U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H9NO3.ClH
Molecular Weight 203.623
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRIDOXAL HYDROCHLORIDE

SMILES

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

InChI

InChIKey=FCHXJFJNDJXENQ-UHFFFAOYSA-N
InChI=1S/C8H9NO3.ClH/c1-5-8(12)7(4-11)6(3-10)2-9-5;/h2,4,10,12H,3H2,1H3;1H

HIDE SMILES / InChI
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

Sources: N. Y. (Geneva) Agr. Expt. Sta., Ann. Rept. (1943), No. 1, 75 pp.

Approval Year

Targets
PubMed

PubMed

TitleDatePubMed
Stereospecificity for the hydrogen transfer of pyridoxal enzyme reactions.
2001
Neuroprotective effects of pyridoxal phosphate and pyridoxal against ischemia in monkeys.
2001
Isoprenoid biosynthesis via 1-deoxy-D-xylulose 5-phosphate/2-C-methyl-D-erythritol 4-phosphate (DOXP/MEP) pathway.
2001
Biosynthesis of biotin and lipoic acid.
2001
Biosynthesis of vitamin B6 and structurally related derivatives.
2001
Effect of energy restriction and exercise on vitamin B-6 status of women during lactation.
2001 Apr
Production of pyridoxal phosphate by a mutant strain of Schizosaccharomyces pombe.
2001 Aug
Experimental model of pyridoxine (B6) deficiency-induced neuropathy.
2001 Aug
The pdx genetic marker adjacent to the chloramphenicol biosynthesis gene cluster in Streptomyces venezuelae ISP5230: functional characterization.
2001 Aug
Structure of human cystathionine beta-synthase: a unique pyridoxal 5'-phosphate-dependent heme protein.
2001 Aug 1
Pyridoxal 5'-phosphate inhibits DNA binding of HNF1.
2001 Dec 19
Electrophysiologic endpoint measures in a multicenter ALS drug trial.
2001 Feb 15
Occurrence of D-Amino Acids and a pyridoxal 5'-phosphate-dependent aspartate racemase in the acidothermophilic archaeon, Thermoplasma acidophilum.
2001 Feb 23
Purification and characterization of tyrosine decarboxylase of Lactobacillus brevis IOEB 9809 isolated from wine.
2001 Feb 5
Pyridoxal 5'-phosphate-dependent alpha,beta-elimination reactions: mechanism of O-acetylserine sulfhydrylase.
2001 Jan
Abnormal vitamin B6 metabolism in alkaline phosphatase knock-out mice causes multiple abnormalities, but not the impaired bone mineralization.
2001 Jan
Phosphorylation of 1-deoxy-D-xylulose by D-xylulokinase of Escherichia coli.
2001 Jan
Purification and some properties of alanine racemase from a bivalve mollusc Corbicula japonica.
2001 Jan 1
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
Strain is more important than electrostatic interaction in controlling the pKa of the catalytic group in aspartate aminotransferase.
2001 Jan 16
Influence of pyridoxal 5'-phosphate alone and in combination with vigabatrin on brain GABA measured by 1H-NMR-spectroscopy.
2001 Jul 1
Vitamin B1 and B6 retention in milk after continuous-flow microwave and conventional heating at high temperatures.
2001 Jun
Cassette mutagenesis of lysine 130 of human glutamate dehydrogenase. An essential residue in catalysis.
2001 Jun
Complexities of measuring antagonist potency at P2X(7) receptor orthologs.
2001 Mar
A model for enzyme-substrate interaction in alanine racemase.
2001 Mar 28
Proteinuria and plasma total homocysteine levels in chronic renal disease patients with a normal range serum creatinine: critical impact of true glomerular filtration rate.
2001 Nov
Pyridoxal 5'-phosphate and pyridoxal inhibit angiogenesis in serum-free rat aortic ring assay.
2001 Nov
Long-range interactions in the dimer interface of ornithine decarboxylase are important for enzyme function.
2001 Nov 6
Seizures induced by intracerebral administration of pyridoxal-5'-phosphate: effect of GABAergic drugs and glutamate receptor antagonists.
2001 Oct
