Pyridoxal-5'-(dihydrogenphosphat)

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

Appreciable

28 mg/mL

Light yellow powder; [Acros Organics MSDS]

Solid

153.2 Ų [M+Na-2H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

150.8 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

151.4 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

165.05 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]

152.4 Ų [M+H]+

This chemical does not meet GHS hazard criteria for 66.7% (4 of 6) of all reports.

Warning

H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 6 reports by companies from 2 notifications to the ECHA C&L Inventory.

Chemical: 4-Pyridinecarboxaldehyde, 3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-

Regulation (EC) No 178/2002 (amended)

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

pyridoxal phosphate

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

The two major forms of vitamin B6 are pyridoxine and pyridoxamine. In the liver they are converted to pyridoxal phosphate (PLP) which is a cofactor in many reactions of amino acid metabolism. PLP also is necessary for the enzymatic reaction governing the release of glucose from glycogen. Pyroluria is one potential cause of vitamin B6 deficiency.

Pyridoxal Phosphate is a coenzyme of many enzymatic reactions. It is the active form of vitamin B6 which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. Pyridoxal phosphate acts as a coenzyme in all transamination reactions, and in some oxylation and deamination reactions of amino acids. The aldehyde group of pyridoxal phosphate forms a Schiff-base linkage with the epsilon-amino group of a specific lysine group of the aminotransferase enzyme. The alpha-amino group of the amino acid substrate displaces the epsilon-amino group of the active-site lysine residue. The resulting aldimine becomes deprotonated to become a quinoid intermediate, which in turn accepts a proton at a different position to become a ketimine. Ketimine becomes hydrolyzed so that the amino group remains on the protein complex.

MC-1 is a biologically active natural product which can be regarded as a chemical entity that has been evolutionarily selected and validated for binding to particular protein domains. Thus, its underlying structural architecture, or scaffold, has already been biologically established as safe and active, providing a powerful guiding principle for novel drug and library development.