Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:02 UTC
HMDB IDHMDB00182
Secondary Accession NumbersNone
Metabolite Identification
Common NameL-Lysine
DescriptionL-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. (http://www.dcnutrition.com).
Structure
Thumb
Synonyms
  1. (+)-S-Lysine
  2. (S)-2,6-diamino-Hexanoate
  3. (S)-2,6-diamino-Hexanoic acid
  4. (S)-2,6-Diaminohexanoate
  5. (S)-2,6-Diaminohexanoic acid
  6. (S)-a,e-Diaminocaproate
  7. (S)-a,e-Diaminocaproic acid
  8. (S)-Lysine
  9. 2,6-Diaminohexanoate
  10. 2,6-Diaminohexanoic acid
  11. 6-Amino-Aminutrin
  12. 6-Amino-L-Norleucine
  13. a-Lysine
  14. alpha-Lysine
  15. Aminutrin
  16. h-Lys-oh
  17. L-(+)-Lysine
  18. L-2,6-Diainohexanoate
  19. L-2,6-Diainohexanoic acid
  20. L-2,6-Diaminocaproate
  21. L-2,6-Diaminocaproic acid
  22. L-Lys
  23. Lys
  24. Lysine
  25. Lysine acid
Chemical FormulaC6H14N2O2
Average Molecular Weight146.1876
Monoisotopic Molecular Weight146.105527702
IUPAC Name(2S)-2,6-diaminohexanoic acid
Traditional IUPAC NameL-lysine
CAS Registry Number56-87-1
SMILES
NCCCC[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1
InChI KeyKDXKERNSBIXSRK-YFKPBYRVSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassAmino Acids and Derivatives
Sub ClassAlpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Amino Fatty Acids
  • Common amino acids(KEGG)
  • L-alpha-amino acid(ChEBI)
  • Organic Compounds
  • Straight Chain Fatty Acids
  • lysine(ChEBI)
Substituents
  • Carboxylic Acid
  • Polyamine
  • Primary Aliphatic Amine (Alkylamine)
Direct ParentAlpha Amino Acids and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
  • Plant
Biofunction
  • Component of Aminoacyl-tRNA biosynthesis
  • Component of Lysine biosynthesis
  • Essential amino acids
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point224.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP-3.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility105 g/LALOGPS
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 area89.34ChemAxon
rotatable bond count5ChemAxon
refractivity37.81ChemAxon
polarizability16.01ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
  • Peroxisome
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Biotin MetabolismSMP00066map00780
Carnitine SynthesisSMP00465Not Available
Lysine DegradationSMP00037map00310
Transcription/TranslationSMP00019Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified190.0 +/- 60.0 uMNewborn (0-30 days old)Not SpecifiedNormal
  • Geigy Scient...
BloodDetected and Quantified164.0 +/- 28.0 uMChildren (1-13 year old)FemaleNormal
  • Geigy Scient...
BloodDetected and Quantified198.0 +/- 31.0 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
BloodDetected and Quantified183.0 +/- 34.0 uMAdult (>18 years old)FemaleNormal
  • Geigy Scient...
BloodDetected and Quantified434.0 +/- 23.0 uMAdult (>18 years old)BothNormal
BloodDetected and Quantified178.6 +/- 58.2 uMAdult (>18 years old)Not SpecifiedNormal
BloodDetected and Quantified188.0 (156.0-220.0) uMAdult (>18 years old)BothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified21.7 +/- 3.7 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified29.0 +/- 13.0 uMNot SpecifiedBothNormal
Cerebrospinal Fluid (CSF)Detected and Quantified27.7 +/- 8.0 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified31.5 +/- 5.7 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified25.7 +/- 5.3 uMAdult (>18 years old)Not SpecifiedNormal
Cerebrospinal Fluid (CSF)Detected and Quantified23.9 (18.1-29.7) uMAdult (>18 years old)BothNormal
SalivaDetected and Quantified>10 uMAdult (>18 years old)BothNormal
UrineDetected and Quantified31.45 +/- 52.32 umol/mmol creatinineInfant (0-1 year old)BothNormal
UrineDetected and Quantified18.0 (7.0-29.0) umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified3.42-75.29 umol/mmol creatinineAdult (>18 years old)BothNormal
  • David F. Put...
