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Key Documents

N7381

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide hydrate

Grade AA-1

Synonym(s):

β-DPN, β-NAD, Coenzyme 1, Cozymase, DPN, Diphosphopyridine nucleotide, NAD, Nadide

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About This Item

Empirical Formula (Hill Notation):
C21H27N7O14P2 · xH2O
CAS Number:
Molecular Weight:
663.43 (anhydrous basis)
MDL number:
UNSPSC Code:
41106305
eCl@ss:
39200202
PubChem Substance ID:
NACRES:
NA.55

biological source

yeast

type

Grade AA-1

form

powder

IVD

not for in vitro diagnostic use

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 (β-NAD) is a ubiquitous biomolecule containing 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.

Application

β-Nicotinamide adenine dinucleotide hydrate has been used as a supplement in chocolate agar plates for Haemophilus influenzae growth.

Biochem/physiol Actions

β-Nicotinamide adenine dinucleotide (β-NAD) is an electron carrier and a cofactor, significantly involved in enzyme-catalyzed oxido-reduction processes and many genetic processes. NAD 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. β-NAD acts as a substrate for various enzymes in several cellular processes.
Electron acceptor

Packaging

Packaged by solid weight.

Preparation Note

Produced by fermentation.

Other Notes

This is the common form of NAD.

Pictograms

Health hazard

Signal Word

Warning

Hazard Statements

Hazard Classifications

STOT SE 2

Target Organs

Eyes,Central nervous system

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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Iron-binding proteins in sputum of chronic bronchitis patients with Haemophilus influenzae infections
Vogel L, et al.
The European Respiratory Journal, 10(10), 2327-2333 (1997)
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)
Extracellular beta-nicotinamide adenine dinucleotide (beta-NAD) promotes the endothelial cell barrier integrity via PKA-and EPAC1/Rac1-dependent actin cytoskeleton rearrangement
Umapathy NS, et al.
Journal of Cellular Physiology, 223(1), 215-223 (2010)
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)
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)

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