Record Information
Version1.0
Creation Date2016-09-30 22:44:00 UTC
Update Date2020-05-21 15:38:42 UTC
BMDB IDBMDB0001314
Secondary Accession Numbers
  • BMDB01314
Metabolite Identification
Common NameCyclic GMP
DescriptionCyclic GMP, also known as CGMP or GMP, cyclic, 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. Cyclic GMP is possibly soluble (in water) and a moderately basic compound (based on its pKa). Cyclic GMP exists in all living species, ranging from bacteria to humans. In cattle, cyclic GMP is involved in the metabolic pathway called ion channels and their functional role in vascular endothelium pathway.
Structure
Thumb
Synonyms
ValueSource
CGMPChEBI
Guanosine 3',5'-cyclic monophosphateChEBI
Guanosine 3',5'-cyclic phosphateChEBI
Guanosine cyclic monophosphateChEBI
Guanosine 3',5'-cyclic monophosphoric acidGenerator
Guanosine 3',5'-cyclic phosphoric acidGenerator
Guanosine cyclic monophosphoric acidGenerator
3',5'-Cyclic GMPHMDB
3',5'-GuanosineHMDB
3',5'-Guanosine monophosphateHMDB
Cyclic 3',5'-guanosine monophosphateHMDB
Cyclic guanosine 3',5'-monophosphateHMDB
Cyclic-GMPHMDB
Guanosine 3',5'-cyclic-monophosphateHMDB
Guanosine 3',5'-monophosphateHMDB
Guanosine cyclic-monophosphateHMDB
Guanosine-cyclic-phosphoric-acidHMDB
Cyclic 3',5'-monophosphate, guanosineHMDB
GMP, CyclicHMDB
Guanosine cyclic-3',5'-monophosphateHMDB
monoPhosphate, guanosine cyclicHMDB
3',5'-monoPhosphate, guanosine cyclicHMDB
Cyclic-3',5'-monophosphate, guanosineHMDB
Guanosine cyclic 3',5'-monophosphateHMDB
Guanosine cyclic 3,5 monophosphateHMDB
Cyclic monophosphate, guanosineHMDB
Guanosine cyclic 3',5' monophosphateHMDB
Chemical FormulaC10H12N5O7P
Average Molecular Weight345.2053
Monoisotopic Molecular Weight345.047434275
IUPAC Name9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one
Traditional Namecyclic-GMP
CAS Registry Number7665-99-8
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
InChI Identifier
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
InChI KeyZOOGRGPOEVQQDX-UUOKFMHZSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent3',5'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 3',5'-cyclic purine ribonucleotide
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Vinylogous amide
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Golgi
  • Nucleus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-2.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.05ChemAxon
pKa (Strongest Basic)1.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m³·mol⁻¹ChemAxon
Polarizability29.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-2972000000-80320c485cef8d6d91adView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-001i-2972000000-80320c485cef8d6d91adView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f76-3901000000-c970aad6713a547b2d8fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4590100000-edbc82f84eca5a64f5a5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uec-2904000000-85af5865e64af24e7691View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0904000000-e34bb3204af3b18ddf11View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-35925bce602ee60e24eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0904000000-93fabfb961527e02671eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0907000000-60b56b2fcc437a04a7b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udj-0908000000-16c413e42a41fa5e7262View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udl-3904000000-051a745d5db4f607a935View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0901000000-a2a6721a5a98c3d3e945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0907000000-ae3d3b4dfb6aefdd34c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udj-0904000000-fd635f17953dbbff039bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0902000000-36d8b1a240f9f6471886View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-4c75be42ba8dbd671bbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-06ee1dc93418cde4fe39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-db6612a4a4b92db51507View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-8455683aa1bc0141dd38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0900000000-196c267f58b468d3a8f5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-7637808812023bf3fb33View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-34c09019debbbd2ef2a6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0009000000-db049b28da12291887ceView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0904000000-65ab088e129c01a9b140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-fc45e23a1d622d9a6848View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0900000000-d7d3bc38b1c32086753eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-1709000000-881760c573673e832db8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-2900000000-f74b8ec55fbea3fdf8cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003u-9600000000-d7f00c8f8cec474c7304View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Golgi
  • Nucleus
Biospecimen Locations
  • Kidney
  • Liver
  • Mammary Gland
  • Platelet
  • Smooth Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Smooth MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001314
DrugBank IDDB02315
Phenol Explorer Compound IDNot Available
FooDB IDFDB030764
KNApSAcK IDC00019673
Chemspider ID22734
KEGG Compound IDC00942
BioCyc IDNot Available
BiGG ID1485267
Wikipedia LinkCyclic guanosine monophosphate
METLIN ID6152
PubChem Compound24316
PDB IDNot Available
ChEBI ID16356
References
Synthesis ReferenceSekhar, Konjeti R.; Grondin, Pascal; Francis, Sharron H.; Corbin, Jackie D. Design and synthesis of xanthines and cyclic GMP analogs as potent inhibitors of PDE5. Phosphodiesterase Inhibitors (1996), 135-146.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Signal transduction mechanisms
Specific function:
Mediates responses to nitric oxide (NO) by catalyzing the biosynthesis of the signaling molecule cGMP.