UrineDetected and Quantified10.9(2.105-19.7) umol/mmol creatinineAdult (>18 years old)BothNormal
    UrineDetected and Quantified17.2 (3.7-51.3) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
    UrineDetected and Quantified0.0026 - 0.0388 umol/mmol creatinineAdult (>18 years old)BothNormal
    UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothCommentNormal
    UrineDetected and Quantified10.28 +/- 5.34 umol/mmol creatinineAdult (>18 years old)BothNormal
    UrineDetected and Quantified0.9 (0.17-1.84) umol/mmol creatinineNewborn (0-30 days old)BothNormal
    • Geigy Scient...
    • West Cadwell...
    • Basel, Switz...
    UrineDetected and Quantified32.0 +/- 27.0 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scient...
    • West Cadwell...
    • Basel, Switz...
    UrineDetected and Quantified29.0 +/- 21.7 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scient...
    • West Cadwell...
    • Basel, Switz...
    UrineDetected and Quantified17.9 (3.6-56.1) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
    UrineDetected and Quantified4.7 umol/mmol creatinineAdult (>18 years old)BothNormal
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReference
    BloodDetected and Quantified128.2 +/- 55.3 uMAdult (>18 years old)Not SpecifiedHeart Transplant
    BloodDetected and Quantified216.7 +/- 54.5 uMElderly (>65 years old)BothAlzheimer's disease
    BloodDetected and Quantified128.0 +/- 9.0 uMAdult (>18 years old)BothRefractory localization-related epilepsy (RLE)
    Cerebrospinal Fluid (CSF)Detected and Quantified44.6 +/- 10.8 uMAdult (>18 years old)BothAlzheimer's disease
    Cerebrospinal Fluid (CSF)Detected and Quantified26.9 +/- 11.1 uMChildren (1-13 year old)Not SpecifiedLeukemia
    Cerebrospinal Fluid (CSF)Detected and Quantified21.9 +/- 6.2 uMChildren (1-13 year old)Not SpecifiedCommentLeukemia
    UrineDetected and Quantified2750.0 (500.0-5000.0) umol/mmol creatinineChildren (1-13 year old)BothCarbamoyl phosphate synthetase deficiency
    UrineDetected and Quantified1075.0 (150.0-2000.0) umol/mmol creatinineChildren (1-13 year old)BothCystinuria
    UrineDetected and Quantified0.0039 - 0.0116 umol/mmol creatinineAdult (>18 years old)BothADPKD
    UrineDetected and Quantified5.5 +/- 1.74 umol/mmol creatinineAdult (>18 years old)BothAlzheimer's disease
    UrineDetected and Quantified600.00 (200.00-1000.00) umol/mmol creatinineChildren (1-13 year old)BothHyperdibasic aminoaciduria I
    UrineDetected and Quantified67.5 (10.00-125.00) umol/mmol creatinineChildren (1-13 year old)BothLysinuric protein intolerance
    UrineDetected and Quantified101 +/- 13 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia
    UrineDetected and Quantified452.1 +/- 60.2 umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I
    UrineDetected and Quantified321.8 +/- 15.4 umol/mmol creatinineAdult (>18 years old)BothTyrosinemia I
    UrineDetected and Quantified397.5 +/- 16.6 umol/mmol creatinineAdult (>18 years old)BothAminoaciduria
    Associated Disorders and Diseases
    Disease References
    Alzheimer's disease
    • Fonteh AN, Harrington RJ, Tsai A, Liao P, Harrington MG: Free amino acid and dipeptide changes in the body fluids from Alzheimer's disease subjects. Amino Acids. 2007 Feb;32(2):213-24. Epub 2006 Oct 10. Pubmed: 17031479
    Carbamoyl Phosphate Synthetase Deficiency
    Cystinuria
    Leukemia
    • Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
    Lysinuric protein intolerance
    Refractory localization-related epilepsy
    • Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
    Hyperdibasic aminoaciduria I
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB000474
    KNApSAcK IDC00001378
    Chemspider ID5747
    KEGG Compound IDC00047
    BioCyc IDLYS
    BiGG ID33655
    Wikipedia LinkL-Lysine
    NuGOwiki LinkHMDB00182
    Metagene LinkHMDB00182
    METLIN ID5200
    PubChem Compound5962
    PDB ID1BBU
    ChEBI ID18019
    References
    Synthesis ReferenceRothstein, Morton. DL-Lysine-6-C14 and DL-a-aminoadipic acid-6-C14. Biochemical Preparations (1961), 8 85-8.
