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Identification
NameD-Lysine
Accession NumberDB03252  (EXPT01219)
TypeSmall Molecule
GroupsExperimental
DescriptionAn 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
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNII3HQ6U6424Q
CAS number923-27-3
WeightAverage: 146.1876
Monoisotopic: 146.105527702
Chemical FormulaC6H14N2O2
InChI KeyKDXKERNSBIXSRK-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][C@@](N)(CCCCN)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Alanine racemase, catabolicProteinunknownNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Q9HTQ2 details
Diaminopimelate decarboxylaseProteinunknownNot AvailableEscherichia coli (strain K12)P00861 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
References
Synthesis Reference

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

US5723321
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Taxonomy
DescriptionThis 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.
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 acyl
  • Fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors

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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23