A NAD analog
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3-Acetylpyridine NAD

Item No. 21884

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
adenosine 5'-(trihydrogen diphosphate), P’→5’-ester with 3-acetyl-1-β-D-ribofuranosylpyridinium, inner salt
CAS Number
86-08-8
Synonyms
  • APAD
  • NSC 20275
Molecular Formula
C22H28N6O14P2
Formula Weight
662.4
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
λmax
261 nm
SMILES
O[C@H]1[C@H](N2C=NC3=C2N=CN=C3N)O[C@H](COP(OP(OC[C@@H]4[C@@H](O)[C@@H](O)[C@H]([N+]5=CC(C(C)=O)=CC=C5)O4)([O-])=O)(O)=O)[C@H]1O
InChi Code
InChI=1S/C22H28N6O14P2/c1-10(29)11-3-2-4-27(5-11)21-17(32)15(30)12(40-21)6-38-43(34,35)42-44(36,37)39-7-13-16(31)18(33)22(41-13)28-9-26-14-19(23)24-8-25-20(14)28/h2-5,8-9,12-13,15-18,21-22,30-33H,6-7H2,1H3,(H3-,23,24,25,34,35,36,37)/t12-,13-,15-,16-,17-,18-,21-,22-/m1/s1
InChi Key
KPVQNXLUPNWQHM-RBEMOOQDSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 mg

    $103

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    50 mg

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    100 mg

    $363

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    250 mg

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    Product Description

    3-Acetylpyridine NAD (APAD) is an analog of NAD+ (free acid) (nicotinamide adenine dinucleotide; Item No. 16077), a signaling molecule and cofactor or substrate for many enzymes.1,2 APAD has been used to study the mechanisms of oxidative phosphorylation.3 It can be reduced by transdehydrogenase from NADH (sodium salt) (Item No. 16078).4 It can be reduced more efficiently and is more stable than NAD+; thus, it is useful as a substitute.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Houtkooper, R.H., Cantó, C., Wanders, R.J., et al. The secret life of NAD+: An old metabolite controlling new metabolic signaling pathways. Endocr. Rev. 31(2), 194-223 (2010).

    2. Ciaccio, E.I. The inhibition of lactate dehydrogenase by 3-acetylpyridine adenine dinucleotide and bisulfite. The Journal of Biological Chemisty 241(7), 1581-1586 (1966).

    3. Birrell, J.A., and Hirst, J. Investigation of NADH binding, hydride transfer, and NAD(+) dissociation during NADH oxidation by mitochondrial complex I using modified nicotinamide nucleotides. Biochemistry 52(23), 4048-4055 (2013).

    4. Stilwell, S.N., Bizouam, T., and Jackson, J.B. The reduction of acetylpyridine adenine dinucleotide by NADH: is it a significant reaction of proton-translocating transhydrogenase, or an artefact? Biochim. Biophys. Acta 1320(1), 83-94 (1997).

    5. Lee, H.J., Lee, S.H., Park, C.B., et al. Coenzyme analogs: Excellent substitutes (not poor imitations) for electrochemical regeneration. Chem. Commun. (Camb.) 47(46), 12538-12540 (2011).