N5755

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide phosphate hydrate

Synonym(s):
β-NADP, Coenzyme II, TPN, NADP, Triphosphopyridine nucleotide
Empirical Formula (Hill Notation):
C21H28N7O17P3 · xH2O
CAS Number:
Molecular Weight:
743.41 (anhydrous basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.51

Quality Level

assay

≥95% (HPLC)
≥95% (spectrophotometric assay)

solubility

H2O: soluble 50 mg/mL, clear, colorless to faintly yellow

cation traces

sodium and potassium: ≤0.04%

storage temp.

−20°C

SMILES string

O.NC(=O)c1ccc[n+](c1)[C@@H]2O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](OP(O)(O)=O)[C@@H]3O)n4cnc5c(N)ncnc45)[C@@H](O)[C@H]2O

InChI

1S/C21H28N7O17P3.H2O/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32;/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39);1H2/t10-,11-,13-,14-,15-,16-,20-,21-;/m1./s1

InChI key

ZKJOXOJMGXFSPF-QYZPTAICSA-N

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Related Categories

Application

β-Nicotinamide adenine dinucleotide phosphate hydrate is suitable for use in:
  • the measurement of Glucose-6-phosphate dehydrogenase activity
  • the Cytochrome P450 3A4 assay as a part of NADPH-regenerating system
  • the Cytochrome P450 2D6 assay as a part of NADPH-regenerating system
  • the determination of Glucose-6-phosphate content

Packaging

1 g in glass bottle
100, 250, 500 mg in glass bottle

Biochem/physiol Actions

β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH is generated in vivio by the pentose phosphate pathway (PPP).
Electron acceptor

Other Notes

Packaged based on solid weight.
This is a common form of NADP.

pictograms

Exclamation mark

signalword

Warning

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

T M Lilley et al.
Oecologia, 175(3), 811-823 (2014-05-20)
Harmful reactive oxygen species (ROS) produced during metabolism and immune responses are neutralized in part by a powerful enzymatic antioxidant system. Inter-species variability in the baseline activity of antioxidant enzymes may be explained by a variety of life history traits....
Bent H Hellum et al.
Basic & clinical pharmacology & toxicology, 101(5), 350-358 (2007-10-04)
The six commonly used trade herbal products, St. John's wort, common valerian, common sage, Ginkgo biloba, Echinacea purpurea and horse chestnut, and ethanol, were investigated for their in vitro inhibitory potential of cytochrome P450 2D6 (CYP2D6)-mediated metabolism. Herbal components were...
Raoul G Rosenthal et al.
Nature chemical biology, 10(1), 50-55 (2013-11-19)
The pyridine nucleotides NADH and NADPH (NAD(P)H) are ubiquitous redox coenzymes that are present in all living cells. Although about 16% of all characterized enzymes use pyridine nucleotides as hydride donors or acceptors during catalysis, a detailed understanding of how...
Bent H Hellum et al.
Basic & clinical pharmacology & toxicology, 102(5), 466-475 (2008-03-12)
Extracts of six commonly used commercially available herbal products, St. John's wort, common valerian, common sage, Ginkgo biloba, Echinacea purpurea and horse chestnut were investigated for their in vitro inhibitory potential of CYP3A4 mediated metabolism and P-glycoprotein efflux transport activity....
Yin Wang et al.
Molecular neurobiology, 48(1), 49-61 (2013-04-03)
Glycogen, the largest cytosolic macromolecule, is soluble because of intricate construction generating perfect hydrophilic-surfaced spheres. Little is known about neuronal glycogen function and metabolism, though progress is accruing through the neurodegenerative epilepsy Lafora disease (LD) proteins laforin and malin. Neurons...

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