Showing Compound Picolinic acid (FDB022926)

Record Information

Version

1.0

Creation date

2011-09-21 00:21:48 UTC

Update date

2015-10-09 22:33:15 UTC

Primary ID

FDB022926

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Picolinic acid

Description

Picolinic acid is a metabolite of the tryptophan catabolism. Picolinic acid is produced under inflammatory conditions and a costimulus with interferon-gamma (IFNgamma) of macrophage (Mphi) effector functions, is a selective inducer of the Mphi inflammatory protein-1alpha (MIP-1alpha) and -1beta (MIPs), two chemokines/cytokines involved in the elicitation of the inflammatory reactions and in the development of the Th1 responses. IFNgamma and picolinic acid have reciprocal effects on the production of MIPs chemokines and the expression of their receptor. The concerted action of IFNgamma and picolinic acid on MIP-1alpha/beta chemokine/receptor system is likely to be of pathophysiological significance and to represent an important regulatory mechanism for leukocyte recruitment and distribution into damaged tissues during inflammatory responses. Picolinic acid has an effect on the production of L-arginine-derived reactive nitrogen intermediates in macrophages, by augmenting IFN-gamma-induced NO2- production, and acts synergistically with IFN-gamma in activating macrophages. Children with acrodermatitis enteropathica (AE) are treated with oral zinc dipicolinate (zinc-PA). The concentration of picolinic acid in the plasma of asymptomatic children with AE was significantly less than that of normal children. However, oral treatment with PA alone is ineffective. The results support the hypothesis that the genetic defect in AE is in the tryptophan pathway, although the role of PA in zinc metabolism remains to be defined. (PMID: 15206716, 8473748, 1701787, 6694049) [HMDB]

CAS Number

98-98-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Carboxypyridine	ChEBI
2-Picolinic acid	ChEBI
2-Pyridinecarboxylic acid	ChEBI
alpha-Picolinic acid	ChEBI
alpha-Pyridinecarboxylic acid	ChEBI
O-Pyridinecarboxylic acid	ChEBI
PYRIDINE-2-carboxylIC ACID	ChEBI
2-Picolinate	Generator
2-Pyridinecarboxylate	Generator
a-Picolinate	Generator
a-Picolinic acid	Generator
alpha-Picolinate	Generator
Α-picolinate	Generator
Α-picolinic acid	Generator
a-Pyridinecarboxylate	Generator
a-Pyridinecarboxylic acid	Generator
alpha-Pyridinecarboxylate	Generator
Α-pyridinecarboxylate	Generator
Α-pyridinecarboxylic acid	Generator
O-Pyridinecarboxylate	Generator
PYRIDINE-2-carboxylate	Generator
Picolinate	Generator
2-Methoxy-5-aminopyridine	HMDB
4,5-Dehydropipecolic acid	HMDB
5-amino-2-Fluoropyridine	HMDB
5-amino-2-Methoxypyridine	HMDB
5-amino-2-Pyridinecarboxylic acid	HMDB
5-Aminopicolinic acid	HMDB
5-Aminopyridine-2-carboxylic acid	HMDB
6-Methoxy-pyridin-3-ylamine	HMDB
Acide picolique	HMDB
L-Baikiain	HMDB
Phenyl-(2-pyridyl)acetonitrile	HMDB
PLA	HMDB
Pyridine-carboxylique-2	HMDB
Pyridinecarboxylic acid-(2)	HMDB
Iron(III) picolinate	MeSH, HMDB
Zinc picolinate	MeSH, HMDB
Picolinic acid, sodium salt	MeSH, HMDB
2-Pyridine carboxylic acid	MeSH, HMDB
Calcium dipicolinate trihydrate	MeSH, HMDB
Picolinic acid, hydrochloride	MeSH, HMDB
Chromium picolinate	MeSH, HMDB
2-methoxy-5-aminopyridine	hmdb
5-Amino-2-fluoropyridine	hmdb
5-Amino-2-methoxypyridine	hmdb
acide picolique	hmdb
o-Pyridinecarboxylic acid	hmdb
Pyridine-2-carboxylic acid	hmdb
α-picolinate	Generator
α-picolinic acid	Generator
α-pyridinecarboxylate	Generator
α-pyridinecarboxylic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	61.1 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-0.65	ChemAxon
logS	-0.3	ALOGPS
pKa (Strongest Acidic)	1	ChemAxon
pKa (Strongest Basic)	5.52	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.19 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	30.79 m³·mol⁻¹	ChemAxon
Polarizability	11.38 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

