Organism class: human
UniProt ID: Q8WY07 Link_out
Gene: SLC7A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Hosokawa H, Sawamura T, Kobayashi S, Ninomiya H, Miwa S, Masaki T: Cloning and characterization of a brain-specific cationic amino acid transporter. J Biol Chem. 1997 Mar 28;272(13):8717-22. Pubmed
  4. Humphrey BD, Stephensen CB, Calvert CC, Klasing KC: Lysine deficiency and feed restriction independently alter cationic amino acid transporter expression in chickens (Gallus gallus domesticus). Comp Biochem Physiol A Mol Integr Physiol. 2006 Feb;143(2):218-27. Epub 2006 Jan 10. Pubmed

4. Low-affinity cationic amino acid transporter 2

Pharmacological action: unknown

Low-affinity, high capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine)

Organism class: human
UniProt ID: P52569 Link_out
Gene: SLC7A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Low BC, Grigor MR: Angiotensin II stimulates system y+ and cationic amino acid transporter gene expression in cultured vascular smooth muscle cells. J Biol Chem. 1995 Nov 17;270(46):27577-83. Pubmed
  4. Rotoli BM, Bussolati O, Sala R, Gazzola GC, Dall’Asta V: The transport of cationic amino acids in human airway cells: expression of system y+L activity and transepithelial delivery of NOS inhibitors. FASEB J. 2005 May;19(7):810-2. Epub 2005 Mar 3. Pubmed
  5. Schwartz D, Schwartz IF, Gnessin E, Wollman Y, Chernichovsky T, Blum M, Iaina A: Differential regulation of glomerular arginine transporters (CAT-1 and CAT-2) in lipopolysaccharide-treated rats. Am J Physiol Renal Physiol. 2003 Apr;284(4):F788-95. Epub 2002 Dec 10. Pubmed

5. Lysyl-tRNA synthetase

Pharmacological action: unknown
Organism class: human
UniProt ID: Q15046 Link_out
Gene: KARS Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  2. Chou TF, Wagner CR: Lysyl-tRNA synthetase-generated lysyl-adenylate is a substrate for histidine triad nucleotide binding proteins. J Biol Chem. 2007 Feb 16;282(7):4719-27. Epub 2006 Dec 8. Pubmed
  3. Kamenski P, Kolesnikova O, Jubenot V, Entelis N, Krasheninnikov IA, Martin RP, Tarassov I: Evidence for an adaptation mechanism of mitochondrial translation via tRNA import from the cytosol. Mol Cell. 2007 Jun 8;26(5):625-37. Pubmed
  4. Kwon I, Wang P, Tirrell DA: Design of a bacterial host for site-specific incorporation of p-bromophenylalanine into recombinant proteins. J Am Chem Soc. 2006 Sep 13;128(36):11778-83. Pubmed
Transporters

1. Monocarboxylate transporter 10

Actions: substrate, inhibitor

Sodium-independent transporter that mediates the update of aromatic acid. Can function as a net efflux pathway for aromatic amino acids in the basosolateral epithelial cells (By similarity)

UniProt ID: Q8TF71 Link_out
Gene: SLC16A10 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kim DK, Kanai Y, Chairoungdua A, Matsuo H, Cha SH, Endou H: Expression cloning of a Na+-independent aromatic amino acid transporter with structural similarity to H+/monocarboxylate transporters. J Biol Chem. 2001 May 18;276(20):17221-8. Epub 2001 Feb 20. Pubmed
  2. Kim DK, Kanai Y, Matsuo H, Kim JY, Chairoungdua A, Kobayashi Y, Enomoto A, Cha SH, Goya T, Endou H: The human T-type amino acid transporter-1: characterization, gene organization, and chromosomal location. Genomics. 2002 Jan;79(1):95-103. Pubmed

2. Organic cation/carnitine transporter 1

Actions: inhibitor

Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET)

UniProt ID: Q9H015 Link_out
Gene: SLC22A4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19