L-ISOLEUCINE
Relevant Data
Food Additives Approved in the United States
General Information
| CAS number: | 73-32-5 |
| JECFA number: | 2118 |
| FEMA number: | 4675 |
| Functional Class: |
Flavouring Agent FLAVOURING_AGENT |
From apps.who.int
Evaluations
| Evaluation year: | 2012 |
| ADI: | No safety concern at current levels of intake when used as a flavouring agent |
| Specs Code: | N |
| Report: | TRS 974-JECFA 76 |
| Tox Monograph: | FAS 67 JECFA 76 |
| Specification: | Compendium of FAO food additive specifications |
From apps.who.int
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6306 |
| IUPAC Name | (2S,3S)-2-amino-3-methylpentanoic acid |
| 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 |
| InChI Key | AGPKZVBTJJNPAG-WHFBIAKZSA-N |
| Canonical SMILES | CCC(C)C(C(=O)O)N |
| Molecular Formula | C6H13NO2 |
| Wikipedia | L-Isoleucine |
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 | 103.0 |
| 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 K 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 | 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 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| 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 |
From admetSAR
ADMET Predicted Profile --- Regression
| 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 |
From admetSAR
Toxicity Profile
| Route of Exposure | Absorbed from the small intestine by a sodium-dependent active-transport process |
|---|---|
| Mechanism of Toxicity | (Applies to Valine, Leucine and Isoleucine) <br/>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. <br/>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. <br/>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 | 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 | 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 | 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. |
From ClassyFire
Targets
- General Function:
- Isoleucine-trna ligase activity
- Gene Name:
- IARS
- Uniprot ID:
- P41252
- Molecular Weight:
- 144496.915 Da
References
- Pezo V, Metzgar D, Hendrickson TL, Waas WF, Hazebrouck S, Doring V, Marliere P, Schimmel P, De Crecy-Lagard V: Artificially ambiguous genetic code confers growth yield advantage. Proc Natl Acad Sci U S A. 2004 Jun 8;101(23):8593-7. Epub 2004 May 26. [15163798 ]
- General Function:
- Isoleucine-trna ligase activity
- Gene Name:
- IARS2
- Uniprot ID:
- Q9NSE4
- Molecular Weight:
- 113790.565 Da
References
- Fukunaga R, Yokoyama S: Structural basis for substrate recognition by the editing domain of isoleucyl-tRNA synthetase. J Mol Biol. 2006 Jun 16;359(4):901-12. Epub 2006 Apr 25. [16697013 ]
- 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: Inborn errors of isoleucine degradation: a review. Mol Genet Metab. 2006 Dec;89(4):289-99. Epub 2006 Sep 6. [16950638 ]
- 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
- Madsen SM, Beck HC, Ravn P, Vrang A, Hansen AM, Israelsen H: Cloning and inactivation of a branched-chain-amino-acid aminotransferase gene from Staphylococcus carnosus and characterization of the enzyme. Appl Environ Microbiol. 2002 Aug;68(8):4007-14. [12147502 ]
- 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 ]
From T3DB