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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-12 21:50:34 UTC
Update Date2023-02-21 17:16:42 UTC
HMDB IDHMDB0003484
Secondary Accession Numbers
  • HMDB0006495
  • HMDB03484
  • HMDB06495
Metabolite Identification
Common NameO-Phosphohomoserine
DescriptionO-Phosphohomoserine, also known as homoserine phosphate, 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-Phosphohomoserine exists in all living species, ranging from bacteria to plants to humans. O-Phosphohomoserine has been detected, but not quantified in, several different foods, such as cape gooseberries (Physalis peruviana), green cabbages (Brassica oleracea var. sabauda L.), white bread, beech nuts (Fagus), and jerusalem artichokes (Helianthus tuberosus). This could make O-phosphohomoserine a potential biomarker for the consumption of these foods. O-Phosphohomoserine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on O-Phosphohomoserine.
Structure
Thumb
Synonyms
ValueSource
Homoserine phosphateChEBI
L-Homoserine, dihydrogen phosphate (ester)ChEBI
Homoserine phosphoric acidGenerator
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
O-Phosphohomoserine, (DL)-isomerMeSH, HMDB
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 KeyFXDNYOANAXWZHG-VKHMYHEASA-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
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • 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
Physiological effectNot Available
Disposition
Route of exposureSource
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.82Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023182
KNApSAcK IDC00007385
Chemspider ID133252
KEGG Compound IDC01102
BioCyc IDO-PHOSPHO-L-HOMOSERINE
BiGG ID36811
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151187
PDB IDNot Available
ChEBI ID15961
Food Biomarker OntologyNot Available
VMH IDPHOM
MarkerDB IDNot Available
Good Scents IDNot Available
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. [PubMed: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. [PubMed: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. [PubMed:17665876 ]