| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation Date | 2016-09-30 22:20:30 UTC |
|---|
| Update Date | 2020-06-04 22:12:11 UTC |
|---|
| BMDB ID | BMDB0000172 |
|---|
| Secondary Accession Numbers | |
|---|
| Metabolite Identification |
|---|
| Common Name | L-Isoleucine |
|---|
| Description | L-Isoleucine, also known as I, belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives 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. Thus, L-isoleucine is considered to be a fatty acid lipid molecule. L-Isoleucine exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. L-Isoleucine exists in all living species, ranging from bacteria to humans. L-Isoleucine is a potentially toxic compound. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| (2S,3S)-2-Amino-3-methylpentanoic acid | ChEBI | | 2-Amino-3-methylvaleric acid | ChEBI | | alpha-Amino-beta-methylvaleric acid | ChEBI | | I | ChEBI | | Ile | ChEBI | | ISOLEUCINE | ChEBI | | (2S,3S)-2-Amino-3-methylpentanoate | Generator | | 2-Amino-3-methylvalerate | Generator | | a-Amino-b-methylvalerate | Generator | | a-Amino-b-methylvaleric acid | Generator | | alpha-Amino-beta-methylvalerate | Generator | | Α-amino-β-methylvalerate | Generator | | Α-amino-β-methylvaleric acid | Generator | | (2S,3S)-2-Amino-3-methyl-pentanoate | HMDB | | (2S,3S)-2-Amino-3-methyl-pentanoic acid | HMDB | | (2S,3S)-a-Amino-b-methyl-N-valerate | HMDB | | (2S,3S)-a-Amino-b-methyl-N-valeric acid | HMDB | | (2S,3S)-a-Amino-b-methylvalerate | HMDB | | (2S,3S)-a-Amino-b-methylvaleric acid | HMDB | | (2S,3S)-Alph-amino-beta-methylvalerate | HMDB | | (2S,3S)-Alph-amino-beta-methylvaleric acid | HMDB | | (2S,3S)-alpha-Amino-beta-merthyl-N-valerate | HMDB | | (2S,3S)-alpha-Amino-beta-merthyl-N-valeric acid | HMDB | | (2S,3S)-alpha-Amino-beta-merthylvalerate | HMDB | | (2S,3S)-alpha-Amino-beta-merthylvaleric acid | HMDB | | (2S,3S)-alpha-Amino-beta-methyl-N-valerate | HMDB | | (2S,3S)-alpha-Amino-beta-methyl-N-valeric acid | HMDB | | (2S,3S)-alpha-Amino-beta-methylvalerate | HMDB | | (2S,3S)-alpha-Amino-beta-methylvaleric acid | HMDB | | (S)-Isoleucine | HMDB | | (S,S)-Isoleucine | HMDB | | 2-Amino-3-methylpentanoate | HMDB | | 2-Amino-3-methylpentanoic acid | HMDB | | 2S,3S-Isoleucine | HMDB | | Erythro-L-isoleucine | HMDB | | Iso-leucine | HMDB | | L-(+)-Isoleucine | HMDB | | L-Ile | HMDB | | [S-(R*,r*)]-2-amino-3-methylpentanoate | HMDB | | [S-(R*,r*)]-2-amino-3-methylpentanoic acid | HMDB | | Isoleucine, L-isomer | HMDB | | Alloisoleucine | HMDB | | Isoleucine, L isomer | HMDB | | L-Isomer isoleucine | HMDB | | 2S-Amino-3S-methylpentanoate | HMDB | | L-Isoleucine | KEGG |
|
|---|
| Chemical Formula | C6H13NO2 |
|---|
| Average Molecular Weight | 131.1729 |
|---|
| Monoisotopic Molecular Weight | 131.094628665 |
|---|
| IUPAC Name | (2S,3S)-2-amino-3-methylpentanoic acid |
|---|
| Traditional Name | L-isoleucine |
|---|
| CAS Registry Number | 73-32-5 |
|---|
| SMILES | CC[C@H](C)[C@H](N)C(O)=O |
|---|
| InChI Identifier | 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 |
|---|
| Chemical Taxonomy |
|---|
| Description | belongs to the class of organic compounds known as isoleucine and derivatives. Isoleucine and derivatives 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organic acids and derivatives |
|---|
| Class | Carboxylic acids and derivatives |
|---|
| Sub Class | Amino acids, peptides, and analogues |
|---|
| Direct Parent | Isoleucine and derivatives |
|---|
| Alternative Parents | |
|---|
| 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
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
| Status | Detected and Quantified |
|---|
| Origin | |
|---|
| Biofunction | Not Available |
|---|
| Application | Not Available |
|---|
| Cellular locations | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 285.5 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 35 mg/mL | Human Metabolome Project | | LogP | -1.7 | HANSCH,C ET AL. (1995) |
|
|---|
| Predicted Properties | |
|---|
| Spectra |
|---|
| Spectra | |
|---|
| Biological Properties |
|---|
| Cellular Locations | |
|---|
| Biospecimen Locations | - All Tissues
- Blood
- Colostrum
- Liver
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Placenta
- Prostate Tissue
- Ruminal Fluid
- Semen
- Semimembranosus Muscle
- Testis
|
|---|
| Pathways | |
|---|
| Normal Concentrations |
|---|
| |
| All Tissues | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 71.5 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 76-101 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 72.05 uM | Not Specified | Both | Normal | | details | | Blood | Detected and Quantified | 101-122 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 63-118 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 95-103 uM | Not Specified | Not Specified | Normal | | details | | Blood | Detected and Quantified | 153 +/- 14 uM | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Liver | Detected and Quantified | 178 +/- 29 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 107 +/- 22 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 5.15 +/- 1.64 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3 - 14 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 2 - 13 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.9 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.5 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.5 