PYRIDOXAL

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H9NO3
Molecular Weight	167.162
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC=C(CO)C(C=O)=C1O

InChI

InChIKey=RADKZDMFGJYCBB-UHFFFAOYSA-N

InChI=1S/C8H9NO3/c1-5-8(12)7(4-11)6(3-10)2-9-5/h2,4,10,12H,3H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25052410 | https://www.ncbi.nlm.nih.gov/pubmed/20532028 | https://www.ncbi.nlm.nih.gov/pubmed/12213051 | https://www.ncbi.nlm.nih.gov/pubmed/23510563

Pyridoxal is a pyridinecarbaldehyde and a form of vitamin B 6 which is converted to pyridoxal phosphate. Pyridoxal 5'-phosphate is involved in a wide range of biochemical reactions, including the metabolism of amino acids and glycogen, the synthesis of nucleic acids, hemoglobin, sphingomyelin, and other sphingolipids, and the synthesis of the neurotransmitters serotonin, dopamine, norepinephrine and gamma-aminobutyric acid (GABA). Pyridoxal is one of the natural forms available of vitamin B6, therefore, it is used for nutritional supplementation and for treating dietary shortage or imbalances. 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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
cytokine secretion involved in immune response 5 Target ID: GO:0002374 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27085010	Modulator 828
Steroid 5-alpha-reductase 15 Target ID: CHEMBL2096664 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1421208	Inhibitor 8297
Aldehyde oxidase 7 Target ID: CHEMBL3257 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7365745	Inhibitor 8297	30.0 µM [Ki]

PubMed

Title	Date	PubMed
[Depression of serum pyridoxal levels in theophylline-related seizures].	2000 Jul	10916367
Molecular heterogeneity of O-acetylserine sulfhydrylase by two-photon excited fluorescence fluctuation spectroscopy.	2001 Apr	11259310
Pyridoxal 5'-phosphate inhibits DNA binding of HNF1.	2001 Dec 19	11786225
Computational studies on nonenzymatic and enzymatic pyridoxal phosphate catalyzed decarboxylations of 2-aminoisobutyrate.	2001 Feb 6	11170465
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.	2001 Jan	11168365
Identification of lysine 346 as a functionally important residue for pyridoxal 5'-phosphate binding and catalysis in lysine 2, 3-aminomutase from Bacillus subtilis.	2001 Jan 16	11148055
Strain is more important than electrostatic interaction in controlling the pKa of the catalytic group in aspartate aminotransferase.	2001 Jan 16	11148029
Effect of feeding on circulating micronutrient concentrations in the Burmese python (Python molurus).	2001 Jun	11423336
Cassette mutagenesis of lysine 130 of human glutamate dehydrogenase. An essential residue in catalysis.	2001 Jun	11389722
Circular permutation of 5-aminolevulinate synthase. Mapping the polypeptide chain to its function.	2001 Jun 1	11279050
Low circulating vitamin B(6) is associated with elevation of the inflammation marker C-reactive protein independently of plasma homocysteine levels.	2001 Jun 12	11401933
Pyridoxal 5'-phosphate and pyridoxal inhibit angiogenesis in serum-free rat aortic ring assay.	2001 Nov	11605018
Distribution of B6 vitamers in Escherichia coli as determined by enzymatic assay.	2001 Nov 15	11700988
Long-range interactions in the dimer interface of ornithine decarboxylase are important for enzyme function.	2001 Nov 6	11683631
COMT genotype, micronutrients in the folate metabolic pathway and breast cancer risk.	2001 Oct	11577006
Glycogen and glycogen phosphorylase associated with sarcoplasmic reticulum: effects of fatiguing activity.	2001 Oct	11568145
The iron chelator pyridoxal isonicotinoyl hydrazone inhibits mitochondrial lipid peroxidation induced by Fe(II)-citrate.	2001 Sep 28	11779035
Significance of two distinct types of tryptophan synthase beta chain in Bacteria, Archaea and higher plants.	2002	11806827
Purification and biochemical characterization of some of the properties of recombinant human kynureninase.	2002 Apr	11985583
Study of substrate-enzyme interaction between immobilized pyridoxamine and recombinant porcine pyridoxal kinase using surface plasmon resonance biosensor.	2002 Apr 1	11983425
Structure and function of threonine synthase from yeast.	2002 Apr 5	11756443
Determination of vitamin B6 vitamers and pyridoxic acid in plasma: development and evaluation of a high-performance liquid chromatographic assay.	2002 Jun 1	12018948
Methanococcus jannaschii uses a pyruvoyl-dependent arginine decarboxylase in polyamine biosynthesis.	2002 Jun 28	11980912
Cysteine synthase of an extremely thermophilic bacterium, Thermus thermophilus HB8.	2002 Mar	12005048
Crystal structure of the beta Ser178--> Pro mutant of tryptophan synthase. A "knock-out" allosteric enzyme.	2002 Mar 22	11756454
Reactive intermediate formation from the 2-(Fluoromethoxy)-1,1,3,3,3-pentafluoro-1-propene (compound A)-derived cysteine S-conjugate S-[2-(Fluoromethoxy)-1,1,3,3,3-pentafluoropropyl]-L-cysteine in pyridoxal model systems.	2002 May	12018982
Structure of external aldimine of Escherichia coli CsdB, an IscS/NifS homolog: implications for its specificity toward selenocysteine.	2002 May	11983074

Patents

Sample Use Guides

In Vivo Use Guide

10 mg

Route of Administration: Oral

Name

Type

Language

PYRIDOXAL

Common Name

English

PYRIDOXALDEHYDE

Common Name

English

3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYLPYRIDINE-4-CARBOXALDEHYDE

Systematic Name

English

4-PYRIDINECARBOXALDEHYDE, 3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYL-

Systematic Name

English

6-methyl-1,3-Dihydro-furo[3,4-c]pyridine-1,7-diol

Systematic Name

English

3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYL-4-PYRIDINECARBOXALDEHYDE

Systematic Name

English

3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYLISONICOTINALDEHYDE

Systematic Name

English

2-METHYL-3-HYDROXY-4-FORMYL-5-HYDROXYMETHYLPYRIDINE

Systematic Name

English

PIRIDOXAL

Common Name

English

Pyridoxal [WHO-DD]

Common Name

English

PYRIDOXAL [MI]

Common Name

English

1,3-Dihydro-6-methylfuro[3,4-c]pyridine-1,7-diol

Systematic Name

English

Classification Tree Code System Code

LOINC

75041-4