Record Information
Version1.0
Creation date2010-04-08 22:04:36 UTC
Update date2019-11-26 02:54:57 UTC
Primary IDFDB000546
Secondary Accession Numbers
  • FDB030970
Chemical Information
FooDB NameL-Pipecolic acid
DescriptionL-Pipecolic acid, also known as (S)-pipecolate or L-homoproline, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. L-Pipecolic acid has been detected, but not quantified in, several different foods, such as butternuts (Juglans cinerea), squashberries (Viburnum edule), annual wild rice (Zizania aquatica), rocket salads (Eruca vesicaria), and wakames (Undaria pinnatifida). This could make L-pipecolic acid a potential biomarker for the consumption of these foods. L-Pipecolic acid, with regard to humans, has been linked to several inborn metabolic disorders including peroxisomal biogenesis defect and adrenoleukodystrophy. Based on a literature review a significant number of articles have been published on L-Pipecolic acid.
CAS Number3105-95-1
Structure
Thumb
Synonyms
SynonymSource
(S)-(-)-Pipecolic acidChEBI
(S)-Pipecolic acidChEBI
(S)-Piperidine-2-carboxylic acidChEBI
2-Piperidinecarboxylic acidChEBI
L-(-)-Pipecolic acidChEBI
Pipecolic acidChEBI
Pipecolinic acidChEBI
(S)-(-)-PipecolateGenerator
(S)-PipecolateGenerator
(S)-Piperidine-2-carboxylateGenerator
2-PiperidinecarboxylateGenerator
L-(-)-PipecolateGenerator
PipecolateGenerator
PipecolinateGenerator
L-PipecolateGenerator
(-)-PipecolateHMDB
(-)-Pipecolic acidHMDB
(S)-(-)-2-PiperidinecarboxylateHMDB
(S)-(-)-2-Piperidinecarboxylic acidHMDB
(S)-2-PiperidinecarboxylateHMDB
(S)-2-Piperidinecarboxylic acidHMDB
(S)-PipecolinateHMDB
(S)-Pipecolinic acidHMDB
L-HomoprolineHMDB
L-PipecolinateHMDB
L-Pipecolinic acidHMDB
L-Piperidine-2-carboxylateHMDB
L-Piperidine-2-carboxylic acidHMDB
Pipecolic acid, (+,-)-isomerHMDB
Pipecolic acid, 14C-labeled CPD, (+,-)-isomerHMDB
Homopipecolic acidHMDB
Pipecolic acid, ion(1-), (+,-)-isomerHMDB
Pipecolic acid, ion(1-), (S)-isomerHMDB
Pipecolic acid hydrochloride, (+-)-isomerHMDB
Pipecolic acid, (S)-isomerHMDB
Pipecolic acid, (R)-isomerHMDB
Pipecolic acid, ion (1-)HMDB
Pipecolic acid, monopotassium saltHMDB
(2S)-2-Piperidinecarboxylic acidHMDB
(-)-Pipecolinic acidHMDB
(2S)-Piperidine-2-carboxylic acidHMDB
(RS)-2-Piperidinecarboxylic acidHMDB
(±)-2-piperidinecarboxylic acidHMDB
(±)-pipecolic acidHMDB
(±)-pipecolinic acidHMDB
2-CarboxypiperidineHMDB
2-Pipecolinic acidHMDB
2-Piperidinylcarboxylic acidHMDB
DL-2-Piperidinecarboxylic acidHMDB
DL-Pipecolic acidHMDB
DL-Pipecolinic acidHMDB
DihydrobaikianeHMDB
Hexahydro-2-picolinic acidHMDB
HomoprolineHMDB
Piperidine-6-carboxylic acidHMDB
Piperolinic acidHMDB
alpha-Pipecolinic acidHMDB
Α-pipecolinic acidHMDB
L-Pipecolic acidPhytoBank
(s)-(-)-pipecolatebiospider
(s)-(-)-pipecolic acidbiospider
(s)-pipecolatebiospider
(s)-pipecolic acidbiospider
(s)-pipecolinatebiospider
(s)-pipecolinic acidbiospider
2-Piperidinecarboxylic acid, 9CI; L-formdb_source
L-(-)-pipecolatebiospider
L-(-)-pipecolic acidbiospider
L-homoprolinebiospider
L-pipecolatebiospider
L-pipecolic acidbiospider
L-pipecolinatebiospider
L-pipecolinic acidbiospider
Pipecolic acid, (s)-(-)-biospider
Pipecolic acid, l-biospider
Pipecolic acid, l-(-)-biospider
Predicted Properties
PropertyValueSource
Water Solubility158 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.67 m³·mol⁻¹ChemAxon
Polarizability13.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H11NO2
IUPAC name(2S)-piperidine-2-carboxylic acid
InChI IdentifierInChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1
InChI KeyHXEACLLIILLPRG-YFKPBYRVSA-N
Isomeric SMILESOC(=O)[C@@H]1CCCCN1
Average Molecular Weight129.157
Monoisotopic Molecular Weight129.078978601
Classification
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Piperidinecarboxylic acid
  • Piperidine
  • Amino acid
  • Carboxylic acid
  • Secondary aliphatic amine
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 55.80%; H 8.58%; N 10.84%; O 24.77%DFC
