Details of Metabolite

General Information of MET (ID: META00146)
Name Pipecolic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
()-Piperidine-2-carboxylic acid; (+/-)-2-piperidinecarboxylate; (+/-)-2-piperidinecarboxylic acid; (+/-)-pipecolate; (+/-)-pipecolic acid; (+/-)-pipecolinate; (+/-)-pipecolinic acid; (.+/-.)-2-piperidinecarboxylic acid; (RS)-2-Piperidinecarboxylate; (RS)-2-Piperidinecarboxylic acid; .alpha.-pipecolinic acid; 2-Carboxypiperidine; 2-Pipecolinic acid; 2-Piperidinecarboxylate; 2-Piperidinecarboxylic acid; 2-Piperidinylcarboxylic acid; Acide pipecolique; Acide piperidine-carboxylique-2; DL-2-Piperidinecarboxylate; DL-2-Piperidinecarboxylic acid; DL-Homoproline; DL-Pipecolate; DL-Pipecolic acid; DL-Pipecolinate; DL-Pipecolinic acid; Dihydrobaikiane; Hexahydro-2-picolinate; Hexahydro-2-picolinic acid; Hexahydropicolinate; Hexahydropicolinic acid; Homopipecolic acid; Homoproline; L-Pipecolic acid; Pipecolate; Pipecolic acid; Pipecolic acid free base; Pipecolic acid hydrochloride, (+-)-isomer; Pipecolic acid, (+,-)-isomer; Pipecolic acid, (R)-isomer; Pipecolic acid, (S)-isomer; Pipecolic acid, 14C-labeled CPD, (+,-)-isomer; Pipecolic acid, ion (1-); Pipecolic acid, ion(1-), (+,-)-isomer; Pipecolic acid, ion(1-), (S)-isomer; Pipecolic acid, monopotassium salt; Pipecolinate; Pipecolinic acid; Piperidine-2-carboxylate; Piperidine-2-carboxylic acid; Piperolinate; Piperolinic acid; a-Pipecolinate; a-Pipecolinic acid; alpha-Pipecolinate; alpha-Pipecolinic acid
Source Endogenous;Escherichia Coli Metabolite;Yeast Metabolite;Food
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
849
HMDB ID
HMDB0000070
Formula
C6H11NO2
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
C00408
ChEBI ID
17964
FooDB ID
FDB000545
ChemSpider ID
826
METLIN ID
50
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
Pipecolic acid is a metabolite of lysine found in human physiological fluids such as urine, plasma and CSF. However, it is uncertain if pipecolic acid originates directly from food intake or from mammalian or intestinal bacterial enzyme metabolism. Recent studies suggest that plasma pipecolic acid, particularly the D-isomer, originates mainly from the catabolism of dietary lysine by intestinal bacteria rather than by direct food intake. In classic Zellweger syndrome (a cerebro-hepato-renal genetic disorder, OMIM 214100) pipecolic acid accumulate in the plasma of the patients. It is known that plasma pipecolic acid levels are also elevated in patients with chronic liver diseases. Pipecolic acid is moderately elevated in patients with pyridoxine-dependent seizures and might therefore be a possible biochemical marker for selecting candidates for pyridoxine therapy (Plecko et al 2000). Pipecolic acid was also elevated in CSF in these vitamin B6-responsive patients. Pipecolic acid is found to be associated with adrenoleukodystrophy, infantile Refsum disease, and peroxisomal biogenesis defect, which are also inborn errors of metabolism. Pipecolic acid is a biomarker for the consumption of dried and cooked beans.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) 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 (shRNA) of SULF1
                      Induced Change Pipecolic acid concentration: decrease (FC = 0.43 / 0.44)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the decrease of pipecolic acid levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.

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