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Sigma-Aldrich

β-Nicotinamide adenine dinucleotide, reduced disodium salt hydrate

≥95.0% (HPLC)

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Synonym(s):
β-DPNH, β-NADH, DPNH, Diphosphopyridine nucleotide, reduced form, NADH
Empirical Formula (Hill Notation):
C21H27N7Na2O14P2 · xH2O
CAS Number:
Molecular Weight:
709.40 (anhydrous basis)
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

Assay

≥95.0% (HPLC)

form

powder

cation traces

Ca: ≤200 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤20 mg/kg
Fe: ≤5 mg/kg
K: ≤200 mg/kg
Mg: ≤200 mg/kg
Mn: ≤5 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

absorbance ratio

A260/340 nm ≤2.40

storage temp.

−20°C

SMILES string

O.[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.H2O/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);;;1H2/q;2*+1;/p-2/t10-,11-,13-,14-,15-,16-,20-,21-;;;/m1.../s1

InChI key

FWBNCIFELNNJCX-UHOVGGJYSA-L

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This Item
N8129N6005N1161
Quality Level

200

Quality Level

300

Quality Level

200

Quality Level

200

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

form

powder

form

powder

form

powder

form

powder

cation traces

Ca: ≤200 mg/kg

cation traces

-

cation traces

-

cation traces

-

absorbance ratio

A260/340 nm ≤2.40

absorbance ratio

-

absorbance ratio

-

absorbance ratio

-

Application

As a reagent, NADH can be used in enzyme cycling assays to amplify detection of activity of biologically relevant enzymes or metabolites present in low concentrations.
Nicotinamide adenine dinucleotide (NAD) and NADH form a redox pair. NAD/NADH is a coenzyme that supports redox reactions via the transport of electrons in a vast array of applications. NAD is also involved in post-translational (Poly(ADP-ribose) polymerization) modifications of proteins.

Biochem/physiol Actions

NADH is a coenzyme that functions as a regenerating electron donor in catabolic processes including glycolysis, β-oxidation and the citric acid cycle (Krebs cycle, TCA cycle). It participates in cell signaling events as well, for example as a substrate for the poly (ADP-ribose) polymerases (PARPs) during the DNA damage response. The NAD+/NADH dependent sirtuins play key roles in stress responses during events involving energy metabolism, with implications in cancer biology, diabetes and neurodegenerative disease.
As a reagent, NADH can be used in enzyme cycling assays to amplify detection of activity of biologically relevant enzymes or metabolites present in low concentrations.

Packaging

Packaged by solid weight.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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D.Dolphin, R.Poulson, O.Avramovic, eds.
Chemical, Biochemical and Medical Aspects, 759-759 (1987)
Chemical, Biochemical and Medical Aspects, 776-776 null
D D'Amours et al.
The Biochemical journal, 342 ( Pt 2), 249-268 (1999-08-24)
Poly(ADP-ribosyl)ation is a post-translational modification of proteins. During this process, molecules of ADP-ribose are added successively on to acceptor proteins to form branched polymers. This modification is transient but very extensive in vivo, as polymer chains can reach more than
V A Soldatenkov et al.
Current drug targets, 5(4), 357-365 (2004-05-12)
Poly(ADP-ribose) polymerization is a unique post-translation protein modification that utilizes an ADP-ribose moiety from NAD+ to form long and branched polymers attached via glutamic acid residues to nuclear acceptor proteins. The corresponding enzyme, poly(ADP-ribose) polymerase (PARP-1), is a zinc finger-containing
Mi Young Kim et al.
Genes & development, 19(17), 1951-1967 (2005-09-06)
Poly(ADP-ribose) (PAR) and the PAR polymerases (PARPs) that catalyze its synthesis from donor nicotinamide adenine dinucleotide (NAD+) molecules have received considerable attention in the recent literature. Poly(ADP-ribosyl)ation (PARylation) plays diverse roles in many molecular and cellular processes, including DNA damage

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