Melting PointMp 259-260°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -30.6 (c, 1 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Pipecolic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-c7875e682dfb275cdf1eSpectrum
GC-MSL-Pipecolic acid, 1 TMS, GC-MS Spectrumsplash10-001i-9100000000-07741b1b7d650447197eSpectrum
GC-MSL-Pipecolic acid, 2 TMS, GC-MS Spectrumsplash10-0a4i-1900000000-1b1313072749567d8a9eSpectrum
GC-MSL-Pipecolic acid, 1 MEOX; 2 TMS, GC-MS Spectrumsplash10-0pb9-3960000000-8e89c177d71b5faabdb2Spectrum
GC-MSL-Pipecolic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-0900000000-c7875e682dfb275cdf1eSpectrum
GC-MSL-Pipecolic acid, non-derivatized, GC-MS Spectrumsplash10-0a4i-1900000000-1b1313072749567d8a9eSpectrum
GC-MSL-Pipecolic acid, non-derivatized, GC-MS Spectrumsplash10-0pb9-3960000000-8e89c177d71b5faabdb2Spectrum
GC-MSL-Pipecolic acid, non-derivatized, GC-MS Spectrumsplash10-001i-9100000000-07741b1b7d650447197eSpectrum
Predicted GC-MSL-Pipecolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9100000000-335cf7f41fca5cbc84cfSpectrum
Predicted GC-MSL-Pipecolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fu-9700000000-8003521353d4d37af49fSpectrum
Predicted GC-MSL-Pipecolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Pipecolic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Pipecolic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSL-Pipecolic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-001i-8900000000-b67eb6eabd8fb1b2824a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9000000000-b01a5574139ce1222c4d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-0a4i-9000000000-d80733b289711920626b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0900000000-6d82525e15d98dd794db2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0900000000-abb8b4f2daaa91bfa7582012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-1900000000-b668d1df137fa1685b6d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9000000000-5ec763c9c55715bd01df2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0002-9000000000-5a62167bd787768808f72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-001i-0900000000-edd41fa2c224ec5f5a1e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-001i-9100000000-7ed3d7197cd0f23403b62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-001i-9000000000-e5b2220b7410a3429b952012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-001i-9000000000-baf8dab4263881ac49ea2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0a59-9000000000-d1dc7829582bfd61d47b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-6d82525e15d98dd794db2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0900000000-abb8b4f2daaa91bfa7582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-1900000000-b668d1df137fa1685b6d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-5ec763c9c55715bd01df2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9000000000-5a62167bd787768808f72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-001i-0900000000-edd41fa2c224ec5f5a1e2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-3900000000-bf71d20a7c8e71d335e52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9400000000-fa70645b026293d659de2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053u-9000000000-f849cc3c4b11bc7d4de72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-bf800b5cd197887a11d52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-7900000000-8a0e9f51df40067408632017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9000000000-effc196b5c15971f985a2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID388365
ChEMBL IDCHEMBL322883
KEGG Compound IDC00408
Pubchem Compound ID439227
Pubchem Substance IDNot Available
ChEBI ID30913
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00716
CRC / DFC (Dictionary of Food Compounds) IDBDK62-V:BDK66-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID34890
KNApSAcK IDNot Available
HET IDYCP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Lysine DegradationSMP00037 map00310
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference