cyclic AMP   Click here for help

GtoPdb Ligand ID: 2352

Abbreviated name: cAMP
Synonyms: 3' 5'-adenosine monophosphate | 3',5'-cyclic AMP | cyclic adenosine monophosphate
PDB Ligand
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 10
Hydrogen bond donors 3
Rotatable bonds 1
Topological polar surface area 164.65
Molecular weight 329.05
XLogP -2.49
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OC1C2OP(=O)(O)OCC2OC1n1cnc2c1ncnc2N
Isomeric SMILES O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1ncnc2N
InChI InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/t4-,6-,7-,10-/m1/s1
1. Bradley J, Li J, Davidson N, Lester HA, Zinn K. (1994)
Heteromeric olfactory cyclic nucleotide-gated channels: a subunit that confers increased sensitivity to cAMP.
Proc Natl Acad Sci USA, 91 (19): 8890-4. [PMID:7522325]
2. Bönigk W, Bradley J, Müller F, Sesti F, Boekhoff I, Ronnett GV, Kaupp UB, Frings S. (1999)
The native rat olfactory cyclic nucleotide-gated channel is composed of three distinct subunits.
J Neurosci, 19 (13): 5332-47. [PMID:10377344]
3. Chen S, Wang J, Siegelbaum SA. (2001)
Properties of hyperpolarization-activated pacemaker current defined by coassembly of HCN1 and HCN2 subunits and basal modulation by cyclic nucleotide.
J Gen Physiol, 117 (5): 491-504. [PMID:11331358]
4. Fawcett L, Baxendale R, Stacey P, McGrouther C, Harrow I, Soderling S, Hetman J, Beavo JA, Phillips SC. (2000)
Molecular cloning and characterization of a distinct human phosphodiesterase gene family: PDE11A.
Proc Natl Acad Sci USA, 97 (7): 3702-7. [PMID:10725373]
5. Fisher DA, Smith JF, Pillar JS, St Denis SH, Cheng JB. (1998)
Isolation and characterization of PDE8A, a novel human cAMP-specific phosphodiesterase.
Biochem Biophys Res Commun, 246 (3): 570-7. [PMID:9618252]
6. Fisher DA, Smith JF, Pillar JS, St Denis SH, Cheng JB. (1998)
Isolation and characterization of PDE9A, a novel human cGMP-specific phosphodiesterase.
J Biol Chem, 273 (25): 15559-64. [PMID:9624146]
7. Fujishige K, Kotera J, Michibata H, Yuasa K, Takebayashi S, Okumura K, Omori K. (1999)
Cloning and characterization of a novel human phosphodiesterase that hydrolyzes both cAMP and cGMP (PDE10A).
J Biol Chem, 274 (26): 18438-45. [PMID:10373451]
8. Gardner C, Robas N, Cawkill D, Fidock M. (2000)
Cloning and characterization of the human and mouse PDE7B, a novel cAMP-specific cyclic nucleotide phosphodiesterase.
Biochem Biophys Res Commun, 272 (1): 186-92. [PMID:10872825]
9. Hayashi M, Matsushima K, Ohashi H, Tsunoda H, Murase S, Kawarada Y, Tanaka T. (1998)
Molecular cloning and characterization of human PDE8B, a novel thyroid-specific isozyme of 3',5'-cyclic nucleotide phosphodiesterase.
Biochem Biophys Res Commun, 250 (3): 751-6. [PMID:9784418]
10. Lee HM, Park YS, Kim W, Park CS. (2001)
Electrophysiological characteristics of rat gustatory cyclic nucleotide--gated channel expressed in Xenopus oocytes.
J Neurophysiol, 85 (6): 2335-49. [PMID:11387380]
11. Liman ER, Buck LB. (1994)
A second subunit of the olfactory cyclic nucleotide-gated channel confers high sensitivity to cAMP.
Neuron, 13 (3): 611-21. [PMID:7522482]
12. Ludwig A, Zong X, Jeglitsch M, Hofmann F, Biel M. (1998)
A family of hyperpolarization-activated mammalian cation channels.
Nature, 393 (6685): 587-91. [PMID:9634236]
13. Michaeli T, Bloom TJ, Martins T, Loughney K, Ferguson K, Riggs M, Rodgers L, Beavo JA, Wigler M. (1993)
Isolation and characterization of a previously undetected human cAMP phosphodiesterase by complementation of cAMP phosphodiesterase-deficient Saccharomyces cerevisiae.
J Biol Chem, 268 (17): 12925-32. [PMID:8389765]
14. Nache V, Zimmer T, Wongsamitkul N, Schmauder R, Kusch J, Reinhardt L, Bönigk W, Seifert R, Biskup C, Schwede F et al.. (2012)
Differential regulation by cyclic nucleotides of the CNGA4 and CNGB1b subunits in olfactory cyclic nucleotide-gated channels.
Sci Signal, 5 (232): ra48. [PMID:22786723]
15. Peng C, Rich ED, Thor CA, Varnum MD. (2003)
Functionally important calmodulin-binding sites in both NH2- and COOH-terminal regions of the cone photoreceptor cyclic nucleotide-gated channel CNGB3 subunit.
J Biol Chem, 278 (27): 24617-23. [PMID:12730238]
16. Wang J, Chen S, Siegelbaum SA. (2001)
Regulation of hyperpolarization-activated HCN channel gating and cAMP modulation due to interactions of COOH terminus and core transmembrane regions.
J Gen Physiol, 118 (3): 237-50. [PMID:11524455]
17. Yu WP, Grunwald ME, Yau KW. (1996)
Molecular cloning, functional expression and chromosomal localization of a human homolog of the cyclic nucleotide-gated ion channel of retinal cone photoreceptors.
FEBS Lett, 393 (2-3): 211-5. [PMID:8814292]