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N4256

Sigma-Aldrich

Nicotinic acid adenine dinucleotide sodium salt

≥98%

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Synonym(s):
Deamido NAD, Deamido NAD Sodium Salt, NAAD, NAAD Sodium Salt, Nicotinic Acid Adenine Dinucleotide Sodium Salt, Nicotinic Acid NAD Sodium Salt, Nicotinic acid NAD
Empirical Formula (Hill Notation):
C21H25N6O15P2Na
CAS Number:
104809-30-5
Molecular Weight:
686.39
MDL number:
MFCD00082430
UNSPSC Code:
41106305
PubChem Substance ID:
24897698
NACRES:
NA.51

Quality Level

200

Assay

≥98%

form

powder

storage temp.

−20°C

SMILES string

[Na].Nc1ncnc2n(cnc12)C3OC(COP(O)(=O)OP(O)(=O)OCC4OC(C(O)C4O)[N]5=CC(=CC=C5)C(O)=O)C(O)C3O

InChI

1S/C21H27N6O15P2.Na.H/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(31)14(29)11(41-20)6-39-44(36,37)42-43(34,35)38-5-10-13(28)15(30)19(40-10)26-3-1-2-9(4-26)21(32)33;;/h1-4,7-8,10-11,13-16,19-20,28-31H,5-6H2,(H,32,33)(H,34,35)(H,36,37)(H2,22,23,24);;

InChI key

JSOFOHZYBCRUNK-UHFFFAOYSA-N

General description

Nicotinic acid adenine dinucleotide (deamido-NAD, NAAD) is a closely related analog of NAD+. It is used to study the structure of nicotinate mononucleotide adenylyltransferase(s) (NMN/NaMN). NAAD is used as a substrate to study the specificity and kinetics of nicotinamide adenine dinucleotide synthetase(s) (NADS). In addition, it is also used as a co-substrate to study mechanisms of members of the Sir2 class of NAD+-dependent deacetylase.

Application

Nicotinic acid adenine dinucleotide sodium salt has been used as an internal standard during high performance liquid chromatography (HPLC) metabolite measurement. It has also been used as a substrate in nicotinamide adenine dinucleotide (NAD) biosynthesis.

Other Notes

Analog of β-NAD

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Mechanism of sirtuin inhibition by nicotinamide: altering the NAD+ co-substrate specificity of a Sir2 enzyme
Avalos JL, et al.
Molecular Cell, 17(6), 855-868 (2005)
Alexei Gorelik et al.
The FEBS journal, 284(21), 3718-3726 (2017-09-13)
The ecto-nucleotide pyrophosphatase/phosphodiesterase (NPP) family of proteins mediates purinergic signaling by degrading extracellular nucleotides and also participates in phospholipid metabolism. NPP5 (ENPP5) is the least characterized member of this group and its specific role is unknown. This enzyme does not
Ralf Jauch et al.
The Journal of biological chemistry, 280(15), 15131-15140 (2005-02-09)
Nicotinamide adenine dinucleotide synthetases (NADS) catalyze the amidation of nicotinic acid adenine dinucleotide (NAAD) to yield the enzyme cofactor nicotinamide adenine dinucleotide (NAD). Here we describe the crystal structures of the ammonia-dependent homodimeric NADS from Escherichia coli alone and in
The SARM1 toll/interleukin-1 receptor domain possesses intrinsic NAD+ cleavage activity that promotes pathological axonal degeneration
Essuman K, et al.
Neuron, 93(6), 1334-1343 (2017)
Shanyun Lu et al.
Acta crystallographica. Section F, Structural biology and crystallization communications, 64(Pt 10), 893-898 (2008-10-22)
Nicotinic acid mononucleotide adenylyltransferase (NaMNAT; EC 2.7.7.18) is the penultimate enzyme in the biosynthesis of NAD(+) and catalyzes the adenylation of nicotinic acid mononucleotide (NaMN) by ATP to form nicotinic acid adenine dinucleotide (NaAD). This enzyme is regarded as a
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