Record Information
Version2.0
Creation Date2012-05-31 14:27:00 -0600
Update Date2015-06-03 17:19:17 -0600
Secondary Accession Numbers
  • ECMDB20092
Identification
Name:4-Hydroxy-L-threonine
Description4-hydroxy-L-threonine is a member of the chemical class known as Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).4-hydroxyl-L-threonine is involved in pyridoxine biosynthesis. This result is consistent with a model in which 4-phospho-hydroxy-L-threonine (synonym, 3-hydroxyhomoserine phosphate), rather than 4-hydroxy-L-threonine, is an obligatory intermediate in pyridoxal 5'-phosphate biosynthesis. (PMID 8595869)
Structure
Thumb
Synonyms:
  • (2S,3S)-2-amino-3,4-dihydroxybutanoate
  • (2S,3S)-2-amino-3,4-dihydroxybutanoic acid
  • 2-Amino-3,4-dihydroxy-(S-(R*,R*))-L-Threonate
  • 2-Amino-3,4-dihydroxy-(S-(R*,R*))-L-Threonic acid
  • 3-Hydroxyhomoserine
  • a-amino-b,g-Dihydroxybutyrate
  • a-amino-b,g-Dihydroxybutyric acid
  • Alpha-Amino-beta,gamma-dihydroxybutyrate
  • Alpha-Amino-beta,gamma-dihydroxybutyric acid
  • Hydroxythreonine
  • α-amino-β,γ-Dihydroxybutyrate
  • α-amino-β,γ-Dihydroxybutyric acid
Chemical Formula:C4H9NO4
Weight:Average: 135.1186
Monoisotopic: 135.053157781
InChI Key:JBNUARFQOCGDRK-GBXIJSLDSA-N
InChI:InChI=1S/C4H9NO4/c5-3(4(8)9)2(7)1-6/h2-3,6-7H,1,5H2,(H,8,9)/t2-,3+/m1/s1
CAS number:21768-45-6
IUPAC Name:(2S,3S)-2-amino-3,4-dihydroxybutanoic acid
Traditional IUPAC Name:hydroxythreonine
SMILES:N[C@@H]([C@H](O)CO)C(O)=O
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
  • 1,3-aminoalcohol
  • 1,2-diol
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Alcohol
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility357 g/LALOGPS
logP-3.4ALOGPS
logP-4.5ChemAxon
logS0.42ALOGPS
pKa (Strongest Acidic)1.92ChemAxon
pKa (Strongest Basic)8.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area103.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28 m³·mol⁻¹ChemAxon
Polarizability12.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ec-9000000000-ed89b9334f5be14dc8c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-4900000000-dbd9d3d88c247a29f9c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9100000000-2070d819d44de1960ae0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9100000000-283552f8bd87ff9d06d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-8900000000-75b8c2945f1960264b7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pw9-9400000000-43e8a71f87678ae42e12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-437c14b312f426383b44View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28330
HMDB IDNot Available
Pubchem Compound ID193577
Kegg IDC06056
ChemSpider ID167988
Wikipedia IDNot Available
BioCyc IDCPD0-2189
EcoCyc IDCPD0-2189
Ligand ExpoTH6

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the gamma-elimination of phosphate from L- phosphohomoserine and the beta-addition of water to produce L- threonine. To a lesser extent, is able to slowly catalyze the deamination of L-threonine into alpha-ketobutyrate and that of L- serine and 3-chloroalanine into pyruvate. Is also able to rapidly convert vinylglycine to threonine, which proves that the pyridoxal p-quinonoid of vinylglycine is an intermediate in the TS reaction
Gene Name:
thrC
Uniprot ID:
P00934
Molecular weight:
47113
Reactions
O-phospho-L-homoserine + H(2)O = L-threonine + phosphate.