Milk Composition Database: Showing metabocard for Pipecolic acid (BMDB0000070)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:19:15 UTC

Update Date

2020-05-11 20:46:18 UTC

MCDB ID

BMDB0000070

Secondary Accession Numbers

BMDB00070

Metabolite Identification

Common Name

Pipecolic acid

Description

DL-Pipecolic acid, also known as pipecolinate or homoproline, 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). DL-Pipecolic acid exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. DL-Pipecolic acid exists in all living species, ranging from bacteria to humans. DL-Pipecolic acid has been found to be associated with several diseases known as malaria, schizophrenia, rhizomelic chondrodysplasia punctata, and perillyl alcohol administration for cancer treatment; also dl-pipecolic acid has been linked to the inborn metabolic disorders including adrenoleukodystrophy.

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	264 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	314 mg/mL	Not Available
LogP	-2.31	TSAI,RS ET AL. (1991)

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0a4i-0910000000-d9cfd443adb5187a3f21	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9200000000-5c4f6059bcc868ca23fd	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05fu-9700000000-8003521353d4d37af49f	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0060-9900000000-c5b5bf28424d5d5d1bda	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-001i-9000000000-92660ad26bff36fba7ef	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0a59-9000000000-b779372fa816467754c1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-001i-9300000000-26dee47121401990f1c1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-001i-9000000000-929057dfd61546bee24d	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-0900000000-6595801dc6a322f712f0	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-6595801dc6a322f712f0	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-0900000000-99a7a942cee58c76115a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9300000000-26dee47121401990f1c1	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-9000000000-929057dfd61546bee24d	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-9600000000-9631d0fbc984509f8d1e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-9000000000-b244255a58ffb3b92be5	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-001i-9000000000-c3041e7b5b1f5118c1ec	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-3900000000-b2ceb4c88f50a6524604	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9400000000-d3fab76e3fbfbe92c14d	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5c-9000000000-20464a5c62992da01ab7	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-6fac2bf48ffe4d910118	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-8900000000-81b6d69c7a568e36b49f	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-6332d1986eb0da0057fd	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-b487cd2a72f17977a8cd	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1900000000-83b59287dc6d3e726326	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0036-9200000000-3ca813e7348e686ed922	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-9300000000-cb8df30f7267d610fd8d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9000000000-72c8691eb15dce6e0abb	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-053r-9000000000-c7623c5058ad6c879ec3	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-16	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected but not Quantified	Not Applicable		PMID: 23438684	details
Detected but not Quantified	Not Applicable		PMID: 28306241	details

External Links

HMDB ID

HMDB0000070

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pipecolic_acid

METLIN ID

PubChem Compound

849

PDB ID

Not Available

ChEBI ID

17964

References

Synthesis Reference

Asher, Vikram; Becu, Christian; Anteunis, Marc J. O.; Callens, Roland. New synthesis of pipecolic acid and analogs. Tetrahedron Letters (1981), 22(2), 141-4.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
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 ]

Showing metabocard for Pipecolic acid (BMDB0000070)

Structure for BMDB0000070 (Pipecolic acid)