Common NamePyridoxal
DescriptionPyridoxal is a pyridinecarbaldehyde that is pyridine-4-carbaldehyde bearing methyl, hydroxy and hydroxymethyl substituents at positions 2, 3 and 5 respectively. Pyridoxal, also known as pyridoxaldehyde, belongs to the class of organic compounds known as pyridoxals and derivatives. Pyridoxals and derivatives are compounds containing a pyridoxal moiety, which consists of a pyridine ring substituted at positions 2, 3, 4, and 5 by a methyl group, a hydroxyl group, a carbaldehyde group, and a hydroxymethyl group, respectively. Pyridoxal is one form of vitamin B6. Pyridoxal exists in all living species, ranging from bacteria to humans. In humans, pyridoxal is involved in glycine and serine metabolism. Pyridoxal has been detected, but not quantified in several different foods, such as sourdoughs, lichee, arctic blackberries, watercress, and cottonseeds. Some medically relevant bacteria, such as those in the genera Granulicatella and Abiotrophia, require pyridoxal for growth. This nutritional requirement can lead to the culture phenomenon of satellite growth. In in vitro culture, these pyridoxal-dependent bacteria may only grow in areas surrounding colonies of bacteria from other genera ("satellitism") that are capable of producing pyridoxal. Pridoxal has a role as a cofactor, a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite.
Structure
Molecular FormulaC8H9NO3
Average Mass167.16200
Monoisotopic Mass167.05824
IUPAC Name3-hydroxy-5-(hydroxymethyl)-2-methylpyridine-4-carbaldehyde
Traditional NamePyridoxal
CAS Registry Number66-72-8
SMILESCc1ncc(CO)c(C=O)c1O
InChI IdentifierInChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3
InChI KeyRADKZDMFGJYCBB-UHFFFAOYSA-N
CHEBI IDCHEBI:17310
HMDB IDHMDB0001545
Pathways
NameSMPDB/PathBank
Valine, leucine and isoleucine degradation
Vitamin B6 Metabolism
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency
3-Methylglutaconic Aciduria Type I
3-Methylglutaconic Aciduria Type III
3-Methylglutaconic Aciduria Type IV
Beta-Ketothiolase Deficiency
Maple Syrup Urine Disease
Methylmalonic Aciduria
Propionic Acidemia
3-Methylcrotonyl Coa Carboxylase Deficiency Type I
Isovaleric Aciduria
Methylmalonate Semialdehyde Dehydrogenase Deficiency
Hypophosphatasia
3-hydroxyisobutyric acid dehydrogenase deficiency
3-hydroxyisobutyric aciduria
Isobutyryl-coa dehydrogenase deficiency
Isovaleric acidemia
StateNot Available
Water Solubility1.17e+01 g/l
logP0.02
logS-1.16
pKa (Strongest Acidic)7.97
pKa (Strongest Basic)4.11
Hydrogen Acceptor Count4
Hydrogen Donor Count2
Polar Surface Area70.42 Ų
Rotatable Bond Count2
Physiological Charge0
Formal Charge0
Refractivity43.87 m³·mol⁻¹
Polarizability16.26

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