Details of Metabolite

General Information of MET (ID: META00403)
Name 2,3-Bisphosphoglycerate
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(2R)-2,3-Bis(phosphonooxy)-propanoate; (2R)-2,3-Bis(phosphonooxy)-propanoic acid; (2R)-2,3-Bis(phosphonooxy)propanoic acid; (2R)-2,3-Bis(phosphonooxy)propionic acid; (R)-2,3-Bis(phosphonooxy)-propanoate; (R)-2,3-Bis(phosphonooxy)-propanoic acid; 2,3 Bisphosphoglycerate; 2,3 Diphosphoglycerate; 2,3 Diphosphoglyceric acid; 2,3-BPG; 2,3-Bis(phosphonooxy)-propanoate; 2,3-Bis(phosphonooxy)-propanoic acid; 2,3-Bis(phosphonooxy)propanoic acid; 2,3-Bis(phosphonooxy)propionic acid; 2,3-Bisphosphate, glycerate; 2,3-Bisphospho-D-glycerate; 2,3-Bisphospho-D-glyceric acid; 2,3-Bisphosphoglycerate; 2,3-Bisphosphoglyceric acid; 2,3-DPG; 2,3-Diphospho-D-glycerate; 2,3-Diphospho-D-glyceric acid; 2,3-Diphospho-D-glyceric acid pentasodium salt; 2,3-Diphosphoglycerate; 2,3-Diphosphoglycerate, (D)-isomer; 2,3-Diphosphoglyceric acid; 2,3-Diphosphonooxypropanoic acid; 2,3-Diphosphonooxypropionic acid; 2,3-Disphospho-D-glycerate; 2,3-Disphospho-D-glyceric acid; D-Glyceric acid bis; D-Glyceric acid bis(dihydrogen phosphate); D-Greenwald ester; DPG; Diphosphoglycerate; Diphosphoglyceric acid; Glycerate 2,3-bisphosphate; Glycerate 2,3-diphosphate; Glycerate bis(dihydrogen phosphate); Glycerate diphosphate; Glyceric acid bis(dihydrogen phosphate); Glyceric acid bis(dihydrogen phosphoric acid); Glyceric acid diphosphate; Glyceric acid diphosphoric acid
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food;Microbial
Structure Type   Carbohydrates and carbohydrate conjugates  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic oxygen compounds
Organooxygen compounds
Carbohydrates and carbohydrate conjugates
PubChem CID
186004
HMDB ID
HMDB0001294
Formula
C3H8O10P2
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
C01159
ChEBI ID
17720
FooDB ID
FDB022538
ChemSpider ID
161681
METLIN ID
153
Physicochemical Properties Molecular Weight 266.04 Topological Polar Surface Area 171
XlogP -3.7 Complexity 311
Heavy Atom Count 15 Rotatable Bond Count 6
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 10
Function
2,3-Bisphosphoglycerate (CAS: 138-81-8), also known as 2,3-BPG or 2,3-diphosphoglycerate, is a three-carbon isomer of the glycolytic intermediate 1,3-bisphosphoglycerate and is present at high levels in the human red blood cell (RBC; erythrocyte) at the same molar concentration as hemoglobin. It is notable because it binds to deoxygenated hemoglobin in RBCs. In doing so, it allosterically upregulates the ability of RBCs to release oxygen near tissues that need it most. Its function was discovered in 1967 by Reinhold Benesch and Ruth Benesch.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Lyases (EC 4)
            Cystathionine gamma-lyase (CTH) 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 Cth
                      Induced Change 2,3-Bisphosphoglycerate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Organic acid disorderss [ICD-11: 5C50]
                      Details It is reported that knockout of Cth leads to the increase of 2,3-bisphosphoglycerate levels compared with control group.
      Transcription factor (TF)
            Forkhead box protein O1 (FOXO1) 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 Overexpression of Foxo1
                      Induced Change 2,3-Bisphosphoglycerate concentration: increase (FC = 1.80)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Foxo1 leads to the increase of 2,3-bisphosphoglycerate levels compared with control group.
      Transferases (EC 2)
            Sphingosine kinase 1 (SPHK1) 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 Knockout of Sphk1
                      Induced Change 2,3-Bisphosphoglycerate concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Chronic kidney disease [ICD-11: GB61]
                      Details It is reported that knockout of Sphk1 leads to the decrease of 2,3-bisphosphoglycerate levels compared with control group.
            Transaldolase (TALDO1) 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 [4]
                      Introduced Variation Knockout of Taldo1
                      Induced Change 2,3-Bisphosphoglycerate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that knockout of Taldo1 leads to the increase of 2,3-bisphosphoglycerate levels compared with control group.
References
1 Hydrogen Sulfide Is a Regulator of Hemoglobin Oxygen-Carrying Capacity via Controlling 2,3-BPG Production in Erythrocytes. Oxid Med Cell Longev. 2021 Feb 13;2021:8877691.
2 Metabolomic analysis of C2C12 myoblasts induced by the transcription factor FOXO1. FEBS Lett. 2019 Jun;593(12):1303-1312.
3 Erythrocyte Metabolic Reprogramming by Sphingosine 1-Phosphate in Chronic Kidney Disease and Therapies. Circ Res. 2020 Jul 17;127(3):360-375.
4 Two isoforms of TALDO1 generated by alternative translational initiation show differential nucleocytoplasmic distribution to regulate the global metabolic network. Sci Rep. 2016 Oct 5;6:34648.

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