481973

NADPH, Tetrasodium Salt

A ubiquitous coenzyme that acts as an electron donor in many reactions utilizing dehydrogenase and reductase enzymes.

• Synonym(s): NADPH, Tetrasodium Salt, β-Nicotinamide-adenine Dinucleotide Phosphate, Reduced, 4Na
• Empirical Formula (Hill Notation): C₂₁H₂₆N₇O₁₇P₃ · 4Na
• CAS Number: 2646-71-1
• Molecular Weight: 833.35
• MDL number: MFCD00674870
• UNSPSC Code: 41106305
• NACRES: NA.51
• Assay: ≥90% (HPLC), ≥93% (enzymatic)
• Form: solid
• Solubility: water: 50 mg/mL
• Storage temp.: −20°C

Properties

• Quality Segment: 100
• description: Merck USA index - 14, 6348
• assay: ≥90% (HPLC), ≥93% (enzymatic)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, desiccated (hygroscopic)
• color: yellow
• solubility: water: 50 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: [P](=O)(O[P](=O)(OC[C@H]3O[C@H]([C@@H]([C@@H]3O)O[P](=O)(O)O)[n]4c5ncnc(c5nc4)N)O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N2C=C(CC=C2)C(=O)N)O
• InChI: 1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
• InChI key: ACFIXJIJDZMPPO-NNYOXOHSSA-N

Description

General description

A ubiquitous coenzyme that acts as an electron donor in many reactions utilizing dehydrogenase and reductase enzymes. It is generated by reduction of the electron acceptor NADP⁺. The following biological pathways involve NADPH: formation of carbohydrate from CO₂ during photosynthesis, maintenance of high levels of reduced glutathione in erythrocytes, reduction of thioredoxin.

Application

NADPH, tetrasodium salt, has been used:

• as a cofactor in the enzymatic synthesis of epoxidized metabolites from polyunsaturated fatty acids, facilitating the epoxidation reaction catalyzed by the cytochrome P450 enzyme BM3[1]
• in microsomal assays to evaluate the metabolic stability of CHD1L inhibitors[2]
• in conjunction with glutathione to reduce S-glutathionylated cysteine groups during the biotin switch assay, facilitating the detection of protein S-glutathionylation in the study of HLTF-deleted colorectal cancer models

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable