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N2630

Sigma-Aldrich

Nicotinamide 1,N6-ethenoadenine dinucleotide

≥98%

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Synonym(s):
ε-NAD, 1,N6-Etheno NAD, 1,N6-Ethenonicotinamide adenine dinucleotide
Empirical Formula (Hill Notation):
C23H27N7O14P2
CAS Number:
38806-38-1
Molecular Weight:
687.45
MDL number:
MFCD00063546
UNSPSC Code:
41106305
PubChem Substance ID:
24897579
NACRES:
NA.51

Quality Level

200

Assay

≥98%

form

powder

storage temp.

−20°C

SMILES string

NC(=O)C1=CC=C[N](=C1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5c4ncn6ccnc56)C(O)C2O

InChI

1S/C23H28N7O14P2/c24-19(35)11-2-1-4-28(6-11)22-17(33)15(31)12(42-22)7-40-45(36,37)44-46(38,39)41-8-13-16(32)18(34)23(43-13)30-10-26-14-20-25-3-5-29(20)9-27-21(14)30/h1-6,9-10,12-13,15-18,22-23,31-34H,7-8H2,(H2,24,35)(H,36,37)(H,38,39)

InChI key

AVLUSNAXLARRGJ-UHFFFAOYSA-N

Application

Nicotinamide 1,N6-ethenoadenine dinucleotide (ε-NAD) is an NAD fluorescent analog (fluorophore) that may be used to study ADP-ribosylation reactions and the structure/kinetics of NAD+ binding enzymes by assays such as etheno-NAD+ assay.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Hélène Muller-Steffner et al.
ACS chemical biology, 12(7), 1787-1795 (2017-05-10)
SmNACE is a NAD catabolizing enzyme expressed on the outer tegument of S. mansoni, a human parasite that is one of the major agents of the neglected tropical disease schistosomiasis. Recently, we identified aroylhydrazone derivatives capable of inhibiting the recombinant
ADP-ribosylation and NAD+
Utilizing Enzymes
Paul Chang
Methods in Molecular Biology, 77-90 (2018)
R G Lowery et al.
The Journal of biological chemistry, 263(32), 16714-16719 (1988-11-15)
The enzyme that catalyzes the ADP-ribosylation and concomitant inactivation of dinitrogenase reductase in Rhodospirillum rubrum has been purified greater than 19,000-fold to near homogeneity. We propose dinitrogenase reductase ADP-ribosyltransferase (DRAT) as the working name for the enzyme. DRAT activity is
James N Wilson et al.
Organic & biomolecular chemistry, 4(23), 4265-4274 (2006-11-15)
We describe the design, synthesis, and properties of nucleoside monomers in which the DNA base is replaced by fluorescent hydrocarbons and heterocycles, and the assembly of these monomers into DNA-like molecules in which the all bases are fluorescent. As monomers
Y I Henis et al.
European journal of biochemistry, 112(1), 59-73 (1980-11-01)
The binding of nicotinamide--adenine dinucleotide (NAD+), nicotinamide--1,N6-ethenoadenine dinucleotide (epsilon NAD+), acetylpyridine--adenine dinucleotide (AcPyAD+), ATP, and adenosine diphosphoribose (ADP-ribose) to rabbit muscle glyceraldehyde-3-phosphate dehydrogenase (the enzyme) was examined. NAD+ and epsilon NAD+ were found to bind to the apoenzyme in a
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