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N6660

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide, reduced disodium salt

~98%, pkg of 0.2 mg (per vial)

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Synonym(s):
β-DPNH, β-NADH, Coenzyme I reduced disodium salt, Diphosphopyridine nucleotide reduced disodium salt
Empirical Formula (Hill Notation):
C21H27N7Na2O14P2
CAS Number:
Molecular Weight:
709.40
Beilstein:
5230241
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Assay

~98%

Quality Level

form

powder

packaging

pkg of 0.2 mg (per vial)

SMILES string

[Na+].[Na+].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](O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@H](O)[C@@H]2O

InChI

1S/C21H29N7O14P2.2Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33;;/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25);;/q;2*+1/p-2/t10-,11+,13-,14+,15-,16+,20-,21+;;/m0../s1

InChI key

QRGNQKGQENGQSE-QUWMEQBESA-L

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This Item
N0786N6785N9535
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

packaging

pkg of 0.2 mg (per vial)

packaging

pkg of 1 mg (per vial)

packaging

pkg of 10 mg (per vial)

packaging

pkg of 25-30 mg (per vial)

General description

β-Nicotinamide adenine dinucleotide (β-NAD) regulates energy metabolism and immunity. It is a cofactor for mitochondrial deacetylase sirtuin-3 enzyme and modulates inflammasome assembly. β-NAD supresses interleukin-1β levels in monocytic cells in inflammatory syndromes. β-NAD released by neurosecretory cells is a potential neurotransmitter. β-NAD is a vascular mediator in lung endothelial cells and may play a protective role against cytokine mediated inflammation.

Application

β-Nicotinamide adenine dinucleotide (NAD+) and β-Nicotinamide adenine dinucleotide, reduced (NADH) comprise a coenzyme redox pair (NAD+:NADH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. In addition to its redox function, NAD+/NADH is a donor of ADP-ribose units in ADP-ribosylaton (ADP-ribosyltransferases; poly(ADP-ribose) polymerases ) reactions and a precursor of cyclic ADP-ribose (ADP-ribosyl cyclases).
β-Nicotinamide adenine dinucleotide, reduced disodium salt has been used:
  • for the standard curve generation in neurotoxity assay of cortical neurons
  • in triosephosphate isomerase assay in jurkat JE6-1 cells
  • in lactate dehydrogenase assay

Biochem/physiol Actions

Electron donor

Reconstitution

Solutions should be prepared fresh and used promptly.

Other Notes

Packaged based on NADH content as determined by UV-Vis.
This is the common form of NADH; do not confuse with α-NADH.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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beta-Nicotinamide adenine dinucleotide attenuates lipopolysaccharide-induced inflammatory effects in a murine model of acute lung injury
Umapathy N, et al.
Experimental Lung Research, 38(5), 223-232 (2012)
Deficiency of ATP13A2 leads to lysosomal dysfunction, alpha-synuclein accumulation, and neurotoxicity
Usenovic M, et al.
The Journal of Neuroscience, 32(12), 4240-4246 (2012)
beta-Nicotinamide Adenine Dinucleotide (beta-NAD) Inhibits ATP-Dependent IL-1beta Release from Human Monocytic Cells
Hiller SD, et al.
International Journal of Molecular Sciences, 19(4), 1126-1126 (2018)
13C MR Hyperpolarization of Lactate by Using ParaHydrogen and Metabolic Transformation in Vitro
Cavallari E, et al.
Chemistry?A European Journal , 23(5), 1200-1204 (2017)
beta-Nicotinamide adenine dinucleotide is an enteric inhibitory neurotransmitter in human and nonhuman primate colons
Hwang SJ, et al.
Gastroenterology, 140(2), 608-617 (2011)

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