Identification
NameCyclic Guanosine Monophosphate
Accession NumberDB02315  (EXPT02518, DB04536)
TypeSmall Molecule
GroupsExperimental
Description

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)

Structure
Thumb
Synonyms
Guanosine-3',5'-monophosphate
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIIH2D2X058MU
CAS number7665-99-8
WeightAverage: 345.2053
Monoisotopic: 345.047434275
Chemical FormulaC10H12N5O7P
InChI KeyZOOGRGPOEVQQDX-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-2λ⁵-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[[email protected]]3[[email protected]]2O)C(=O)N1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
cGMP-dependent 3',5'-cyclic phosphodiesteraseProteinunknownNot AvailableHumanO00408 details
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2ProteinunknownNot AvailableHumanQ9UL51 details
cAMP-dependent protein kinase type I-alpha regulatory subunitProteinunknownNot AvailableHumanP10644 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.79 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m3·mol-1ChemAxon
Polarizability29.19 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.8903
Blood Brain Barrier+0.8984
Caco-2 permeable-0.7164
P-glycoprotein substrateNon-substrate0.6627
P-glycoprotein inhibitor INon-inhibitor0.9244
P-glycoprotein inhibitor IINon-inhibitor0.9844
Renal organic cation transporterNon-inhibitor0.9263
CYP450 2C9 substrateNon-substrate0.8264
CYP450 2D6 substrateNon-substrate0.8382
CYP450 3A4 substrateNon-substrate0.5285
CYP450 1A2 substrateNon-inhibitor0.8406
CYP450 2C9 inhibitorNon-inhibitor0.904
CYP450 2D6 inhibitorNon-inhibitor0.9159
CYP450 2C19 inhibitorNon-inhibitor0.9055
CYP450 3A4 inhibitorNon-inhibitor0.9535
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9816
Ames testNon AMES toxic0.7791
CarcinogenicityNon-carcinogens0.8908
BiodegradationNot ready biodegradable0.9675
Rat acute toxicity2.4826 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9861
hERG inhibition (predictor II)Non-inhibitor0.849
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-001i-2972000000-80320c485cef8d6d91adView in MoNA
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 - LC-ESI-TOF , 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
Taxonomy
ClassificationNot classified

Targets

Kind
Protein
Organism
Human
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 Mitochondrial cAMP Levels and Respiration.
Gene Name:
PDE2A
Uniprot ID:
O00408
Molecular Weight:
105715.85 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:10592235 ]
Kind
Protein
Organism
Human
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 transport ammonium in the distal nephron. Produces a large instantaneous current. Modulated by intracellular chloride ions and pH; acidic pH shifts the activation to more negative voltages (By similarity).
Gene Name:
HCN2
Uniprot ID:
Q9UL51
Molecular Weight:
96949.43 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:10592235 ]
Kind
Protein
Organism
Human
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
Molecular Weight:
42981.28 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. 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. [PubMed:17016423 ]
  3. 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. [PubMed:10592235 ]

Transporters

Kind
Protein
Organism
Human
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 molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. 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. [PubMed:9228014 ]
Drug created on June 13, 2005 07:24 / Updated on July 18, 2017 17:08