Details of Metabolite

General Information of MET (ID: META00225)
Name Phosphoenolpyruvate
Synonyms   Click to Show/Hide Synonyms of This Metabolite
2-(Phosphonooxy)-2-propenoate; 2-(Phosphonooxy)-2-propenoic acid; 2-Hydroxy-acrylic acid dihydrogen phosphate; 2-PHOSPHOENOLPYRUVIC ACID; 2-PHOSPHOENOLPYRUVate; 2-Phosphonooxyprop-2-enoate; 2-Phosphonooxyprop-2-enoic acid; P-enol-Pyruvate; PEP; PHOSPHOENOLPYRUVATE
Source Aliphatic acyclic compounds
Structure Type   Phosphate esters  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Organic phosphoric acids and derivatives
Phosphate esters
PubChem CID
1005
HMDB ID
HMDB0000263
Formula
C3H5O6P
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
C00074
DrugBank ID
DB01819
ChEBI ID
44897
FooDB ID
FDB031112
Physicochemical Properties Molecular Weight 168.04 Topological Polar Surface Area 104
XlogP -1.1 Complexity 201
Heavy Atom Count 10 Rotatable Bond Count 3
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 6
Function
Phosphoenolpyruvate (PEP) is an important chemical compound in biochemistry. It has a high energy phosphate bond, and is involved in glycolysis and gluconeogenesis. In glycolysis, PEP is formed by the action of the enzyme enolase on 2-phosphoglycerate. Metabolism of PEP to pyruvate by pyruvate kinase (PK) generates 1 molecule of adenosine triphosphate (ATP) via substrate-level phosphorylation. ATP is one of the major currencies of chemical energy within cells. In gluconeogenesis, PEP is formed from the decarboxylation of oxaloacetate and hydrolysis of 1 guanosine triphosphate molecule. This reaction is catalyzed by the enzyme phosphoenolpyruvate carboxykinase (PEPCK). This reaction is a rate-limiting step in gluconeogenesis.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      GPCR rhodopsin (GPCR-1)
            Adrenergic receptor beta-3 (ADRB3) 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 Agonist (CL-316,243) of Adrb3
                      Induced Change Phosphoenolpyruvate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that agonist of ADRB3 leads to the increase of phosphoenolpyruvate levels compared with control group.
      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 [2]
                      Introduced Variation Knockout of Gcgr
                      Induced Change Phosphoenolpyruvate concentration: decrease (FC = 2.3)
                      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 decrease of phosphoenolpyruvate levels compared with control group.
      Oxidoreductases (EC 1)
            Alcohol dehydrogenase iron 1 (ADHFE1) 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 Overexpression of ADHFE1
                      Induced Change Phosphoenolpyruvate concentration: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Breast cancer [ICD-11: 2C60]
                      Details It is reported that overexpression of ADHFE1 leads to the increase of phosphoenolpyruvate 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 [4]
                      Introduced Variation Overexpression of Foxo1
                      Induced Change Phosphoenolpyruvate concentration: increase (FC = 1.70)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Healthy individual
                      Details It is reported that overexpression of Foxo1 leads to the increase of phosphoenolpyruvate levels compared with control group.
            Myc proto-oncogene protein (MYC) 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 [5]
                      Introduced Variation Knockdown (siRNA) of MYC
                      Induced Change Phosphoenolpyruvate concentration: decrease
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colorectal cancer [ICD-11: 2B91]
                      Details It is reported that knockdown of MYC leads to the decrease of phosphoenolpyruvate levels compared with control group.
References
1 Metabolic changes in adipose tissues in response to 3 -adrenergic receptor activation in mice. J Cell Biochem. 2019 Jan;120(1):821-835.
2 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.
3 ADHFE1 is a breast cancer oncogene and induces metabolic reprogramming. J Clin Invest. 2018 Jan 2;128(1):323-340.
4 Metabolomic analysis of C2C12 myoblasts induced by the transcription factor FOXO1. FEBS Lett. 2019 Jun;593(12):1303-1312.
5 Global metabolic reprogramming of colorectal cancer occurs at adenoma stage and is induced by MYC. Proc Natl Acad Sci U S A. 2017 Sep 12;114(37):E7697-E7706.

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