ATP   Click here for help

GtoPdb Ligand ID: 1713

Synonyms: 5'-ATP | adenosine 5' triphosphate | adenosine triphosphate
PDB Ligand
Click here for help
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: atp

2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 17
Hydrogen bond donors 7
Rotatable bonds 8
Topological polar surface area 308.56
Molecular weight 507
XLogP -5.53
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES OC1C(COP(=O)(OP(=O)(OP(=O)(O)O)O)O)OC(C1O)n1cnc2c1ncnc2N
Isomeric SMILES O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
InChI InChI=1S/C10H16N5O13P3/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(26-10)1-25-30(21,22)28-31(23,24)27-29(18,19)20/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H,23,24)(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
1. A-González N, Castrillo A. (2011)
Liver X receptors as regulators of macrophage inflammatory and metabolic pathways.
Biochim Biophys Acta, 1812 (8): 982-94. [PMID:21193033]
2. Bhattacharjee A, Joiner WJ, Wu M, Yang Y, Sigworth FJ, Kaczmarek LK. (2003)
Slick (Slo2.1), a rapidly-gating sodium-activated potassium channel inhibited by ATP.
J Neurosci, 23 (37): 11681-91. [PMID:14684870]
3. Bogdanov YD, Wildman SS, Clements MP, King BF, Burnstock G. (1998)
Molecular cloning and characterization of rat P2Y4 nucleotide receptor.
Br J Pharmacol, 124 (3): 428-30. [PMID:9647463]
4. Buccioni M, Marucci G, Dal Ben D, Giacobbe D, Lambertucci C, Soverchia L, Thomas A, Volpini R, Cristalli G. (2011)
Innovative functional cAMP assay for studying G protein-coupled receptors: application to the pharmacological characterization of GPR17.
Purinergic Signal, 7 (4): 463-8. [PMID:21773766]
5. Chu X, Li D. (2003)
Cloning, expression, and purification of His-tagged rat mevalonate kinase.
Protein Expr Purif, 27 (1): 165-70. [PMID:12509999]
6. Chu X, Li D. (2003)
Expression, purification, and characterization of His20 mutants of rat mevalonate kinase.
Protein Expr Purif, 32 (1): 75-82. [PMID:14680942]
7. Chu X, Yu W, Wu L, Liu X, Li N, Li D. (2007)
Effect of a disulfide bond on mevalonate kinase.
Biochim Biophys Acta, 1774 (12): 1571-81. [PMID:17964869]
8. Communi D, Robaye B, Boeynaems JM. (1999)
Pharmacological characterization of the human P2Y11 receptor.
Br J Pharmacol, 128 (6): 1199-206. [PMID:10578132]
9. Fu Z, Voynova NE, Herdendorf TJ, Miziorko HM, Kim JJ. (2008)
Biochemical and structural basis for feedback inhibition of mevalonate kinase and isoprenoid metabolism.
Biochemistry, 47 (12): 3715-24. [PMID:18302342]
10. Hechler B, Vigne P, Léon C, Breittmayer JP, Gachet C, Frelin C. (1998)
ATP derivatives are antagonists of the P2Y1 receptor: similarities to the platelet ADP receptor.
Mol Pharmacol, 53 (4): 727-33. [PMID:9547364]
11. Herdendorf TJ, Miziorko HM. (2006)
Phosphomevalonate kinase: functional investigation of the recombinant human enzyme.
Biochemistry, 45 (10): 3235-42. [PMID:16519518]
12. Herdendorf TJ, Miziorko HM. (2007)
Functional evaluation of conserved basic residues in human phosphomevalonate kinase.
Biochemistry, 46 (42): 11780-8. [PMID:17902708]
13. Hinson DD, Chambliss KL, Toth MJ, Tanaka RD, Gibson KM. (1997)
Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways.
J Lipid Res, 38 (11): 2216-23. [PMID:9392419]
14. Inagaki N, Gonoi T, Clement 4th JP, Namba N, Inazawa J, Gonzalez G, Aguilar-Bryan L, Seino S, Bryan J. (1995)
Reconstitution of IKATP: an inward rectifier subunit plus the sulfonylurea receptor.
Science, 270 (5239): 1166-70. [PMID:7502040]
15. Inagaki N, Gonoi T, Clement JP, Wang CZ, Aguilar-Bryan L, Bryan J, Seino S. (1996)
A family of sulfonylurea receptors determines the pharmacological properties of ATP-sensitive K+ channels.
Neuron, 16 (5): 1011-7. [PMID:8630239]
16. Jacobson KA, Ivanov AA, de Castro S, Harden TK, Ko H. (2009)
Development of selective agonists and antagonists of P2Y receptors.
Purinergic Signal, 5 (1): 75-89. [PMID:18600475]
17. Jacobson KA, Jarvis MF, Williams M. (2002)
Purine and pyrimidine (P2) receptors as drug targets.
