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
Compound class: Metabolite or derivative
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
InChI Key IVOMOUWHDPKRLL-KQYNXXCUSA-N
References
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]