L-Leucine
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Basic Info
| Common Name | L-Leucine(F05358) |
| 2D Structure | |
| Description | Leucine (abbreviated as Leu or L)[2] is a branched-chain л±-amino acid with the chemical formulaHO2CCH(NH2)CH2CH(CH3)2. Leucine is classified as a hydrophobic amino acid due to its aliphatic isobutyl side chain. It is encoded by six codons (UUA, UUG, CUU, CUC, CUA, and CUG) and is a major component of the subunits in ferritin, astacin, and other 'buffer' proteins. Leucine is an essential amino acid, meaning that the human body cannot synthesize it, and it therefore must be ingested. It is important for hemoglobin formation. |
| FRCD ID | F05358 |
| CAS Number | 61-90-5 |
| PubChem CID | 6106 |
| Formula | C6H13NO2 |
| IUPAC Name | (2S)-2-amino-4-methylpentanoic acid |
| InChI Key | ROHFNLRQFUQHCH-YFKPBYRVSA-N |
| 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 |
| Canonical SMILES | CC(C)CC(C(=O)O)N |
| Isomeric SMILES | CC(C)C[C@@H](C(=O)O)N |
| Wikipedia | L-Leucine |
| Synonyms |
(S)-Leucine
L-Norvaline, 4-methyl-
L-leucine
leucine
61-90-5
(S)-2-Amino-4-methylpentanoic acid
H-Leu-OH
(2S)-2-amino-4-methylpentanoic acid
(S)-(+)-Leucine
Leucin
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| 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. |
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 |
| Monoisotopic Mass | 131.095 |
| Exact Mass | 131.095 |
| XLogP | -1.5 |
| 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 |
ADMET
| 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 |
| 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 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Lactobacillus plantarum IS-10506 activates intestinal stem cells in a rodentmodel. | Benef Microbes | 2018 May 4:1-6 | 29726283 |
| Catalytic amino acid production from biomass-derived intermediates. | Proc Natl Acad Sci U S A | 2018 May 15 | 29712826 |
| Serum metabolomic profile of incident diabetes. | Diabetologia | 2018 May | 29556673 |
| Characterization of H9N2 avian influenza viruses from the Middle Eastdemonstrates heterogeneity at amino acid position 226 in the hemagglutinin andpotential for transmission to mammals. | Virology | 2018 May | 29524835 |
| Molecular Characterization and Overexpression of VpRPW8s from Vitispseudoreticulata Enhances Resistance to Phytophthora capsici in Nicotianabenthamiana. | Int J Mol Sci | 2018 Mar 13 | 29534026 |
| Molecular characterization of fluoroquinolone and/or cephalosporin resistance in Shigella sonnei isolates from yaks. | BMC Vet Res | 2018 Jun 7 | 29879965 |
| Detoxification of Aflatoxin B1 by Antifungal Compounds from Lactobacillus brevis and Lactobacillus paracasei, Isolated from Dairy Products. | Probiotics Antimicrob Proteins | 2018 Jun | 29150754 |
| Diversity and Probiotic Potential of Lactic Acid Bacteria Isolated from Horreh, aTraditional Iranian Fermented Food. | Probiotics Antimicrob Proteins | 2018 Jun | 28527125 |
| The island cotton NBS-LRR gene GbaNA1 confers resistance to the non-race 1Verticillium dahliae isolate Vd991. | Mol Plant Pathol | 2018 Jun | 29052967 |
| Frequency of Mutations in Quinolone Resistance-Determining Regions andPlasmid-Mediated Quinolone Resistance in Shigella Isolates Recovered fromPediatric Patients in Tehran, Iran: An Overlooked Problem. | Microb Drug Resist | 2018 Jul/Aug | 29148915 |
| Metabolism of sulfamethoxazole in Arabidopsis thaliana cells and cucumberseedlings. | Environ Pollut | 2018 Jul 27 | 30078686 |
| DEAD-box helicase 6 (DDX6) is a new negative regulator for milk synthesis andproliferation of bovine mammary epithelial cells. | In Vitro Cell Dev Biol Anim | 2018 Jan | 28842848 |
| Varying the ratio of Lys:Met while maintaining the ratios of Thr:Phe, Lys:Thr,Lys:His, and Lys:Val alters mammary cellular metabolites, mammalian target ofrapamycin signaling, and gene transcription. | J Dairy Sci | 2018 Feb | 29248224 |
| Effects of maternal treatment with β-hydroxy-β-metylbutyrate and 2-oxoglutaricacid on femur development in offspring of minks of the standard dark brown type. | J Anim Physiol Anim Nutr (Berl) | 2018 Feb | 28503899 |
| Changes in maize transcriptome in response to maize Iranian mosaic virusinfection. | PLoS One | 2018 Apr 10 | 29634778 |
| Effects of tryptophan-containing peptides on angiotensin-converting enzymeactivity and vessel tone ex vivo and in vivo. | Eur J Nutr | 2018 Apr | 28102435 |
| Generation of 2 induced pluripotent stem cell lines derived from patients withParkinson's disease carrying LRRK2 G2385R variant. | Stem Cell Res | 2018 Apr | 29414410 |
| The Fungal bZIP Transcription Factor AtfB Controls Virulence-Associated Processes in Aspergillus parasiticus. | Toxins (Basel) | 2017 Sep 16 | 28926946 |
| Effects of multi-carbohydrase and phytase on standardized ileal digestibility of amino acids and apparent metabolizable energy in canola meal fed to broilerchicks. | Poult Sci | 2017 Sep 1 | 28854754 |
| 13 C metabolic flux profiling of Pichia pastoris grown in aerobic batch cultures on glucose revealed high relative anabolic use of TCA cycle and limitedincorporation of provided precursors of branched-chain amino acids. | FEBS J | 2017 Sep | 28731268 |
Targets
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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-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
- Chen CD, Huang TF, Lin CH, Guan HH, Hsieh YC, Lin YH, Huang YC, Liu MY, Chang WC, Chen CJ: Purification, crystallization and preliminary X-ray crystallographic analysis of branched-chain aminotransferase from Deinococcus radiodurans. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2007 Jun 1;63(Pt 6):492-4. Epub 2007 May 5. [17554170 ]
- 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
- Ma JJ, Zhao MW, Wang ED: Split leucine-specific domain of leucyl-tRNA synthetase from the hyperthermophilic bacterium Aquifex aeolicus. Biochemistry. 2006 Dec 12;45(49):14809-16. [17144674 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
- 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 ]