Record Information
Version1.0
Creation date2010-04-08 22:04:35 UTC
Update date2018-05-29 00:29:12 UTC
Primary IDFDB000474
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Lysine
DescriptionDietary supplement, nutrient. Found widely in protein hydrolysates, e.g. casein, egg albumen, fibrin, gelatin, beet molasses. Flavouring agent for a variety of foods Lysine (abbreviated as Lys or K) is an alpha-amino acid with the chemical formula HO2CCH(NH2)(CH2)4NH2. It is an essential amino acid, which means that the human body cannot synthesize it. Its codons are AAA and AAG. L-Lysine is found in many foods, some of which are rocket salad (sspecies), lingonberry, japanese persimmon, and welsh onion.
CAS Number56-87-1
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)-α,epsilon-diaminocaproateGenerator
(S)-α,epsilon-diaminocaproic acidGenerator
FEMA 3847db_source
L-Lysinedb_source
Lysine, 9CI, INN, USAN; L-formdb_source
S-6-amino-L-Norleucinebiospider
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 49.30%; H 9.65%; N 19.16%; O 21.89%DFC
Melting PointMp 224-225 dec. (darkens at 210°)DFC
Boiling PointNot Available
Experimental Water Solubility1000 mg/mL at 20 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.05HANSCH,C ET AL. (1995)
Experimental pKapKa3 10.54 (25°, 0.1M NaClO4)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +37.9 (5M HCl)DFC
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 ID5747
ChEMBL IDCHEMBL8085
KEGG Compound IDC00047
Pubchem Compound ID5962
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB03252
HMDB IDHMDB00182
CRC / DFC (Dictionary of Food Compounds) IDBCS45-Z:BCS47-B
EAFUS ID2071
Dr. Duke IDLYSINE
BIGG ID33655
KNApSAcK IDC00001378
HET ID1BBU
Flavornet IDNot Available
GoodScent IDrw1107871
SuperScent IDNot Available
Wikipedia IDLysine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti alkaloticDUKE
anti herpetic22587 A substance that destroys or inhibits replication of viruses.DUKE
essentialDUKE
hypoarginanemicDUKE
Enzymes
NameGene NameUniProt ID
Aminoadipate-semialdehyde synthaseAASSA4D0W4
BiotinidaseBTDP43251
Lysine--tRNA ligaseKARSQ15046
Lysine-specific demethylase 2AKDM2AQ9Y2K7
Lysine-specific demethylase 2BKDM2BQ8NHM5
Pathways
NameSMPDB LinkKEGG Link
Biotin MetabolismSMP00066 map00780
Carnitine SynthesisSMP00465 Not Available
Lysine DegradationSMP00037 map00310
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
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).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).