Record Information
Version1.0
Creation date2010-04-08 22:10:25 UTC
Update date2019-11-27 17:23:19 UTC
Primary IDFDB012887
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nameepsilon-Polylysine
DescriptionFood additive Allysine is a derivative of lysine, used in the production of elastin and collagen. It is produced by the actions of the enzyme lysyl oxidase on lysine in the extracellular matrix and is essential in the crosslink formation that stabilizes collagen and elastin.; Insures the adequate absorption of calcium; L-Lysine is a necessary building block for all protein in the body. L-Lysine plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies.; 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. (http://www.dcnutrition.com); Lysine (abbreviated as Lys or K) is an ?-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.; Lysine is a base, as are arginine and histidine. The ?-amino group often participates in hydrogen bonding and as a general base in catalysis. Common posttranslational modifications include methylation of the ?-amino group, giving methyl-, dimethyl-, and trimethyllysine. The latter occurs in calmodulin. Other posttranslational modifications at lysine residues include acetylation and ubiquitination. 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.; The 1993 film Jurassic Park, which is based on the 1990 Michael Crichton novel Jurassic Park, features dinosaurs that were genetically altered so they could not produce lysine. This was supposed to prevent the cloned dinosaurs from leaving the park, forcing them to depend on lysine supplements provided by the park's veterinary staff. Most vertebrates cannot produce lysine by default (it is an essential amino acid).; The 2002 Max Tundra single "Lysine" (featuring Becky Jacobs) is a tribute to the advantages of lysine.
CAS Number25104-18-1
Structure
Thumb
Synonyms
SynonymSource
(S)-2,6-Diaminohexanoic acidChEBI
(S)-alpha,epsilon-Diaminocaproic acidChEBI
(S)-LysineChEBI
6-Ammonio-L-norleucineChEBI
KChEBI
L-2,6-Diaminocaproic acidChEBI
L-LysinChEBI
LysChEBI
LysinaChEBI
LysineChEBI
Lysine acidChEBI
LysinumChEBI
2,6-Diaminohexanoic acidKegg
(S)-2,6-DiaminohexanoateGenerator
(S)-a,epsilon-DiaminocaproateGenerator
(S)-a,epsilon-Diaminocaproic acidGenerator
(S)-alpha,epsilon-DiaminocaproateGenerator
(S)-Α,epsilon-diaminocaproateGenerator
(S)-Α,epsilon-diaminocaproic acidGenerator
L-2,6-DiaminocaproateGenerator
2,6-DiaminohexanoateGenerator
(+)-S-LysineHMDB
(S)-2,6-Diamino-hexanoateHMDB
(S)-2,6-Diamino-hexanoic acidHMDB
(S)-a,e-DiaminocaproateHMDB
(S)-a,e-Diaminocaproic acidHMDB
6-Amino-aminutrinHMDB
6-Amino-L-norleucineHMDB
a-LysineHMDB
alpha-LysineHMDB
AminutrinHMDB
H-Lys-OHHMDB
L-(+)-LysineHMDB
L-2,6-DiainohexanoateHMDB
L-2,6-Diainohexanoic acidHMDB
L-LysHMDB
Acetate, lysineHMDB
EnisylHMDB
Lysine hydrochlorideHMDB
L LysineHMDB
Lysine acetateHMDB
(s)-a,e-diaminocaproic acidbiospider
1ozvbiospider
1yxdbiospider
3H-Lysinebiospider
6-amino-Aminutrinbiospider
6-amino-L-Norleucinebiospider
A-lysinebiospider
Alpha-lysinebiospider
DLYbiospider
Gidrolizinbiospider
H-LYS-ohbiospider
Hydrolysinbiospider
Hydrolysinebiospider
L-lysinbiospider
L-lysine monohydratebiospider
L-lysine, homopolymerbiospider
L-lysine, labeled with tritiumbiospider
L-lysine, monoacetatebiospider
Lisinabiospider
LYSbiospider
LYS (iupac abbreviation)biospider
Lysine (usan/inn)biospider
Lysine [usan:inn]biospider
Lysine homopolymer, l-biospider
Polylysinebiospider
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 Area89.34 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.81 m³·mol⁻¹ChemAxon
Polarizability15.84 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H14N2O2
IUPAC name(2S)-2,6-diaminohexanoic acid
InChI IdentifierInChI=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
Isomeric SMILESNCCCC[C@H](N)C(O)=O
Average Molecular Weight146.1876
Monoisotopic Molecular Weight146.105527702
Classification
Description 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 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
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point224.5 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-3.05HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-00di-3910000000-98c565675de67aa87900View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0ab9-1910000000-87ef8534f592041f50f2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0a4i-1921000000-84f7815b0f650fa17444View in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-001i-9600000000-823408dba509cb204acfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-00di-3910000000-4f5578af5e7d8b6c49f7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0adi-1921000000-4e56d95e623e792f9e6bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-0921000000-eeb49e57bc1a75193058View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ab9-0921000000-ebb902be0f3754225b2fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-3910000000-98c565675de67aa87900View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ab9-1910000000-87ef8534f592041f50f2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0fdk-3923000000-15b84c2649c1b0455de1View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-1921000000-84f7815b0f650fa17444View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-9600000000-823408dba509cb204acfView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00di-3910000000-4f5578af5e7d8b6c49f7View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0adi-1921000000-4e56d95e623e792f9e6bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0abi-1900000000-9ad174122e4d6e003eb8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0089-9100000000-974cc55c9130ed5213ebView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ue9-9700000000-57b24ae819b6ec26bfd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-003r-8900000000-470a0beb4f338ed89bcaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-74e9193d9d33c2509bfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-9000000000-822c4e78250fffa56e39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0002-0900000000-04f9a62a77fb5a37ca22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-9000000000-035035ecfa084671479bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-5bb15839f86f4fca0d0bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-6c8ef03aa83eb1cab35bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-01ot-0910000000-c182a7dcdbc260666978View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4j-0900000000-6c5f378cef2f14204e15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-41e1a6499097748934b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-03di-0390000000-7270a0b85b9e3f9f6373View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-a997e809874357908880View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-2900000000-f64110414f82c93e1fe8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-014m-9200000000-33a38e6370811c5ddc82View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-3a8b0b6e62f5c66d3720View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-d5167570d11d77fd541eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0002-0900000000-a46231bd529176101129View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-9200000000-f8b9f01b2a9886c51df9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-ace0361476d939043e98View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-5b06b6e9dcf9faf8e89cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-053r-9000000000-2894ef6d7f72ea71688eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - CE-ESI-TOF (CE-system connected to 6210 Time-of-Flight MS, Agilent) , Positivesplash10-0002-0900000000-290902f43cf851e8ef5eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9300000000-f81193f6b50235ec8147View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9300000000-8931d2193adab166d5e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0002-0900000000-b4825cc64fcb830c6967View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHND72-V:HND72-V
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).