C6H5NO2

IUPAC name

pyridine-2-carboxylic acid

InChI Identifier

InChI=1S/C6H5NO2/c8-6(9)5-3-1-2-4-7-5/h1-4H,(H,8,9)

InChI Key

SIOXPEMLGUPBBT-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C1=CC=CC=N1

Average Molecular Weight

123.1094

Monoisotopic Molecular Weight

123.032028409

Classification

Description

Belongs to the class of organic compounds known as pyridinecarboxylic acids. Pyridinecarboxylic acids are compounds containing a pyridine ring bearing a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Pyridinecarboxylic acids and derivatives

Direct Parent

Pyridinecarboxylic acids

Alternative Parents

Substituents

Pyridine carboxylic acid
Heteroaromatic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyridinemonocarboxylic acid (CHEBI:28747 )
Piperidine alkaloids (C10164 )

Ontology

Disposition

Source:

Endogenous

Biological location:

Biofluid and excreta:

Organ and components:

Prostate

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
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	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Picolinic acid, non-derivatized, GC-MS Spectrum	splash10-001r-0900000000-3d42fed18a7170ac902c	Spectrum
GC-MS	Picolinic acid, 1 TMS, GC-MS Spectrum	splash10-005i-4900000000-ceebd42c8dcc23fdf3e4	Spectrum
GC-MS	Picolinic acid, non-derivatized, GC-MS Spectrum	splash10-0fb9-9000000000-bab2bcb7bd27b0be1f51	Spectrum
GC-MS	Picolinic acid, non-derivatized, GC-MS Spectrum	splash10-001r-0900000000-3d42fed18a7170ac902c	Spectrum
GC-MS	Picolinic acid, non-derivatized, GC-MS Spectrum	splash10-005i-4900000000-ceebd42c8dcc23fdf3e4	Spectrum
GC-MS	Picolinic acid, non-derivatized, GC-MS Spectrum	splash10-001r-0900000000-7276adde2578b546a8f2	Spectrum
Predicted GC-MS	Picolinic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05i0-9400000000-7356d3453f3427cc9d89	Spectrum
Predicted GC-MS	Picolinic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05fr-9500000000-5d9f84aec4ab264b04db	Spectrum
Predicted GC-MS	Picolinic acid, non-derivatized, 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, Positive (Annotated)	splash10-0adi-3900000000-7fac959b15471dc94406	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-004i-9000000000-0e912cf3a3db8f8ee5df	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0fb9-9000000000-6d29f5dc4ddc1bb1adb5	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (MX-1303) , Positive	splash10-0fb9-9000000000-bab2bcb7bd27b0be1f51	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-05fr-0900000000-e169ce1e815eac2ad211	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-056s-9500000000-cd5fe946f692da4957ca	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-004i-9000000000-927c599edd5deaf854f0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-004i-9000000000-1d63eb2db32cd991a084	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9000000000-219a58c586353210f1a3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-00di-0900000000-fe37c7a3e725d6a622fd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-05fs-4900000000-b85a7afe0ba03853cfbf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-05fr-0900000000-59ec49f98e7a39b33252	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-056s-9500000000-cd5fe946f692da4957ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-927c599edd5deaf854f0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-1d63eb2db32cd991a084	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-004i-9000000000-219a58c586353210f1a3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-3900000000-9fd4a6ac15261e2c8d8e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-02t9-9600000000-bc378bb03dd26ace9a39	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-fe37c7a3e725d6a622fd	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-b09ed1d66b009b4624ee	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-a4d3409ab064e87942a9	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-ddbf2ed02e3b712aca5d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-2900000000-7de5e81309a53ea848ef	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00fr-8900000000-0143384039159388b6eb	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-85d472523e404d49ec06	2015-04-25	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