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N7505 Sigma-Aldrich

β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt hydrate

≥97% (HPLC)

Synonym: β-NADPH, 2′-NADPH hydrate, Coenzyme II reduced tetrasodium salt, Dihydronicotinamide adenine dinucleotide phosphate tetrasodium salt, NADPH Na4, TPNH2 Na4, Triphosphopyridine nucleotide reduced tetrasodium salt



Related Categories Application Index, Biochemicals and Reagents, Bulk vials, Cancer Metabolism, Cancer Research,
Quality Level   300
assay   ≥97% (HPLC)
  ≥97% (spectrophotometric assay)
solubility   10 mM NaOH: soluble 50 mg/mL, clear
storage temp.   −20°C
SMILES string   [Na+].[Na+].[Na+].[Na+].NC(=O)C1=CN(C=CC1)[C@H]2O[C@@H](COP([O-])(=O)OP([O-])(=O)OC[C@H]3O[C@H]([C@H](OP([O-])([O-])=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@H](O)[C@@H]2O
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



1 g in poly bottle

25, 100, 250, 500 mg in poly bottle

Biochem/physiol Actions

NADPH is an electron donor and a cofactor for many redox enzymes including nitric oxide synthetase.

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).

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

Preparation Note

Chemically reduced

Other Notes

Packaged based on solid weight.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
NONH for all modes of transport
WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles


Fatty Acid Synthesis and Metabolism in Cancer Cells

Proliferatively active cells require fatty acids for functions such as membrane generation, protein modification, and bioenergetic requirements. These fatty acids are derived either from dietary sour...
BioFiles v7 n4
Keywords: Apoptosis, Cancer, Carboxylations, Catalysis, Citric Acid Cycle, Gene expression, Glycolysis, Metabolism, Oxidations, Phosphorylations

Nucleotide Synthesis in Cancer Cells

Neoplastic cells are highly dependent on the de novo synthesis of nucleotides to maintain sufficient pools to support DNA replication and the production of RNA. The metabolic pathways supporting nucl...
BioFiles v7 n4
Keywords: Cancer, Catalysis, Citric Acid Cycle, DNA replication, Gene expression, Glycolysis, Metabolic Pathways, Metabolism, Metabolites, Nucleotide Synthesis, Pentose phosphate pathway, Pyrimidine synthesis

Peer-Reviewed Papers


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