Tmic
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Toxin, Toxin Target Database.
Record Information
Version2.0
Creation Date2014-08-29 06:35:36 UTC
Update Date2014-12-24 20:26:47 UTC
Accession NumberT3D4368
Identification
Common NameL-Threonine
ClassSmall Molecule
DescriptionThreonine is an essential amino acid in humans. It is abundant in human plasma, particularly in newborns. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals. Threonine is an immunostimulant which promotes the growth of thymus gland. It also can probably promote cell immune defense function. This amino acid has been useful in the treatment of genetic spasticity disorders and multiple sclerosis at a dose of 1 gram daily. It is highly concentrated in meat products, cottage cheese and wheat germ. The threonine content of most of the infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Due to this high threonine content the plasma threonine concentrations are up to twice as high in premature infants fed these formulas than in infants fed human milk. The whey proteins which are used for infant formulas are sweet whey proteins. Sweet whey results from cheese production. Threonine catabolism in mammals appears to be due primarily (70-80%) to the activity of threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate, which forms glycine and acetyl CoA, whereas threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia, is significantly less active. Increasing the threonine plasma concentrations leads to accumulation of threonine and glycine in the brain. Such accumulation affects the neurotransmitter balance which may have consequences for the brain development during early postnatal life. Thus, excessive threonine intake during infant feeding should be avoided. (1).
Compound Type
  • Amine
  • Amino Acid, Essential
  • Animal Toxin
  • Dietary Supplement
  • Drug
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Micronutrient
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • Supplement
Chemical Structure
Thumb
Synonyms
Synonym
(2S)-threonine
(2S,3R)-(-)-Threonine
(2S,3R)-2-Amino-3-hydroxybutyrate
(2S,3R)-2-Amino-3-hydroxybutyric acid
(R-(R*,S*))-2-Amino-3-hydroxybutanoate
(R-(R*,S*))-2-Amino-3-hydroxybutanoic acid
(S)-Threonine
2-Amino-3-hydroxybutanoate
2-Amino-3-hydroxybutanoic acid
2-Amino-3-hydroxybutyrate
2-Amino-3-hydroxybutyric acid
L-(-)-Threonine
L-2-Amino-3-hydroxybutyrate
L-2-Amino-3-hydroxybutyric acid
L-alpha-Amino-beta-hydroxybutyrate
L-alpha-Amino-beta-hydroxybutyric acid
L-Threonin
L-α-amino-β-hydroxybutyric acid
Thr
Threonin
Threonine
[R-(R*,S*)]-2-amino-3-hydroxy-Butanoate
[R-(R*,S*)]-2-amino-3-hydroxy-Butanoic acid
[R-(R*,S*)]-2-Amino-3-hydroxybutanoate
[R-(R*,S*)]-2-Amino-3-hydroxybutanoic acid
Chemical FormulaC4H9NO3
Average Molecular Mass119.119 g/mol
Monoisotopic Mass119.058 g/mol
CAS Registry Number72-19-5
IUPAC Name(2S,3R)-2-amino-3-hydroxybutanoic acid
Traditional NameL-threonine
SMILES[H][C@](C)(O)[C@]([H])(N)C(O)=O
InChI IdentifierInChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1
InChI KeyInChIKey=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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • All Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
Threonine and 2-Oxobutanoate DegradationSMP00452 Not Available
Transcription/TranslationSMP00019 Not Available
Hartnup DisorderSMP00189 Not Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point256 dec°C
Boiling PointNot Available
Solubility9.7E+004 mg/L (at 25°C)
LogP-2.94
Predicted Properties
PropertyValueSource
Water Solubility477 g/LALOGPS
logP-3ALOGPS
logP-3.5ChemAxon
logS0.6ALOGPS
pKa (Strongest Acidic)2.21ChemAxon
pKa (Strongest Basic)9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area83.55 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.46 m³·mol⁻¹ChemAxon
