ChemFOnt: Showing chemical card for 3-Pyridylacetic acid (CFc000001182)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:45 UTC

Chemfont ID

CFc000001182

Molecule Identification

Common Name

3-Pyridylacetic acid

Definition

3-Pyridylacetic acid is a breakdown product of nicotine (and other tobacco alkaloids) and is part of the nicotine degradation pathway. It is formed from 4-(3-pyridyl)-butanoate. One alkaloid in particular, myosmine, appears to be a major source for 3-pyridylacetic acid. The alkaloid myosmine is present not only in tobacco products but also in various foods. Myosmine is easily nitrosated, yielding 4-hydroxy-1-(3-pyridyl)-1-butanone (HPB) and the esophageal tobacco carcinogen N'-nitrosonornicotine. The two major metabolites of myosmine metabolism have been identified as 3-pyridylacetic acid (20-26%) and 4-oxo-4-(3-pyridyl)butyric acid (50-60%) (PMID:16079272 ). 3-pyridylacetatic acid is an analog of nicotinic acid. (PMID 13898750 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-Pyridylacetate	Generator
2-(3-Pyridyl)acetate	HMDB
2-(3-Pyridyl)acetic acid	HMDB
2-(Pyridin-3-yl)acetate	HMDB
2-(Pyridin-3-yl)acetic acid	HMDB
3-Carboxymethylpyridine	HMDB
a-(3-Pyridyl)acetate	HMDB
a-(3-Pyridyl)acetic acid	HMDB
alpha-(3-Pyridyl)acetate	HMDB
alpha-(3-Pyridyl)acetic acid	HMDB
Coletin	HMDB
Lessterol	HMDB
Lioxone	HMDB
Minedil	HMDB
Piridil	HMDB
Piristerol	HMDB
Pyridin-3-ylacetate	HMDB
Pyridin-3-ylacetic acid	HMDB
Toneon	HMDB
2-(3-Pyridine)acetic acid	MeSH, HMDB
3-Pyridineacetic acid	MeSH, HMDB

Chemical Formula

C₇H₇NO₂

Average Molecular Weight

137.136

Monoisotopic Molecular Weight

137.047678473

IUPAC Name

2-(pyridin-3-yl)acetic acid

Traditional Name

3-pyridylacetic acid

CAS Registry Number

501-81-5

SMILES

OC(=O)CC1=CN=CC=C1

InChI Identifier

InChI=1S/C7H7NO2/c9-7(10)4-6-2-1-3-8-5-6/h1-3,5H,4H2,(H,9,10)

InChI Key

WGNUNYPERJMVRM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridines and derivatives. Pyridines and derivatives are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Not Available

Direct Parent

Pyridines and derivatives

Alternative Parents

Substituents

Pyridine
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
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:86390 )
pyridines (CHEBI:86390 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14765546)

Source

Endogenous

Endogenous (HMDB: HMDB0001538)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	58.3 g/L	ALOGPS
logP	0.43	ALOGPS
logP	-0.59	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Acidic)	3.61	ChemAxon
pKa (Strongest Basic)	4.97	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	2	ChemAxon
Refractivity	35.21 m³·mol⁻¹	ChemAxon
Polarizability	13.18 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

External Links

HMDB ID

HMDB0001538

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022679

KNApSAcK ID

Not Available

Chemspider ID

106

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6308

PubChem Compound

108

PDB ID

Not Available

ChEBI ID

86390

Food Biomarker Ontology

Not Available

References

Synthesis Reference

aquet, Andre; Marison, Ian W.; Meyer, Hans Peter; Von Stockar, Urs. Choice of a method for in situ recovery of 3-pyridylacetic acid formed by biotransformation with Pseudomonas oleovorans. Chimia (1996), 50(9), 426-427.

Showing chemical card for 3-Pyridylacetic acid (CFc000001182)

MOL for CFc000001182 (3-Pyridylacetic acid)

3D MOL for CFc000001182 (3-Pyridylacetic acid)

3D SDF for CFc000001182 (3-Pyridylacetic acid)

3D-SDF for CFc000001182 (3-Pyridylacetic acid)

PDB for CFc000001182 (3-Pyridylacetic acid)

3D PDB for CFc000001182 (3-Pyridylacetic acid)

SMILES for CFc000001182 (3-Pyridylacetic acid)

INCHI for CFc000001182 (3-Pyridylacetic acid)

Structure for CFc000001182 (3-Pyridylacetic acid)

3D Structure for CFc000001182 (3-Pyridylacetic acid)