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Record Information
Version1.0
Creation Date2016-09-30 22:20:26 UTC
Update Date2020-06-04 22:06:16 UTC
BMDB IDBMDB0000167
Secondary Accession Numbers
  • BMDB00167
Metabolite Identification
Common NameL-Threonine
DescriptionL-Threonine, also known as (2S)-threonine or L threonine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Threonine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Threonine exists in all living species, ranging from bacteria to humans. L-Threonine is a potentially toxic compound. L-Threonine has been found to be associated with several diseases known as crohn's disease, rheumatoid arthritis, eosinophilic esophagitis, and heart failure; also l-threonine has been linked to the inborn metabolic disorders including fumarase deficiency.
Structure
Thumb
Synonyms
ValueSource
(2S)-ThreonineChEBI
(2S,3R)-(-)-ThreonineChEBI
(2S,3R)-2-Amino-3-hydroxybutanoic acidChEBI
2-Amino-3-hydroxybutyric acidChEBI
L-(-)-ThreonineChEBI
L-2-Amino-3-hydroxybutyric acidChEBI
L-alpha-Amino-beta-hydroxybutyric acidChEBI
L-ThreoninChEBI
TChEBI
ThrChEBI
THREONINEChEBI
(2S,3R)-2-Amino-3-hydroxybutanoateGenerator
2-Amino-3-hydroxybutyrateGenerator
L-2-Amino-3-hydroxybutyrateGenerator
L-a-Amino-b-hydroxybutyrateGenerator
L-a-Amino-b-hydroxybutyric acidGenerator
L-alpha-Amino-beta-hydroxybutyrateGenerator
L-Α-amino-β-hydroxybutyrateGenerator
L-Α-amino-β-hydroxybutyric acidGenerator
(2S,3R)-2-Amino-3-hydroxybutyrateHMDB
(2S,3R)-2-Amino-3-hydroxybutyric acidHMDB
(R-(R*,s*))-2-amino-3-hydroxybutanoateHMDB
(R-(R*,s*))-2-amino-3-hydroxybutanoic acidHMDB
(S)-ThreonineHMDB
2-Amino-3-hydroxybutanoateHMDB
2-Amino-3-hydroxybutanoic acidHMDB
ThreoninHMDB
[R-(R*,s*)]-2-amino-3-hydroxy-butanoateHMDB
[R-(R*,s*)]-2-amino-3-hydroxy-butanoic acidHMDB
[R-(R*,s*)]-2-amino-3-hydroxybutanoateHMDB
[R-(R*,s*)]-2-amino-3-hydroxybutanoic acidHMDB
L ThreonineHMDB
Chemical FormulaC4H9NO3
Average Molecular Weight119.1192
Monoisotopic Molecular Weight119.058243159
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number72-19-5
SMILESNot Available
InChI Identifier
InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1
InChI KeyAYFVYJQAPQTCCC-GBXIJSLDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Hydroxy acid
  • Fatty acid
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Amine
  • 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 Point256 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility97.0 mg/mLNot Available
LogP-2.94HANSCH,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 and Quantified51.9 uMNot SpecifiedNot Specified
Normal
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified78.6 uMNot SpecifiedBothNormal details
BloodDetected and Quantified58-76 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified71-110 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified72-79 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified74 +/- 12 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
ColostrumDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected and Quantified377 +/- 95 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Longissimus Thoracis MuscleDetected and Quantified194 +/- 80 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 Quantified1 - 46 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified12592.428 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12592.428 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12592.428 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12592.428 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12592.428 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12592.428 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12592.428 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified9 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified8 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified8 +/- 1 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
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MuscleDetected and Quantified570 +/- 280 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified690 +/- 310 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified690 +/- 270 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified640 +/- 270 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • S. F. Graham, T. ...
details
MuscleDetected and Quantified193-468 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 Quantified28 +/- 7 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified35 +/- 22 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified41 +/- 29 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified25 +/- 8 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified25 +/- 8 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified53-153 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified29.9 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified36.4 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified41.3 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified23.1 uMNot SpecifiedNot Specified
Normal
details
Ruminal FluidDetected and Quantified113.5 (37.0 - 190.0) uMAdultBoth
Normal
details
Ruminal FluidDetected and Quantified658 +/- 301 uMNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Ruminal FluidDetected and Quantified24.45 +/- 7.32 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 Quantified193 +/- 32 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
TestisDetected and Quantified140 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
TestisDetected and Quantified232 +/- 51 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • Aidin Foroutan, C...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 and Quantified39.9 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy negative
details
BloodDetected and Quantified48.5 uMNot SpecifiedNot Specified
Bovine spongiform encephalopathy positive
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
All Mycobacterium avium subsp. paratuberculosis-infected
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 Quantified39.07 +/- 29.55 uMNot SpecifiedNot SpecifiedRumen acidosis
    • Fozia Saleem, Sou...
details
HMDB IDHMDB0000167
DrugBank IDDB00156
Phenol Explorer Compound IDNot Available
FooDB IDFDB011999
KNApSAcK IDC00001394
Chemspider ID6051
KEGG Compound IDC00188
BioCyc IDTHR
BiGG ID34186
Wikipedia LinkThreonine
METLIN ID32
PubChem Compound6288
PDB IDNot Available
ChEBI ID16857
References
Synthesis ReferenceFujita, Chuzo; Nara, Takashi; Samejima, Hirotoshi; Kinoshita, Shukuo. L-Threonine fermentation. I. Microbial conversion of L-homoserine to L-threonine. Nippon Nogei Kagaku Kaishi (1965), 39(6), 2
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. 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 ]
  3. 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 ]
  4. 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.
  5. 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.
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
SDS
Uniprot ID:
Q0VCW4
Molecular weight:
34441.0
Reactions
L-Threonine → 2-Ketobutyric acid + Ammoniadetails
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Catalyzes the attachment of threonine to tRNA(Thr) in a two-step reaction: threonine is first activated by ATP to form Thr-AMP and then transferred to the acceptor end of tRNA(Thr). Also edits incorrectly charged tRNA(Thr) via its editing domain, at the post-transfer stage.
Gene Name:
TARS3
Uniprot ID:
A6QNM8
Molecular weight:
83076.0
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Catalyzes the NAD(+)-dependent oxidation of L-threonine to 2-amino-3-ketobutyrate, mediating L-threonine catabolism.
Gene Name:
TDH
Uniprot ID:
Q2KIR8
Molecular weight:
41846.0
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Catalyzes the attachment of threonine to tRNA(Thr) in a two-step reaction: threonine is first activated by ATP to form Thr-AMP and then transferred to the acceptor end of tRNA(Thr). Also edits incorrectly charged tRNA(Thr) via its editing domain, at the post-transfer stage.
Gene Name:
TARS1
Uniprot ID:
Q3ZBV8
Molecular weight:
83492.0
Reactions
Adenosine triphosphate + L-Threonine + tRNA(Thr) → Adenosine monophosphate + Pyrophosphate + L-Threonyl-tRNA(Thr)details
General function:
Not Available
Specific function:
Not Available
Gene Name:
TARS2
Uniprot ID:
F1MX06
Molecular weight:
80993.0
Reactions
Adenosine triphosphate + L-Threonine + tRNA(Thr) → Adenosine monophosphate + Pyrophosphate + L-Threonyl-tRNA(Thr)details