AFCDB: L-Pipecolic acid (FDB000546)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:36 UTC

Update date

2019-11-26 02:54:57 UTC

Primary ID

FDB000546

Secondary Accession Numbers

FDB030970

Chemical Information

FooDB Name

L-Pipecolic acid

Description

L-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 Number

3105-95-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	158 g/L	ALOGPS
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	13.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H11NO2

IUPAC name

(2S)-piperidine-2-carboxylic acid

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 Key

HXEACLLIILLPRG-YFKPBYRVSA-N

Isomeric SMILES

OC(=O)[C@@H]1CCCCN1

Average Molecular Weight

129.157

Monoisotopic Molecular Weight

129.078978601

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

pipecolic acid (CHEBI:30913 )
Piperidine alkaloids (C00408 )

Ontology

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Liver

Subcellular:

Peroxisome

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 55.80%; H 8.58%; N 10.84%; O 24.77%	DFC
Melting Point	Mp 259-260°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -30.6 (c, 1 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Pipecolic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-c7875e682dfb275cdf1e	Spectrum
GC-MS	L-Pipecolic acid, 1 TMS, GC-MS Spectrum	splash10-001i-9100000000-07741b1b7d650447197e	Spectrum
GC-MS	L-Pipecolic acid, 2 TMS, GC-MS Spectrum	splash10-0a4i-1900000000-1b1313072749567d8a9e	Spectrum
GC-MS	L-Pipecolic acid, 1 MEOX; 2 TMS, GC-MS Spectrum	splash10-0pb9-3960000000-8e89c177d71b5faabdb2	Spectrum
GC-MS	L-Pipecolic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-0900000000-c7875e682dfb275cdf1e	Spectrum
GC-MS	L-Pipecolic acid, non-derivatized, GC-MS Spectrum	splash10-0a4i-1900000000-1b1313072749567d8a9e	Spectrum
GC-MS	L-Pipecolic acid, non-derivatized, GC-MS Spectrum	splash10-0pb9-3960000000-8e89c177d71b5faabdb2	Spectrum
GC-MS	L-Pipecolic acid, non-derivatized, GC-MS Spectrum	splash10-001i-9100000000-07741b1b7d650447197e	Spectrum
Predicted GC-MS	L-Pipecolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-9100000000-335cf7f41fca5cbc84cf	Spectrum
Predicted GC-MS	L-Pipecolic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fu-9700000000-8003521353d4d37af49f	Spectrum
Predicted GC-MS	L-Pipecolic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Pipecolic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Pipecolic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Pipecolic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-001i-8900000000-b67eb6eabd8fb1b2824a	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-001i-9000000000-b01a5574139ce1222c4d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0a4i-9000000000-d80733b289711920626b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-004i-0900000000-6d82525e15d98dd794db	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-0900000000-abb8b4f2daaa91bfa758	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-1900000000-b668d1df137fa1685b6d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9000000000-5ec763c9c55715bd01df	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0002-9000000000-5a62167bd787768808f7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-001i-0900000000-edd41fa2c224ec5f5a1e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-001i-9100000000-7ed3d7197cd0f23403b6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-001i-9000000000-e5b2220b7410a3429b95	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-001i-9000000000-baf8dab4263881ac49ea	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a59-9000000000-d1dc7829582bfd61d47b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-6d82525e15d98dd794db	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-0900000000-abb8b4f2daaa91bfa758	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-1900000000-b668d1df137fa1685b6d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-5ec763c9c55715bd01df	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-9000000000-5a62167bd787768808f7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-001i-0900000000-edd41fa2c224ec5f5a1e	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3900000000-bf71d20a7c8e71d335e5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9400000000-fa70645b026293d659de	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053u-9000000000-f849cc3c4b11bc7d4de7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-bf800b5cd197887a11d5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-7900000000-8a0e9f51df4006740863	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-effc196b5c15971f985a	2017-09-01	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

30913

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00716

CRC / DFC (Dictionary of Food Compounds) ID

BDK62-V:BDK66-Z

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34890

KNApSAcK ID

Not Available

HET ID

YCP

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Lysine Degradation	SMP00037	map00310

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

L-Pipecolic acid (FDB000546)

Structure for FDB000546 (L-Pipecolic acid)