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N7785

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

vial of 10 mg, ~95%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C21H26N7Na4O17P3
Molecular Weight:
833.35
UNSPSC Code:
41106305
PubChem Substance ID:
24897841
EC Number:
214-664-6
NACRES:
NA.51
MDL number:
MFCD00036263
Assay:
~95%
Form:
powder
Solubility:
0.1 mg/mL, clear, colorless (0.01 N NaOH)
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assay

~95%

Quality Level

200

form

powder

packaging

vial of 10 mg

solubility

0.1 mg/mL, clear, colorless (0.01 N NaOH)

SMILES string

[Na+].[Na+].[Na+].[Na+].[P](=O)([O-])([O-])O[C@H]1[C@@H](O[C@@H]([C@H]1O)CO[P](=O)([O-])O[P](=O)([O-])OC[C@@H]4O[C@@H]([C@H]([C@H]4O)O)N5C=C(CC=C5)C(=O)N)[n]2c3ncnc(c3nc2)N

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

InChI key

WYWWVJHQDVCHKF-MPUNMZHWSA-J

Application

β-Nicotinamide adenine dinucleotide 2′-phosphate reduced tetrasodium salt has been used in the Griess reagent assay of culture medium to reduce nitrate to nitrite and in glutathione peroxidase assay.
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).
Electron donor; cofactor for many redox enzymes including nitric oxide synthetase

Preparation Note

Chemically reduced

Other Notes

Packaged based on NADPH content as determined by UV-Vis.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCG5053
SLBR2676V
SLBM5569V
SLBG2401V
SLBB6544V

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Assays for nitric oxide expression
Stone WL, et al.
Methods in Molecular Biology, 245-256 (2006)
Lithium potentiate oxidative burden and reduced antioxidant status in different rat organs system
Joshi DK, et al.
Int J Toxicol Pharmacol Res, 5(1), 9-14 (2013)
Xiao-Chuan Cai et al.
eLife, 8 (2019-10-29)
CARM1 is a cancer-relevant protein arginine methyltransferase that regulates many aspects of transcription. Its pharmacological inhibition is a promising anti-cancer strategy. Here SKI-73 (6a in this work) is presented as a CARM1 chemical probe with pro-drug properties. SKI-73 (6a) can
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Global Trade Item Number

SKUGTIN
N7785-15VL04061834118237
N7785-1VL04061837143878