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Record Information
Version4.0
Creation Date2006-08-12 20:14:46 UTC
Update Date2017-09-27 08:24:21 UTC
HMDB IDHMDB0003405
Secondary Accession Numbers
  • HMDB03405
Metabolite Identification
Common NameD-Lysine
DescriptionD-Lysine is an essential amino acid. It is often added to animal feed.
Structure
Thumb
Synonyms
ValueSource
(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
(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
(+)-S-LysineHMDB
(S)-2,6-diamino-HexanoateHMDB
(S)-2,6-diamino-Hexanoic acidHMDB
(S)-a,e-DiaminocaproateHMDB
(S)-a,e-Diaminocaproic acidHMDB
2,6-DiaminohexanoateHMDB
2,6-Diaminohexanoic 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, lysineMeSH
EnisylMeSH
Lysine hydrochlorideMeSH
L LysineMeSH
Lysine acetateMeSH
Chemical FormulaC6H14N2O2
Average Molecular Weight146.1876
Monoisotopic Molecular Weight146.105527702
IUPAC Name(2S)-2,6-diaminohexanoic acid
Traditional NameL-lysine
CAS Registry Number923-27-3
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
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 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
Disposition

Biological Location:

  Subcellular:

Source:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Metabolism and nutrition disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
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
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Feces
Tissue Location
  • Neuron
Pathways
NameSMPDB/PathwhizKEGG
2-aminoadipic 2-oxoadipic aciduriaPw000696Pw000696 greyscalePw000696 simpleNot Available
Biotin MetabolismPw000013Pw000013 greyscalePw000013 simpleMap00780
Biotinidase DeficiencyPw000092Pw000092 greyscalePw000092 simpleNot Available
Carnitine SynthesisPw000016Pw000016 greyscalePw000016 simpleNot Available
Glutaric Aciduria Type IPw000111Pw000111 greyscalePw000111 simpleNot Available
Displaying entries 1 - 5 of 11 in total
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Infant (0-1 year old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023163
KNApSAcK IDNot Available
Chemspider ID51793
KEGG Compound IDC00739
BioCyc IDCPD-219
BiGG IDNot Available
Wikipedia LinkLysine
METLIN ID6919
PubChem Compound57449
PDB IDDLY
ChEBI ID16855
References
Synthesis ReferenceFurui, Masakatsu; Takahashi, Eiji; Seko, Hiroyasu. Process for preparing D-lysine. Eur. Pat. Appl. (1996), 7 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wakisaka K, Arano Y, Uezono T, Akizawa H, Ono M, Kawai K, Ohomomo Y, Nakayama M, Saji H: A novel radioiodination reagent for protein radiopharmaceuticals with L-lysine as a plasma-stable metabolizable linkage to liberate m-iodohippuric acid after lysosomal proteolysis. J Med Chem. 1997 Aug 1;40(16):2643-52. [PubMed:9258371 ]
  2. Darling PB, Bross R, Wykes LJ, Ball RO, Pencharz PB: Isotopic enrichment of amino acids in urine following oral infusions of L-[1-(13)C]phenylalanine and L-[1-(13)C]lysine in humans: confounding effect of D-[13C]amino acids. Metabolism. 1999 Jun;48(6):732-7. [PubMed:10381147 ]
  3. Bross R, Ball RO, Pencharz PB: Development of a minimally invasive protocol for the determination of phenylalanine and lysine kinetics in humans during the fed state. J Nutr. 1998 Nov;128(11):1913-9. [PubMed:9808642 ]
  4. Hayman MW, Smith KH, Cameron NR, Przyborski SA: Growth of human stem cell-derived neurons on solid three-dimensional polymers. J Biochem Biophys Methods. 2005 Mar 31;62(3):231-40. Epub 2004 Dec 30. [PubMed:15733583 ]