A reduced form of NADP+
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Alternative(s)
9000743NADPH (sodium salt)
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NADPH (cyclohexyl ammonium salt)

Item No. 20945

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
tetracyclohexanamine (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-5-((((((((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1(4H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methoxy)oxidophosphoryl)oxy)oxidophosphoryl)oxy)methyl)-4-hydroxytetrahydrofuran-3-yl phosphate
CAS Number
100929-71-3
Synonyms
  • Nicotinamide adenine dinucleotide phosphate
Molecular Formula
C21H30N7O17P3 • 4C6H13N
Formula Weight
1142.1
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 0.2 mg/mlDMSO: 20 mg/mlEthanol: 1 mg/mlPBS (pH 7.2): 5 mg/ml
λmax
258, 336 nm
SMILES
O[C@H]1[C@@H](OP(O)(O)=O)[C@H](N2C=NC3=C2N=CN=C3N)O[C@@H]1COP(OP(OC[C@@H]4[C@@H](O)[C@@H](O)[C@H](N5C=C(C(N)=O)CC=C5)O4)(O)=O)(O)=O.NC6CCCCC6.NC7CCCCC7.NC8CCCCC8.NC9CCCCC9
InChi Code
InChI=1S/C21H30N7O17P3.4C6H13N/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;4*7-6-4-2-1-3-5-6/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23
InChi Key
PTKRUDMLGIIORX-ITGWJZMWSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $32

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    10 mg

    $54

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    25 mg

    $120

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    50 mg

    $160

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    Product Description

    NADPH is the reduced form of the electron acceptor nicotinamide adenine dinucleotide phosphate (NADP+) and acts as an electron donor in various biological reactions. In plants, NADPH is produced by ferredoxin-NADP+ reductase in the last step of the electron chain during photosynthesis. In animals it is predominantly produced by the pentose phosphate pathway, but it is also generated by key mitochondrial enzymes. NADPH provides the reducing equivalents for biosynthetic reactions and the oxidation-reduction involved in protecting against the toxicity of reactive oxygen species.1,2,3 It is also used for the synthesis of lipids and cholesterol and during the process of fatty acid chain elongation.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sumimoto, H. Structure, regulation and evolution of Nox-family NADPH oxidases that produce reactive oxygen species. FEBS J. 275(13), 3249-3277 (2008).

    2. Sutherland, M.W., Nelson, J., Harrison, G., et al. Effects of t-butyl hydroperoxide on NADPH, glutathione, and the respiratory burst of rat alveolar machrophages. Arch. Biochem. Biophys. 243(2), 325-331 (1985).

    3. Nauseef, W.M. Biological roles for the NOX family NADPH oxidases. The Journal of Biological Chemisty 283(25), 16961-16965 (2008).

    4. Tserng, K.Y., and Jin, S.J. NADPH-dependent reductive metabolism of cis-5 unsaturated fatty acids. A revised pathway for the β-oxidation of oleic acid. The Journal of Biological Chemisty 266(18), 11614-11620 (1990).