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Record Information
Version3.6
Creation Date2006-08-12 21:50:34 UTC
Update Date2016-02-11 01:06:20 UTC
HMDB IDHMDB03484
Secondary Accession Numbers
  • HMDB06495
Metabolite Identification
Common NameO-Phosphohomoserine
DescriptionO-phosphohomoserine is a naturally occurring analogue of phosphonate amino acids. O-phosphohomoserine has been found in trace amounts in shotgun-metabolomics analysis in mouse tissue extracts, and is the substrate of a threonine analog enzyme in murine species. O-phosphohomoserine, an analogue of the excitatory amino acid antagonist 2-amino-phosphonovalerate is an N-methyl-D-aspartate (NMDA) antagonist. (PMID: 3528930 , 17034760 , 17665876 ).
Structure
Thumb
Synonyms
ValueSource
Homoserine phosphateChEBI
L-Homoserine, dihydrogen phosphate (ester)ChEBI
O-PhosphohomoserineChEBI
Homoserine phosphoric acidGenerator
(2S)-2-amino-4-PhosphonooxybutanoateGenerator
L-Homoserine, dihydrogen phosphoric acid (ester)Generator
2-amino-4-Hydroxy-butyric acid phosphateHMDB
L-2-amino-4-Hydroxy-butyric acid dihydrogen phosphate (ester)HMDB
O-phospho-HomoserineHMDB
O-phospho-L-HomoserineHMDB
Chemical FormulaC4H10NO6P
Average Molecular Weight199.0991
Monoisotopic Molecular Weight199.024573569
IUPAC Name(2S)-2-amino-4-(phosphonooxy)butanoic acid
Traditional NameO-phosphohomoserine
CAS Registry Number4210-66-6
SMILES
N[C@@H](CCOP(O)(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H10NO6P/c5-3(4(6)7)1-2-11-12(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)/t3-/m0/s1
InChI KeyInChIKey=FXDNYOANAXWZHG-VKHMYHEASA-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
  • 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
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
LogP-3.82Not Available
Predicted Properties
PropertyValueSource
Water Solubility18.1 mg/mLALOGPS
logP-2.3ALOGPS
logP-3.2ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.52ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area130.08 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity37.78 m3·mol-1ChemAxon
Polarizability15.86 Å3ChemAxon
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-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2920000000-4ad8858fcdd6c7235181View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-9400000000-0f8e18482c6cb4d65640View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-5e53d50c26289d23a51dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-6900000000-7771f160a034ddf9f1b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-8d6f322a6a23b8822896View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a90f429c8931d6b68915View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
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 IDFDB023182
KNApSAcK IDNot Available
Chemspider ID133252
KEGG Compound IDC01102
BioCyc IDO-PHOSPHO-L-HOMOSERINE
BiGG ID36811
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03484
Metagene LinkHMDB03484
METLIN IDNot Available
PubChem Compound151187
PDB IDNot Available
ChEBI ID15961
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Connick JH, Heywood GC, Smith DA, Stone TW: O-phosphohomoserine, a naturally occurring analogue of phosphonate amino acid antagonists, is an N-methyl-D-aspartate (NMDA) antagonist in rat hippocampus. Neurosci Lett. 1986 Jul 24;68(2):249-51. [3528930 ]
  2. Donini S, Percudani R, Credali A, Montanini B, Sartori A, Peracchi A: A threonine synthase homolog from a mammalian genome. Biochem Biophys Res Commun. 2006 Dec 1;350(4):922-8. Epub 2006 Sep 29. [17034760 ]
  3. Sun G, Yang K, Zhao Z, Guan S, Han X, Gross RW: Shotgun metabolomics approach for the analysis of negatively charged water-soluble cellular metabolites from mouse heart tissue. Anal Chem. 2007 Sep 1;79(17):6629-40. Epub 2007 Aug 1. [17665876 ]