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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-11-01 11:41:11 UTC
Update Date2017-12-07 02:29:42 UTC
HMDB IDHMDB0011185
Secondary Accession Numbers
  • HMDB11185
Metabolite Identification
Common NameO-Phosphothreonine
DescriptionPhosphothreonine is a phosphoamino acid. It is the phosphorylated ester of threonine. There are three amino acids that are typically phosphorylated in eukaryotes: serine, threonine, and tyrosine. Threonine residues in endogenous proteins undergo phosphorylation through the action of a threonine kinase. Small amounts of free phosphothreonine can be detected in urine [PMID: 7693088 ].
Structure
Thumb
Synonyms
ValueSource
(2S,3R)-2-amino-3-Hydroxybutanoic acid 3-phosphateChEBI
L-Threonine O-3-phosphateChEBI
L-Threonine phosphateChEBI
O3-PhosphothreonineChEBI
PhosphothreonineChEBI
Threonine phosphate esterChEBI
Threoninium dihydrogen phosphateChEBI
(2S,3R)-2-amino-3-Hydroxybutanoate 3-phosphateGenerator
(2S,3R)-2-amino-3-Hydroxybutanoic acid 3-phosphoric acidGenerator
L-Threonine O-3-phosphoric acidGenerator
L-Threonine phosphoric acidGenerator
Threonine phosphoric acid esterGenerator
Threoninium dihydrogen phosphoric acidGenerator
Phosphate, threonineMeSH
Threonine phosphateMeSH
Chemical FormulaC4H10NO6P
Average Molecular Weight199.0991
Monoisotopic Molecular Weight199.024573569
IUPAC Name(2S,3R)-2-amino-3-(phosphonooxy)butanoic acid
Traditional Namephosphothreonine
CAS Registry Number1114-81-4
SMILES
C[C@@H](OP(O)(O)=O)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H10NO6P/c1-2(3(5)4(6)7)11-12(8,9)10/h2-3H,5H2,1H3,(H,6,7)(H2,8,9,10)/t2-,3+/m1/s1
InChI KeyUSRGIUJOYOXOQJ-GBXIJSLDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acid
  • Alkyl phosphate
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.5 g/LALOGPS
logP-1.9ALOGPS
logP-2.7ChemAxon
logS-0.93ALOGPS
pKa (Strongest Acidic)1.21ChemAxon
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.08 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.33 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-7e906e7246b3ef636b98View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9110000000-0b27bac67efac2895d49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6900000000-6cd4ab972cda9b9e8854View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-9300000000-7755990490f9b0d090c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-f7e90830423c5451204bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-ad7260fbe15d44575ebfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9500000000-c0ec684a681c34652a92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-d20cfbbcad9f78ca2901View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.036 +/- 0.0009 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB027954
    KNApSAcK IDNot Available
    Chemspider ID2497038
    KEGG Compound IDC12147
    BioCyc IDPHOSPHOTHREONINE
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN IDNot Available
    PubChem Compound3246323
    PDB IDTPO
    ChEBI ID37525
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Kataoka H, Nakai K, Katagiri Y, Makita M: Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection. Biomed Chromatogr. 1993 Jul-Aug;7(4):184-8. [PubMed:7693088 ]