J Med Chem, 45 (19): 4057-93. [PMID:12213051]
18. Jones CA, Chessell IP, Simon J, Barnard EA, Miller KJ, Michel AD, Humphrey PP. (2000)
Functional characterization of the P2X(4) receptor orthologues.
Br J Pharmacol, 129 (2): 388-94. [PMID:10694247]
19. 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]
20. Kim HS, Ravi RG, Marquez VE, Maddileti S, Wihlborg AK, Erlinge D, Malmsjö M, Boyer JL, Harden TK, Jacobson KA. (2002)
Methanocarba modification of uracil and adenine nucleotides: high potency of Northern ring conformation at P2Y1, P2Y2, P2Y4, and P2Y11 but not P2Y6 receptors.
J Med Chem, 45 (1): 208-18. [PMID:11754592]
21. Lazarowski ER, Watt WC, Stutts MJ, Boucher RC, Harden TK. (1995)
Pharmacological selectivity of the cloned human P2U-purinoceptor: potent activation by diadenosine tetraphosphate.
Br J Pharmacol, 116 (1): 1619-27. [PMID:8564228]
22. 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]
23. Michihara A, Akasaki K, Yamori Y, Tsuji H. (2002)
Purification and characterization of mouse mevalonate pyrophosphate decarboxylase.
Biol Pharm Bull, 25 (3): 302-6. [PMID:11913522]
24. Michihara A, Sawamura M, Nara Y, Ikeda K, Yamori Y. (1997)
Purification and characterization of two mevalonate pyrophosphate decarboxylases from rat liver: a novel molecular species of 37 kDa.
J Biochem, 122 (3): 647-54. [PMID:9348097]
25. Nilius B, Prenen J, Voets T, Droogmans G. (2004)
Intracellular nucleotides and polyamines inhibit the Ca2+-activated cation channel TRPM4b.
Pflugers Arch, 448 (1): 70-5. [PMID:14758478]
26. Potter D, Miziorko HM. (1997)
Identification of catalytic residues in human mevalonate kinase.
J Biol Chem, 272 (41): 25449-54. [PMID:9325256]
27. Potter D, Wojnar JM, Narasimhan C, Miziorko HM. (1997)
Identification and functional characterization of an active-site lysine in mevalonate kinase.
J Biol Chem, 272 (9): 5741-6. [PMID:9038186]
28. Qiu Y, Gao J, Guo F, Qiao Y, Li D. (2007)
Mutation and inhibition studies of mevalonate 5-diphosphate decarboxylase.
Bioorg Med Chem Lett, 17 (22): 6164-8. [PMID:17888661]
29. Qiu Y, Li D. (2006)
Inhibition of mevalonate 5-diphosphate decarboxylase by fluorinated substrate analogs.
Biochim Biophys Acta, 1760 (7): 1080-7. [PMID:16626865]
30. Sawada K, Echigo N, Juge N, Miyaji T, Otsuka M, Omote H, Yamamoto A, Moriyama Y. (2008)
Identification of a vesicular nucleotide transporter.
Proc Natl Acad Sci USA, 105 (15): 5683-6. [PMID:18375752]
31. Schachter JB, Harden TK. (1997)
An examination of deoxyadenosine 5'(alpha-thio)triphosphate as a ligand to define P2Y receptors and its selectivity as a low potency partial agonist of the P2Y1 receptor.
Br J Pharmacol, 121 (2): 338-44. [PMID:9154346]
32. Tanaka RD, Schafer BL, Lee LY, Freudenberger JS, Mosley ST. (1990)
Purification and regulation of mevalonate kinase from rat liver.
J Biol Chem, 265 (4): 2391-8. [PMID:2153681]
33. Ullrich ND, Voets T, Prenen J, Vennekens R, Talavera K, Droogmans G, Nilius B. (2005)
Comparison of functional properties of the Ca2+-activated cation channels TRPM4 and TRPM5 from mice.
Cell Calcium, 37 (3): 267-78. [PMID:15670874]
34. Voynova NE, Fu Z, Battaile KP, Herdendorf TJ, Kim JJ, Miziorko HM. (2008)
Human mevalonate diphosphate decarboxylase: characterization, investigation of the mevalonate diphosphate binding site, and crystal structure.
Arch Biochem Biophys, 480 (1): 58-67. [PMID:18823933]
35. Waldo GL, Corbitt J, Boyer JL, Ravi G, Kim HS, Ji XD, Lacy J, Jacobson KA, Harden TK. (2002)
Quantitation of the P2Y(1) receptor with a high affinity radiolabeled antagonist.
Mol Pharmacol, 62 (5): 1249-57. [PMID:12391289]
36. White PJ, Webb TE, Boarder MR. (2003)
Characterization of a Ca2+ response to both UTP and ATP at human P2Y11 receptors: evidence for agonist-specific signaling.
Mol Pharmacol, 63 (6): 1356-63. [PMID:12761346]
37. Yamada M, Isomoto S, Matsumoto S, Kondo C, Shindo T, Horio Y, Kurachi Y. (1997)
Sulphonylurea receptor 2B and Kir6.1 form a sulphonylurea-sensitive but ATP-insensitive K+ channel.
J Physiol (Lond.), 499 ( Pt 3): 715-20. [PMID:9130167]