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Record Information
Version1.0
Creation Date2016-09-30 22:20:30 UTC
Update Date2020-06-04 22:12:11 UTC
BMDB IDBMDB0000172
Secondary Accession Numbers
  • BMDB00172
Metabolite Identification
Common NameL-Isoleucine
DescriptionL-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
Thumb
Synonyms
ValueSource
(2S,3S)-2-Amino-3-methylpentanoic acidChEBI
2-Amino-3-methylvaleric acidChEBI
alpha-Amino-beta-methylvaleric acidChEBI
IChEBI
IleChEBI
ISOLEUCINEChEBI
(2S,3S)-2-Amino-3-methylpentanoateGenerator
2-Amino-3-methylvalerateGenerator
a-Amino-b-methylvalerateGenerator
a-Amino-b-methylvaleric acidGenerator
alpha-Amino-beta-methylvalerateGenerator
Α-amino-β-methylvalerateGenerator
Α-amino-β-methylvaleric acidGenerator
(2S,3S)-2-Amino-3-methyl-pentanoateHMDB
(2S,3S)-2-Amino-3-methyl-pentanoic acidHMDB
(2S,3S)-a-Amino-b-methyl-N-valerateHMDB
(2S,3S)-a-Amino-b-methyl-N-valeric acidHMDB
(2S,3S)-a-Amino-b-methylvalerateHMDB
(2S,3S)-a-Amino-b-methylvaleric acidHMDB
(2S,3S)-Alph-amino-beta-methylvalerateHMDB
(2S,3S)-Alph-amino-beta-methylvaleric acidHMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valerateHMDB
(2S,3S)-alpha-Amino-beta-merthyl-N-valeric acidHMDB
(2S,3S)-alpha-Amino-beta-merthylvalerateHMDB
(2S,3S)-alpha-Amino-beta-merthylvaleric acidHMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valerateHMDB
(2S,3S)-alpha-Amino-beta-methyl-N-valeric acidHMDB
(2S,3S)-alpha-Amino-beta-methylvalerateHMDB
(2S,3S)-alpha-Amino-beta-methylvaleric acidHMDB
(S)-IsoleucineHMDB
(S,S)-IsoleucineHMDB
2-Amino-3-methylpentanoateHMDB
2-Amino-3-methylpentanoic acidHMDB
2S,3S-IsoleucineHMDB
Erythro-L-isoleucineHMDB
Iso-leucineHMDB
L-(+)-IsoleucineHMDB
L-IleHMDB
[S-(R*,r*)]-2-amino-3-methylpentanoateHMDB
[S-(R*,r*)]-2-amino-3-methylpentanoic acidHMDB
Isoleucine, L-isomerHMDB
AlloisoleucineHMDB
Isoleucine, L isomerHMDB
L-Isomer isoleucineHMDB
2S-Amino-3S-methylpentanoateHMDB
L-IsoleucineKEGG
Chemical FormulaC6H13NO2
Average Molecular Weight131.1729
Monoisotopic Molecular Weight131.094628665
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number73-32-5
SMILESNot Available
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 KeyAGPKZVBTJJNPAG-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentIsoleucine 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility35 mg/mLHuman Metabolome Project
LogP-1.7HANSCH,C ET AL. (1995)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
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
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified71.5 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
    • Jiyuan Li, Everes...
details
BloodDetected and Quantified76-101 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified72.05 uMNot SpecifiedBothNormal details
BloodDetected and Quantified101-122 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified63-118 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified95-103 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified153 +/- 14 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified178 +/- 29 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Longissimus Thoracis MuscleDetected and Quantified107 +/- 22 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5.15 +/- 1.64 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3 - 14 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified2 - 13 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified3.9 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15247.0518 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15247.0518 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15247.0518 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15247.0518 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15247.0518 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15247.0518 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15247.0518 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified4.33 +/- 1.74 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.4 +/- 0.5 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.2 +/- 0.2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3.9 +/- 0.6 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.7 +/- 0.7 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified4.20 +/- 1.53 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified215.92 +/- 14.82 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified43-231 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified46.75 +/- 3.37 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified387770 +/- 50250 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified2360 +/- 380 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified640 +/- 70 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified970 +/- 120 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified370 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified72.44 +/- 10.27 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified85.7 +/- 14.97 uMNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified5-11 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified160-588 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified151.8 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified266.9 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified182.9 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified173.8 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified123-1210 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified137 +/- 40 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified235 +/- 62 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified183 +/- 74 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified147 +/- 42 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified147 +/- 42 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified48-144 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Hanne Christine B...
details
Ruminal FluidDetected and Quantified124 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified222 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified148 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified144 uMNot SpecifiedNot Specified
Normal
    • Burim NA, Qendrim...
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified556 +/- 127 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified173.85 +/- 19.76 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Semimembranosus MuscleDetected and Quantified116 +/- 23 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified30 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
TestisDetected and Quantified79 +/- 14 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Treated with growth-promoting hormones
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
High dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Low dose Mycobacterium avium subsp. paratuberculosis-infected
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis
details
BloodDetected and Quantified76.9 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy negative
details
BloodDetected and Quantified82.3 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy positive
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Commercial Product/bacterial growth on ground beef
details
Ruminal FluidDetected and Quantified182.86 +/- 71.9 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000172
DrugBank IDDB00167
Phenol Explorer Compound IDNot Available
FooDB IDFDB012397
KNApSAcK IDC00001374
Chemspider ID6067
KEGG Compound IDC00407
BioCyc IDILE
BiGG ID34887
Wikipedia LinkIsoleucine
METLIN ID5193
PubChem Compound6306
PDB IDNot Available
ChEBI ID17191
References
Synthesis ReferenceMarvel, C. S. L-Isoleucine. Organic Syntheses (1941), 21 60-4.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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.
  9. 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.
  10. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
BCAT1
Uniprot ID:
A4IFQ7
Molecular weight:
43185.0
General function:
Amino acid transport and metabolism
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 (By similarity).
Gene Name:
BCAT2
Uniprot ID:
Q5EA40
Molecular weight:
44648.0
Reactions
L-Isoleucine + Oxoglutaric acid → 3-Methyl-2-oxovaleric acid + L-Glutamic aciddetails
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
BCAT2
Uniprot ID:
Q0V8J6
Molecular weight:
44274.0
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
BCAT2
Uniprot ID:
Q5E9U7
Molecular weight:
40447.0
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Not Available
Gene Name:
IARS1
Uniprot ID:
A7MBC5
Molecular weight:
144642.0
Reactions
Adenosine triphosphate + L-Isoleucine + tRNA(Ile) → Adenosine monophosphate + Pyrophosphate + L-Isoleucyl-tRNA(Ile)details