Identification
- Generic Name
- Cyclic GMP
- DrugBank Accession Number
- DB02315
- Background
Cyclic guanosine monophosphate (Cyclic GMP) is a guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed)
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Cyclic GMP (DB02315)
- Weight
- Average: 345.2053
Monoisotopic: 345.047434275 - Chemical Formula
- C10H12N5O7P
- Synonyms
- 3',5'-cyclic GMP
- cGMP
- Cyclic GMP
- Cyclic guanosine monophosphate
- Guanosine 3',5'-cyclic monophosphate
- Guanosine 3',5'-cyclic phosphate
- Guanosine cyclic monophosphate
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UcGMP-dependent 3',5'-cyclic phosphodiesterase Not Available Humans UPotassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 Not Available Humans UcAMP-dependent protein kinase type I-alpha regulatory subunit Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleotides
- Sub Class
- Cyclic purine nucleotides
- Direct Parent
- 3',5'-cyclic purine nucleotides
- Alternative Parents
- Pentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Pyrimidones / N-substituted imidazoles / Organic phosphoric acids and derivatives / Vinylogous amides show 9 more
- Substituents
- 3',5'-cyclic purine ribonucleotide / 6-oxopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound show 26 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- 3',5'-cyclic purine nucleotide, guanyl ribonucleotide (CHEBI:16356) / 3',5'-Cyclic nuclcleotides (C00942)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- H2D2X058MU
- CAS number
- 7665-99-8
- InChI Key
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N
- 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
- IUPAC Name
- 9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one
- SMILES
- NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0001314
- KEGG Compound
- C00942
- PubChem Compound
- 24316
- PubChem Substance
- 46508914
- ChemSpider
- 22734
- BindingDB
- 50369127
- ChEBI
- 16356
- ChEMBL
- CHEMBL395336
- ZINC
- ZINC000004095501
- PDBe Ligand
- 35G
- Wikipedia
- Cyclic_guanosine_monophosphate
- PDB Entries
- 1be4 / 1bhn / 1mc0 / 1q3e / 1rl3 / 2gx5 / 2k31 / 2ouu / 2q0a / 3cl1 … show 46 more
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 3.79 mg/mL ALOGPS logP -2 ALOGPS logP -2.1 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 1.85 Chemaxon pKa (Strongest Basic) 0.5 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 170.52 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 71.72 m3·mol-1 Chemaxon Polarizability 29.39 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8903 Blood Brain Barrier + 0.8984 Caco-2 permeable - 0.7164 P-glycoprotein substrate Non-substrate 0.6627 P-glycoprotein inhibitor I Non-inhibitor 0.9244 P-glycoprotein inhibitor II Non-inhibitor 0.9844 Renal organic cation transporter Non-inhibitor 0.9263 CYP450 2C9 substrate Non-substrate 0.8264 CYP450 2D6 substrate Non-substrate 0.8382 CYP450 3A4 substrate Non-substrate 0.5285 CYP450 1A2 substrate Non-inhibitor 0.8406 CYP450 2C9 inhibitor Non-inhibitor 0.904 CYP450 2D6 inhibitor Non-inhibitor 0.9159 CYP450 2C19 inhibitor Non-inhibitor 0.9055 CYP450 3A4 inhibitor Non-inhibitor 0.9535 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9816 Ames test Non AMES toxic 0.7791 Carcinogenicity Non-carcinogens 0.8908 Biodegradation Not ready biodegradable 0.9675 Rat acute toxicity 2.4826 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9861 hERG inhibition (predictor II) Non-inhibitor 0.849
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tpr domain binding
- Specific Function
- Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.Isoform PDE2A2: Regulates Mit...
- Gene Name
- PDE2A
- Uniprot ID
- O00408
- Uniprot Name
- cGMP-dependent 3',5'-cyclic phosphodiesterase
- Molecular Weight
- 105715.85 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Voltage-gated sodium channel activity
- Specific Function
- Hyperpolarization-activated ion channel exhibiting weak selectivity for potassium over sodium ions. Contributes to the native pacemaker currents in heart (If) and in neurons (Ih). Can also transpor...
- Gene Name
- HCN2
- Uniprot ID
- Q9UL51
- Uniprot Name
- Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2
- Molecular Weight
- 96949.43 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Ubiquitin protein ligase binding
- Specific Function
- Regulatory subunit of the cAMP-dependent protein kinases involved in cAMP signaling in cells.
- Gene Name
- PRKAR1A
- Uniprot ID
- P10644
- Uniprot Name
- cAMP-dependent protein kinase type I-alpha regulatory subunit
- Molecular Weight
- 42981.28 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Sekine T, Watanabe N, Hosoyamada M, Kanai Y, Endou H: Expression cloning and characterization of a novel multispecific organic anion transporter. J Biol Chem. 1997 Jul 25;272(30):18526-9. [Article]
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:14