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Record Information
Version1.0
Creation Date2016-10-03 18:14:16 UTC
Update Date2020-04-22 15:43:09 UTC
BMDB IDBMDB0011185
Secondary Accession Numbers
  • BMDB11185
Metabolite Identification
Common NameO-Phosphothreonine
DescriptionO-Phosphothreonine, also known as L-threonine phosphate or phosphate, 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-Phosphothreonine is a very strong basic compound (based on its pKa). O-Phosphothreonine exists in all living organisms, ranging from bacteria to humans.
Structure
Thumb
Synonyms
ValueSource
L-Threonine phosphateKegg
O-Phospho-L-threonineKegg
L-Threonine phosphoric acidGenerator
(2S,3R)-2-Amino-3-hydroxybutanoic acid 3-phosphateHMDB
L-Threonine O-3-phosphateHMDB
O3-PhosphothreonineHMDB
PhosphothreonineHMDB
Threonine phosphate esterHMDB
Threoninium dihydrogen phosphateHMDB
(2S,3R)-2-Amino-3-hydroxybutanoate 3-phosphateHMDB
(2S,3R)-2-Amino-3-hydroxybutanoic acid 3-phosphoric acidHMDB
L-Threonine O-3-phosphoric acidHMDB
Threonine phosphoric acid esterHMDB
Threoninium dihydrogen phosphoric acidHMDB
Phosphate, threonineHMDB
Threonine phosphateHMDB
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
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
  • 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
StatusExpected but not 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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011185
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027954
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC12147
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThreonine
METLIN IDNot Available
PubChem Compound3246323
PDB IDTPO
ChEBI ID37525
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Activates the ADP-ribosyltransferase (exoS) activity of bacterial origin. Induces ARHGEF7 activity on RAC1 as well as lamellipodia and membrane ruffle formation (By similarity). In neurons, regulates spine maturation through the modulation of ARHGEF7 activity (By similarity).
Gene Name:
YWHAZ
Uniprot ID:
P63103
Molecular weight:
27745.0
General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negatively regulates the kinase activity of PDPK1 (By similarity).
Gene Name:
YWHAH
Uniprot ID:
P68509
Molecular weight:
28212.0
General function:
Involved in insulin-like growth factor receptor binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner.
Gene Name:
YWHAG
Uniprot ID:
P68252
Molecular weight:
28253.0
General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negative regulator of osteogenesis. Blocks the nuclear translocation of the phosphorylated form (by AKT1) of SRPK2 and antagonizes its stimulatory effect on cyclin D1 expression resulting in blockage of neuronal apoptosis elicited by SRPK2. Negative regulator of signaling cascades that mediate activation of MAP kinases via AKAP13.
Gene Name:
YWHAB
Uniprot ID:
P68250
Molecular weight:
28081.0
General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. Negatively regulates the kinase activity of PDPK1 (By similarity).
Gene Name:
YWHAQ
Uniprot ID:
Q3SZI4
Molecular weight:
27764.0
General function:
Not Available
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways (PubMed:7931346). Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif (PubMed:7931346). Binding generally results in the modulation of the activity of the binding partner (PubMed:7931346). Positively regulates phosphorylated protein HSF1 nuclear export to the cytoplasm (By similarity).
Gene Name:
YWHAE
Uniprot ID:
P62261
Molecular weight:
29174.0
General function:
Involved in protein domain specific binding
Specific function:
Adapter protein implicated in the regulation of a large spectrum of both general and specialized signaling pathways. Binds to a large number of partners, usually by recognition of a phosphoserine or phosphothreonine motif. Binding generally results in the modulation of the activity of the binding partner. When bound to KRT17, regulates protein synthesis and epithelial cell growth by stimulating Akt/mTOR pathway. May also regulate MDM2 autoubiquitination and degradation and thereby activate p53/TP53 (By similarity).
Gene Name:
SFN
Uniprot ID:
Q0VC36
Molecular weight:
27849.0