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Identification
NameL-Lysine
Accession NumberDB00123  (NUTR00037)
TypeSmall Molecule
GroupsApproved, 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
Synonyms
SynonymLanguageCode
(S)-2,6-diaminohexanoic acidNot AvailableNot Available
(S)-lysineNot AvailableNot Available
(S)-α,ε-diaminocaproic acidNot AvailableNot Available
6-ammonio-L-norleucineNot AvailableNot Available
L-lysNot AvailableNot Available
LYSNot AvailableNot Available
lysine acidNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number56-87-1
WeightAverage: 146.1876
Monoisotopic: 146.105527702
Chemical FormulaC6H14N2O2
InChI KeyKDXKERNSBIXSRK-MLHKIVSYNA-N
InChI
InChI=1/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/s2
IUPAC Name
(2S)-2,6-diaminohexanoic acid
SMILES
NCCCC[C@H](N)C(O)=O
Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Pharmacology
IndicationSupplemental L-lysine has putative anti-herpes simplex virus activity. There is preliminary research suggesting that it may have some anti-osteoporotic activity.
PharmacodynamicsInsures 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 actionProteins 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.
AbsorptionAbsorbed from the lumen of the small intestine into the enterocytes by an active transport process
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 2C19 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Neoprofen 20 mg/2 ml vial304.5USD ml
Cayston 75 mg inhal solution63.24USD ml
L-lysine ointment0.16USD g
Lysine hcl powder0.16USD g
Ra l-lysine 1000 mg tablet0.08USD tablet
L-lysine hcl 500 mg tablet0.07USD tablet
L-lysine 1000 mg tablet0.04USD tablet
L-lysine 500 mg tablet0.04USD tablet
CVS Pharmacy l-lysine 500 mg tablet0.03USD tablet
Lysine 500 mg tablet0.02USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point224.5 dec °CPhysProp
water solubility1E+006 mg/L (at 20 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-3.05HANSCH,C ET AL. (1995)
pKa3.12 (at 0 °C)KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility105.0 mg/mLALOGPS
logP-3.8ALOGPS
logP-3.2ChemAxon
logS-0.14ALOGPS
pKa (Strongest Acidic)2.74ChemAxon
pKa (Strongest Basic)10.29ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area89.34 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.81 m3·mol-1ChemAxon
Polarizability15.84 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.31 KB)
SpectraNot Available
References
Synthesis Reference

Joseph Michael Stevens, Thomas P. Binder, “Process for making granular L-lysine.” U.S. Patent US5990350, issued 0000.

US5990350
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
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (73.3 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. High affinity cationic amino acid transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
High affinity cationic amino acid transporter 1 P30825 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cationic amino acid transporter 4 O43246 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cationic amino acid transporter 3 Q8WY07 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Low affinity cationic amino acid transporter 2 P52569 Details

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. Lysine--tRNA ligase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Lysine--tRNA ligase Q15046 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Monocarboxylate transporter 10 Q8TF71 Details

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. Solute carrier family 22 member 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08