Gene Name:
GUCY1B1
Uniprot ID:
P16068
Molecular weight:
70502.0
Reactions
Guanosine triphosphate → Cyclic GMPdetails
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
As cone-specific cGMP phosphodiesterase, it plays an essential role in light detection and cone phototransduction by rapidly decreasing intracellular levels of cGMP.
Gene Name:
PDE6C
Uniprot ID:
P16586
Molecular weight:
98798.0
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
This protein participates in processes of transmission and amplification of the visual signal.
Gene Name:
PDE6A
Uniprot ID:
P11541
Molecular weight:
99341.0
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
This protein participates in processes of transmission and amplification of the visual signal. Necessary for the formation of a functional phosphodiesterase holoenzyme.
Gene Name:
PDE6B
Uniprot ID:
P23439
Molecular weight:
98331.0
General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase a
Specific function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6H
Uniprot ID:
P22571
Molecular weight:
9102.0
General function:
Involved in 3',5'-cyclic-GMP phosphodiesterase activity
Specific function:
Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP (PubMed:8530505). Specifically regulates nitric-oxide-generated cGMP (By similarity).
Gene Name:
PDE5A
Uniprot ID:
Q28156
Molecular weight:
98627.0
General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase a
Specific function:
Participates in processes of transmission and amplification of the visual signal. cGMP-PDEs are the effector molecules in G-protein-mediated phototransduction in vertebrate rods and cones.
Gene Name:
PDE6G
Uniprot ID:
P04972
Molecular weight:
9669.0
General function:
Signal transduction mechanisms
Specific function:
Receptor for the C-type natriuretic peptide NPPC/CNP hormone. Has guanylate cyclase activity upon binding of its ligand. May play a role in the regulation of skeletal growth.
Gene Name:
NPR2
Uniprot ID:
P46197
Molecular weight:
117146.0
General function:
Signal transduction mechanisms
Specific function:
Responsible for the synthesis of cyclic GMP (cGMP) in rods and cones of photoreceptors (PubMed:9571173, PubMed:9175772). Plays an essential role in phototransduction, by mediating cGMP replenishment (PubMed:9571173, PubMed:9175772). May also participate in the trafficking of membrane-asociated proteins to the photoreceptor outer segment membrane (By similarity).
Gene Name:
GUCY2F
Uniprot ID:
O02740
Molecular weight:
124262.0
General function:
Signal transduction mechanisms
Specific function:
Not Available
Gene Name:
GUCY1A1
Uniprot ID:
P19687
Molecular weight:
77533.0
Reactions
Guanosine triphosphate → Cyclic GMPdetails
General function:
Signal transduction mechanisms
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
O77690
Molecular weight:
122710.0
General function:
Signal transduction mechanisms
Specific function:
Catalyzes the synthesis of cyclic GMP (cGMP) in rods and cones of photoreceptors. Plays an essential role in phototransduction, by mediating cGMP replenishment (PubMed:8102054). May also participate in the trafficking of membrane-asociated proteins to the photoreceptor outer segment membrane (By similarity).
