L-LEUCINE
Relevant Data
Food Additives Approved by WHO:
Flavouring Substances Approved by European Union:
General Information
| Mainterm | L-LEUCINE |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 61-90-5 |
| Regnum |
172.320 172.804 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6106 |
| IUPAC Name | (2S)-2-amino-4-methylpentanoic acid |
| InChI | InChI=1S/C6H13NO2/c1-4(2)3-5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t5-/m0/s1 |
| InChI Key | ROHFNLRQFUQHCH-YFKPBYRVSA-N |
| Canonical SMILES | CC(C)CC(C(=O)O)N |
| Molecular Formula | C6H13NO2 |
| Wikipedia | L-Leucine |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 131.175 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 101.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B i 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 D S j B g A Q C 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 C I A A A 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 = = |
| Topological Polar Surface Area | 63.3 |
| Monoisotopic Mass | 131.095 |
| Exact Mass | 131.095 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| 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+ | 0.6686 |
| Human Intestinal Absorption | HIA+ | 0.9785 |
| Caco-2 Permeability | Caco2- | 0.8958 |
| P-glycoprotein Substrate | Non-substrate | 0.6833 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9767 |
| Non-inhibitor | 0.9875 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9617 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.7172 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8483 |
| CYP450 2D6 Substrate | Non-substrate | 0.7693 |
| CYP450 3A4 Substrate | Non-substrate | 0.7389 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9045 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9543 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9336 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9608 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9558 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9910 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9929 |
| Non-inhibitor | 0.9760 | |
| AMES Toxicity | Non AMES toxic | 0.8892 |
| Carcinogens | Non-carcinogens | 0.7139 |
| Fish Toxicity | High FHMT | 0.7410 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.6849 |
| Honey Bee Toxicity | Low HBT | 0.5810 |
| Biodegradation | Ready biodegradable | 0.7417 |
| Acute Oral Toxicity | III | 0.6794 |
| Carcinogenicity (Three-class) | Non-required | 0.6822 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.1813 | LogS |
| Caco-2 Permeability | 0.2633 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5061 | LD50, mol/kg |
| Fish Toxicity | 2.9289 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.6956 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | This group of essential amino acids are identified as the branched-chain amino acids, BCAAs. Because this arrangement of carbon atoms cannot be made by humans, these amino acids are an essential element in the diet. The catabolism of all three compounds initiates in muscle and yields NADH and FADH2 which can be utilized for ATP generation. The catabolism of all three of these amino acids uses the same enzymes in the first two steps. The first step in each case is a transamination using a single BCAA aminotransferase, with a-ketoglutarate as amine acceptor. As a result, three different a-keto acids are produced and are oxidized using a common branched-chain a-keto acid dehydrogenase, yielding the three different CoA derivatives. Subsequently the metabolic pathways diverge, producing many intermediates. The principal product from valine is propionylCoA, the glucogenic precursor of succinyl-CoA. Isoleucine catabolism terminates with production of acetylCoA and propionylCoA; thus isoleucine is both glucogenic and ketogenic. Leucine gives rise to acetylCoA and acetoacetylCoA, and is thus classified as strictly ketogenic. There are a number of genetic diseases associated with faulty catabolism of the BCAAs. The most common defect is in the branched-chain a-keto acid dehydrogenase. Since there is only one dehydrogenase enzyme for all three amino acids, all three a-keto acids accumulate and are excreted in the urine. The disease is known as Maple syrup urine disease because of the characteristic odor of the urine in afflicted individuals. Mental retardation in these cases is extensive. Unfortunately, since these are essential amino acids, they cannot be heavily restricted in the diet; ultimately, the life of afflicted individuals is short and development is abnormal The main neurological problems are due to poor formation of myelin in the CNS. |
| Metabolism | None |
| 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 | None |
| 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 |
| Direct Parent | Leucine and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Leucine or derivatives - Alpha-amino acid - L-alpha-amino acid - Branched fatty acid - Methyl-branched fatty acid - Fatty acid - Fatty acyl - Amino acid - Monocarboxylic acid or derivatives - Carboxylic acid - Organic oxide - Organopnictogen compound - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Carbonyl group - Organic oxygen compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. |
From ClassyFire
Targets
- General Function:
- Leucine-trna ligase activity
- Specific Function:
- Catalyzes the specific attachment of an amino acid to its cognate tRNA in a two 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. Exhibits a post-transfer editing activity to hydrolyze mischarged tRNAs.