Polarizability11.08 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0gb9-0930000000-045341234639d940688bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gb9-0930000000-08f448150a2533471625View in MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0159-1910000000-98a39d63665a1a1855ddView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1960000000-82e1bd8ff2e302e6b51bView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0159-0910000000-d36a7a07f0444e55e38fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0980000000-ebba7965f95f804648abView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-0930000000-045341234639d940688bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-0930000000-08f448150a2533471625View in MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0ffa-3921000000-05359581d7eb97866c8fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-1910000000-98a39d63665a1a1855ddView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1960000000-82e1bd8ff2e302e6b51bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9000000000-a05d200d324c3242c239View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fdk-8930000000-c4701f28963821b700b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9300000000-85dce837b0f965e73c8aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-221510fd551c0b52c362View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9100000000-6ee11649899572cd4867View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-fde7ef1951fddff4b817View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-8900000000-2d7e5609618437e59272View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-4b43567f4a446aed0828View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-4900000000-45382d9abd25be948e5bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-071b61d3ea723715c1c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a59-9000000000-c8320d0556dbe72049caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-8900000000-9945ecd06408cb733177View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0ufr-8900000000-c9804e2bfc51ec0e8593View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-02t9-0692200000-f96dba3c74726ede32deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-9000000000-94eeca12e76e23c1695eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-0930000000-efff9b10ae39f6ce6095View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-0190000000-74ab3cba7b57b1b1b681View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-1900000000-d9348197a5df9756d30cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9100000000-9008bb1dfd2806e9f87dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-47fd01696817c86aecc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-ba9cd5b3e37ded5d3764View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-1900000000-3fa8bd5efd825e5ac3faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0kn9-9200000000-063cffd047551fca9ee6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-8b82bffd35f30875a7c0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-1748dd9a759c98e1c5eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-e9069de219196460cc61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-6900000000-d30fcc60bda11aeb88b4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityL-Threonine is a precursor to the amino acids glycine and serine. It acts as a lipotropic in controlling fat build-up in the liver. May help combat mental illness and may be very useful in indigestion and intestinal malfunctions. Also, threonine prevents excessive liver fat. Nutrients are more readily absorbed when threonine is present.
MetabolismHepatic
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesL-Threonine makes up collagen, elastin, and enamel protein. It aids proper fat metabolism in the liver, helps the digestive and intestinal tracts function more smoothly, and assists in metabolism and assimilation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00156
HMDB IDHMDB00167
PubChem Compound ID6288
ChEMBL IDCHEMBL291747
ChemSpider ID6051
KEGG IDC00188
UniProt IDNot Available
OMIM ID
ChEBI ID16857
BioCyc IDTHR
CTD IDNot Available
Stitch IDNot Available
PDB IDTHR
ACToR IDNot Available
Wikipedia LinkL-Threonine
References
Synthesis Reference

Masato Terasawa, Yukie Satoo, Hideaki Yukawa, “Method for production of l-threonine.” U.S. Patent US5019503, issued June, 1967.

MSDSLink
General References
  1. Boehm G, Cervantes H, Georgi G, Jelinek J, Sawatzki G, Wermuth B, Colombo JP: Effect of increasing dietary threonine intakes on amino acid metabolism of the central nervous system and peripheral tissues in growing rats. Pediatr Res. 1998 Dec;44(6):900-6. [9853925 ]
  2. Vold BS, Keith DE Jr, Slavik M: Urine levels of N-[9-(beta-D-ribofuranosyl)purin-6-ylcarbamoyl]-L-threonine, N6-(delta 2-isopentenyl)adenosine, and 2'-O-methylguanosine as determined by radioimmunoassay for normal subjects and cancer patients. Cancer Res. 1982 Dec;42(12):5265-9. [7139629 ]
