A reduced form of NADP+
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Alternative(s)
20945NADPH (cyclohexyl ammonium salt)
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NADPH (sodium salt)

Item No. 9000743

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
P'→5'-ester with 1,4-dihydro-1-β-D-ribofuranosyl-3-pyridinecarboxamide 2'-(dihydrogen phosphate) adenosine 5'-(trihydrogen diphosphate) sodium salt
CAS Number
2646-71-1
Synonyms
  • Nicotinamide adenine dinucleotide phosphate
Molecular Formula
C21H26N7O17P3 • 4Na
Formula Weight
833.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
258, 336
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.[Na+].[Na+].[Na+].[Na+]
InChi Code
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
InChi Key
WYWWVJHQDVCHKF-ITGWJZMWSA-J
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    5 mg

    $32

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    10 mg

    $61

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    25 mg

    $96

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    50 mg

    $128

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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 is it predominantly produced by the pentose phosphate pathway, but 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).

    Product Citations

    Deventer, M.H., Emanuele, M.C., Stang, B.N., et al. Identification and investigation of the intrinsic receptor activation potential and metabolization of the new oxo-pyridyl synthetic cannabinoid receptor agonist CH-FUBBMPDORA. Drug Test. Anal. (2025).

    Norman, C., Deventer, M.H., Dremann, O., et al. In vitro cannabinoid receptor activity, metabolism, and detection in seized samples of CH-PIATA, a new indole-3-acetamide synthetic cannabinoid. Drug Test. Anal. 1-12 (2023).

    Kuhn, M.J., and Sordillo, L.M. Inhibition of 20-hydroxyeicosatetraenoic acid biosynthesis by vitamin E analogs in human and bovine cytochrome P450 microsomes. J. Anim. Physiol. Anim. Nutr. (Berl.) 1-6 (2021).

    Lyu, H., Petukhov, P.A., Banta, P.R., et al. Characterization of lead compounds targeting the selenoprotein thioredoxin glutathione reductase for treatment of schistosomiasis. ACS Infect. Dis. 6(3), 393-405 (2020).

    Krotulski, A.J., Papsun, D.M., Noble, C., et al. Brorphine-investigation and quantitation of a new potent synthetic opioid in forensic toxicology casework using liquid chromatography-mass spectrometry. J. Forensic Sci. 66(2), 664-676 (2021).

    Presley, B.C., Logan, B.K., and Jansen-Varnum, S.A. In vitro metabolic profile elucidation of synthetic cannabinoid APP-CHMINACA (PX-3). J. Anal. Chem. 1-11 (2019).