A secondary messenger that induces calcium mobilization
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NAADP (sodium salt)

Item No. 25992

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2′-(dihydrogen phosphate), adenosine 5′-(trihydrogen diphosphate), P′→5′-ester with 3-carboxy-1-β-D-ribofuranosylpyridinium, inner salt, tetrasodium salt
Synonyms
  • Nicotinic Acid adenine dinucleotide phosphate
Molecular Formula
C21H23N6O18P3 • 4Na
Formula Weight
832.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Water: 50 mg/ml
λmax
259 nm
SMILES
NC1=NC=NC2=C1N=CN2[C@H]3[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](COP(OP(OC[C@@H]4[C@@H](O)[C@@H](O)[C@H]([N+]5=CC(C([O-])=O)=CC=C5)O4)([O-])=O)([O-])=O)O3.[Na+].[Na+].[Na+].[Na+]
InChi Code
InChI=1S/C21H27N6O18P3.4Na/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(44-46(33,34)35)14(29)11(43-20)6-41-48(38,39)45-47(36,37)40-5-10-13(28)15(30)19(42-10)26-3-1-2-9(4-26)21(31)32;;;;/h1-4,7-8,10-11,13-16,19-20,28-30H,5-6H2,(H6-,22,23,24,31,32,33,34,35,36,37,38,39);;;;/q;4*+1/p-4/t10-,11-,13-,14-,15-,16-,19-,20-;;;;/m1..../s1
InChi Key
NWKIGVGTZIAOCW-MCNGMCCKSA-J
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $69

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    Product Description

    Nicotinic acid adenine dinucleotide phosphate (NAADP) is a secondary messenger that induces calcium mobilization.1,2 It induces calcium release from endosomes and lysosomes via two-pore channel 2 (TPC2) and TPC1, which then stimulates large-scale calcium release from granules and the endoplasmic reticulum mediated by type 1 ryanodine receptors (RyR2s), RyR3s, and inositol-(1,4,5)-triphosphate receptors (IP3Rs).1,3 NAADP induces calcium mobilization in sea urchin and starfish eggs post fertilization to block polyspermy and activate embryogenesis.3 NAADP-induced calcium mobilization induces VEGF-mediated angiogenesis in human umbilical vein endothelial cells (HUVECs). It also alkalizes lysosomal pH thereby inhibiting fusion between autophagosomes and lysosomes and arresting autophagic flux in mouse embryonic stem cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gerasimenko, J.V., Charlesworth, R.M., Sherwood, M.W., et al. Both RyRs and TPCs are required for NAADP-induced intracellular Ca²⁺ release. Cell Calcium 58(3), 237-245 (2015).

    2. Lee, H.C. Mechanisms of calcium signaling by cyclic ADP-ribose and NAADP. Physiol. Rev. 77(4), 1133-1164 (1997).

    3. Parrington, J., Lear, P., and Hachem, A. Calcium signals regulated by NAADP and two-pore channels - their role in development, differentiation and cancer. Int. J. Dev. Biol. 59(7-9), 341-355 (2015).

    4. Lu, Y., Hao, B., Graeff, R., et al. NAADP/TPC2/Ca2+ Signaling Inhibits Autophagy. Commun. Integr. Biol. 6(6), e27595 (2013).