D-Lysine (CHEM003379)

Record Information
Version1.0
Creation Date2014-08-29 06:51:11 UTC
Update Date2026-05-14 17:48:54 UTC
Accession NumberCHEM003379
Identification
Common NameD-Lysine
ClassSmall Molecule
Description
D-Lysine is an essential amino acid. It is often added to animal feed.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
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 Mass146.190 g/mol
Monoisotopic Mass146.106 g/mol
CAS Registry Number923-27-3
IUPAC Name(2R)-2,6-diaminohexanoic acid
Traditional NameD-lysine
SMILESNCCCC[C@@H](N)C(O)=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Neuron
Pathways
NameSMPDB LinkKEGG Link
Lysinuric Protein IntoleranceSMP00197 Not Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB03252
HMDB IDHMDB0003405
FooDB IDFDB023163
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-219
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLysine
Chemspider ID51793
ChEBI ID16855
PubChem Compound ID57449
Kegg Compound IDC00739
YMDB IDNot Available
ECMDB IDM2MDB004926
References
Synthesis Reference

Masakatsu Furui, Eiji Takahashi, Hiroyasu Seko, “Process for preparing D-lysine.” U.S. Patent US5723321, issued June, 1992.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10571145
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=125972
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=15561717
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=15914930
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16595662
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=17259313
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=22569959
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23023754
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23090865
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=2435906
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=2493343
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=2503300
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=2510957
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=4359655
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=4391118
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=4710063
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=5128165
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=6448848
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=7563967
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=77880
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=8063049
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=8234494
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=8405749
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=9163947
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=9430472
27. Furui, Masakatsu; Takahashi, Eiji; Seko, Hiroyasu. Process for preparing D-lysine. Eur. Pat. Appl. (1996), 7 pp.
28. 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.
29. 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.
30. 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.
31. 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.