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Record Information
Version1.0
Creation Date2016-09-30 22:19:15 UTC
Update Date2020-05-11 20:46:18 UTC
MCDB ID BMDB0000070
Secondary Accession Numbers
  • BMDB00070
Metabolite Identification
Common NamePipecolic acid
DescriptionDL-Pipecolic acid, also known as pipecolinate or homoproline, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-Pipecolic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. DL-Pipecolic acid exists in all living species, ranging from bacteria to humans. DL-Pipecolic acid has been found to be associated with several diseases known as malaria, schizophrenia, rhizomelic chondrodysplasia punctata, and perillyl alcohol administration for cancer treatment; also dl-pipecolic acid has been linked to the inborn metabolic disorders including adrenoleukodystrophy.
Structure
Thumb
Synonyms
ValueSource
2-Piperidinecarboxylic acidChEBI
HomoprolineChEBI
Pipecolinic acidChEBI
2-PiperidinecarboxylateGenerator
PipecolinateGenerator
PipecolateGenerator
()-Piperidine-2-carboxylic acidHMDB
(+/-)-2-piperidinecarboxylateHMDB
(+/-)-2-piperidinecarboxylic acidHMDB
(+/-)-pipecolateHMDB
(+/-)-pipecolic acidHMDB
(+/-)-pipecolinateHMDB
(+/-)-pipecolinic acidHMDB
(.+/-.)-2-piperidinecarboxylic acidHMDB
(RS)-2-PiperidinecarboxylateHMDB
(RS)-2-Piperidinecarboxylic acidHMDB
.alpha.-pipecolinic acidHMDB
2-CarboxypiperidineHMDB
2-Pipecolinic acidHMDB
2-Piperidinylcarboxylic acidHMDB
a-PipecolinateHMDB
a-Pipecolinic acidHMDB
Acide pipecoliqueHMDB
Acide piperidine-carboxylique-2HMDB
alpha-PipecolinateHMDB
alpha-Pipecolinic acidHMDB
DihydrobaikianeHMDB
DL-2-PiperidinecarboxylateHMDB
DL-2-Piperidinecarboxylic acidHMDB
DL-HomoprolineHMDB
DL-PipecolateHMDB, Generator
DL-Pipecolic acidHMDB
DL-PipecolinateHMDB
DL-Pipecolinic acidHMDB
hexahydro-2-PicolinateHMDB
hexahydro-2-Picolinic acidHMDB
HexahydropicolinateHMDB
Hexahydropicolinic acidHMDB
Pipecolic acid free baseHMDB
Piperidine-2-carboxylic acidHMDB
PiperolinateHMDB
Piperolinic acidHMDB
L-Pipecolic acidMeSH, HMDB
Pipecolic acid, (R)-isomerMeSH, HMDB
Pipecolic acid, ion (1-)MeSH, HMDB
Pipecolic acid, monopotassium saltMeSH, HMDB
Pipecolic acid hydrochloride, (+-)-isomerMeSH, HMDB
Pipecolic acid, (S)-isomerMeSH, HMDB
Pipecolic acid, 14C-labeled CPD, (+,-)-isomerMeSH, HMDB
Homopipecolic acidMeSH, HMDB
Pipecolic acid, (+,-)-isomerMeSH, HMDB
Pipecolic acid, ion(1-), (+,-)-isomerMeSH, HMDB
Pipecolic acid, ion(1-), (S)-isomerMeSH, HMDB
Piperidine-2-carboxylateGenerator, HMDB
Pipecolic acidMeSH
Chemical FormulaC6H11NO2
Average Molecular Weight129.157
Monoisotopic Molecular Weight129.078978601
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number535-75-1
SMILESNot Available
InChI Identifier
InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)
InChI KeyHXEACLLIILLPRG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Piperidinecarboxylic acid
  • Piperidine
  • Amino acid
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Secondary aliphatic amine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point264 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility314 mg/mLNot Available
LogP-2.31TSAI,RS ET AL. (1991)
Predicted PropertiesNot Available
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000070
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000545
KNApSAcK IDC00001387
Chemspider ID826
KEGG Compound IDC00408
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPipecolic_acid
METLIN ID50
PubChem Compound849
PDB IDNot Available
ChEBI ID17964
References
Synthesis ReferenceAsher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland. New synthesis of pipecolic acid and analogs. Tetrahedron Letters (1981), 22(2), 141-4.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]