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

• ChemBase编号: 1
• 分子式: C8H10NO6P
• 平均质量: 247.141861
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: [(4-formyl-5-hydroxy-6-methylpyridin-3-yl)methoxy]phosphonic acid
• IUPAC传统名: pyridoxal phosphate
• 商标名: Hairoxal; Hiadelon; Himitan; Vitazechs; Biosechs; Pidopidon
• 别名: 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

登记号

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

理论计算性质

JChem

• Acid pKa: 1.6802986
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): -2.3409967
• LogD (pH = 7.4): -3.1810691
• Log P: -2.0856087
• 摩尔折射率: 54.7463 cm^3
• 极化性: 20.725895 Å^3
• 极化表面积: 116.95 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.55
• LOG S: -1.64
• 溶解度: 5.70e+00 g/l

分子性质

理化性质

• 溶解度: Appreciable
• 外观: powder
• 熔点: 140-143 °C; 140-143°C
• 疏水性(logP): -1.2

安全信息

• 保存条件: 0°C
• RTECS编号: UV1208000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: ~98%; ≥98%; 95+%
• 适用性: suitable for cell culture

详细说明

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).

参考文献

• 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)