Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:05:17 UTC |
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Update date | 2020-09-17 15:38:31 UTC |
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Primary ID | FDB021926 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | L-Phosphoserine |
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Description | Phosphoserine, also known as dexfosfoserine or fosforina, 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. The L-enantiomer of O-phosphoserine. Phosphoserine is a very strong basic compound (based on its pKa). Phosphoserine exists in all living species, ranging from bacteria to humans. Within humans, phosphoserine participates in a number of enzymatic reactions. In particular, phosphoserine and oxoglutaric acid can be biosynthesized from phosphohydroxypyruvic acid and L-glutamic acid; which is catalyzed by the enzyme phosphoserine aminotransferase. In addition, phosphoserine can be converted into L-serine; which is mediated by the enzyme phosphoserine phosphatase. In humans, phosphoserine is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. |
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CAS Number | 407-41-0 |
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Structure | |
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Synonyms | Synonym | Source |
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(+)-L-Serine dihydrogen phosphate (ester) | ChEBI | (2S)-2-Amino-3-(phosphonooxy)propanoic acid | ChEBI | (S)-2-Amino-3-hydroxypropanoic acid 3-phosphate | ChEBI | 3-Phosphoserine | ChEBI | Dexfosfoserine | ChEBI | L-O-Phosphoserine | ChEBI | O-Phosphoserine | ChEBI | 3-Phospho-L-serine | Kegg | (+)-L-Serine dihydrogen phosphoric acid (ester) | Generator | (2S)-2-Amino-3-(phosphonooxy)propanoate | Generator | (S)-2-Amino-3-hydroxypropanoate 3-phosphate | Generator | (S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acid | Generator | 3-O-Phosphoserine | HMDB | Fosforina | HMDB | L-3-Phosphoserine | HMDB | L-O-Serine phosphate | HMDB | L-Phosphoserine | HMDB | L-Serine dihydrogen phosphate (ester) | HMDB | L-Serine phosphate | HMDB | L-Serinephosphorate | HMDB | L-Serinephosphoric acid | HMDB | L-Seryl phosphate | HMDB | Plasmenylserine | HMDB | (+)-L-Serine dihydrogen ate (ester) | ChEBI | (+)-L-Serine dihydrogen ic acid (ester) | Generator | (2S)-2-amino-3-(Onooxy)propanoate | Generator | (2S)-2-amino-3-(Onooxy)propanoic acid | ChEBI | (S)-2-amino-3-Hydroxypropanoate 3-ate | Generator | (S)-2-amino-3-Hydroxypropanoic acid 3-ate | ChEBI | (S)-2-amino-3-Hydroxypropanoic acid 3-ic acid | Generator | 3-O-Oserine | HMDB | 3-Oserine | ChEBI | Dexfosfoserine, INN | db_source | L-3-Oserine | HMDB | L-O-Oserine | ChEBI | L-O-Serine ate | HMDB | L-Oserine | HMDB | L-Serine ate | HMDB | L-Serine dihydrogen ate (ester) | HMDB | L-Serineorate | HMDB | L-Serineoric acid | HMDB | L-Seryl ate | HMDB | O-O-L-Serine | ChEBI | O-Oserine | ChEBI | Oserine | ChEBI | S-Phosphoserine | manual |
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Predicted Properties | |
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Chemical Formula | C3H8NO6P |
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IUPAC name | (2S)-2-amino-3-(phosphonooxy)propanoic acid |
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InChI Identifier | InChI=1S/C3H8NO6P/c4-2(3(5)6)1-10-11(7,8)9/h2H,1,4H2,(H,5,6)(H2,7,8,9)/t2-/m0/s1 |
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InChI Key | BZQFBWGGLXLEPQ-REOHCLBHSA-N |
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Isomeric SMILES | N[C@@H](COP(O)(O)=O)C(O)=O |
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Average Molecular Weight | 185.0725 |
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Monoisotopic Molecular Weight | 185.008923505 |
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Classification |
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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. |
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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
- Phosphoethanolamine
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Amino acid
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Primary amine
- Organopnictogen compound
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Amine
- Primary aliphatic amine
- Carbonyl group
- Organic oxide
- Hydrocarbon derivative
