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Pyridoxal 5′-phosphate

Pyridoxal 5′-phosphate structure

CAS No:
54-47-7
Formula:
C8H10NO6P
Chemical Name:
Pyridoxal 5′-phosphate
Synonyms:
4-Pyridinecarboxaldehyde,3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-;Pyridoxal,5-(dihydrogen phosphate);Pyridoxal phosphate;3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde;Codecarboxylase;2-Methyl-3-hydroxy-4-formyl-5-pyridylmethylphosphoric acid;Phosphopyridoxal;Phosphopyridoxal coenzyme;PLP;Pyridoxal 5-phosphate;Pyridoxal 5′-phosphate;Vitamin B6 phosphate (ester);Pyridoxaldehyde phosphate;Pyridoxal P;PAL-P;Pyridoxal monophosphate;Pyridoxal 5-monophosphoric acid ester;3-Hydroxy-5-(hydroxymethyl)-2-methylisonicotinaldehyde 5-phosphate;Pyromijin;Sechvitan;Vitazechs;Pyridoxyl phosphate;Apolon B6;Hairoxal;Hiadelon;Biosechs;Hi-Pyridoxin;Vitahexin P;Piodel;Pydoxal;Hexermin P;Coenzyme B6;Vitamin B6 phosphate;NSC 82388;[(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid;(4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate;52064-48-9;52441-27-7;1071665-72-9
Categories:
Cosmetic Ingredient > Skin Conditioning

Description

Pyridoxal phosphate is the active form of vitamin B6, acts as an inhibitor of reverse transcriptases, and is used for the treatment of tardive dyskinesia.

Solid

Pyridoxal 5'-phosphate is the monophosphate ester obtained by condensation of phosphoric acid with the primary hydroxy group of pyridoxal. It has a role as a coenzyme, a human metabolite, an Escherichia coli metabolite, a Saccharomyces cerevisiae metabolite, a mouse metabolite, an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor and a cofactor. It is a vitamin B6 phosphate, a member of methylpyridines, a monohydroxypyridine and a pyridinecarbaldehyde. It derives from a pyridoxal. It is a conjugate acid of a pyridoxal 5'-phosphate(2-).|This is the active form of vitamin B6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (pyridoxamine).|This is the active form of VITAMIN B 6 serving as a coenzyme for synthesis of amino acids, neurotransmitters (serotonin, norepinephrine), sphingolipids, aminolevulinic acid. During transamination of amino acids, pyridoxal phosphate is transiently converted into pyridoxamine phosphate (PYRIDOXAMINE).

Pyridoxal 5′-phosphate Basic Attributes

Molecular Weight：

247.14

Exact Mass：

247.14

EC Number：

200-208-3

UNII：

F06SGE49M6

NSC Number：

82388

DSSTox ID：

DTXSID4048351

ATC Code：

A - Alimentary tract and metabolism

HScode：

2933399090

Characteristics

PSA：

117

XLogP3：

-1.1

Appearance：

powder

Density：

1.6±0.1 g/cm3

Melting Point：

255 °C

Boiling Point：

565.7°C at 760 mmHg

Flash Point：

296.0±32.9 °C

Refractive Index：

1.641

Water Solubility：

H2O: 28 mg/mL

Storage Conditions：

−20°C

Collision Cross Section：

151.4 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|146.34 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]|154.76 Å² [M+H]+ [CCS Type: DT, Method: stepped-field]|165.05 Å² [M+Na]+ [CCS Type: DT, Method: stepped-field]|150.54 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|151.3 Å² [M+H]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|160.8 Å² [M+Na]+ [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|149.4 Å² [M-H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|153.2 Å² [M+Na-2H]- [CCS Type: DT, Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]|150.8 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|151.94 Å² [M+H]+ [CCS Type: DT, Method: stepped-field]|161.4 Å² [M+Na]+ [CCS Type: DT, Method: stepped-field]|153.2 Å² [M-2H+Na]-

Safety Information

wgk germany：

safety instructions：

22-24/25

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Drug Information

Drug Indication：

For nutritional supplementation and for treating dietary shortage or imbalance.

Pharmacology：

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.

MeSH：

A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

Mechanism of Action：

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.

MeSH Entry Terms：

Phosphate, Pyridoxal

Pyridoxal 5′-phosphate Use and Manufacturing

Methods of Manufacturing

Pyridoxamine dihydrochloride reacts with anhydrous phosphoric acid to form pyridoxamine phosphate, which is then oxidized by manganese dioxide.

Uses

Vitamin (enzyme co-factor).

Manufacturing Info：

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

Use Classification：

Human drugs -> Rare disease (orphan)|Cosmetics -> Skin conditioning

Computed Properties

Molecular Weight:247.14
XLogP3:-1.1
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:4
Exact Mass:247.02457404
Monoisotopic Mass:247.02457404
Topological Polar Surface Area:117
Heavy Atom Count:16
Complexity:292
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Manganese oxide (MnO2)

Pyridoxine

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Guide of Pyridoxal 5′-phosphate

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Material
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