cyclic GMP   Click here for help

GtoPdb Ligand ID: 2347

Abbreviated name: cGMP
Synonyms: 3',5'-cyclic GMP | 3',5'-guanosine monophosphate | cyclic guanosine monophosphate
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 10
Hydrogen bond donors 4
Rotatable bonds 1
Topological polar surface area 184.62
Molecular weight 345.05
XLogP -2.44
No. Lipinski's rules broken 0
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Canonical SMILES OC1C2OP(=O)(O)OCC2OC1n1cnc2c1nc(N)[nH]c2=O
Isomeric SMILES O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O
InChI InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/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. Chen TY, Illing M, Molday LL, Hsu YT, Yau KW, Molday RS. (1994)
Subunit 2 (or beta) of retinal rod cGMP-gated cation channel is a component of the 240-kDa channel-associated protein and mediates Ca(2+)-calmodulin modulation.
Proc Natl Acad Sci USA, 91 (24): 11757-61. [PMID:7526403]
3. Dhallan RS, Macke JP, Eddy RL, Shows TB, Reed RR, Yau KW, Nathans J. (1992)
Human rod photoreceptor cGMP-gated channel: amino acid sequence, gene structure, and functional expression.
J Neurosci, 12 (8): 3248-56. [PMID:1379636]
4. Dryja TP, Finn JT, Peng YW, McGee TL, Berson EL, Yau KW. (1995)
Mutations in the gene encoding the alpha subunit of the rod cGMP-gated channel in autosomal recessive retinitis pigmentosa.
Proc Natl Acad Sci USA, 92 (22): 10177-81. [PMID:7479749]
5. 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]
6. Finn JT, Krautwurst D, Schroeder JE, Chen TY, Reed RR, Yau KW. (1998)
Functional co-assembly among subunits of cyclic-nucleotide-activated, nonselective cation channels, and across species from nematode to human.
Biophys J, 74 (3): 1333-45. [PMID:9512030]
7. 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]
8. 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]
9. 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]
10. 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]
11. Gordon SE, Zagotta WN. (1995)
A histidine residue associated with the gate of the cyclic nucleotide-activated channels in rod photoreceptors.
Neuron, 14 (1): 177-83. [PMID:7530019]
12. 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]
13. 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]
14. 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]
15. 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]
16. 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]
17. 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]
18. Paoletti P, Young EC, Siegelbaum SA. (1999)
C-Linker of cyclic nucleotide-gated channels controls coupling of ligand binding to channel gating.
J Gen Physiol, 113 (1): 17-34. [PMID:9874685]
19. 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]
20. Wissinger B, Müller F, Weyand I, Schuffenhauer S, Thanos S, Kaupp UB, Zrenner E. (1997)
Cloning, chromosomal localization and functional expression of the gene encoding the alpha-subunit of the cGMP-gated channel in human cone photoreceptors.
Eur J Neurosci, 9 (12): 2512-21. [PMID:9517456]
21. 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]
22. Zheng J, Trudeau MC, Zagotta WN. (2002)
Rod cyclic nucleotide-gated channels have a stoichiometry of three CNGA1 subunits and one CNGB1 subunit.
Neuron, 36 (5): 891-6. [PMID:12467592]