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Record Information
Version1.0
Creation Date2016-07-13 19:40:51 UTC
Update Date2016-09-23 18:44:30 UTC
LmdbLMDB00031
Secondary Accession NumbersNone
Metabolite Identification
Common NamePipecolic acid
DescriptionPipecolic acid is a metabolite of lysine found in animal 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 ).
Structure
Thumb
Synonyms
ValueSource
2-Piperidinecarboxylic acidChEBI
HomoprolineChEBI
Pipecolinic acidChEBI
2-PiperidinecarboxylateGenerator
PipecolateGenerator
PipecolinateGenerator
()-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
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
Pipecolic acid, (R)-isomerMeSH
Pipecolic acid, ion (1-)MeSH
Pipecolic acid, monopotassium saltMeSH
Pipecolic acid hydrochloride, (+-)-isomerMeSH
Pipecolic acid, (S)-isomerMeSH
Pipecolic acid, 14C-labeled CPD, (+,-)-isomerMeSH
Homopipecolic acidMeSH
Pipecolic acid, (+,-)-isomerMeSH
Pipecolic acid, ion(1-), (+,-)-isomerMeSH
Pipecolic acid, ion(1-), (S)-isomerMeSH
Chemical FormulaC6H11NO2
Average Molecular Weight129.157
Monoisotopic Molecular Weight129.078978601
IUPAC Namepiperidine-2-carboxylic acid
Traditional Name(+,-)-pipecolic acid
CAS Registry Number535-75-1
SMILES
OC(=O)C1CCCCN1
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
DescriptionThis compound belongs to the class of chemical entities 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).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.2ALOGPS
logP-2.1ChemAxon
logS0.09ALOGPS
pKa (Strongest Acidic)2.06ChemAxon
pKa (Strongest Basic)10.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.67 m3·mol-1ChemAxon
Polarizability13.47 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0a4i-0910000000-d9cfd443adb5187a3f21View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0060-9900000000-c5b5bf28424d5d5d1bdaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-92660ad26bff36fba7efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0a59-9000000000-b779372fa816467754c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-001i-9300000000-26dee47121401990f1c1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positivesplash10-001i-9000000000-929057dfd61546bee24dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-0900000000-6595801dc6a322f712f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0900000000-99a7a942cee58c76115aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-9600000000-9631d0fbc984509f8d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-b2ceb4c88f50a6524604View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9400000000-d3fab76e3fbfbe92c14dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a5c-9000000000-20464a5c62992da01ab7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-6fac2bf48ffe4d910118View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-8900000000-81b6d69c7a568e36b49fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-6332d1986eb0da0057fdView in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Milk
  • Plasma
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB00070
FooDB IDFDB000545
Phenol Explorer IDNot Available
KNApSAcK IDC00001387
BiGG IDNot Available
BioCyc ID5-HYDROXY-PIPECOLATE
METLIN ID50
PDB IDNot Available
Wikipedia LinkPipecolic_acid
Chemspider ID826
ChEBI ID17964
PubChem Compound ID849
Kegg Compound IDC00408
YMDB IDNot Available
ECMDB IDECMDB21385
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Baas JC, van de Laar R, Dorland L, Duran M, Berger R, Poll-The BT, de Koning TJ: Plasma pipecolic acid is frequently elevated in non-peroxisomal disease. J Inherit Metab Dis. 2002 Dec;25(8):699-701. [12705501 ]