Details of Metabolite

General Information of MET (ID: META00559)
Name D-Pipecolic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-Pipecolic acid; (+)-Pipecolinic acid; (2R)-2-Piperidinecarboxylic acid; (2R)-Piperidine-2-carboxylic acid; (R)-()-2-Piperidinecarboxylic acid; (R)-(+)-Pipecolic acid; (R)-2-Piperidinecarboxylic acid; (R)-Pipecolate; (R)-Pipecolic acid; (R)-Pipecolinic acid; (R)-Piperidine-2-carboxylate; (R)-Piperidine-2-carboxylic acid; 6-CARBOXYPIPERIDINE; D-(+)- Pipecolic acid; D-(+)-Pipecolic acid; D-Homoproline; D-Pipecolate; D-Pipecolinic acid; D-Piperidine-2-carboxylic acid
Source Endogenous;Yeast Metabolite;Food;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
736316
HMDB ID
HMDB0005960
Formula
C6H11NO2
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=736316"></iframe>
3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
41582
FooDB ID
FDB023791
ChemSpider ID
643442
Physicochemical Properties Molecular Weight 129.16 Topological Polar Surface Area 49.3
XlogP -2.3 Complexity 114
Heavy Atom Count 9 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
D-Pipecolic acid is a normal human metabolite found in human biofluids. Normal adults excrete pipecolic acid primarily as the D-enantiomer even though it is present in the blood stream mainly as the L-enantiomer. It is believed that D-pipecolic acid originates from the metabolism of intestinal bacteria and from dietary sources. High levels of D-pipecolic acid are not found in plasma, but they are increased in urine of patients with chronic liver disease.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      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 [1]
                      Introduced Variation Knockdown (siRNA) of GGT1
                      Induced Change D-Pipecolic acid 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 D-Pipecolic acid levels compared with control group.
      Pore-forming PNC peptide (PNC)
            Cellular tumor antigen p53 (TP53) 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 TP53
                      Induced Change D-Pipecolic acid concentration: increase (Log2 FC=1.22)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Colon cancer [ICD-11: 2B90]
                      Details It is reported that knockout of TP53 leads to the increase of D-Pipecolic acid levels compared with control group.
References
1 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.
2 Integrative omics analysis of p53-dependent regulation of metabolism. FEBS Lett. 2018 Feb;592(3):380-393.

If you find any error in data or bug in web service, please kindly report it to Dr. Zhang and Dr. Mou.