Adenophostin

Adenophostin A

Names
IUPAC name [(2R,3R,4R,5R)-2-(6-Amino-9-purinyl)-4-[[(2R,3R,4R,5R,6R)-3-hydroxy-6-(hydroxymethyl)-4,5-diphosphonooxy-2-tetrahydropyranyl]oxy]-5-(hydroxymethyl)-3-tetrahydrofuranyl] dihydrogen phosphate
Identifiers
CAS Number	149091-92-9
ChEMBL	ChEMBL204385
ChemSpider	110268
IUPHAR/BPS	4124
Jmol 3D model	Interactive image
PubChem	123695
InChI InChI=1S/C16H26N5O18P3/c17-13-7-14(19-3-18-13)21(4-20-7)15-12(39-42(31,32)33)9(5(1-22)34-15)36-16-8(24)11(38-41(28,29)30)10(6(2-23)35-16)37-40(25,26)27/h3-6,8-12,15-16,22-24H,1-2H2,(H2,17,18,19)(H2,25,26,27)(H2,28,29,30)(H2,31,32,33)/t5-,6-,8-,9-,10-,11-,12-,15-,16-/m1/s1 Key: RENVITLQVBEFDT-MZQFDOALSA-N InChI=1/C16H26N5O18P3/c17-13-7-14(19-3-18-13)21(4-20-7)15-12(39-42(31,32)33)9(5(1-22)34-15)36-16-8(24)11(38-41(28,29)30)10(6(2-23)35-16)37-40(25,26)27/h3-6,8-12,15-16,22-24H,1-2H2,(H2,17,18,19)(H2,25,26,27)(H2,28,29,30)(H2,31,32,33)/t5-,6-,8-,9-,10-,11-,12-,15-,16-/m1/s1 Key: RENVITLQVBEFDT-MZQFDOALBO
SMILES O=P(O)(O)O[C@@H]4[C@H](O[C@H]1O[C@@H]([C@@H](OP(=O)(O)O)[C@H](OP(=O)(O)O)[C@H]1O)CO)[C@H](O[C@H]4n2c3ncnc(N)c3nc2)CO
Properties
Chemical formula	C16H26N5O18P3
Molar mass	669.32 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Adenophostin A is a potent inositol triphosphate (IP₃) receptor agonist, but is much more potent than IP₃.

IPR3 is a ligand-gated intracellular Ca²⁺ release channel that plays a central role in modulating cytoplasmic free Ca²⁺ concentration (Ca²⁺i). Adenophostin A is structurally different from IP₃ but could elicit distinct calcium signals in cells.^[1]

References

1. Mak, D.-O. D.; McBride, S; Foskett, JK (2001). "ATP-dependent Adenophostin Activation of Inositol 1,4,5-Trisphosphate Receptor Channel Gating: Kinetic Implications for the Durations of Calcium Puffs in Cells". The Journal of General Physiology 117 (4): 299–314. doi:10.1085/jgp.117.4.299. PMC 2217258. PMID 11279251.