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
    2. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
    3. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. Pubmed: 6696735
    4. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
    5. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. Pubmed: 6198473
    6. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. Pubmed: 15911239
    7. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. Pubmed: 12297216
    8. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. Pubmed: 14992292
    9. Kranz BR: Detection of rare malignant cells and their apoptotic fragments in cerebrospinal fluid. Lancet. 2000 Oct 7;356(9237):1242-4. Pubmed: 11072949
    10. Hajishengallis G, Koga T, Russell MW: Affinity and specificity of the interactions between Streptococcus mutans antigen I/II and salivary components. J Dent Res. 1994 Sep;73(9):1493-502. Pubmed: 7523469
    11. Pahler A, Parker J, Dekant W: Dose-dependent protein adduct formation in kidney, liver, and blood of rats and in human blood after perchloroethene inhalation. Toxicol Sci. 1999 Mar;48(1):5-13. Pubmed: 10330678
    12. Faraasen S, Voros J, Csucs G, Textor M, Merkle HP, Walter E: Ligand-specific targeting of microspheres to phagocytes by surface modification with poly(L-lysine)-grafted poly(ethylene glycol) conjugate. Pharm Res. 2003 Feb;20(2):237-46. Pubmed: 12636162

    Enzymes

    Gene Name:
    BTD
    Uniprot ID:
    P43251
    Reactions
    Biocytin + Water unknown Biotin + L-Lysinedetails
    Gene Name:
    KARS
    Uniprot ID:
    Q15046
    Reactions
    Adenosine triphosphate + L-Lysine + tRNA(Lys) unknown Adenosine monophosphate + Pyrophosphate + L-lysyl-tRNA(Lys)details
    Adenosine triphosphate + L-Lysine + tRNA(Lys) unknown Adenosine monophosphate + Pyrophosphate + L-Lysyl-tRNAdetails
    Gene Name:
    AASS
    Uniprot ID:
    Q9UDR5
    Reactions
    N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NADP + Water unknown L-Lysine + Oxoglutaric acid + NADPHdetails
    Saccharopine + NADP + Water unknown L-Lysine + Oxoglutaric acid + NADPH + Hydrogen Iondetails
    Gene Name:
    PRDM2
    Uniprot ID:
    Q13029
    Gene Name:
    AASS
    Uniprot ID:
    A4D0W4
    Gene Name:
    CARNS1
    Uniprot ID:
    A5YM72
    Reactions
    Adenosine triphosphate + L-Lysine + Beta-Alanine unknown Adenosine monophosphate + Pyrophosphate + beta-Alanyl-L-lysinedetails
    Gene Name:
    WHSC1L1
    Uniprot ID:
    Q9BZ95
    Gene Name:
    KDM2A
    Uniprot ID:
    Q9Y2K7
    Gene Name:
    KDM2B
    Uniprot ID:
    Q8NHM5