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N5755

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide phosphate hydrate

Synonym(s):

β-NADP, Coenzyme II, NADP, TPN, Triphosphopyridine nucleotide

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About This Item

Empirical Formula (Hill Notation):
C21H28N7O17P3 · xH2O
CAS Number:
53-59-8
Molecular Weight:
743.41 (anhydrous basis)
MDL number:
MFCD10567218
UNSPSC Code:
41106305
PubChem Substance ID:
24897747
NACRES:
NA.51

Assay

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

form

powder

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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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

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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
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
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.
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