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Human Metabolome Database Version 3.5

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Showing metabocard for O-Phosphothreonine (HMDB11185)

Record Information
Version 3.5
Creation Date 2008-11-01 05:41:11 -0600
Update Date 2013-02-08 17:25:51 -0700
HMDB ID HMDB11185
Secondary Accession Numbers None
Metabolite Identification
Common Name O-Phosphothreonine
Description Phosphothreonine 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 Link_out].
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2S,3R)-2-amino-3-hydroxybutanoate
  2. (2S,3R)-2-amino-3-hydroxybutanoic acid
  3. (2S,3R)-2-amino-3-hydroxybutanoic acid 3-phosphate
  4. L-Threonine O-3-phosphate
  5. L-Threonine O-phosphate
  6. L-Threonine phosphate
  7. O-Phospho-L-threonine
  8. O-Phosphono-L-threonine
  9. O3-phosphothreonine
  10. Phospho-L-threonine
  11. Phosphothreonine
  12. Synonyms Sources
  13. Threonine phosphate ester
  14. Threoninium dihydrogen phosphate
Chemical Formula C4H10NO6P
Average Molecular Weight 199.0991
Monoisotopic Molecular Weight 199.024573569
IUPAC Name (2S,3R)-2-amino-3-(phosphonooxy)butanoic acid
Traditional IUPAC Name O-phospho-L-threonine
CAS Registry Number 1114-81-4
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 Key USRGIUJOYOXOQJ-GBXIJSLDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Amino Acids and Derivatives
Sub Class Alpha Amino Acids and Derivatives
Other Descriptors
  • Aliphatic Acyclic Compounds
  • O-phosphoamino acid(ChEBI)
  • threonine derivative(ChEBI)
Substituents
  • Carboxylic Acid
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoethanolamine
  • Phosphoric Acid Ester
  • Primary Aliphatic Amine (Alkylamine)
Direct Parent Alpha Amino Acids and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 23.5 g/L ALOGPS
LogP -1.86 ALOGPS
LogP -2.7 ChemAxon
LogS -0.93 ALOGPS
pKa (strongest acidic) 1.21 ChemAxon
pKa (strongest basic) 9.47 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 130.08 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 37.33 ChemAxon
Polarizability 15.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.036 +/- 0.0009 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027954
KNApSAcK ID Not Available
Chemspider ID 2497038 Link_out
KEGG Compound ID C12147 Link_out
BioCyc ID PHOSPHOTHREONINE Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11185 Link_out
Metagene Link HMDB11185 Link_out
METLIN ID Not Available
PubChem Compound 3246323 Link_out
PDB ID TPO Link_out
ChEBI ID 37525 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available