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Merck

N6785

β-Nicotinamide adenine dinucleotide, reduced disodium salt

~98%, pkg of 10 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:
Molecular Weight:
709.40
UNSPSC Code:
41106305
NACRES:
NA.51
PubChem Substance ID:
EC Number:
210-123-3
Beilstein/REAXYS Number:
5230241
MDL number:
Form:
powder
Assay:
~98%
Solubility:
10 mM NaOH: soluble-1 mg/mL, clear, colorless
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assay

~98%

Quality Level

form

powder

packaging

pkg of 10 mg (per vial)

solubility

10 mM NaOH: soluble-1 mg/mL, clear, colorless

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

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).

Biochem/physiol Actions

Electron donor

Preparation Note

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.


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Shin-Ichiro Imai
Biochimica et biophysica acta, 1804(8), 1584-1590 (2009-11-10)
SIR2 (silent information regulator 2) proteins, now called "sirtuins," are an evolutionarily conserved family of NAD-dependent protein deacetylases/ADP-ribosyltransferases. Sirtuins have recently attracted major attention in the field of aging research, and it has been demonstrated that SIR2 and its orthologs
Arvind Venkat Namuduri et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 34(2), 2269-2286 (2020-01-08)
SUMOylation is a dynamic, reversible, enzymatic drug-targetable post-translational modification (PTM) reaction where the Small Ubiquitin-like Modifier (SUMO) moieties are attached to proteins. This reaction regulates various biological functions like cell growth, differentiation, and it is crucial for maintaining organ homeostasis.
Richard P Ebstein et al.
FEBS letters, 585(11), 1529-1536 (2011-05-12)
Increasing evidence suggests that the nonapeptide, oxytocin (OT), helps shape social and affiliative behaviors not only in lower mammals but also in humans. Recently, an essential mediator of brain OT release has been discovered, ADP-ribosyl cyclase and/or CD38. We have