Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H30N7O17P3 |
Molecular Weight | 745.4209 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 8 / 8 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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)N4C=NC5=C4N=CN=C5N)[C@@H](O)[C@H]2O
InChI
InChIKey=ACFIXJIJDZMPPO-NNYOXOHSSA-N
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
Nicotinamide-adenine dinucleotide phosphate, reduced (NADPH) is the reduced form of the electron acceptor 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. It is also used for the synthesis of lipids and cholesterol and during the process of fatty acid chain elongation. 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 protects against redox stress by providing reducing equivalents to antioxidants such as glutathione and thioredoxin. NADPH levels decline with aging in several tissues, but whether this is a major driving force for the aging process has not been well established. Both NADPH and NAD+ have been reported to have potent neuroprotective effects against ischemic neuronal injury. The combination of NADPH and NAD+ may provide a novel effective therapy for ischemic stroke.
Approval Year
PubMed
Title | Date | PubMed |
---|---|---|
[Production of cytoplasmic NADPH2 other than by the pentose cycle in adipose tissue]. | 1967 |
|
Studies on the mechanism of metabolic stimulation in polymorphonuclear leucocytes during phagocytosis. I. Evidence for superoxide anion involvement in the oxidation of NADPH2. | 1975 Apr 7 |
|
Memo is a copper-dependent redox protein with an essential role in migration and metastasis. | 2014 Jun 10 |
|
Cytoplasmic and Mitochondrial NADPH-Coupled Redox Systems in the Regulation of Aging. | 2019 Feb 27 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29164394
In in vivo studies, NAD+ (12.5–50 mg/kg) or NADPH (2.5
or 7.5 mg/kg), dissolved in 0.9% saline solution, was administered to mice via tail vein at the onset of reperfusion or at the
indicated time after reperfusion.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12642631
Insect ganglia were directly incubated in an NADPHd staining solution of 0.2 mM nicotinamide-adenine dinucleotide phosphate, reduced (β-NADPH) and 0.2 mM nitroblue tetrazolium (NBT) in Tris-Tx for 1–3 hr at RT.
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381Q4X082D
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16474
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200-177-6
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5884
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m7702
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NADPH
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57783
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DTXSID001018921
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SUB22887
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DB02338
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SUBSTANCE RECORD