L-Isoleucine
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Basic Info
| Common Name | L-Isoleucine(F05357) |
| 2D Structure | |
| Description | L-Isoleucine is one of the essential amino acids that cannot be made by the body and is known for its ability to help endurance and assist in the repair and rebuilding of muscle. This amino acid is important to body builders as it helps boost energy and helps the body recover from training. L-Isoleucine is also classified as a branched-chain amino acid (BCAA). It helps promote muscle recovery after exercise. Isoleucine is actually broken down for energy within the muscle tissue. It is important in hemoglobin synthesis and regulation of blood sugar and energy levels. |
| FRCD ID | F05357 |
| CAS Number | 73-32-5 |
| PubChem CID | 6306 |
| Formula | C6H13NO2 |
| IUPAC Name | (2S,3S)-2-amino-3-methylpentanoic acid |
| InChI Key | AGPKZVBTJJNPAG-WHFBIAKZSA-N |
| InChI | InChI=1S/C6H13NO2/c1-3-4(2)5(7)6(8)9/h4-5H,3,7H2,1-2H3,(H,8,9)/t4-,5-/m0/s1 |
| Canonical SMILES | CCC(C)C(C(=O)O)N |
| Isomeric SMILES | CC[C@H](C)[C@@H](C(=O)O)N |
| Wikipedia | L-Isoleucine |
| Synonyms |
(2S,3S)-2-Amino-3-methylpentanoic acid
l-isoleucine
Isoleucine
73-32-5
(S)-Isoleucine
(S,S)-Isoleucine
2S,3S-Isoleucine
2-Amino-3-methylvaleric acid
erythro-L-Isoleucine
L-(+)-Isoleucine
|
| 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 | Isoleucine and derivatives |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Isoleucine 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 isoleucine and derivatives. These are compounds containing isoleucine or a derivative thereof resulting from reaction of isoleucine 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 | 103 |
| Monoisotopic Mass | 131.095 |
| Exact Mass | 131.095 |
| XLogP | -1.7 |
| Formal Charge | 0 |
| Heavy Atom Count | 9 |
| Defined Atom Stereocenter Count | 2 |
| 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+ | 0.7800 |
| Human Intestinal Absorption | HIA+ | 0.9677 |
| Caco-2 Permeability | Caco2- | 0.7966 |
| P-glycoprotein Substrate | Non-substrate | 0.7385 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9825 |
| Non-inhibitor | 0.9739 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9696 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.6198 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8513 |
| CYP450 2D6 Substrate | Non-substrate | 0.8372 |
| CYP450 3A4 Substrate | Non-substrate | 0.7827 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.8536 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8762 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9000 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9386 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9155 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9700 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9921 |
| Non-inhibitor | 0.9735 | |
| AMES Toxicity | Non AMES toxic | 0.9030 |
| Carcinogens | Non-carcinogens | 0.6320 |
| Fish Toxicity | High FHMT | 0.6029 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.5156 |
| Honey Bee Toxicity | Low HBT | 0.5386 |
| Biodegradation | Ready biodegradable | 0.5166 |
| Acute Oral Toxicity | III | 0.6522 |
| Carcinogenicity (Three-class) | Non-required | 0.5962 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | 0.2002 | LogS |
| Caco-2 Permeability | 0.5153 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.5846 | LD50, mol/kg |
| Fish Toxicity | 3.2390 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.9153 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| A novel calcium-binding peptide from Antarctic krill protein hydrolysates andidentification of binding sites of calcium-peptide complex. | Food Chem | 2018 Mar 15 | 29146354 |
| Comparative Metabolomic Analyses of Ipomoea lacunosa Biotypes with ContrastingGlyphosate Tolerance Captures Herbicide-Induced Differential Perturbations inCellular Physiology. | J Agric Food Chem | 2018 Feb 28 | 29278495 |
| 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 |
| 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 |
| Milk protein responses to balanced amino acid and removal of Leucine and Argininesupplied from jugular-infused amino acid mixture in lactating dairy cows. | J Anim Physiol Anim Nutr (Berl) | 2017 Oct | 27862398 |
