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Merck

N5130

β-Nicotinamide adenine dinucleotide phosphate, reduced tetra(cyclohexylammonium) salt

≥93%

Synonym(s):

β-NADPH, NADPH, TPNH, Triphosphopyridine nucleotide, reduced form

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About This Item

Empirical Formula (Hill Notation):
C21H30N7O17P3 · 4C6H13N
CAS Number:
100929-71-3
Molecular Weight:
1142.12
NACRES:
NA.51
PubChem Substance ID:
329818651
UNSPSC Code:
41106305
MDL number:
MFCD00079504

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Product Name

β-Nicotinamide adenine dinucleotide phosphate, reduced tetra(cyclohexylammonium) salt, ≥93%

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,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35);4*6H,1-5,7H2/t10-,11-,13-,14-,15-,16-,20-,21-;;;;/m1..../s1

SMILES string

NC1CCCCC1.NC2CCCCC2.NC3CCCCC3.NC4CCCCC4.NC(=O)C5=CN(C=CC5)[C@@H]6O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]7O[C@H]([C@H](OP(O)(O)=O)[C@@H]7O)n8cnc9c(N)ncnc89)[C@@H](O)[C@H]6O

InChI key

PTKRUDMLGIIORX-ITGWJZMWSA-N

assay

≥93%

form

powder

cation traces

Na: ≤0.1%

storage temp.

−20°C

Quality Level

200

Related Categories

Application

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

Electron donor; cofactor for nitric oxide synthetase

Preparation Note

Chemically reduced.

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
0000509397
0000509397
0000477320
0000477320
0000448626

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Nataliia Kovalchuk et al.
Toxicological sciences : an official journal of the Society of Toxicology, 177(2), 334-346 (2020-09-26)
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Chen-Hua Huang et al.
ACS omega, 6(40), 26065-26076 (2021-10-19)
Mutations far from the center of chemical activity in dihydrofolate reductase (DHFR) can affect several steps in the catalytic cycle. Mutations at highly conserved positions and the distal distance of the catalytic center (Met-42, Thr-113, and Gly-121) were designed, including
Xue-Qian Sun et al.
International immunopharmacology, 74, 105634-105634 (2019-06-30)
Heme oxygenase-1 (HO-1) plays a critical protective role in various insults-induced acute lung injury (ALI) through its strong anti-inflammatory, anti-oxidant, and anti-apoptotic properties, but its protective role and mechanism on seawater aspiration-induced acute lung injury remains unclear. This study aimed
Paul A Fraser
Free radical biology & medicine, 51(5), 967-977 (2011-06-30)
The brain endothelium constitutes a barrier to the passive movement of substances from the blood into the cerebral microenvironment, and disruption of this barrier after a stroke or trauma has potentially fatal consequences. Reactive oxygen species (ROS), which are formed
Estrogen signaling and neuroprotection in cerebral ischemia.
Brann D, Raz L, Wang R, et al.
Journal of Neuroendocrinology, 24(1), 34-47 (2011)
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Product Information Sheet - N5130

Product Information Sheet

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