You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-08-12 20:14:46 UTC
Update Date2019-07-23 05:45:46 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
Data?1563860746
Synonyms
ValueSource
(R)-2,6-Diaminohexanoic acidChEBI
D-2,6-Diaminohexanoic acidChEBI
D-LysinChEBI
DLYChEBI
(R)-2,6-DiaminohexanoateGenerator
D-2,6-DiaminohexanoateGenerator
Chemical FormulaC6H14N2O2
Average Molecular Weight146.19
Monoisotopic Molecular Weight146.105527699
IUPAC Name(2R)-2,6-diaminohexanoic acid
Traditional NameD-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-/m1/s1
InChI KeyKDXKERNSBIXSRK-RXMQYKEDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentD-alpha-amino acids
Alternative Parents
Substituents
  • D-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
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

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
Polarizability15.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f8a-2900000000-d5972dfce0860da55a0aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-9700000000-d8e3259076e214ba9a3fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-0b901a2eb0a82d41fc3dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-603377bb44b83d433b77JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-3900000000-e5d6ccb8cd7879780fafJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9100000000-e7f9a18ab48141069feeJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Feces
Tissue Locations
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB03252
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023163
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00739
BioCyc IDCPD-219
BiGG IDNot Available
Wikipedia LinkLysine
METLIN IDNot Available
PubChem Compound57449
PDB IDNot Available
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 ]