| Record Information |
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| Version | 1.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2021-07-01 14:27:28 UTC |
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| NP-MRD ID | NP0000094 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Phosphoserine |
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| Description | Phosphoserine is the phosphoric acid ester of the amino acid serine. It is found in essentially all living organisms ranging from microbes to plants to mammals. Phosphoserine is a component of many proteins as the result of posttranslational modifications to the native protein’s serine residue(s). The phosphorylation of the hydroxyl functional group in serine to produce phosphoserine is catalyzed by various types of kinases. Serine is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Free phosphoserine is found in many biofluids and likely arises from the proteolysis of proteins containing phosphoserine residues (PMID: 7693088 ). |
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| Structure | N[C@@H](COP(O)(O)=O)C(O)=O 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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| Synonyms | | Value | 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 |
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| Chemical Formula | C3H8NO6P |
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| Average Mass | 185.0725 Da |
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| Monoisotopic Mass | 185.00892 Da |
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| IUPAC Name | (2S)-2-amino-3-(phosphonooxy)propanoic acid |
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| Traditional Name | phosphoserine |
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| CAS Registry Number | 407-41-0 |
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| SMILES | N[C@@H](COP(O)(O)=O)C(O)=O |
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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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| Spectra |
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| | Spectrum Type | Description | Depositor ID | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | Wishart Lab | 2021-06-20 | View Spectrum | | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Wishart Lab | 2021-06-20 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Species Where Detected | |
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| Chemical Taxonomy |
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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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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 170 - 171 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 71 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Molina JA, Jimenez-Jimenez FJ, Gomez P, Vargas C, Navarro JA, Orti-Pareja M, Gasalla T, Benito-Leon J, Bermejo F, Arenas J: Decreased cerebrospinal fluid levels of neutral and basic amino acids in patients with Parkinson's disease. J Neurol Sci. 1997 Sep 10;150(2):123-7. [PubMed:9268238 ]
- Kataoka H, Nakai K, Katagiri Y, Makita M: Analysis of free and bound O-phosphoamino acids in urine by gas chromatography with flame photometric detection. Biomed Chromatogr. 1993 Jul-Aug;7(4):184-8. [PubMed:7693088 ]
- Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
- Kataoka H, Sakiyama N, Makita M: Occurrence of free O-phosphoserine and O-phosphothreonine in porcine liver. Agric Biol Chem. 1990 Jul;54(7):1731-3. [PubMed:1368590 ]
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