Gene Name:
GUCY2D
Uniprot ID:
P55203
Molecular weight:
120369.0
General function:
Involved in ATP binding
Specific function:
Serine/threonine protein kinase that acts as key mediator of the nitric oxide (NO)/cGMP signaling pathway. GMP binding activates PRKG1, which phosphorylates serines and threonines on many cellular proteins. Numerous protein targets for PRKG1 phosphorylation are implicated in modulating cellular calcium, but the contribution of each of these targets may vary substantially among cell types. Proteins that are phosphorylated by PRKG1 regulate platelet activation and adhesion, smooth muscle contraction, cardiac function, gene expression, feedback of the NO-signaling pathway, and other processes involved in several aspects of the CNS like axon guidance, hippocampal and cerebellar learning, circadian rhythm and nociception. Smooth muscle relaxation is mediated through lowering of intracellular free calcium, by desensitization of contractile proteins to calcium, and by decrease in the contractile state of smooth muscle or in platelet activation. Regulates intracellular calcium levels via several pathways: phosphorylates MRVI1/IRAG and inhibits IP3-induced Ca(2+) release from intracellular stores, phosphorylation of KCNMA1 (BKCa) channels decreases intracellular Ca(2+) levels, which leads to increased opening of this channel. PRKG1 phosphorylates the canonical transient receptor potential channel (TRPC) family which inactivates the associated inward calcium current. Another mode of action of NO/cGMP/PKGI signaling involves PKGI-mediated inactivation of the Ras homolog gene family member A (RhoA). Phosphorylation of RHOA by PRKG1 blocks the action of this protein in myriad processes: regulation of RHOA translocation; decreasing contraction; controlling vesicle trafficking, reduction of myosin light chain phosphorylation resulting in vasorelaxation. Activation of PRKG1 by NO signaling alters also gene expression in a number of tissues. In smooth muscle cells, increased cGMP and PRKG1 activity influence expression of smooth muscle-specific contractile proteins, levels of proteins in the NO/cGMP signaling pathway, down-regulation of the matrix proteins osteopontin and thrombospondin-1 to limit smooth muscle cell migration and phenotype. Regulates vasodilator-stimulated phosphoprotein (VASP) functions in platelets and smooth muscle (By similarity).
Gene Name:
PRKG1
Uniprot ID:
P00516
Molecular weight:
76419.0
General function:
Involved in 3',5'-cyclic-nucleotide phosphodiesterase a
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.
Gene Name:
PDE2A
Uniprot ID:
P14099
Molecular weight:
103228.0
General function:
Involved in calcium ion binding
Specific function:
Intracellular channel that mediates calcium release from the endoplasmic reticulum following stimulation by inositol 1,4,5-trisphosphate. Involved in the regulation of epithelial secretion of electrolytes and fluid through the interaction with AHCYL1 Plays a role in ER stress-induced apoptosis. Cytoplasmic calcium released from the ER triggers apoptosis by the activation of CaM kinase II, eventually leading to the activation of downstream apoptosis pathways.
Gene Name:
ITPR1
Uniprot ID:
Q9TU34
Molecular weight:
308318.0
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Subunit of the rod cyclic GMP-gated cation channel, which is involved in the final stage of the phototransduction pathway. When light hits rod photoreceptors, cGMP concentrations decrease causing rapid closure of CNGA1/CNGB1 channels and, therefore, hyperpolarization of the membrane potential.
Gene Name:
CNGA1
Uniprot ID:
Q00194
Molecular weight:
79602.0
General function:
Signal transduction mechanisms
Specific function:
Visual signal transduction is mediated by a G-protein coupled cascade using cGMP as second messenger. This protein can be activated by cyclic GMP which leads to an opening of the cation channel and thereby causing a depolarization of cone photoreceptors. Essential for the generation of light-evoked electrical responses in the red-, green- and blue sensitive cones Induced a flickering channel gating, weakened the outward rectification in the presence of extracellular calcium, increased sensitivity for L-cis diltiazem and enhanced the cAMP efficacy of the channel when coexpressed with CNGB3 (By similarity). Could be responsible for cGMP-induced calcium entry in cells other than sensory cells. Might be involved in chemotaxis of sperm.
Gene Name:
CNGA3
Uniprot ID:
Q29441
Molecular weight:
81132.0