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V900401

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide hydrate

Vetec™, reagent grade, ≥96.5%

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Synonym(s):
β-DPN, β-NAD, Coenzyme 1, Cozymase, DPN, Diphosphopyridine nucleotide, NAD, Nadide
Empirical Formula (Hill Notation):
C21H27N7O14P2 · xH2O
CAS Number:
53-84-9
Molecular Weight:
663.43 (anhydrous basis)
EC Number:
200-184-4
MDL number:
MFCD00036253
PubChem Substance ID:
329829810

grade

reagent grade

product line

Vetec™

Assay

≥96.5%

form

powder

color

white to off-white

storage temp.

−20°C

SMILES string

NC1=NC=NC2=C1N=CN2.O[C@@H]3[C@@H](COP(O)(OP(OC[C@@H](O4)[C@@H](O)[C@@H](O)[C@H]4[N+]5=CC=CC(C(N)=O)=C5)([O-])=O)=O)OC[C@@H]3O

InChI

1S/C21H27N7O14P2/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/h1-4,7-8,10-11,13-16,20-21,29-32H,5-6H2,(H5-,22,23,24,25,33,34,35,36,37)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

InChI key

BAWFJGJZGIEFAR-NNYOXOHSSA-N

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General description

β-Nicotinamide adenine dinucleotide (NAD) is a ubiquitously found electron carrier and a cofactor. NAD+ contains an adenylic acid and a nicotinamide-5′-ribonucleotide group linked together by a pyrophosphate moiety. In NAD+ complexes, the enzyme-cofactor interactions are highly conserved.

Biochem/physiol Actions

β-Nicotinamide adenine dinucleotide (NAD) significantly participates in enzyme-catalyzed oxido-reduction processes and many genetic processes. It cycles between the oxidized (NAD+) and reduced (NADH) forms to maintain a redox balance necessary for continued cell growth. NAD is also involved in microbial catabolism.
Electron acceptor

Packaging

Packaged by solid weight.

Other Notes

This is the common form of NAD.

Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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A Mechanism of Adsorption of beta-Nicotinamide Adenine Dinucleotide on Graphene Sheets: Experiment and Theory
Pumera M, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 15(41), 10851-10856 (2009)
Experimental and theoretical electron density studies in large molecules: NAD+, beta-nicotinamide adenine dinucleotide
Guillot B, et al.
The Journal of Physical Chemistry B, 107(34), 9109-9121 (2003)
Metabolic engineering of Escherichia coli: increase of NADH availability by overexpressing an NAD+-dependent formate dehydrogenase.
Berrios-Rivera S J, et al.
Metabolic engineering, 4(3), 217-229 (2002)
Christian Dölle et al.
The FEBS journal, 280(15), 3530-3541 (2013-04-27)
Mitochondrial metabolism is intimately connected to the universal coenzyme NAD. In addition to its role in redox reactions of energy transduction, NAD serves as substrate in regulatory reactions that lead to its degradation. Importantly, all types of the known NAD-consuming
Brian J North et al.
The EMBO journal, 33(13), 1438-1453 (2014-05-16)
Mice overexpressing the mitotic checkpoint kinase gene BubR1 live longer, whereas mice hypomorphic for BubR1 (BubR1(H/H)) live shorter and show signs of accelerated aging. As wild-type mice age, BubR1 levels decline in many tissues, a process that is proposed to
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