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N4505

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide, reduced dipotassium salt

Synonym(s):

β-DPNH, β-NADH, DPNH, Diphosphopyridine nucleotide, reduced form, NADH

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About This Item

Linear Formula:
C21H27N7O14P2K2
CAS Number:
104809-32-7
Molecular Weight:
741.62
MDL number:
MFCD00079494
UNSPSC Code:
41106305
PubChem Substance ID:
24897704
NACRES:
NA.51

biological source

synthetic

Quality Level

200

Assay

≥95%

form

powder

solubility

10 mM NaOH: soluble-100 mg/mL, clear to hazy, faintly yellow to yellow

storage temp.

−20°C

SMILES string

[K].NC(=O)C1=CN(C=CC1)C2OC(COP(O)(=O)OP(O)(=O)OCC3OC(C(O)C3O)n4cnc5c(N)ncnc45)C(O)C2O

InChI

1S/C21H29N7O14P2.K.H/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);;

InChI key

KMRPNNQOKAHXEZ-UHFFFAOYSA-N

Gene Information

human ... IMPDH2(3615)

Application

β-Nicotinamide adenine dinucleotide (NAD+) and β-Nicotinamide adenine dinucleotide, reduced (NADH) comprise a coenzyme redox pair (NAD+:NADH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. In addition to its redox function, NAD+/NADH is a donor of ADP-ribose units in ADP-ribosylaton (ADP-ribosyltransferases; poly(ADP-ribose) polymerases ) reactions and a precursor of cyclic ADP-ribose (ADP-ribosyl cyclases).

Biochem/physiol Actions

Electron donor

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Luisa Schwarzmann et al.
Bioscience reports, 41(1) (2021-01-05)
Nicotinamide adenine dinucleotide (NAD) is a coenzyme in metabolic reactions and cosubstrate in signaling pathways of cells. While the intracellular function of NAD is well described, much less is known about its importance as an extracellular molecule. Moreover, there is
Sritama De Sarkar et al.
Parasitology research, 118(1), 335-345 (2018-11-25)
Berberine chloride, a plant-derived isoquinoline alkaloid, has been demonstrated to have leishmanicidal activity, which is mediated by generation of a redox imbalance and depolarization of the mitochondrial membrane, resulting in a caspase-independent apoptotic-like cell death. However, its impact on mitochondrial
Peter M Fernandes et al.
The FEBS journal, 287(13), 2847-2861 (2019-12-16)
Trypanosomatids possess glycosome organelles that contain much of the glycolytic machinery, including phosphofructokinase (PFK). We present kinetic and structural data for PFK from three human pathogenic trypanosomatids, illustrating intriguing differences that may reflect evolutionary adaptations to differing ecological niches. The
Justin P Hardee et al.
Molecular metabolism, 45, 101157-101157 (2020-12-29)
Preferential damage to fast, glycolytic myofibers is common in many muscle-wasting diseases, including Duchenne muscular dystrophy (DMD). Promoting an oxidative phenotype could protect muscles from damage and ameliorate the dystrophic pathology with therapeutic relevance, but developing efficacious strategies requires understanding
Yuan Liu et al.
Nature communications, 9(1), 4429-4429 (2018-10-26)
It is well known that high-risk human papilloma virus (HR-HPV) infection is strongly associated with cervical cancer and E7 was identified as one of the key initiators in HPV-mediated carcinogenesis. Here we show that lactate dehydrogenase A (LDHA) preferably locates
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