| Effect of elevated dietary amino acid levels in high canola meal diets onproductive traits and cecal microbiota population of broiler chickens in apair-feeding study. | Poult Sci | 2017 May 1 | 27811325 |
| Organochlorine pesticide residues in dried cocoa beans obtained from cocoa storesat Ondo and Ile-Ife, Southwestern Nigeria. | Toxicol Rep | 2017 Mar 6 | 28959635 |
| Effect of a high-concentrate diet on milk components and mammary health inHolstein dairy cows. | Genet Mol Res | 2017 Mar 22 | 28340261 |
| Ileal endogenous losses in pigs feeding a protein-free diet or diets withdifferent contents of casein or crystalline amino acids. | Arch Anim Nutr | 2017 Jun | 28429994 |
| Plasma protein and supplemental isoleucine in milk replacers for dairy calves. | J Dairy Sci | 2017 Jan | 27865507 |
| Temporal trends of mercury and organohalogen contaminants in great blue heroneggs from the St. Lawrence River, Québec, Canada, 1991-2011, and relationshipswith tracers of feeding ecology. | Sci Total Environ | 2017 Dec 31 | 28797142 |
| Effect of dietary fiber levels on performance, gizzard development, intestinalmorphology, and nutrient utilization in meat ducks from 1 to 21 days of age. | Poult Sci | 2017 Dec 1 | 29053831 |
| Optimal in-feed amino acid ratio for broiler breeder hens based on deletionstudies. | J Anim Physiol Anim Nutr (Berl) | 2017 Dec | 27862400 |
| Colistin Resistance Gene mcr-1 and Its Variant in Escherichia coli Isolates from Chickens in China. | Antimicrob Agents Chemother | 2017 Apr 24 | 28242671 |
| Structure-function relationships of brazzein variants with altered interactionswith the human sweet taste receptor. | Protein Sci | 2016 Mar | 26701738 |
| Characterization of aspartate kinase and homoserine dehydrogenase from Corynebacterium glutamicum IWJ001 and systematic investigation of L-isoleucine biosynthesis. | J Ind Microbiol Biotechnol | 2016 Jun | 27033538 |
| Effect of dietary excess of branched-chain amino acids on performance and serumconcentrations of amino acids in growing pigs. | J Anim Physiol Anim Nutr (Berl) | 2016 Feb | 25873515 |
| A simple method using two-step hot embossing technique with shrinking forfabrication of cross microchannels on PMMA substrate and its application toelectrophoretic separation of amino acids in functional drinks. | Talanta | 2016 Dec 1 | 27769450 |
| Formation of Peptide Bound Pyrraline in the Maillard Model Systems with DifferentLys-Containing Dipeptides and Tripeptides. | Molecules | 2016 Apr 7 | 27070556 |
| Purification and identification of anti-inflammatory peptides derived fromsimulated gastrointestinal digests of velvet antler protein (Cervus elaphusLinnaeus). | J Food Drug Anal | 2016 Apr | 28911592 |
Targets
- 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
- Goto M, Miyahara I, Hayashi H, Kagamiyama H, Hirotsu K: Crystal structures of branched-chain amino acid aminotransferase complexed with glutamate and glutarate: true reaction intermediate and double substrate recognition of the enzyme. Biochemistry. 2003 Apr 8;42(13):3725-33. [12667063 ]
- General Function:
- Isoleucine-trna ligase activity
- Gene Name:
- IARS
- Uniprot ID:
- P41252
- Molecular Weight:
- 144496.915 Da
References
- Crasto CF, Forrest AK, Karoli T, March DR, Mensah L, O'Hanlon PJ, Nairn MR, Oldham MD, Yue W, Banwell MG, Easton CJ: Synthesis and activity of analogues of the isoleucyl tRNA synthetase inhibitor SB-203207. Bioorg Med Chem. 2003 Jul 3;11(13):2687-94. [12788342 ]
- General Function:
- Oxidoreductase activity, acting on the ch-ch group of donors, with a flavin as acceptor
- Specific Function:
- Has greatest activity toward short branched chain acyl-CoA derivative such as (s)-2-methylbutyryl-CoA, isobutyryl-CoA, and 2-methylhexanoyl-CoA as well as toward short straight chain acyl-CoAs such as butyryl-CoA and hexanoyl-CoA. Can use valproyl-CoA as substrate and may play a role in controlling the metabolic flux of valproic acid in the development of toxicity of this agent.
- Gene Name:
- ACADSB
- Uniprot ID:
- P45954
- Molecular Weight:
- 47485.035 Da
References
- Korman SH, Andresen BS, Zeharia A, Gutman A, Boneh A, Pitt JJ: 2-ethylhydracrylic aciduria in short/branched-chain acyl-CoA dehydrogenase deficiency: application to diagnosis and implications for the R-pathway of isoleucine oxidation. Clin Chem. 2005 Mar;51(3):610-7. Epub 2004 Dec 22. [15615815 ]
- 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-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 ]