| Record Information |
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| Version | 4.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2006-08-12 21:50:34 UTC |
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| Update Date | 2017-12-07 01:52:21 UTC |
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| HMDB ID | HMDB0003484 |
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| Secondary Accession Numbers | - HMDB0006495
- HMDB03484
- HMDB06495
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| Metabolite Identification |
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| Common Name | O-Phosphohomoserine |
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| Description | O-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 ). |
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| Structure | |
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| Synonyms | | Value | Source |
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| Homoserine phosphate | ChEBI | | L-Homoserine, dihydrogen phosphate (ester) | ChEBI | | Homoserine phosphoric acid | Generator | | L-Homoserine, dihydrogen phosphoric acid (ester) | Generator | | 2-amino-4-Hydroxy-butyric acid phosphate | HMDB | | L-2-amino-4-Hydroxy-butyric acid dihydrogen phosphate (ester) | HMDB | | O-phospho-Homoserine | HMDB | | O-phospho-L-Homoserine | HMDB | | O-Phosphohomoserine, (DL)-isomer | MeSH |
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| Chemical Formula | C4H10NO6P |
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| Average Molecular Weight | 199.0991 |
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| Monoisotopic Molecular Weight | 199.024573569 |
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| IUPAC Name | (2S)-2-amino-4-(phosphonooxy)butanoic acid |
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| Traditional Name | O-phosphohomoserine |
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| CAS Registry Number | 4210-66-6 |
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| SMILES | N[C@@H](CCOP(O)(O)=O)C(O)=O |
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| 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 |
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| InChI Key | FXDNYOANAXWZHG-VKHMYHEASA-N |
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| Chemical Taxonomy |
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| Description | This 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. |
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| Kingdom | Organic compounds |
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| Super Class | Organic acids and derivatives |
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| Class | Carboxylic acids and derivatives |
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| Sub Class | Amino acids, peptides, and analogues |
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| Direct Parent | L-alpha-amino acids |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aliphatic acyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Route of exposure: Source: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | -3.82 | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| General References | - 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 ]
- 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 ]
- 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 ]
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