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N6660

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide, reduced disodium salt

~98%, pkg of 0.2 mg (per vial)

Synonym(s):

β-DPNH, β-NADH, Coenzyme I reduced disodium salt, Diphosphopyridine nucleotide reduced disodium salt

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About This Item

Empirical Formula (Hill Notation):
C21H27N7Na2O14P2
CAS Number:
606-68-8
Molecular Weight:
709.40
Beilstein:
5230241
EC Number:
210-123-3
MDL number:
MFCD00036200
UNSPSC Code:
41106305
PubChem Substance ID:
24897788
NACRES:
NA.51

Assay

~98%

Quality Level

200

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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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.

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
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 (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)
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