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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-04-22 23:28:10 UTC
HMDB IDHMDB0001084
Secondary Accession Numbers
  • HMDB0062778
  • HMDB01084
  • HMDB62778
Metabolite Identification
Common Name1-Piperideine-2-carboxylic acid
Description1-Piperideine-2-carboxylic acid (P2C), also known as Δ1-pipecolic acid, is classified as a member of the tetrahydropyridines. Tetrahydropyridines are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms. 1-Piperideine-2-carboxylic acid is considered to be slightly soluble (in water) and acidic. 1-Piperideine-2-carboxylic acid is an intermediate of the L-lysine metabolic pathway in the brain; the uptake of P2C into the synaptosome of the cerebral cortex was Na+ and temperature-dependent (PMID: 7654748 ).
Structure
Data?1582752175
Synonyms
ValueSource
1,2-Didehydropiperidine-2-carboxylateChEBI
Delta(1)-Piperidine-2-carboxylic acidChEBI
1-Piperideine-2-carboxylateKegg
1,2-Didehydropiperidine-2-carboxylic acidGenerator
delta(1)-Piperidine-2-carboxylateGenerator
Δ(1)-piperidine-2-carboxylateGenerator
Δ(1)-piperidine-2-carboxylic acidGenerator
D-1-Piperideine-2-carboxylateHMDB
delta(1)-Piperideine-2-carboxylateHMDB
Delta1-Piperideine-2-carboxylateHMDB
1-p-2-CAHMDB
delta 1-Piperideine-2-carboxylateHMDB
delta1-Piperideine-2-carboxylic acidHMDB
Δ1-piperideine-2-carboxylateHMDB
Δ1-piperideine-2-carboxylic acidHMDB
3,4,5,6-Tetrahydro-2-pyridinecarboxylateHMDB
3,4,5,6-Tetrahydro-2-pyridinecarboxylic acidHMDB
D-1-Piperideine-2-carboxylic acidHMDB
delta1-Pipecolic acidHMDB
delta1-Piperidine-2-carboxylateHMDB
delta1-Piperidine-2-carboxylic acidHMDB
Δ1-pipecolic acidHMDB
Δ1-piperidine-2-carboxylateHMDB
Δ1-piperidine-2-carboxylic acidHMDB
P2CHMDB
1-Piperideine-2-carboxylic acidGenerator
Chemical FormulaC6H9NO2
Average Molecular Weight127.1412
Monoisotopic Molecular Weight127.063328537
IUPAC Name3,4,5,6-tetrahydropyridine-2-carboxylic acid
Traditional Name1-piperideine-2-carboxylate
CAS Registry Number2756-89-0
SMILES
OC(=O)C1=NCCCC1
InChI Identifier
InChI=1S/C6H9NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H2,(H,8,9)
InChI KeyGEJXSVNGWOSZPC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tetrahydropyridines. These are derivatives of pyridine in which two double bonds in the pyridine moiety are reduced by adding four hydrogen atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydropyridines
Direct ParentTetrahydropyridines
Alternative Parents
Substituents
  • Tetrahydropyridine
  • Ketimine
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.18 g/LALOGPS
logP10(0.65) g/LALOGPS
logP10(0.97) g/LChemAxon
logS10(-1.4) g/LALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)1.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.66 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability12.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+126.54931661259
DarkChem[M+H]+126.54931661259
DarkChem[M-H]-120.93831661259
DarkChem[M-H]-120.93831661259
AllCCS[M+H]+126.34532859911
AllCCS[M-H]-124.71532859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Piperideine-2-carboxylic acid,1TMS,#1C[Si](C)(C)OC(=O)C1=NCCCC11321.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
1-Piperideine-2-carboxylic acid,1TBDMS,#1CC(C)(C)[Si](C)(C)OC(=O)C1=NCCCC11526.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Piperideine-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-faef06ea65c53c738e072017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Piperideine-2-carboxylic acid GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9200000000-e6b57b9a445998c98d4e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Piperideine-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Piperideine-2-carboxylic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 10V, Positive-QTOFsplash10-01t9-3900000000-7acf87e49673fc08eeaa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 20V, Positive-QTOFsplash10-001i-9400000000-b9fc4be5234b4880569a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 40V, Positive-QTOFsplash10-0zgl-9000000000-0cfd0825acb043e7a48b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 10V, Negative-QTOFsplash10-004i-2900000000-18bc515d926da96e59022017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 20V, Negative-QTOFsplash10-003r-7900000000-c3dfec63b6da113b8afd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 40V, Negative-QTOFsplash10-001i-9100000000-469c9a3eba0aab2bcedf2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 10V, Negative-QTOFsplash10-004i-1900000000-c001ef1bb3af1a3e99e52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 20V, Negative-QTOFsplash10-003r-9500000000-da3a51be6597bb1a56512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 40V, Negative-QTOFsplash10-001i-9000000000-a4a99a49d0d9a62928322021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 10V, Positive-QTOFsplash10-0059-6900000000-de321d632b2b23a4f2cc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 20V, Positive-QTOFsplash10-001i-9000000000-73e218e05fb16ed082542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Piperideine-2-carboxylic acid 40V, Positive-QTOFsplash10-053r-9000000000-9e9e210b523e73dbdd642021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022415
KNApSAcK IDNot Available
Chemspider ID1157
KEGG Compound IDC04092
BioCyc IDNot Available
BiGG ID35015
Wikipedia LinkNot Available
METLIN ID5992
PubChem Compound1194
PDB IDNot Available
ChEBI ID30912
Food Biomarker OntologyNot Available
VMH ID1PIPDN2C
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNoguchi, Yuichi; Kanda, Kiyoo; Hosoda, Taku; Akiyama, Katsumi. D1-Piperidine-2-carboxylic acid isolation from fermentatin broth. Jpn. Tokkyo Koho (1971), 5 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang YF, Charles AK: Uptake and metabolism of delta 1-piperidine-2-carboxylic acid by synaptosomes from rat cerebral cortex. Biochim Biophys Acta. 1995 Aug 23;1238(1):29-33. [PubMed:7654748 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Metabolizes sarcosine, L-pipecolic acid and L-proline.
Gene Name:
PIPOX
Uniprot ID:
Q9P0Z9
Molecular weight:
44065.515