D-Lysine

Identification

Name
D-Lysine
Accession Number
DB03252  (EXPT01219)
Type
Small Molecule
Groups
Experimental
Description

An essential amino acid. It is often added to animal feed. [PubChem]

Structure
Thumb
Synonyms
  • (R)-2,6-diaminohexanoic acid
  • D-2,6-Diaminohexanoic acid
  • D-Lysin
Categories
Not Available
UNII
3HQ6U6424Q
CAS number
923-27-3
Weight
Average: 146.1876
Monoisotopic: 146.105527702
Chemical Formula
C6H14N2O2
InChI Key
KDXKERNSBIXSRK-RXMQYKEDSA-N
InChI
InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m1/s1
IUPAC Name
(2R)-2,6-diaminohexanoic acid
SMILES
[H][[email protected]@](N)(CCCCN)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAlanine racemase, catabolicNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
UDiaminopimelate decarboxylaseNot AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

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

US5723321
General References
Not Available
External Links
KEGG Compound
C00739
PubChem Compound
57449
PubChem Substance
46506741
ChemSpider
51793
BindingDB
217368
ChEBI
16855
ChEMBL
CHEMBL319497
HET
DLY
PDB Entries
1c4b / 1ko0 / 1rcq / 1ywh / 2ats / 2ki4 / 2ki6 / 2kql / 2m7i / 2q33
show 66 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility105.0 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.81 m3·mol-1ChemAxon
Polarizability15.91 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8514
Blood Brain Barrier+0.7107
Caco-2 permeable-0.7663
P-glycoprotein substrateNon-substrate0.5949
P-glycoprotein inhibitor INon-inhibitor0.9863
P-glycoprotein inhibitor IINon-inhibitor0.9625
Renal organic cation transporterNon-inhibitor0.8878
CYP450 2C9 substrateNon-substrate0.85
CYP450 2D6 substrateNon-substrate0.7525
CYP450 3A4 substrateNon-substrate0.8287
CYP450 1A2 substrateNon-inhibitor0.9379
CYP450 2C9 inhibitorNon-inhibitor0.9643
CYP450 2D6 inhibitorNon-inhibitor0.9749
CYP450 2C19 inhibitorNon-inhibitor0.9653
CYP450 3A4 inhibitorNon-inhibitor0.9338
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9912
Ames testAMES toxic0.8612
CarcinogenicityNon-carcinogens0.8476
BiodegradationReady biodegradable0.8163
Rat acute toxicity1.3190 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9694
hERG inhibition (predictor II)Non-inhibitor0.9525
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
D-alpha-amino acids
Alternative Parents
Medium-chain fatty acids / Amino fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
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
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
lysine, D-alpha-amino acid (CHEBI:16855) / Other amino acids (C00739)

Targets

Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Isomerizes L-alanine to D-alanine which is then oxidized to pyruvate by DadA.
Gene Name
dadX
Uniprot ID
Q9HTQ2
Uniprot Name
Alanine racemase, catabolic
Molecular Weight
38914.32 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Pyridoxal phosphate binding
Specific Function
Specifically catalyzes the decarboxylation of meso-diaminopimelate (meso-DAP) to L-lysine. Is not active against the DD- or LL-isomers of diaminopimelate.
Gene Name
lysA
Uniprot ID
P00861
Uniprot Name
Diaminopimelate decarboxylase
Molecular Weight
46176.975 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:10