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N5755

Sigma-Aldrich

β-Nicotinamide adenine dinucleotide phosphate hydrate

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Synonym(s):
β-NADP, Coenzyme II, NADP, TPN, Triphosphopyridine nucleotide
Empirical Formula (Hill Notation):
C21H28N7O17P3 · xH2O
CAS Number:
Molecular Weight:
743.41 (anhydrous basis)
MDL number:
PubChem Substance ID:
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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This Item
N301443410N8160
cation traces

sodium and potassium: ≤0.04%

cation traces

-

cation traces

Ca: ≤200 mg/kg, Cd: ≤50 mg/kg, Co: ≤50 mg/kg, Cr: ≤50 mg/kg, Cu: ≤50 mg/kg, Fe: ≤50 mg/kg, K: ≤50 mg/kg, Mg: ≤100 mg/kg, Mn: ≤50 mg/kg, Na: ≤1000 mg/kg, Ni: ≤50 mg/kg, Pb: ≤50 mg/kg, Zn: ≤50 mg/kg

cation traces

-

form

powder

form

powder

form

powder or crystals

form

powder

solubility

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

solubility

H2O: 50 mg/mL

solubility

H2O: 0.1 g/mL at 20 °C, clear, H2O: freely soluble

solubility

water: 0.05 g/L

assay

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

assay

≥96.5% (HPLC), ≥96.5% (spectrophotometric assay)

assay

≥95% (HPLC)

assay

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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.
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.
William B. Wood
Biochemistry: A Problems Approach, 195-195 null
Berg, J.M., et al.
Biochemistry (5th Edition) (2002)

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