General Information of MET (ID: META00230)
Name Phosphoserine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-L-Serine dihydrogen phosphate (ester); (+)-L-Serine dihydrogen phosphoric acid (ester); (2S)-2-Amino-3-(phosphonooxy)propanoate; (2S)-2-Amino-3-(phosphonooxy)propanoic acid; (S)-2-Amino-3-hydroxypropanoate 3-phosphate; (S)-2-Amino-3-hydroxypropanoic acid 3-phosphate; (S)-2-Amino-3-hydroxypropanoic acid 3-phosphoric acid; 3-O-Phosphoserine; 3-Phospho-L-serine; 3-Phosphoserine; Dexfosfoserine; Fosforina; L-3-Phosphoserine; L-O-Phosphoserine; L-O-Serine phosphate; L-Phosphoserine; L-Serine dihydrogen phosphate (ester); L-Serine phosphate; L-Serinephosphorate; L-Serinephosphoric acid; L-Seryl phosphate; O-Phosphoserine; Plasmenylserine
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Drug;Microbial
Structure Type   Amino acids, peptides, and analogues  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Carboxylic acids and derivatives
Amino acids, peptides, and analogues
PubChem CID
68841
HMDB ID
HMDB0000272
Formula
C3H8NO6P
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
KEGG ID
C01005
DrugBank ID
DB04522
ChEBI ID
15811
FooDB ID
FDB021926
ChemSpider ID
62074
METLIN ID
5270
Physicochemical Properties Molecular Weight 185.07 Topological Polar Surface Area 130
XlogP -5.1 Complexity 186
Heavy Atom Count 11 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Function
The phosphoric acid ester of serine. As a constituent (residue) of proteins, its side chain can undergo O-linked glycosylation. This might be important in explaining some of the devastating consequences of diabetes. It is one of three amino acid residues that are commonly phosphorylated by kinases during cell signalling in eukaryotes. Phosphorylated serine residues are often referred to as phosphoserine. Serine proteases are a common type of protease. Serine, organic compound, one of the 20 amino acids commonly found in animal proteins. Only the L-stereoisomer appears in mammalian protein. It is not essential to the human diet, since it can be synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865. Its name is derived from the Latin for silk, sericum. Serine's structure was established in 1902.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Oxidoreductases (EC 1)
            Phosphoglycerate dehydrogenase (PHGDH) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation Knockout of PHGDH
                      Induced Change Phosphoserine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of PHGDH leads to the decrease of phosphoserine levels compared with control group.
      Transferases (EC 2)
            Histone-lysine N-methyltransferase EHMT2 (EHMT2) Click to Show/Hide the Full List of Regulating Pair(s):   2 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair (1) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Inhibition (BIX01294 (BIX)) of EHMT2
                      Induced Change Phosphoserine concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Bone metastasis [ICD-11: 2E03]
                      Details It is reported that inhibition of EHMT2 leads to the decrease of phosphoserine levels compared with control group.
               Regulating Pair (2) Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Overexpression of EHMT2
                      Induced Change Phosphoserine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Bone metastasis [ICD-11: 2E03]
                      Details It is reported that overexpression of EHMT2 leads to the increase of phosphoserine levels compared with control group.
References
1 Phosphoglycerate dehydrogenase diverts glycolytic flux and contributes to oncogenesis. Nat Genet. 2011 Jul 31;43(9):869-74.
2 The histone H3 methyltransferase G9A epigenetically activates the serine-glycine synthesis pathway to sustain cancer cell survival and proliferation. Cell Metab. 2013 Dec 3;18(6):896-907.

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