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T5515

Sigma-Aldrich

Thionicotinamide adenine dinucleotidephosphate sodium salt

≥95%

Synonym(s):

Thionicotinamid-TPN sodium salt, Thionicotinamide-TPN, Triphosphothiopyridine nucleotide sodium salt

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About This Item

Linear Formula:
C21H27N7O16P3S · Na
CAS Number:
19254-05-8
Molecular Weight:
781.45
MDL number:
MFCD00079598
UNSPSC Code:
12352200
PubChem Substance ID:
24278061

Assay

≥95%

solubility

H2O: soluble 50 mg/mL, clear, yellow to very deep yellow

storage temp.

−20°C

SMILES string

[Na+].NC(=S)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/C21H28N7O16P3S.Na/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(43-45(32,33)34)14(30)11(42-21)6-40-47(37,38)44-46(35,36)39-5-10-13(29)15(31)20(41-10)27-3-1-2-9(4-27)18(23)48;/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,48);/q;+1/p-1/t10-,11-,13-,14-,15-,16-,20-,21-;/m1./s1

InChI key

RFGBSJGYGUYCBT-QYZPTAICSA-M

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Application

Thio-NADP has been identified as a compound unique to the β-arrestin CNR2 screening assay4.

Biochem/physiol Actions

Blocks nicotinate adenine dinucleotide phosphate (NAADP)-induced Ca2+ release
Studies using sea-urchin egg homogenates have reported that thio-NADP stimulates partial Ca2+ release at 50 μm and blocks successive challenge with a saturating concentration of nicotinic acid adenine dinucleotide phosphate (NAADP). Subsequent HPLC purification analysis have reported that Ca2+ release function of thio-NADP is because of the presence of NAADP as a contaminant. Hence, this study challenges the NAADP antagonist functions of thio-NADP and indicates that thio-NADP does not function as an NAADP blocker5.

Linkage

Analog of NADP

Preparation Note

Thionicotinamide adenine dinucleotidephosphate (thio-NADP) sodium is soluble in water at 50 mg/ml and yields a clear, yellow to dark yellow solution.

Storage Class Code

13 - Non 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

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Certificates of Analysis (COA)

Lot/Batch Number
074K7049
059F7185
077F7200
058F7330

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J Feeney et al.
Biochemistry, 22(3), 628-633 (1983-02-01)
Transferred nuclear Overhauser effect measurements have been made on complexes of NADP+ and thioNADP+ with Lactobacillus casei dihydrofolate reductase to provide information about the glycosidic bond conformations in these complexes. Both NADP+ and thioNADP+ are shown to have very similar
Arkady S Pivovarov et al.
Regulatory peptides, 111(1-3), 31-39 (2003-03-01)
The effect of seven compounds intracellularly applied by spontaneous diffusion were investigated on the EPYLRFamide-induced reduction of acetylcholine-induced inward current (ACh-current) recorded from identified neurones from Helix lucorum. Inward currents were recorded from neurones LPa2, LPa3, RPa3 and RPa2 in
Hans-Gert Korth et al.
Biochemistry, 51(23), 4693-4703 (2012-05-24)
Mammalian (Clade 3) catalases utilize NADPH as a protective cofactor to prevent one-electron reduction of the central reactive intermediate Compound I (Cpd I) to the catalytically inactive Compound II (Cpd II) species by re-reduction of Cpd I to the enzyme's
M P Patel et al.
Biochemistry, 38(36), 11827-11833 (1999-10-08)
Mycothione reductase from the human pathogen Mycobacterium tuberculosis has been cloned, expressed in Mycobacterium smegmatis, and purified 145-fold to homogeneity in 43% yield. Amino acid sequence alignment of mycothione reductase with the functionally homologous glutathione and trypanothione reductase indicates conservation
M A McTigue et al.
Biochemistry, 32(27), 6855-6862 (1993-07-13)
The role of the 3'-carboxamide substituent of NADPH in the reduction of pteridine substrates as catalyzed by dihydrofolate reductase (EC 1.5.1.3, DHFR) has been investigated by determining crystal structures at 2.3 A of chicken liver DHFR in a binary complex
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