- 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 | Source: Biological location: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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GC-MS | L-Phosphoserine, x TMS, GC-MS Spectrum | splash10-02u1-0930000000-c899f07d021f46de8c59 | Spectrum | GC-MS | L-Phosphoserine, x TMS, GC-MS Spectrum | splash10-02am-0980000000-224ebb540cc8cfeee7bf | Spectrum | GC-MS | L-Phosphoserine, non-derivatized, GC-MS Spectrum | splash10-0k92-0943000000-2c96e781366647a38c1b | Spectrum | GC-MS | L-Phosphoserine, 4 TMS, GC-MS Spectrum | splash10-0rka-2965000000-6295c9d3aab0dbbdbe06 | Spectrum | GC-MS | L-Phosphoserine, non-derivatized, GC-MS Spectrum | splash10-02u1-0930000000-c899f07d021f46de8c59 | Spectrum | GC-MS | L-Phosphoserine, non-derivatized, GC-MS Spectrum | splash10-02am-0980000000-224ebb540cc8cfeee7bf | Spectrum | GC-MS | L-Phosphoserine, non-derivatized, GC-MS Spectrum | splash10-0k92-0943000000-2c96e781366647a38c1b | Spectrum | GC-MS | L-Phosphoserine, non-derivatized, GC-MS Spectrum | splash10-0rka-2965000000-6295c9d3aab0dbbdbe06 | Spectrum | GC-MS | L-Phosphoserine, non-derivatized, GC-MS Spectrum | splash10-052b-0943000000-925dbf1f579400fe1275 | Spectrum | GC-MS | L-Phosphoserine, non-derivatized, GC-MS Spectrum | splash10-03yl-0890000000-f853ba80cc56b6057d3e | Spectrum | Predicted GC-MS | L-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0002-9200000000-579f933727173ebf1101 | Spectrum | Predicted GC-MS | L-Phosphoserine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-9720000000-0c93ad0358d5840580e0 | Spectrum | Predicted GC-MS | L-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Phosphoserine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Phosphoserine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Phosphoserine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Phosphoserine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Phosphoserine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | L-Phosphoserine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-9000000000-07c4d8f30a6ca83b8b55 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-00dr-9000000000-c5a74679d970f7b6e2d5 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0006-9000000000-1d94e50890f1499da7f4 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-000i-3900000000-0424244742b82164682f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-000i-9100000000-f86c85cff0432259c764 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-00kr-9000000000-997762f62b3a2e22b12b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-00di-9000000000-4732d51a493c7bf13c29 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-00kf-9000000000-5d40f9a41d75ac08b4c2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-0002-9000000000-f653dafdf17fa74b83a5 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0002-9000000000-f653dafdf17fa74b83a5 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-3900000000-76c6900db1ecb22c9dc6 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-000i-9100000000-f86c85cff0432259c764 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00kr-9000000000-25381bf668ede8881af0 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00di-9000000000-63cde6935414b6893a5f | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , positive | splash10-00kf-9000000000-5d40f9a41d75ac08b4c2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0002-9000000000-030fc19bab74121b9536 | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-004j-9000000000-78dc68824c37b96fd97f | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-8c715ebc5361358f572d | 2021-09-20 | View Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-000t-5900000000-2acd16447bafd738b8b2 | 2021-09-20 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000l-9800000000-672ba3fb65a9cac25044 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9300000000-e63c25df326283cc3b7f | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-dbc8b3072add030d1711 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-003r-9800000000-10234b7ff1b336489a5a | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9100000000-8a4c753dfa69ac6720e0 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-ebe13ec0e44d8c4f4771 | 2016-09-12 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, D2O, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 62074 |
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ChEMBL ID | CHEMBL284377 |
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KEGG Compound ID | C01005 |
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Pubchem Compound ID | 68841 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | Not Available |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB04522 |
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HMDB ID | HMDB00272 |
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CRC / DFC (Dictionary of Food Compounds) ID | CJC00-O:CJC02-Q |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | Not Available |
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KNApSAcK ID | Not Available |
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HET ID | SEP |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Phosphoserine |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Phosphoserine aminotransferase | PSAT1 | Q9Y617 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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