Vitamin B6 intakes and status assessment of elderly men and women in Taiwan.
2001 Sep
Cloning and overexpression of the oah1 gene encoding O-acetyl-L-homoserine sulfhydrylase of Thermus thermophilus HB8 and characterization of the gene product.
2001 Sep 10
Enzyme catalysis of 1,2-amino shifts: the cooperative action of B6, B12, and aminomutases.
2001 Sep 12
Biocatalysis of isomerization of 1,2-benzisoxazole by bovine serum albumin in an organic solvent.
2001 Sep 20
The iron chelator pyridoxal isonicotinoyl hydrazone inhibits mitochondrial lipid peroxidation induced by Fe(II)-citrate.
2001 Sep 28
Significance of two distinct types of tryptophan synthase beta chain in Bacteria, Archaea and higher plants.
2002
Purification and biochemical characterization of some of the properties of recombinant human kynureninase.
2002 Apr
Characteristics of bovine hemoglobin as a potential source of hemoglobin-vesicles for an artificial oxygen carrier.
2002 Apr
Cold-induced enzyme inactivation: how does cooling lead to pyridoxal phosphate-aldimine bond cleavage in tryptophanase?
2002 Feb 11
Modification of an essential amino group in the mineralocorticoid receptor evidences a differential conformational change of the receptor protein upon binding of antagonists, natural agonists and the synthetic agonist 11,19-oxidoprogesterone.
2002 Feb 13
Inhibition of camel lens zeta-crystallin by aspirin and aspirin-like analgesics.
2002 Jan
Active site structure and stereospecificity of Escherichia coli pyridoxine-5'-phosphate oxidase.
2002 Jan 18
Determination of vitamin B6 vitamers and pyridoxic acid in plasma: development and evaluation of a high-performance liquid chromatographic assay.
2002 Jun 1
Crystals of tryptophan indole-lyase and tyrosine phenol-lyase form stable quinonoid complexes.
2002 Jun 14
Cysteine synthase of an extremely thermophilic bacterium, Thermus thermophilus HB8.
2002 Mar
Purification and characterization of pyridoxal 4-dehydrogenase from Aureobacterium luteolum.
2002 Mar
The Arabidopsis salt overly sensitive 4 mutants uncover a critical role for vitamin B6 in plant salt tolerance.
2002 Mar
Production of diamino propionic acid ammonia lyase by a new strain of Salmonella typhimurium PU011.
2002 Mar 15
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
Structure of external aldimine of Escherichia coli CsdB, an IscS/NifS homolog: implications for its specificity toward selenocysteine.
2002 May
Reaction mechanism of alanine racemase from Bacillus stearothermophilus: x-ray crystallographic studies of the enzyme bound with N-(5'-phosphopyridoxyl)alanine.
2002 May 24
Patents

Sample Use Guides

10 mg
Route of Administration: Oral
Name Type Language
PYRIDOXAL HYDROCHLORIDE
MI   WHO-DD  
Common Name English
NSC-19613
Code English
Pyridoxal hydrochloride [WHO-DD]
Common Name English
3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYL-4-PYRIDINECARBOXALDEHYDE HYDROCHLORIDE
Systematic Name English
PYRIDOXAL HCL
Common Name English
PYRIDOXAL HYDROCHLORIDE [MI]
Common Name English
Code System Code Type Description
PUBCHEM
6171
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-602-5
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY
WIKIPEDIA
Pyridoxal hydrochloride
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY
MERCK INDEX
m9361
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY Merck Index
FDA UNII
1416KF0QBC
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY
NSC
19613
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY
DRUG BANK
DB00147
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID0058774
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY
CAS
65-22-5
Created by admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
PRIMARY