Showing metabocard for L-Pipecolic acid (BMDB0000716)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:35:24 UTC
Update Date2020-05-11 20:21:26 UTC
BMDB IDBMDB0000716
Secondary Accession Numbers
  • BMDB00716
Metabolite Identification
Common 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Pipecolic acid has been linked to several inborn metabolic disorders including peroxisomal biogenesis defect and adrenoleukodystrophy.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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
Chemical FormulaC6H11NO2
Average Molecular Weight129.157
Monoisotopic Molecular Weight129.078978601
IUPAC Name(2S)-piperidine-2-carboxylic acid
Traditional NameL-pipecolic acid
CAS Registry Number3105-95-1
SMILES
OC(=O)[C@@H]1CCCCN1
InChI Identifier
InChI=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
Chemical Taxonomy
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
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Peroxisome
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point272 °CNot 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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.67 m³·mol⁻¹ChemAxon
Polarizability13.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Peroxisome
Biospecimen Locations
  • Liver
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000716
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000546
KNApSAcK IDC00001387
Chemspider ID388365
KEGG Compound IDC00408
BioCyc IDL-PIPECOLATE
BiGG ID34890
Wikipedia LinkPipecolic acid
METLIN ID5684
PubChem Compound439227
PDB IDNot Available
ChEBI ID30913
References
Synthesis ReferenceKisfaludy, Lajos; Korenczki, Ferenc; Katho, Agnes. Works, Gedeon Richter Ltd., Budapest, Hung. One-step synthesis of L-piperidine-2-carboxylic acid. Synthesis (1982), (2), 163.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details
1. Peroxisomal sarcosine oxidase
General function:
Amino acid transport and metabolism
Specific function:
Metabolizes sarcosine, L-pipecolic acid and L-proline.
Gene Name:
PIPOX
Uniprot ID:
Q29RU9
Molecular weight:
43820.0