Details of Metabolite

General Information of MET (ID: META00308)
Name L-Homoserine
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2S)-2-Amino-4-hydroxybutanoate; (2S)-2-Amino-4-hydroxybutanoic acid; (S)-2-Amino-4-hydroxy-butanoate; (S)-2-Amino-4-hydroxy-butanoic acid; (S)-2-Amino-4-hydroxybutanoate; (S)-2-Amino-4-hydroxybutanoic acid; (S)-Homoserine; 2-Amino-4-hydroxy-L-butyrate; 2-Amino-4-hydroxy-L-butyric acid; 2-Amino-4-hydroxy-butyrate; 2-Amino-4-hydroxy-butyric acid; 2-Amino-4-hydroxybutanoate; 2-Amino-4-hydroxybutanoic acid; 2-Amino-4-hydroxybutyrate; 2-Amino-4-hydroxybutyric acid; Homoserine; Homoserine L-isomer; L Isomer OF homoserine; L-Isomer OF homoserine
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
12647
HMDB ID
HMDB0000719
Formula
C4H9NO3
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
C00263
DrugBank ID
DB04193
ChEBI ID
15699
FooDB ID
FDB000521
ChemSpider ID
12126
METLIN ID
5687
Physicochemical Properties Molecular Weight 119.12 Topological Polar Surface Area 83.6
XlogP -4.4 Complexity 83.4
Heavy Atom Count 8 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 4
Function
Homoserine is a more reactive variant of the amino acid serine. In this variant, the hydroxyl side chain contains an additional CH2 group which brings the hydroxyl group closer to its own carboxyl group, allowing it to chemically react to form a five-membered ring. This occurs at the point that amino acids normally join to their neighbours in a peptide bond. Homoserine is therefore unsuitable for forming proteins and has been eliminated from the repertoire of amino acids used by living things. Homoserine is the final product on the C-terminal end of the N-terminal fragment following a cyanogen bromide cleavage. Homoserine is also a microbial metabolite.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR secretin (GPCR-2)
            Glucagon receptor (GCGR) 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 Gcgr
                      Induced Change L-Homoserine concentration: increase (FC = 3)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Type 2 diabetes mellitus [ICD-11: 5A11]
                      Details It is reported that knockout of GCGR leads to the increase of L-homoserine levels compared with control group.
      Hydrolases (EC 3)
            Leukotriene-C4 hydrolase (GGT1) 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 [2]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change L-Homoserine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Renal cell carcinoma [ICD-11: 2C90]
                      Details It is reported that knockdown of GGT1 leads to the increase of L-homoserine levels compared with control group.
      Oxidoreductases (EC 1)
            L-2-hydroxyglutarate dehydrogenase (L2HGDH) 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 [3]
                      Introduced Variation Mutation (Nonsense mutations or missense mutations) of L2hgdh
                      Induced Change L-Homoserine concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Melanoma [ICD-11: 2C30]
                      Details It is reported that mutation (nonsense mutations or missense mutations leading to KMT2D loss) of L2hgdh leads to the increase of L-homoserine levels compared with control group.
References
1 Polyomic profiling reveals significant hepatic metabolic alterations in glucagon-receptor (GCGR) knockout mice: implications on anti-glucagon therapies for diabetes. BMC Genomics. 2011 Jun 1;12:281.
2 Impairment of gamma-glutamyl transferase 1 activity in the metabolic pathogenesis of chromophobe renal cell carcinoma. Proc Natl Acad Sci U S A. 2018 Jul 3;115(27):E6274-E6282.
3 Enhancer Reprogramming Confers Dependence on Glycolysis and IGF Signaling in KMT2D Mutant Melanoma. Cell Rep. 2020 Oct 20;33(3):108293.

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