Livestock Metabolome Database: Showing metabocard for Pipecolic acid (LMDB00031)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:51 UTC

Update Date

2016-09-23 18:44:30 UTC

Lmdb

LMDB00031

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pipecolic acid

Description

Pipecolic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Piperidinecarboxylic acid	ChEBI
Homoproline	ChEBI
Pipecolinic acid	ChEBI
2-Piperidinecarboxylate	Generator
Pipecolinate	Generator
Pipecolate	Generator
()-Piperidine-2-carboxylic acid	HMDB
(+/-)-2-piperidinecarboxylate	HMDB
(+/-)-2-piperidinecarboxylic acid	HMDB
(+/-)-pipecolate	HMDB
(+/-)-pipecolic acid	HMDB
(+/-)-pipecolinate	HMDB
(+/-)-pipecolinic acid	HMDB
(.+/-.)-2-piperidinecarboxylic acid	HMDB
(RS)-2-Piperidinecarboxylate	HMDB
(RS)-2-Piperidinecarboxylic acid	HMDB
.alpha.-pipecolinic acid	HMDB
2-Carboxypiperidine	HMDB
2-Pipecolinic acid	HMDB
2-Piperidinylcarboxylic acid	HMDB
a-Pipecolinate	HMDB
a-Pipecolinic acid	HMDB
Acide pipecolique	HMDB
Acide piperidine-carboxylique-2	HMDB
alpha-Pipecolinate	HMDB
alpha-Pipecolinic acid	HMDB
Dihydrobaikiane	HMDB
DL-2-Piperidinecarboxylate	HMDB
DL-2-Piperidinecarboxylic acid	HMDB
DL-Homoproline	HMDB
DL-Pipecolate	HMDB, Generator
DL-Pipecolic acid	HMDB
DL-Pipecolinate	HMDB
DL-Pipecolinic acid	HMDB
hexahydro-2-Picolinate	HMDB
hexahydro-2-Picolinic acid	HMDB
Hexahydropicolinate	HMDB
Hexahydropicolinic acid	HMDB
Pipecolic acid free base	HMDB
Piperidine-2-carboxylic acid	HMDB
Piperolinate	HMDB
Piperolinic acid	HMDB
L-Pipecolic acid	MeSH, HMDB
Pipecolic acid, (R)-isomer	MeSH, HMDB
Pipecolic acid, ion (1-)	MeSH, HMDB
Pipecolic acid, monopotassium salt	MeSH, HMDB
Pipecolic acid hydrochloride, (+-)-isomer	MeSH, HMDB
Pipecolic acid, (S)-isomer	MeSH, HMDB
Pipecolic acid, 14C-labeled CPD, (+,-)-isomer	MeSH, HMDB
Homopipecolic acid	MeSH, HMDB
Pipecolic acid, (+,-)-isomer	MeSH, HMDB
Pipecolic acid, ion(1-), (+,-)-isomer	MeSH, HMDB
Pipecolic acid, ion(1-), (S)-isomer	MeSH, HMDB
Piperidine-2-carboxylate	Generator, HMDB
Pipecolic acid	MeSH

Chemical Formula

C₆H₁₁NO₂

Average Molecular Weight

129.157

Monoisotopic Molecular Weight

129.078978601

IUPAC Name

piperidine-2-carboxylic acid

Traditional Name

(+,-)-pipecolic acid

CAS Registry Number

535-75-1

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 Key

HXEACLLIILLPRG-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).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

piperidinemonocarboxylic acid (CHEBI:17964 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-2.1	ChemAxon
logS	0.09	ALOGPS
pKa (Strongest Acidic)	2.06	ChemAxon
pKa (Strongest Basic)	10.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	32.67 m³·mol⁻¹	ChemAxon
Polarizability	13.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-5c4f6059bcc868ca23fd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fu-9700000000-8003521353d4d37af49f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0060-9900000000-c5b5bf28424d5d5d1bda	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-92660ad26bff36fba7ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-9000000000-b779372fa816467754c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-26dee47121401990f1c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9000000000-929057dfd61546bee24d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-0900000000-6595801dc6a322f712f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-6595801dc6a322f712f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-0900000000-99a7a942cee58c76115a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9300000000-26dee47121401990f1c1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9000000000-929057dfd61546bee24d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-9600000000-9631d0fbc984509f8d1e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9000000000-b244255a58ffb3b92be5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-9000000000-c3041e7b5b1f5118c1ec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3900000000-b2ceb4c88f50a6524604	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9400000000-d3fab76e3fbfbe92c14d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-9000000000-20464a5c62992da01ab7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-6fac2bf48ffe4d910118	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-8900000000-81b6d69c7a568e36b49f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-6332d1986eb0da0057fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-b487cd2a72f17977a8cd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1900000000-83b59287dc6d3e726326	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0036-9200000000-3ca813e7348e686ed922	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9300000000-cb8df30f7267d610fd8d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-72c8691eb15dce6e0abb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9000000000-c7623c5058ad6c879ec3	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Milk
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	23438684	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Ovine	17249687	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24070026	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000070

FooDB ID

FDB000545

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001387

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]

Showing metabocard for Pipecolic acid (LMDB00031)

Structure for LMDB00031 (Pipecolic acid)