Bovine Metabolome Database: Showing metabocard for L-Threonine (BMDB0000167)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (5) Show 5 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:26 UTC

Update Date

2020-06-04 22:06:16 UTC

BMDB ID

BMDB0000167

Secondary Accession Numbers

BMDB00167

Metabolite Identification

Common Name

L-Threonine

Description

L-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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-Threonine	ChEBI
(2S,3R)-(-)-Threonine	ChEBI
(2S,3R)-2-Amino-3-hydroxybutanoic acid	ChEBI
2-Amino-3-hydroxybutyric acid	ChEBI
L-(-)-Threonine	ChEBI
L-2-Amino-3-hydroxybutyric acid	ChEBI
L-alpha-Amino-beta-hydroxybutyric acid	ChEBI
L-Threonin	ChEBI
T	ChEBI
Thr	ChEBI
THREONINE	ChEBI
(2S,3R)-2-Amino-3-hydroxybutanoate	Generator
2-Amino-3-hydroxybutyrate	Generator
L-2-Amino-3-hydroxybutyrate	Generator
L-a-Amino-b-hydroxybutyrate	Generator
L-a-Amino-b-hydroxybutyric acid	Generator
L-alpha-Amino-beta-hydroxybutyrate	Generator
L-Α-amino-β-hydroxybutyrate	Generator
L-Α-amino-β-hydroxybutyric acid	Generator
(2S,3R)-2-Amino-3-hydroxybutyrate	HMDB
(2S,3R)-2-Amino-3-hydroxybutyric acid	HMDB
(R-(R,s))-2-amino-3-hydroxybutanoate	HMDB
(R-(R,s))-2-amino-3-hydroxybutanoic acid	HMDB
(S)-Threonine	HMDB
2-Amino-3-hydroxybutanoate	HMDB
2-Amino-3-hydroxybutanoic acid	HMDB
Threonin	HMDB
[R-(R,s)]-2-amino-3-hydroxy-butanoate	HMDB
[R-(R,s)]-2-amino-3-hydroxy-butanoic acid	HMDB
[R-(R,s)]-2-amino-3-hydroxybutanoate	HMDB
[R-(R,s)]-2-amino-3-hydroxybutanoic acid	HMDB
L Threonine	HMDB

Chemical Formula

C₄H₉NO₃

Average Molecular Weight

119.1192

Monoisotopic Molecular Weight

119.058243159

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

72-19-5

SMILES

Not 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 Key

AYFVYJQAPQTCCC-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic acyclic compounds

External Descriptors

aspartate family amino acid (CHEBI:16857 )
proteinogenic amino acid (CHEBI:16857 )
L-alpha-amino acid (CHEBI:16857 )
threonine (CHEBI:16857 )
Common amino acids (C00188 )

Ontology

Status

Detected and Quantified

Origin

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	256 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	97.0 mg/mL	Not Available
LogP	-2.94	HANSCH,C ET AL. (1995)

Predicted Properties

Not Available

Spectra

Spectrum Type	Description	Splash 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

Name	SMPDB/Pathwhiz	KEGG
Threonine and 2-Oxobutanoate Degradation		Not Available
Protein Synthesis: Threonine		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
All Tissues	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25372282	details
Blood	Detected and Quantified	51.9 uM	Not Specified	Not Specified	Normal	PMID: 17197001	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25913299	details
Blood	Detected and Quantified	78.6 uM	Not Specified	Both	Normal	PMID: 9374324	details
Blood	Detected and Quantified	58-76 uM	Not Specified	Not Specified	Normal	PMID: 11204708	details
Blood	Detected and Quantified	71-110 uM	Not Specified	Not Specified	Normal	PMID: 3535614	details
Blood	Detected and Quantified	72-79 uM	Not Specified	Not Specified	Normal	PMID: 28036059	details
Blood	Detected and Quantified	74 +/- 12 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24630653	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22361340	details
Liver	Detected and Quantified	377 +/- 95 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Longissimus Thoracis Muscle	Detected and Quantified	194 +/- 80 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected and Quantified	1 - 46 uM	Not Specified	Not Specified	Normal	PMID: 20338431	details
Milk	Detected and Quantified	12592.428 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12592.428 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12592.428 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12592.428 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12592.428 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12592.428 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	12592.428 uM	Not Specified	Not Specified	Normal	Fooddata+, T...	details
Milk	Detected and Quantified	10 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	9 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	8 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	8 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 22361340	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Muscle	Detected and Quantified	570 +/- 280 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	690 +/- 310 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	690 +/- 270 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	640 +/- 270 nmol/g of tissue	Not Specified	Not Specified	Normal	S. F. Graham, T. ...	details
Muscle	Detected and Quantified	193-468 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 30744349	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	28 +/- 7 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	35 +/- 22 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	41 +/- 29 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	25 +/- 8 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	25 +/- 8 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Ruminal Fluid	Detected and Quantified	53-153 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Ruminal Fluid	Detected and Quantified	29.9 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	36.4 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	41.3 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	23.1 uM	Not Specified	Not Specified	Normal	PMID: 22959937	details
Ruminal Fluid	Detected and Quantified	113.5 (37.0 - 190.0) uM	Adult	Both	Normal	PMID: 9581948	details
Ruminal Fluid	Detected and Quantified	658 +/- 301 uM	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Ruminal Fluid	Detected and Quantified	24.45 +/- 7.32 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 5096119	details
Semen	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29634739	details
Semimembranosus Muscle	Detected and Quantified	193 +/- 32 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details
Testis	Detected and Quantified	140 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 5096119	details
Testis	Detected and Quantified	232 +/- 51 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	High dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Low dose Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Blood	Detected and Quantified	39.9 uM	Not Specified	Not Specified	Bovine spongiform encephalopathy negative	PMID: 17197001	details
Blood	Detected and Quantified	48.5 uM	Not Specified	Not Specified	Bovine spongiform encephalopathy positive	PMID: 17197001	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	All Mycobacterium avium subsp. paratuberculosis-infected	PMID: 25372282	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Commercial Product/bacterial growth on ground beef	PMID: 22417363	details
Ruminal Fluid	Detected and Quantified	39.07 +/- 29.55 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0000167

DrugBank ID

DB00156

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

6288

PDB ID

Not Available

ChEBI ID

16857

References

Synthesis Reference

Fujita, 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

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 ]
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 ]
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]

Enzymes

Enzyme Details

1. L-serine dehydratase/L-threonine deaminase

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 + Ammonia	details

Enzyme Details

2. Threonine--tRNA ligase 2, cytoplasmic

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

Enzyme Details

3. L-threonine 3-dehydrogenase, mitochondrial

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

Enzyme Details

4. Threonine--tRNA ligase 1, cytoplasmic

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

Enzyme Details

5. Threonyl-tRNA synthetase 2, mitochondrial

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

Showing metabocard for L-Threonine (BMDB0000167)

Structure for BMDB0000167 (L-Threonine)

Enzymes

Reactions

Reactions

Reactions