[(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid

• ChemBase ID: 1
• Molecular Formular: C8H10NO6P
• Molecular Mass: 247.141861
• Monoisotopic Mass: 247.02457368
• SMILES: P(=O)(OCc1c(c(O)c(nc1)C)C=O)(O)O
• Canonical SMILES: O=Cc1c(COP(=O)(O)O)cnc(c1O)C
• InChI: InChI=1S/C8H10NO6P/c1-5-8(11)7(3-10)6(2-9-5)4-15-16(12,13)14/h2-3,11H,4H2,1H3,(H2,12,13,14)
• InChIKey: NGVDGCNFYWLIFO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
• IUPAC Traditional name: pyridoxal phosphate
• Brand Name: Hairoxal; Hiadelon; Himitan; Vitazechs; Biosechs; Pidopidon
• Synonyms: 3-Hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinecarboxaldehyde; Pyridoxal Phosphate; Pyridoxal 5-(Dihydrogen Phosphate); 2-Methyl-3-hydroxy-4-formyl-5-pyridyl-methylphosphoric Acid; 3-Hydroxy-5-(hydroxymethyl)-2-methyl-isonicotinaldehyde 5-Phosphate; Apolon B6; Biosechs; Coenzyme B6; Hairoxal; Hexermin P; Hi-Pyridoxin; Hiadelon; NSC 82388; Phosphopyridoxal; Piodel; Pydoxal; Pyridoxal Monophosphate; Vitazechs; Pyridoxal 5'-Phosphate; PLP; Pyridoxal 5'-phosphate; Pyridoxal 5-phosphate; Pyridoxal-P; Pyridoxal P; Vitamin B6; Pyridoxal-5P; Codecarboxylase; Pyromijin; Pyridoxal Phosphate; 3-Hydroxy-2-methyl-5-([phosphonooxy]methyl)-4-pyridinecarboxaldehyde; PYRIDOXAL-5-PHOSPHATE MONOHYDRATE; Pyrido; PYRIDOXAL-5-PHOSPHATE; Pyridoxal 5′-phosphate hydrate; (4-Formyl-5-hydroxy-6-methylpyridin-3-yl)methyl dihydrogen phosphate

Database IDs

• CAS Number: 41468-25-1; 853645-22-4; 54-47-7
• EC Number: 200-208-3
• MDL Number: MFCD00006333
• Beilstein Number: 234749
• PubChem SID: 160963464; 46506428; 24898438; 24899020
• PubChem CID: 1051

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.6802986
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.3409967
• LogD (pH = 7.4): -3.1810691
• Log P: -2.0856087
• Molar Refractivity: 54.7463 cm^3
• Polarizability: 20.725895 Å^3
• Polar Surface Area: 116.95 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.55
• LOG S: -1.64
• Solubility (Water): 5.70e+00 g/l

PROPERTIES

Physical Property

• Solubility: Appreciable
• Apperance: powder
• Melting Point: 140-143 °C; 140-143°C
• Hydrophobicity(logP): -1.2

Safety Information

• Storage Condition: 0°C
• RTECS: UV1208000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~98%; ≥98%; 95+%
• Suitability: suitable for cell culture

DETAILS

MP Biomedicals - 02102769

Monohydrate
Purity: ~98%
Off-white crystals Useful for modifying lysyl and valyl residues in proteins.

MP Biomedicals - 02194731

Cell Culture Reagent
Monohydrate
Purity: ~98%

DrugBank - DB00114

• Drug Groups: nutraceutical
• Description: 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). [PubChem]
• 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.
• Affected Organisms: Humans and other mammals
• External Links: Wikipedia; PDRhealth

Sigma Aldrich - P3657

General description
Pyridoxal-phosphate (PLP, pyridoxal-5′-phosphate, P5P) is a prosthetic group of some enzymes. It is the active form of vitamin B6, which comprises three natural organic compounds, pyridoxal, pyridoxamine and pyridoxine. PLP acts as a coenzyme in all transamination reactions, and in some decarboxylation and deamination reactions of amino acids.

Sigma Aldrich - P9255

Application
Enzyme cofactor.Normal coenzyme form of Vitamin B6
包装
1, 5, 25 g in poly bottle
Biochem/physiol Actions
Pyridoxal 5′-phosphate (PLP) is used as a cofactor for a wide range of enzymes including mitochondrial cysteine desulfurase, cystathionine γ-synthase (CGS), ornithine 4,5-aminomutase (OAM), and d-serine dehydratase. PLP is used in the studies of PLP-dependent enzyme active sites.

Toronto Research Chemicals - P991715

Vitamin (enzyme co-factor).

REFERENCES

• Lichstein, et al.: J. Biol. Chem., 161, 311 (1945)
• McPhalen, C., et al.: J. Mol. Biol., 225, 495 (1945)
• Fenn, T., et al.: Biochemistry, 44, 5317 (1945)