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Merck
CN

A5251

3-Acetylpyridine adenine dinucleotide

≥85%

Synonym(s):

3 -Acetyl NAD, APADH, APAD

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About This Item

Empirical Formula (Hill Notation):
C22H28N6O14P2
CAS Number:
86-08-8
Molecular Weight:
662.44
NACRES:
NA.51
PubChem Substance ID:
24890959
UNSPSC Code:
41106305
MDL number:
MFCD00078882

Key Documents

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Product Name

3-Acetylpyridine adenine dinucleotide, ≥85%

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

SMILES string

CC(=O)c1ccc[n+](c1)[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 key

KPVQNXLUPNWQHM-RBEMOOQDSA-N

biological source

Porcine brain

assay

≥85%

form

powder

Quality Level

200

mol wt

662.44 g/mol

concentration

≤100% (3-acetylpyridine-adenine dinucleotide)

color

white to off-white

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

λmax

259-260 nm

fluorescence

λem 15.2- 17.2 (dry basis at pH 7.0)

storage temp.

−20°C

Related Categories

Application

Many molecules use 3-Acetylpyridine adenine dinucleotide as a signaling molecule, cofactor, or substrate. Various dehydrogenase processes use APAD instead of NAD as a hydrogen-accepting cofactor. The oxidative phosphorylation can be studied with ADAP. ADAP can also be used as a suitable substrate.

Biochem/physiol Actions

APAD is an NAD analog with higher oxidation potential than NAD. It can substitute for NAD as a hydrogen-accepting cofactor in many dehydrogenase reactions; e.g. lactate dehydrogenase from Toxoplasma, Clonorchis, and Plasmodium, bacterial lipoamide dehydrogenase, as well as mammalian dehydrogenases. It can also act as a proton acceptor in various transhydrogenation reactions with NADH or NADPH.

General description

3-Acetylpyridine adenine dinucleotide is a crystalline solid. 3-Acetylpyridine adenine dinucleotide is a prominent electron transporter in various enzymatic activities in which it is alternately oxidized. APAD has a more significant oxidation potential than NAD. NAD analogues, APAD, were electrochemically more effectively reduced than genuine NAD, and the stability of their reduced products was also significantly higher than NADH. In transhydrogenation processes with NADH or NADPH, APAD also operates as a proton acceptor.

Other Notes

Analog of NAD

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000486760
0000486759
0000486760
0000486759
0000434681

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P D Bragg et al.
Archives of biochemistry and biophysics, 363(1), 182-190 (1999-03-02)
The pyridine nucleotide transhydrogenase carries out transmembrane proton translocation coupled to transfer of a hydride ion equivalent between NAD+ and NADP+. Previous workers (E. Holmberg et al. Biochemistry 33, 7691-7700, 1994; N. A. Glavas et al. Biochemistry 34, 7694-7702, 1995)
M Yamaguchi et al.
Biochimica et biophysica acta, 1318(1-2), 225-234 (1997-01-16)
The hydrophilic, extramembranous domains I (alpha 1 subunit) and III of the Rhodospirillum rubrum nicotinamide nucleotide transhydrogenase were expressed in Escherichia coli and purified therefrom as soluble proteins. These domains bind NAD(H) and NADP(H). respectively, and together they form the
W A Prütz et al.
Archives of biochemistry and biophysics, 380(1), 181-191 (2000-07-20)
Degradation of the reduced pyridine nucleotides NMNH and NADH by HOCl involves two distinct stages: a fast reaction, k = 4.2 x 10(5) M(-1) s(-1), leads to generation of stable pyridine products (Py/Cl) with a strong absorption band at 275
C O Hewitt et al.
Protein engineering, 10(1), 39-44 (1997-01-01)
This paper describes the testing of a homology model of Plasmodium falciparum lactate dehydrogenase (pfLDH) by protein engineering. The model had been validated in structural terms. It suggests explanations of the unusual properties of pfLDH (compared with all other LDHs).
Todd W Roy et al.
Nucleic acids research, 35(21), e147-e147 (2007-11-16)
The Escherichia coli AlkB protein catalyzes the direct reversal of alkylation damage to DNA; primarily 1-methyladenine (1mA) and 3-methylcytosine (3mC) lesions created by endogenous or environmental alkylating agents. AlkB is a member of the non-heme iron (II) alpha-ketoglutarate-dependent dioxygenase superfamily
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