CHEBI:64342 - 3-hydroxypicolinic acid

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ChEBI Name 3-hydroxypicolinic acid
ChEBI ID CHEBI:64342
Definition A monohydroxypyridine that is picolinic acid in which the hydrogen at position 3 is replaced by a hydroxy group. It is used as a matrix in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry for the analysis of oligonucleotides.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Gerhard Mayer
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Formula C6H5NO3
Net Charge 0
Average Mass 139.10880
Monoisotopic Mass 139.02694
InChI InChI=1S/C6H5NO3/c8-4-2-1-3-7-5(4)6(9)10/h1-3,8H,(H,9,10)
InChIKey BRARRAHGNDUELT-UHFFFAOYSA-N
SMILES OC(=O)c1ncccc1O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Application(s): MALDI matrix material
A compound used to form the matrix for MALDI (matrix-assisted laser desorption/ionization) mass spectrometry. MALDI matrix materials are crystalline compounds with a fairly low molecular weight, so as to allow facile vaporization, have strong absorption at UV or IR wavelengths (to rapidly and efficiently absorb laser irradiation), generally contain polar groups (enabling them to be used in aqueous solutions) and are frequently acidic (so assisting ionisation of the compound being studied, which is contained within the matrix material).
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ChEBI Ontology
Outgoing 3-hydroxypicolinic acid (CHEBI:64342) has role MALDI matrix material (CHEBI:64345)
3-hydroxypicolinic acid (CHEBI:64342) is a monocarboxylic acid (CHEBI:25384)
3-hydroxypicolinic acid (CHEBI:64342) is a monohydroxypyridine (CHEBI:38182)
IUPAC Name
3-hydroxypyridine-2-carboxylic acid
Synonyms Sources
3-hydroxy-2-pyridinecarboxylic acid ChEBI
HPA ChEBI
Manual Xrefs Databases
3-Hydroxypicolinic_acid Wikipedia
C18620 KEGG COMPOUND
HMDB0013188 HMDB
MHW PDBeChem
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Registry Numbers Types Sources
118954 Reaxys Registry Number Reaxys
874-24-8 CAS Registry Number NIST Chemistry WebBook
874-24-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
5902481 PubMed citation Europe PMC
8457722 PubMed citation Europe PMC
Last Modified
23 October 2015
General Comment
2012-04-03 MALDI matrix solution [PubChem_Compound:13401]