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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-12 13:15:45 UTC
Update Date2021-09-14 15:39:04 UTC
HMDB IDHMDB0006802
Secondary Accession Numbers
  • HMDB06802
Metabolite Identification
Common NameO-Phospho-4-hydroxy-L-threonine
DescriptionO-Phospho-4-hydroxy-L-threonine, also known as 4-(phosphonooxy)-threonine, 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. O-Phospho-4-hydroxy-L-threonine is a very strong basic compound (based on its pKa). O-Phospho-4-hydroxy-L-threonine exists in all living species, ranging from bacteria to humans.
Structure
Data?1582752406
Synonyms
ValueSource
4-(Phosphonooxy)-threonineChEBI
4-(Phosphonooxy)-L-threonineKegg
4-Phosphooxy-L-threonineKegg
4-Phosphonooxy-L-threonineHMDB
4-Phospho-hydroxy-threonineHMDB
4-(Phosphohydroxy)-L-threonineHMDB
4-PhosphohydroxythreonineHMDB
4-PhosphothreonineHMDB
Chemical FormulaC4H10NO7P
Average Molecular Weight215.0985
Monoisotopic Molecular Weight215.019488191
IUPAC Name(2S,3S)-2-amino-3-hydroxy-4-(phosphonooxy)butanoic acid
Traditional Name4-(phosphonooxy)-L-threonine
CAS Registry NumberNot Available
SMILES
N[C@@H]([C@H](O)COP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H10NO7P/c5-3(4(7)8)2(6)1-12-13(9,10)11/h2-3,6H,1,5H2,(H,7,8)(H2,9,10,11)/t2-,3+/m1/s1
InChI KeyFKHAKIJOKDGEII-GBXIJSLDSA-N
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
  • Monoalkyl phosphate
  • Hydroxy acid
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acid
  • Amino acid
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Primary aliphatic amine
  • Alcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility22.7 g/LALOGPS
logP10(-2.4) g/LALOGPS
logP10(-3.9) g/LChemAxon
logS10(-0.98) g/LALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)8.93ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area150.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.88 m³·mol⁻¹ChemAxon
Polarizability16.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+145.74731661259
DarkChem[M-H]-140.1931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
O-Phospho-4-hydroxy-L-threonine,1TMS,#1C[Si](C)(C)O[C@H](COP(=O)(O)O)[C@H](N)C(=O)O1906.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,1TMS,#2C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)COP(=O)(O)O1892.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,1TMS,#3C[Si](C)(C)OP(=O)(O)OC[C@@H](O)[C@H](N)C(=O)O1956.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,1TMS,#4C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)COP(=O)(O)O1978.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#1C[Si](C)(C)OC(=O)[C@@H](N)[C@@H](COP(=O)(O)O)O[Si](C)(C)C1899.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#2C[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C)[C@H](N)C(=O)O1945.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#3C[Si](C)(C)N[C@H](C(=O)O)[C@@H](COP(=O)(O)O)O[Si](C)(C)C1954.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#4C[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)COP(=O)(O)O[Si](C)(C)C1946.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#5C[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C)[C@H](O)COP(=O)(O)O1950.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#6C[Si](C)(C)OP(=O)(OC[C@@H](O)[C@H](N)C(=O)O)O[Si](C)(C)C1975.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#7C[Si](C)(C)N[C@H](C(=O)O)[C@H](O)COP(=O)(O)O[Si](C)(C)C2023.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TMS,#8C[Si](C)(C)N([C@H](C(=O)O)[C@H](O)COP(=O)(O)O)[Si](C)(C)C2042.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,1TBDMS,#1CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O)[C@H](N)C(=O)O2154.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,1TBDMS,#2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)COP(=O)(O)O2150.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,1TBDMS,#3CC(C)(C)[Si](C)(C)OP(=O)(O)OC[C@@H](O)[C@H](N)C(=O)O2192.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,1TBDMS,#4CC(C)(C)[Si](C)(C)N[C@H](C(=O)O)[C@H](O)COP(=O)(O)O2211.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)[C@@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2348.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#2CC(C)(C)[Si](C)(C)O[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)[C@H](N)C(=O)O2377.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#3CC(C)(C)[Si](C)(C)N[C@H](C(=O)O)[C@@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2361.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#4CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)[C@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2380.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#5CC(C)(C)[Si](C)(C)N[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@H](O)COP(=O)(O)O2378.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#6CC(C)(C)[Si](C)(C)OP(=O)(OC[C@@H](O)[C@H](N)C(=O)O)O[Si](C)(C)C(C)(C)C2420.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#7CC(C)(C)[Si](C)(C)N[C@H](C(=O)O)[C@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C2443.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
O-Phospho-4-hydroxy-L-threonine,2TBDMS,#8CC(C)(C)[Si](C)(C)N([C@H](C(=O)O)[C@H](O)COP(=O)(O)O)[Si](C)(C)C(C)(C)C2524.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - O-Phospho-4-hydroxy-L-threonine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9200000000-a8f91387710592709ff82016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - O-Phospho-4-hydroxy-L-threonine GC-MS (2 TMS) - 70eV, Positivesplash10-01ow-9711000000-89a880807057686a60b12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - O-Phospho-4-hydroxy-L-threonine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 10V, Positive-QTOFsplash10-00r2-2920000000-c23edaafe01dd32ccd6a2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 20V, Positive-QTOFsplash10-00di-9600000000-fd8c6ec273c259b6d6932015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 40V, Positive-QTOFsplash10-00di-9300000000-42e18773c2868e50da832015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 10V, Negative-QTOFsplash10-03mj-9850000000-0cd651cd24395dbae4a12015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 20V, Negative-QTOFsplash10-004i-9100000000-a925d7c6b56522b6d34b2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 40V, Negative-QTOFsplash10-004i-9000000000-5c41cf86b2bcca5178682015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 10V, Positive-QTOFsplash10-014i-2590000000-a9146bba129194b49abb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 20V, Positive-QTOFsplash10-00di-9200000000-e8dbc889a8d9573cd3962021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 40V, Positive-QTOFsplash10-001j-9000000000-9eec4757ad69989237c02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 10V, Negative-QTOFsplash10-01ta-9030000000-a684f48886db0724b48e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 20V, Negative-QTOFsplash10-004i-9000000000-177256aadc387d9ad2362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - O-Phospho-4-hydroxy-L-threonine 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02609
Phenol Explorer Compound IDNot Available
FooDB IDFDB024088
KNApSAcK IDNot Available
Chemspider ID389731
KEGG Compound IDC06055
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440901
PDB IDNot Available
ChEBI ID18336
Food Biomarker OntologyNot Available
VMH IDPHTHR
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3-phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4-phosphonooxybutanoate to phosphohydroxythreonine (By similarity).
Gene Name:
PSAT1
Uniprot ID:
Q9Y617
Molecular weight:
35188.305
Reactions
O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid → 2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic aciddetails