Picolinic acid
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Basic information
- CAS
32075-31-3- Standard SMILES
O=C(O)c1ccccn1- InChIKey
SIOXPEMLGUPBBT-UHFFFAOYSA-N- Molecular formula
- C6H5NO2
- Average molar mass
- 123.11 g/mol
- Monoisotopic mass
- 123.0320284
Overview
Picolinic acid is a pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan. It has a role as a MALDI matrix material and a human metabolite. It is a conjugate acid of a picolinate.
Names & identifiers
- Preferred name
- Picolinic acid
- IUPAC
- pyridine-2-carboxylic acid
- English name
- nikogamol
- Molecular formula
- C6H5NO2
- Molecular weight
- 123.1094
Names & synonyms
picolinic acid98-98-6Pyridine-2-carboxylic acid2-Pyridinecarboxylic acid2-Carboxypyridineo-Pyridinecarboxylic acidAcide picoliquealpha-Pyridinecarboxylic acid2-pyridine carboxylic acidDTXSID7031903QZV2W997JQDTXCID5011903
Show more names
nikogamol
CHEBI:28747RefChem:863115202-719-72-Picolinic acidalpha-Picolinic acidPYRIDINECARBOXYLIC ACIDPyridine-carboxylique-2MFCD00006293
Database identifiers
- CAS
32075-31-3、88161-53-9、98-98-6- PubChem CID
- 1018
- DTXSID
DTXSID7031903- ChEMBL
CHEMBL72628- ChEBI
CHEBI:28747- UNII
- QZV2W997JQ
- EC Number
- 202-719-7
- Nikkaji
- J45.682I、J452.014I
Properties
Computed structural propertiesFilling in
- XLogP
- 0.8
- Topological polar surface area
- 50.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 114
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Pyridines
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesChemical shift
LogP
0.72
-1.0
Solubility
960 mg/mL at 20 °C
>18.5 [ug/mL] (The mean of the results at pH 7.4)
Melting Point
136.5 °C
136.5 °C
Vapor Pressure0.00789 [mmHg]
Physical Description
White or off-white crystalline powder; [MSDSonline]
Solid
Dissociation Constants0.99
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (93.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 179 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: 2-Pyridinecarboxylic acid
Status: Active Update: 03-07-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24100
2-Pyridinecarboxylic acid: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Hazards SummaryAn eye irritant; [eChemPortal: ERMA] An irritant; [MSDSonline] See Pyridine.
Hazard Classes and CategoriesAcute Tox. 4 (93.9%)
Safety & protection
Protective Action Criteria (PAC)
1.2 [mg/m3]
13 [mg/m3]
78 [mg/m3]
Chemistry & industry
Pharmacology
Pharmacodynamics
PCL-016 or Picolinic acid drug substance is a pyridine carboxylate metabolite of tryptophan. It acts as an anti-infective and immunomodulator through its role in zinc transport. ZFPs are involved in viral replication and packaging as well as normal cell homeostatic functions. Picolinic acid has been shown to be an anti-viral in vitro and in vivo.
Mechanism of ActionAs a therapeutic agent, the molecule works by binding to zinc finger proteins (ZFPs) in a way that changes their structures and disrupts zinc binding, inhibiting function.
MeSH Pharmacological Classification
Organic chemicals that form two or more coordination links with an iron ion. Once coordination has occurred, the complex formed is called a chelate. The iron-binding porphyrin group of hemoglobin is an example of a metal chelate found in biological systems.
Tissue LocationsProstate
Uses & manufacturing
Uses
Iron-chelating agent that inhibits DNA synthesis; may interfere with iron-dependent production of stable free organic radical which is essential for ribonucleotide reductase formation of deoxyribonucleotides. [ChemIDplus]
Synthetic Polymer MALDI Matrix Compounds
General Manufacturing Information2-Pyridinecarboxylic acid: ACTIVE
Additional notes
DefinitionChEBI: Picolinic acid is a pyridinemonocarboxylic acid in which the carboxy group is located at position 2. It is an intermediate in the metabolism of tryptophan. It has a role as a MALDI matrix material and a human metabolite. It is a conjugate acid of a picolinate.
Related reactions
511 records
Compound notes
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