D-Lysine
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Identification
- Generic Name
- D-Lysine
- DrugBank Accession Number
- DB03252
- Background
An essential amino acid. It is often added to animal feed. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 146.1876
Monoisotopic: 146.105527702 - Chemical Formula
- C6H14N2O2
- Synonyms
- (R)-2,6-diaminohexanoic acid
- D-2,6-Diaminohexanoic acid
- D-Lysin
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAlanine racemase, catabolic Not Available Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) UDiaminopimelate decarboxylase Not Available Escherichia 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboxylic acid / D-alpha-amino acid / Fatty acid / Fatty acyl / Hydrocarbon derivative
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- lysine, D-alpha-amino acid (CHEBI:16855) / Other amino acids (C00739)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 3HQ6U6424Q
- CAS number
- 923-27-3
- 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][C@@](N)(CCCCN)C(O)=O
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
- ZINC
- ZINC000001532731
- PDBe Ligand
- DLY
- PDB Entries
- 1c4b / 1ko0 / 1rcq / 1ywh / 2ats / 2ki4 / 2ki6 / 2kql / 2m7i / 2q33 … show 139 more
Clinical Trials
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
Property Value Source Water Solubility 105.0 mg/mL ALOGPS logP -3.8 ALOGPS logP -3.2 Chemaxon logS -0.14 ALOGPS pKa (Strongest Acidic) 2.74 Chemaxon pKa (Strongest Basic) 10.29 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 89.34 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 37.81 m3·mol-1 Chemaxon Polarizability 15.91 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8514 Blood Brain Barrier + 0.7107 Caco-2 permeable - 0.7663 P-glycoprotein substrate Non-substrate 0.5949 P-glycoprotein inhibitor I Non-inhibitor 0.9863 P-glycoprotein inhibitor II Non-inhibitor 0.9625 Renal organic cation transporter Non-inhibitor 0.8878 CYP450 2C9 substrate Non-substrate 0.85 CYP450 2D6 substrate Non-substrate 0.7525 CYP450 3A4 substrate Non-substrate 0.8287 CYP450 1A2 substrate Non-inhibitor 0.9379 CYP450 2C9 inhibitor Non-inhibitor 0.9643 CYP450 2D6 inhibitor Non-inhibitor 0.9749 CYP450 2C19 inhibitor Non-inhibitor 0.9653 CYP450 3A4 inhibitor Non-inhibitor 0.9338 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9912 Ames test AMES toxic 0.8612 Carcinogenicity Non-carcinogens 0.8476 Biodegradation Ready biodegradable 0.8163 Rat acute toxicity 1.3190 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9694 hERG inhibition (predictor II) Non-inhibitor 0.9525
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-9600000000-867c0bee952743ac8810 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-dd9ae886af0691e0035e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-9000000000-fa53aac5a8c9e362a6a6 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-773d2b7a8398ef303561 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-8f53acee07658da412b9 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9000000000-33881e056f19badf7f69 1H NMR Spectrum 1D NMR Not Applicable Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable [1H,13C] 2D NMR Spectrum 2D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 135.8836732 predictedDarkChem Lite v0.1.0 [M-H]- 127.20033 predictedDeepCCS 1.0 (2019) [M+H]+ 136.3408732 predictedDarkChem Lite v0.1.0 [M+H]+ 130.89915 predictedDeepCCS 1.0 (2019) [M+Na]+ 136.3156732 predictedDarkChem Lite v0.1.0 [M+Na]+ 139.80876 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAlanine racemase, catabolic
- 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
2. DetailsDiaminopimelate decarboxylase
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52