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.8 +/- 0.1 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15247.0518 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15247.0518 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15247.0518 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15247.0518 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15247.0518 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15247.0518 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 15247.0518 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.33 +/- 1.74 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.4 +/- 0.5 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.2 +/- 0.2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.9 +/- 0.6 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.7 +/- 0.7 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 4.20 +/- 1.53 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 215.92 +/- 14.82 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 43-231 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 46.75 +/- 3.37 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 387770 +/- 50250 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 2360 +/- 380 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 640 +/- 70 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 970 +/- 120 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 370 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 72.44 +/- 10.27 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 85.7 +/- 14.97 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 5-11 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 160-588 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Placenta | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Prostate Tissue | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 151.8 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 266.9 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 182.9 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 173.8 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 123-1210 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 137 +/- 40 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 235 +/- 62 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 183 +/- 74 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 147 +/- 42 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 147 +/- 42 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 48-144 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 124 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 222 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 148 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 144 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 556 +/- 127 uM | Not Specified | Not Specified | Normal | | details | | Ruminal Fluid | Detected and Quantified | 173.85 +/- 19.76 uM | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semen | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 116 +/- 23 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 30 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Testis | Detected and Quantified | 79 +/- 14 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
|
|---|
| Abnormal Concentrations |
|---|
| |
| Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Treated with growth-promoting hormones | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | All Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | High dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Low dose Mycobacterium avium subsp. paratuberculosis-infected | | details | | Blood | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Sub/clinical ketosis | | details | | Blood | Detected and Quantified | 76.9 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy negative | | details | | Blood | Detected and Quantified | 82.3 uM | Not Specified | Not Specified | Bovine spongiform encephalopathy positive | | details | | Colostrum | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Muscle | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Commercial Product/bacterial growth on ground beef | | details | | Ruminal Fluid | Detected and Quantified | 182.86 +/- 71.9 uM | Not Specified | Not Specified | Rumen acidosis | | details |
|
|---|
| External Links |
|---|
| HMDB ID | HMDB0000172 |
|---|
| DrugBank ID | DB00167 |
|---|
| Phenol Explorer Compound ID | Not Available |
|---|
| FooDB ID | FDB012397 |
|---|
| KNApSAcK ID | C00001374 |
|---|
| Chemspider ID | 6067 |
|---|
| KEGG Compound ID | C00407 |
|---|
| BioCyc ID | ILE |
|---|
| BiGG ID | 34887 |
|---|
| Wikipedia Link | Isoleucine |
|---|
| METLIN ID | 5193 |
|---|
| PubChem Compound | 6306 |
|---|
| PDB ID | Not Available |
|---|
| ChEBI ID | 17191 |
|---|
| References |
|---|
| Synthesis Reference | Marvel, C. S. L-Isoleucine. Organic Syntheses (1941), 21 60-4. |
|---|
| Material Safety Data Sheet (MSDS) | Not Available |
|---|
| General References | - Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
- Sundekilde UK, Poulsen NA, Larsen LB, Bertram HC: Nuclear magnetic resonance metabonomics reveals strong association between milk metabolites and somatic cell count in bovine milk. J Dairy Sci. 2013 Jan;96(1):290-9. doi: 10.3168/jds.2012-5819. Epub 2012 Nov 22. [PubMed:23182357 ]
- Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
- Fooddata+, The Technical University of Denmark (DTU) [Link]
|
|---|