tetrasodium [(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonatooxy)oxolan-2-yl]methyl ({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 153692
• Molecular Formular: C21H26N7Na4O17P3
• Molecular Mass: 833.348203
• Monoisotopic Mass: 833.01887942
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])OC[C@H]1[C@@H]([C@@H]([C@H](O1)N1C=CCC(=C1)C(=O)N)O)O)O)OP(=O)([O-])[O-])N.[Na+].[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@H]1[C@@H](O)[C@@H](O[C@@H]1N1C=CCC(=C1)C(=O)N)COP(=O)(OP(=O)(OC[C@H]1O[C@H]([C@@H]([C@@H]1O)OP(=O)([O-])[O-])n1cnc2c1ncnc2N)[O-])[O-].[Na+].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C21H30N7O17P3.4Na/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);;;;/q;4*+1/p-4/t10-,11+,13-,14+,15-,16+,20-,21+;;;;/m0..../s1
• InChIKey: WYWWVJHQDVCHKF-MPUNMZHWSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrasodium [(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonatooxy)oxolan-2-yl]methyl ({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: tetrasodium [(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonatooxy)oxolan-2-yl]methyl {[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: 2′-NADPH hydrate; β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt hydrate; β-NADPH; 2′-NADPH; NADPH Na4; TPNH2 Na4; Coenzyme II reduced tetrasodium salt; Dihydronicotinamide adenine dinucleotide phosphate tetrasodium salt; Triphosphopyridine nucleotide reduced tetrasodium salt; β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt; 2′-NADPH 水合物; 二氢烟酰胺腺嘌呤二核苷酸磷酸 四钠盐; 还原型三磷酸吡啶核苷酸 四钠盐; 还原型辅酶 II 四钠盐; 还原型 β-烟酰胺腺嘌呤二核苷酸 2′-磷酸 四钠盐 水合物; Coenzyme II reduced 四钠盐; Dihydronicotinamide adenine dinucleotide phosphate 四钠盐; Triphosphopyridine nucleotide reduced 四钠盐

Database IDs

• CAS Number: 2646-71-1(anhydrous)
• EC Number: 220-163-3
• MDL Number: MFCD00036263
• PubChem SID: 24897425; 24897910; 24897780; 24278049; 24889817; 24897841; 24897919; 162247831; 24897509
• PubChem CID: 16218775

CALCULATED PROPERTIES

• Acid pKa: 0.65526855
• H Acceptors: 18
• H Donor: 5
• LogD (pH = 5.5): -10.989814
• LogD (pH = 7.4): -12.689332
• Log P: -6.418074
• Molar Refractivity: 149.3858 cm^3
• Polarizability: 60.81711 Å^3
• Polar Surface Area: 375.47 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 1; 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~95%; ≥90.0% (HPLC); ≥95% (HPLC); ≥95% (spectrophotometric assay); ≥97% (HPLC); ≥97% (spectrophotometric assay); 93-100% (HPLC); 93-100% (spectrophotometric assay)
• Packaging: preweighed vial of 1 mg; vial of 0.30-0.36 mg; vial of 1 mg; vial of 10 mg; vial of 5 mg
• Impurities: ≤12% water
• Clinical: for in vitro diagnostic use
• Quality Level: PREMIUM
• Absorbance ratio: A260/340 nm ≤2.45
• Empirical Formula (Hill Notation): C21H26N7Na4O17P3; C21H26N7Na4O17P3 · xH2O

DETAILS

Sigma Aldrich - N9910

Other Notes
Packaged based on NADPH content as determined by UV-Vis.
Preparation Note
Chemically reduced
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+ and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivo by the pentose phosphate pathway (PPP).
Biochem/physiol Actions
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivo by the pentose phosphate pathway (PPP).

Sigma Aldrich - N9660

Other Notes
Packaged based on NADPH content as determined by UV-Vis.
Preparation Note
Chemically reduced
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).
Biochem/physiol Actions
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivo by the pentose phosphate pathway (PPP).

Sigma Aldrich - 201201

Biochem/physiol Actions
Electron donor; cofactor for many redox enzymes including nitric oxide synthetase
Other Notes
Packaged based on solid weight.
Preparation Note
Chemically reduced

Sigma Aldrich - N6505

Biochem/physiol Actions
Electron donor; cofactor for many redox enzymes including nitric oxide synthetase
Other Notes
Packaged based on solid weight.
Preparation Note
Enzymatically reduced.
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).

Sigma Aldrich - N7505

Biochem/physiol Actions
Electron donor; cofactor for many redox enzymes including nitric oxide synthetase
Other Notes
Packaged based on solid weight.
Preparation Note
Chemically reduced
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).

Sigma Aldrich - N1630

Biochem/physiol Actions
Electron donor; cofactor for many redox enzymes including nitric oxide synthetase
Other Notes
Packaged based on solid weight.
Preparation Note
Chemically reduced.

Sigma Aldrich - N7785

Other Notes
Packaged based on NADPH content as determined by UV-Vis.
Preparation Note
Chemically reduced
Application
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).
Biochem/physiol Actions
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivo by the pentose phosphate pathway (PPP).

Sigma Aldrich - N0411

Other Notes
Packaged based on NADPH content as determined by UV-Vis.
Preparation Note
Chemically reduced
Biochem/physiol Actions
β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivo by the pentose phosphate pathway (PPP).

Sigma Aldrich - 93220

Biochem/physiol Actions
Electron donor; cofactor for many redox enzymes including nitric oxide synthetase
Other Notes
Coenzymes and Cofactors, vol. 2: Pyridine Nucleotide Coenzymes1,2; Studies on steroid 5α-reductase3
Packaged based on solid weight.