Ap4A   Click here for help

GtoPdb Ligand ID: 1732

Synonyms: 5',5'''-diadenosine tetraphosphate | adenosyl-P4 | Ap4A | diadenosine tetraphosphate
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 27
Hydrogen bond donors 6
Rotatable bonds 14
Topological polar surface area 484.53
Molecular weight 832.02
XLogP -7.59
No. Lipinski's rules broken 3
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Canonical SMILES OC1C(COP(=O)(OP(=O)(OP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2cnc3c2ncnc3N)[O-])[O-])[O-])[O-])OC(C1O)n1cnc2c1ncnc2N
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2ncnc3N)[O-])[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
InChI InChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26)/p-4/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
1. Castro E, Pintor J, Miras-Portugal MT. (1992)
Ca(2+)-stores mobilization by diadenosine tetraphosphate, Ap4A, through a putative P2Y purinoceptor in adrenal chromaffin cells.
Br J Pharmacol, 106 (4): 833-7. [PMID:1393282]
2. Kennedy C, Qi AD, Herold CL, Harden TK, Nicholas RA. (2000)
ATP, an agonist at the rat P2Y(4) receptor, is an antagonist at the human P2Y(4) receptor.
Mol Pharmacol, 57 (5): 926-31. [PMID:10779375]
3. Marteau F, Le Poul E, Communi D, Communi D, Labouret C, Savi P, Boeynaems JM, Gonzalez NS. (2003)
Pharmacological characterization of the human P2Y13 receptor.
Mol Pharmacol, 64 (1): 104-12. [PMID:12815166]
4. Patel K, Barnes A, Camacho J, Paterson C, Boughtflower R, Cousens D, Marshall F. (2001)
Activity of diadenosine polyphosphates at P2Y receptors stably expressed in 1321N1 cells.
Eur J Pharmacol, 430 (2-3): 203-10. [PMID:11711032]