Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2020-09-17 15:30:55 UTC
Primary IDFDB011999
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Threonine
DescriptionThreonine, abbreviated Thr or T, is an essential amino acid in humans. It has a side chain containing a hydroxyl group, making it a polar, uncharged amino acid Threonine is catabolized in mammals largely (70-80%) by threonine dehydrogenase (EC 1.1.1.103) that oxidizes threonine to 2-amino-3-oxobutyrate (which forms glycine and acetyl CoA), and much less by threonine dehydratase (EC 4.2.1.16) that catabolizes threonine into 2-oxobutyrate and ammonia. It is highly concentrated in meat products, cottage cheese and wheat germ. It is abundant in human plasma, particularly in newborns. The threonine content of most infant formulas currently on the market is approximately 20% higher than the threonine concentration in human milk. Premature infants fed these formulas have twice the plasma threonine concentrations of breast-fed infants. 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 (PMID 9853925). Threonine is an immunostimulant which promotes the growth of thymus gland and probably promotes 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 g per day. Severe deficiency of threonine causes neurological dysfunction and lameness in experimental animals.
CAS Number72-19-5
Structure
Thumb
Synonyms
SynonymSource
(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
2-amino-3-HydroxybutanoateHMDB
2-amino-3-Hydroxybutanoic acidHMDB
2-amino-3-HydroxybutyrateGenerator
2-amino-3-Hydroxybutyric acidChEBI
L-a-amino-b-HydroxybutyrateGenerator
L-a-amino-b-Hydroxybutyric acidGenerator
L-Thrbiospider
L-Threonine (9CI)biospider
L-α-amino-β-hydroxybutyrateGenerator
L-α-amino-β-hydroxybutyric acidGenerator
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC4H9NO3
IUPAC name(2S,3R)-2-amino-3-hydroxybutanoic acid
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 KeyAYFVYJQAPQTCCC-GBXIJSLDSA-N
Isomeric SMILESC[C@@H](O)[C@H](N)C(O)=O
Average Molecular Weight119.1192
Monoisotopic Molecular Weight119.058243159
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.33%; H 7.62%; N 11.76%; O 40.29%DFC
Melting PointMp 251-253° dec.DFC
Boiling PointNot Available
Experimental Water Solubility97 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-2.94HANSCH,C ET AL. (1995)
Experimental pKapKa2 9.62 (NH2)DFC
Isoelectric pointNot Available
Charge0
Optical Rotation[a]26D -33.9 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)splash10-0gb9-0930000000-045341234639d940688bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gb9-0930000000-08f448150a2533471625JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0159-1910000000-98a39d63665a1a1855ddJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-014i-1960000000-82e1bd8ff2e302e6b51bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0159-0910000000-d36a7a07f0444e55e38fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0980000000-ebba7965f95f804648abJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-0930000000-045341234639d940688bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gb9-0930000000-08f448150a2533471625JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-QQ (Non-derivatized)splash10-0ffa-3921000000-05359581d7eb97866c8fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0159-1910000000-98a39d63665a1a1855ddJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-1960000000-82e1bd8ff2e302e6b51bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9000000000-a05d200d324c3242c239JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0fdk-8930000000-c4701f28963821b700b3JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00di-9300000000-85dce837b0f965e73c8aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4i-9000000000-221510fd551c0b52c362JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a4i-9100000000-6ee11649899572cd4867JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-fde7ef1951fddff4b817JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-8900000000-2d7e5609618437e59272JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-9000000000-4b43567f4a446aed0828JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014i-4900000000-45382d9abd25be948e5bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00di-0900000000-071b61d3ea723715c1c1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a59-9000000000-c8320d0556dbe72049caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-8900000000-9945ecd06408cb733177JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0ufr-8900000000-c9804e2bfc51ec0e8593JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-02t9-0692200000-f96dba3c74726ede32deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-9000000000-94eeca12e76e23c1695eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-0930000000-efff9b10ae39f6ce6095JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-014i-0190000000-74ab3cba7b57b1b1b681JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-014i-1900000000-d9348197a5df9756d30cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00di-9100000000-9008bb1dfd2806e9f87dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-00di-9000000000-47fd01696817c86aecc5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00di-9000000000-ba9cd5b3e37ded5d3764JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-00di-1900000000-3fa8bd5efd825e5ac3faJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0kn9-9200000000-063cffd047551fca9ee6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0a4i-9000000000-8b82bffd35f30875a7c0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0a4i-9000000000-1748dd9a759c98e1c5eeJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a4i-9000000000-e9069de219196460cc61JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-6900000000-d30fcc60bda11aeb88b4JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
ChemSpider ID6051
ChEMBL IDCHEMBL291747
KEGG Compound IDC00188
Pubchem Compound ID6288
Pubchem Substance IDNot Available
ChEBI ID16857
Phenol-Explorer IDNot Available
DrugBank IDDB00156
HMDB IDHMDB00167
CRC / DFC (Dictionary of Food Compounds) IDHCL12-S:HCL15-V
EAFUS ID3669
Dr. Duke IDTHREONINE|L-(-)-THREONINE
BIGG ID34186
KNApSAcK IDC00001394
HET IDTHR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDL-Threonine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti ulcer49201 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.DUKE
essentialDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
Enzymes
NameGene NameUniProt ID
L-serine dehydratase/L-threonine deaminaseSDSP20132
Serine dehydratase-likeSDSLQ96GA7
Threonine--tRNA ligase, cytoplasmicTARSP26639
Threonine synthase-like 1THNSL1Q8IYQ7
Probable threonine--tRNA ligase 2, cytoplasmicTARSL2A2RTX5
Threonine--tRNA ligase, mitochondrialTARS2Q9BW92
Pathways
NameSMPDB LinkKEGG Link
Glycine and Serine MetabolismSMP00004 map00260
Threonine and 2-Oxobutanoate DegradationSMP00452 Not Available
Transcription/TranslationSMP00019 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).