- Gene Name:
- LARS
- Uniprot ID:
- Q9P2J5
- Molecular Weight:
- 134465.155 Da
References
- Dohm JC, Vingron M, Staub E: Horizontal gene transfer in aminoacyl-tRNA synthetases including leucine-specific subtypes. J Mol Evol. 2006 Oct;63(4):437-47. Epub 2006 Sep 4. [16955236 ]
- General Function:
- Leucine-trna ligase activity
- Gene Name:
- LARS2
- Uniprot ID:
- Q15031
- Molecular Weight:
- 101975.43 Da
References
- Lue SW, Kelley SO: A single residue in leucyl-tRNA synthetase affecting amino acid specificity and tRNA aminoacylation. Biochemistry. 2007 Apr 17;46(15):4466-72. Epub 2007 Mar 23. [17378584 ]
- General Function:
- S-adenosylmethionine-dependent methyltransferase activity
- Specific Function:
- Methylates the carboxyl group of the C-terminal leucine residue of protein phosphatase 2A catalytic subunits to form alpha-leucine ester residues.
- Gene Name:
- LCMT1
- Uniprot ID:
- Q9UIC8
- Molecular Weight:
- 38378.695 Da
References
- 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. [17016423 ]
- General Function:
- Trna methyltransferase activity
- Specific Function:
- Probable S-adenosyl-L-methionine-dependent methyltransferase that acts as a component of the wybutosine biosynthesis pathway. Wybutosine is a hyper modified guanosine with a tricyclic base found at the 3'-position adjacent to the anticodon of eukaryotic phenylalanine tRNA (By similarity). May methylate the carboxyl group of leucine residues to form alpha-leucine ester residues.
- Gene Name:
- LCMT2
- Uniprot ID:
- O60294
- Molecular Weight:
- 75601.095 Da
References
- 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. [17016423 ]
- General Function:
- L-valine transaminase activity
- Specific Function:
- Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids.
- Gene Name:
- BCAT2
- Uniprot ID:
- O15382
- Molecular Weight:
- 44287.445 Da
References
- Berger BJ, English S, Chan G, Knodel MH: Methionine regeneration and aminotransferases in Bacillus subtilis, Bacillus cereus, and Bacillus anthracis. J Bacteriol. 2003 Apr;185(8):2418-31. [12670965 ]
- General Function:
- L-valine transaminase activity
- Specific Function:
- Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine.
- Gene Name:
- BCAT1
- Uniprot ID:
- P54687
- Molecular Weight:
- 42965.815 Da
References
- Saito M, Nishimura K, Wakabayashi S, Kurihara T, Nagata Y: Purification of branched-chain amino acid aminotransferase from Helicobacter pylori NCTC 11637. Amino Acids. 2007 Sep;33(3):445-9. Epub 2006 Nov 2. [17077963 ]
- General Function:
- Pyrophosphatase activity
- Specific Function:
- This isozyme may play a role in skeletal mineralization.
- Gene Name:
- ALPL
- Uniprot ID:
- P05186
- Molecular Weight:
- 57304.435 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ALPI
- Uniprot ID:
- P09923
- Molecular Weight:
- 56811.695 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- Phospholipase a2 activator activity
- Specific Function:
- Involved in the maintenance of ubiquitin levels.
- Gene Name:
- PLAA
- Uniprot ID:
- Q9Y263
- Molecular Weight:
- 87156.21 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- L-proline transmembrane transporter activity
- Specific Function:
- Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
- Gene Name:
- SLC36A1
- Uniprot ID:
- Q7Z2H8
- Molecular Weight:
- 53075.045 Da
References
- Thondorf I, Voigt V, Schafer S, Gebauer S, Zebisch K, Laug L, Brandsch M: Three-dimensional quantitative structure-activity relationship analyses of substrates of the human proton-coupled amino acid transporter 1 (hPAT1). Bioorg Med Chem. 2011 Nov 1;19(21):6409-18. doi: 10.1016/j.bmc.2011.08.058. Epub 2011 Sep 5. [21955456 ]
From T3DB