We are currently updating the database - data may be missing for the next 10 minutes. We apologize for any inconvenience.

Bovine Metabolome Database



Showing metabocard for Pipecolic acid (BMDB00070)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-14 10:55:13
Accession Number BMDB00070
Common Name Pipecolic acid
Description 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. (PMID 12705501)
Synonyms
  1. ()-Piperidine-2-carboxylic acid
  2. (+/-)-2-Piperidinecarboxylate
  3. (+/-)-2-Piperidinecarboxylic acid
  4. (+/-)-Pipecolate
  5. (+/-)-Pipecolic acid
  6. (+/-)-Pipecolinate
  7. (+/-)-Pipecolinic acid
  8. (.+/-.)-2-Piperidinecarboxylic acid
  9. (RS)-2-Piperidinecarboxylate
  10. (RS)-2-Piperidinecarboxylic acid
  11. .alpha.-Pipecolinic acid
  12. 2-Carboxypiperidine
  13. 2-Pipecolinic acid
  14. 2-Piperidinecarboxylate
  15. 2-Piperidinecarboxylic acid
  16. 2-Piperidinylcarboxylic acid
  17. a-Pipecolinate
  18. a-Pipecolinic acid
  19. acide pipecolique
  20. acide piperidine-carboxylique-2
  21. alpha-Pipecolinate
  22. alpha-Pipecolinic acid
  23. Dihydrobaikiane
  24. DL-2-Piperidinecarboxylate
  25. DL-2-Piperidinecarboxylic acid
  26. DL-Homoproline
  27. DL-Pipecolate
  28. DL-Pipecolic acid
  29. DL-Pipecolinate
  30. DL-Pipecolinic acid
  31. Hexahydro-2-picolinate
  32. Hexahydro-2-picolinic acid
  33. Hexahydropicolinate
  34. Hexahydropicolinic acid
  35. Homoproline
  36. pipecolate
  37. pipecolic acid
  38. Pipecolic acid free base
  39. Pipecolinate
  40. Pipecolinic acid
  41. piperidine-2-carboxylic acid
  42. Piperolinate
  43. Piperolinic acid
Chemical IUPAC Name Piperidine-2-carboxylic acid
Chemical Formula C6H11NO2
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Amino acids and Amino Acid conjugates
Class
  • Amino Acids
Sub Class
  • NA
Family
  • Mammalian_Metabolite
Species
  • secondary amine; secondary aliphatic amine (dialkylamine); carboxylic acid; heterocyclic compound; alpha-aminoacid
Biofunction
  • Protein synthesis, amino acid biosynthesis
Application
Source
  • Endogenous
Average Molecular Weight 129.157
Monoisotopic Molecular Weight 129.078979
Isomeric SMILES OC(=O)C1CCCCN1
Canonical SMILES OC(=O)C1CCCCN1
KEGG Compound ID C00408 Link Image
BioCyc ID 5-HYDROXY-PIPECOLATE Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 50 Link Image
PubChem Compound 849 Link Image
PubChem Substance 675521 Link Image
ChEBI ID 17964 Link Image
CAS Registry Number 535-75-1
InChI Identifier InChI=1/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)
Synthesis Reference Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland. New synthesis of pipecolic acid and analogs. Tetrahedron Letters (1981), 22(2), 141-4.
Melting Point (Experimental) 264 oC
Experimental Water Solubility 314 mg/mL [HMP experimental] Source: PhysProp
Predicted Water Solubility 74.1 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; 158.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity -2.31 [TSAI,RS ET AL. (1991)] Source: PhysProp
Predicted LogP/Hydrophobicity -2.17 [Predicted by ALOGPS]; -2 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
Show Experimental Conditions Link Image
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
Show Experimental Conditions Link Image
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum
Low Energy
Download File
Show Experimental Conditions Link Image
Medium Energy
Download File
Show Experimental Conditions Link Image
High Energy
Download File
Show Experimental Conditions Link Image
Simplified TOCSY Spectrum Show Image
Show Peaklist
BMRB Spectrum Show Image
Show Peaklist
Cellular Location
  • cytoplasm
  • extracellular
Biofluid Location Not Available
Tissue Location
Tissue References
Gut
Liver
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available