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Record Information
Version3.6
Creation Date2008-11-01 11:41:11 UTC
Update Date2016-02-11 01:20:24 UTC
HMDB IDHMDB11185
Secondary Accession NumbersNone
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
(2S,3R)-2-amino-3-HydroxybutanoateHMDB
(2S,3R)-2-amino-3-Hydroxybutanoic acidHMDB
L-Threonine O-phosphateHMDB
O-phospho-L-ThreonineHMDB
O-phosphono-L-ThreonineHMDB
phospho-L-ThreonineHMDB
Synonyms sourcesHMDB
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 KeyInChIKey=USRGIUJOYOXOQJ-GBXIJSLDSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Phosphoethanolamine
  • Monoalkyl phosphate
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity37.33 m3·mol-1ChemAxon
Polarizability15.43 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
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
NuGOwiki LinkHMDB11185
Metagene LinkHMDB11185
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. [7693088 ]