  3. Peng CT, Wu KH, Lan SJ, Tsai JJ, Tsai FJ, Tsai CH: Amino acid concentrations in cerebrospinal fluid in children with acute lymphoblastic leukemia undergoing chemotherapy. Eur J Cancer. 2005 May;41(8):1158-63. Epub 2005 Apr 14. [15911239 ]
  4. Hallgren P, Lundblad A, Svensson S: A new type of carbohydrate-protein linkage in a glycopeptide from normal human urine. J Biol Chem. 1975 Jul 25;250(14):5312-4. [1141232 ]
  5. Cynober LA: Plasma amino acid levels with a note on membrane transport: characteristics, regulation, and metabolic significance. Nutrition. 2002 Sep;18(9):761-6. [12297216 ]
  6. Rainesalo S, Keranen T, Palmio J, Peltola J, Oja SS, Saransaari P: Plasma and cerebrospinal fluid amino acids in epileptic patients. Neurochem Res. 2004 Jan;29(1):319-24. [14992292 ]
  7. Wevers RA, Engelke U, Wendel U, de Jong JG, Gabreels FJ, Heerschap A: Standardized method for high-resolution 1H-NMR of cerebrospinal fluid. Clin Chem. 1995 May;41(5):744-51. [7729054 ]
  8. Wulf G, Finn G, Suizu F, Lu KP: Phosphorylation-specific prolyl isomerization: is there an underlying theme? Nat Cell Biol. 2005 May;7(5):435-41. [15867923 ]
  9. Takeda DY, Parvin JD, Dutta A: Degradation of Cdt1 during S phase is Skp2-independent and is required for efficient progression of mammalian cells through S phase. J Biol Chem. 2005 Jun 17;280(24):23416-23. Epub 2005 Apr 25. [15855168 ]
  10. Nanda N, Bao M, Lin H, Clauser K, Komuves L, Quertermous T, Conley PB, Phillips DR, Hart MJ: Platelet endothelial aggregation receptor 1 (PEAR1), a novel epidermal growth factor repeat-containing transmembrane receptor, participates in platelet contact-induced activation. J Biol Chem. 2005 Jul 1;280(26):24680-9. Epub 2005 Apr 25. [15851471 ]
  11. Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. [12097436 ]
  12. Boneh A, Korman SH, Sato K, Kanno J, Matsubara Y, Lerer I, Ben-Neriah Z, Kure S: A single nucleotide substitution that abolishes the initiator methionine codon of the GLDC gene is prevalent among patients with glycine encephalopathy in Jerusalem. J Hum Genet. 2005;50(5):230-4. Epub 2005 Apr 29. [15864413 ]
  13. Elzinga M, Maron BJ, Adelstein RS: Human heart and platelet actins are products of different genes. Science. 1976 Jan 9;191(4222):94-5. [1246600 ]
  14. Nicholson JK, O'Flynn MP, Sadler PJ, Macleod AF, Juul SM, Sonksen PH: Proton-nuclear-magnetic-resonance studies of serum, plasma and urine from fasting normal and diabetic subjects. Biochem J. 1984 Jan 15;217(2):365-75. [6696735 ]
  15. Rodriguez-Soriano J, Vallo A, Perez de Nanclares G, Bilbao JR, Castano L: A founder mutation in the CLCNKB gene causes Bartter syndrome type III in Spain. Pediatr Nephrol. 2005 Jul;20(7):891-6. Epub 2005 May 5. [15875219 ]
  16. Hagenfeldt L, Bjerkenstedt L, Edman G, Sedvall G, Wiesel FA: Amino acids in plasma and CSF and monoamine metabolites in CSF: interrelationship in healthy subjects. J Neurochem. 1984 Mar;42(3):833-7. [6198473 ]
  17. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [19212411 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Threonine-trna ligase activity
Specific Function:
Not Available
Gene Name:
TARS
Uniprot ID:
P26639
Molecular Weight:
83434.5 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Torres-Larios A, Sankaranarayanan R, Rees B, Dock-Bregeon AC, Moras D: Conformational movements and cooperativity upon amino acid, ATP and tRNA binding in threonyl-tRNA synthetase. J Mol Biol. 2003 Aug 1;331(1):201-11. [12875846 ]
  4. Ruan B, Bovee ML, Sacher M, Stathopoulos C, Poralla K, Francklyn CS, Soll D: A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases. J Biol Chem. 2005 Jan 7;280(1):571-7. Epub 2004 Oct 26. [15507440 ]
  5. Cusack S, Yaremchuk A, Krikliviy I, Tukalo M: tRNA(Pro) anticodon recognition by Thermus thermophilus prolyl-tRNA synthetase. Structure. 1998 Jan 15;6(1):101-8. [9493271 ]
General Function:
Threonine synthase activity
Specific Function:
Not Available
Gene Name:
THNSL1
Uniprot ID:
Q8IYQ7
Molecular Weight:
83069.54 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
General Function:
Threonine-trna ligase activity
Specific Function:
Not Available
Gene Name:
TARS2
Uniprot ID:
Q9BW92
Molecular Weight:
81035.345 Da
References
  1. Caillet J, Graffe M, Eyermann F, Romby P, Springer M: Mutations in residues involved in zinc binding in the catalytic site of Escherichia coli threonyl-tRNA synthetase confer a dominant lethal phenotype. J Bacteriol. 2007 Oct;189(19):6839-48. Epub 2007 Jul 20. [17644600 ]