L-Lysine
Relevant Data
Food Additives Approved in the United States:
Food Additives Approved by WHO:
General Information
| Chemical name | L-Lysine |
| CAS number | 56-87-1 |
| COE number | 11947 |
| JECFA number | 1439 |
| Flavouring type | substances |
| FL No. | 17.026 |
| Mixture | No |
| Purity of the named substance at least 95% unless otherwise specified | |
| Reference body | EFSA |
From webgate.ec.europa.eu
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 5962 |
| IUPAC Name | (2S)-2,6-diaminohexanoic acid |
| InChI | InChI=1S/C6H14N2O2/c7-4-2-1-3-5(8)6(9)10/h5H,1-4,7-8H2,(H,9,10)/t5-/m0/s1 |
| InChI Key | KDXKERNSBIXSRK-YFKPBYRVSA-N |
| Canonical SMILES | C(CCN)CC(C(=O)O)N |
| Molecular Formula | C6H14N2O2 |
| Wikipedia | L-Lysine |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 146.19 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 5 |
| Complexity | 106.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B j M A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A H g A Q C A A A C C j B g A Q A C A B A A g A I A A C Q C A A A A A A A A A A A A I G A A A A C A B I A g A A A Q A A E E A A A A A G Y S A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A A = = |
| Topological Polar Surface Area | 89.3 |
| Monoisotopic Mass | 146.106 |
| Exact Mass | 146.106 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 10 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.7107 |
| Human Intestinal Absorption | HIA+ | 0.8514 |
| Caco-2 Permeability | Caco2- | 0.7663 |
| P-glycoprotein Substrate | Non-substrate | 0.5949 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9863 |
| Non-inhibitor | 0.9625 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8878 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.5313 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8500 |
| CYP450 2D6 Substrate | Non-substrate | 0.7525 |
| CYP450 3A4 Substrate | Non-substrate | 0.8287 |
| CYP450 1A2 Inhibitor | 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 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9912 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9694 |
| Non-inhibitor | 0.9525 | |
| AMES Toxicity | AMES toxic | 0.8612 |
| Carcinogens | Non-carcinogens | 0.8476 |
| Fish Toxicity | Low FHMT | 0.7653 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.9838 |
| Honey Bee Toxicity | Low HBT | 0.7166 |
| Biodegradation | Ready biodegradable | 0.8163 |
| Acute Oral Toxicity | IV | 0.4919 |
| Carcinogenicity (Three-class) | Non-required | 0.6531 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.8567 | LogS |
| Caco-2 Permeability | 0.5261 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3190 | LD50, mol/kg |
| Fish Toxicity | 3.3127 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.9810 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | Absorbed from the lumen of the small intestine into the enterocytes by an active transport process |
|---|---|
| Mechanism of Toxicity | Proteins of the herpes simplex virus are rich in L-arginine, and tissue culture studies indicate an enhancing effect on viral replication when the amino acid ratio of L-arginine to L-lysine is high in the tissue culture media. When the ratio of L-lysine to L-arginine is high, viral replication and the cytopathogenicity of herpes simplex virus have been found to be inhibited. L-lysine may facilitate the absorption of calcium from the small intestine. |
| Metabolism | Hepatic |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | Chronically high levels of lysine are associated with at least 5 inborn errors of metabolism including: D-2-Hydroxyglutaric Aciduria, Familial Hyperlysinemia I, Hyperlysinemia II, Pyruvate carboxylase deficiency and Saccharopinuria. |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Amino acids and derivatives - Alpha amino acids and derivatives - Alpha amino acids |
| Direct Parent | L-alpha-amino acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | L-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 |
| Description | This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. |
From ClassyFire
Targets
- General Function:
- Low-affinity l-arginine transmembrane transporter activity
- Specific Function:
- Functions as permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine); the affinity for its substrates differs between isoforms created by alternative splicing. Isoform 1 functions as permease that mediates the transport of the cationic amino acids (arginine, lysine and ornithine), and it has much higher affinity for arginine than isoform 2. Isoform 2 functions as low-affinity, high capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) (PubMed:9174363). May play a role in classical or alternative activation of macrophages via its role in arginine transport.
- Gene Name:
- SLC7A2
- Uniprot ID:
- P52569
- Molecular Weight:
- 71672.175 Da
References
- Schwartz D, Schwartz IF, Gnessin E, Wollman Y, Chernichovsky T, Blum M, Iaina A: Differential regulation of glomerular arginine transporters (CAT-1 and CAT-2) in lipopolysaccharide-treated rats. Am J Physiol Renal Physiol. 2003 Apr;284(4):F788-95. Epub 2002 Dec 10. [12475743 ]
- General Function:
- Trna binding
- Specific Function:
- Catalyzes the specific attachment of an amino acid to its cognate tRNA in a 2 step reaction: the amino acid (AA) is first activated by ATP to form AA-AMP and then transferred to the acceptor end of the tRNA. When secreted, acts as a signaling molecule that induces immune response through the activation of monocyte/macrophages. Catalyzes the synthesis of diadenosine oligophosphate (Ap4A), a signaling molecule involved in the activation of MITF transcriptional activity. Interacts with HIV-1 virus GAG protein, facilitating the selective packaging of tRNA(3)(Lys), the primer for reverse transcription initiation.
- Gene Name:
- KARS
- Uniprot ID:
- Q15046
- Molecular Weight:
- 68047.54 Da
References
- Kwon I, Wang P, Tirrell DA: Design of a bacterial host for site-specific incorporation of p-bromophenylalanine into recombinant proteins. J Am Chem Soc. 2006 Sep 13;128(36):11778-83. [16953616 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- High-affinity, low capacity permease involved in the transport of the cationic amino acids (arginine, lysine and ornithine) in non-hepatic tissues. May also function as an ecotropic retroviral leukemia receptor.
- Gene Name:
- SLC7A1
- Uniprot ID:
- P30825
- Molecular Weight:
- 67637.62 Da
References
- Nicholson B, Sawamura T, Masaki T, MacLeod CL: Increased Cat3-mediated cationic amino acid transport functionally compensates in Cat1 knockout cell lines. J Biol Chem. 1998 Jun 12;273(24):14663-6. [9614060 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Mediates the uptake of the cationic amino acids arginine, lysine and ornithine in a sodium-independent manner.
- Gene Name:
- SLC7A3
- Uniprot ID:
- Q8WY07
- Molecular Weight:
- 67168.31 Da
References
- Humphrey BD, Stephensen CB, Calvert CC, Klasing KC: Lysine deficiency and feed restriction independently alter cationic amino acid transporter expression in chickens (Gallus gallus domesticus). Comp Biochem Physiol A Mol Integr Physiol. 2006 Feb;143(2):218-27. Epub 2006 Jan 10. [16406639 ]
- General Function:
- L-ornithine transmembrane transporter activity
- Specific Function:
- Involved in the transport of the cationic amino acids (arginine, lysine and ornithine).
- Gene Name:
- SLC7A4
- Uniprot ID:
- O43246
- Molecular Weight:
- 68267.17 Da
References
- Rotoli BM, Bussolati O, Sala R, Gazzola GC, Dall'Asta V: The transport of cationic amino acids in human airway cells: expression of system y+L activity and transepithelial delivery of NOS inhibitors. FASEB J. 2005 May;19(7):810-2. Epub 2005 Mar 3. [15746185 ]
From T3DB