<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4422</id>
  <title>T3D4368</title>
  <common-name>L-Threonine</common-name>
  <description>Threonine 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.  (A3450).</description>
  <cas>72-19-5</cas>
  <pubchem-id>6288</pubchem-id>
  <chemical-formula>C4H9NO3</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>256 dec°C</melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility>9.7E+004 mg/L (at 25°C)</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure nil="true"/>
  <target nil="true"/>
  <mechanism-of-toxicity>L-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.</mechanism-of-toxicity>
  <metabolism>Hepatic</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>L-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.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms nil="true"/>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-08-29T06:35:36Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:24:20Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>L-Threonine</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C00188</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id>16857</chebi-id>
  <biocyc-id>THR</biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00156</drugbank-id>
  <pdb-id>THR</pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>C[C@@H](O)[C@H](N)C(O)=O</moldb-smiles>
  <moldb-formula>C4H9NO3</moldb-formula>
  <moldb-inchi>InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3+/m1/s1</moldb-inchi>
  <moldb-inchikey>AYFVYJQAPQTCCC-GBXIJSLDSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">119.1192</moldb-average-mass>
  <moldb-mono-mass type="decimal">119.058243159</moldb-mono-mass>
  <origin>Endogenous</origin>
  <state>Solid</state>
  <logp>-2.94</logp>
  <hmdb-id>HMDB00167</hmdb-id>
  <chembl-id>CHEMBL291747</chembl-id>
  <chemspider-id>6051</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Masato Terasawa, Yukie Satoo, Hideaki Yukawa, &amp;#8220;Method for production of l-threonine.&amp;#8221; U.S. Patent US5019503, issued June, 1967.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003328</chemdb-id>
  <dsstox-id>DTXSID2046412</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin>wikipedia.org</stoff-ident-origin>
  <stoff-ident-id>SI00009063</stoff-ident-id>
  <susdat-id>NS00001961</susdat-id>
  <iupac>(2S,3R)-2-amino-3-hydroxybutanoic acid</iupac>
  <moldb-polar-surface-area>83.55</moldb-polar-surface-area>
  <moldb-refractivity>26.4598</moldb-refractivity>
  <moldb-polarizability>11.078258022254147</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>4</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>2.207432028688761</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>9.002504827404067</moldb-pka-strongest-basic>
  <moldb-physiological-charge>0</moldb-physiological-charge>
  <moldb-number-of-rings>0</moldb-number-of-rings>
  <moldb-alogps-logp>-3.01</moldb-alogps-logp>
  <moldb-alogps-logs>0.60</moldb-alogps-logs>
  <moldb-alogps-solubility>4.77e+02 g/l</moldb-alogps-solubility>
</compound>
