Cyclic Guanosine Monophosphate

Identification

Name
Cyclic Guanosine Monophosphate
Accession Number
DB02315  (EXPT02518, DB04536)
Type
Small Molecule
Groups
Experimental
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
Categories
Not Available
UNII
H2D2X058MU
CAS number
7665-99-8
Weight
Average: 345.2053
Monoisotopic: 345.047434275
Chemical Formula
C10H12N5O7P
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-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[C@H]3[C@H]2O)C(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UcGMP-dependent 3',5'-cyclic phosphodiesteraseNot AvailableHuman
UPotassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2Not AvailableHuman
UcAMP-dependent protein kinase type I-alpha regulatory subunitNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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
HET
35G
PDB Entries
1be4 / 1bhn / 1mc0 / 1q3e / 1rl3 / 2gx5 / 2k31 / 2ouu / 2q0a / 3cl1
show 20 more

Clinical Trials

Clinical Trials
Not Available

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
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
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (4 TMS)GC-MSsplash10-001i-2972000000-80320c485cef8d6d91ad
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-2972000000-80320c485cef8d6d91ad
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0904000000-65ab088e129c01a9b140
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900000000-fc45e23a1d622d9a6848
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0900000000-d7d3bc38b1c32086753e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f6x-1709000000-881760c573673e832db8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2900000000-f74b8ec55fbea3fdf8cd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-003u-9600000000-d7f00c8f8cec474c7304
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0uec-2904000000-85af5865e64af24e7691
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0904000000-e34bb3204af3b18ddf11
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0908000000-35925bce602ee60e24ee
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0904000000-93fabfb961527e02671e
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0907000000-60b56b2fcc437a04a7b8
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udj-0908000000-16c413e42a41fa5e7262
MS/MS Spectrum - , negativeLC-MS/MSsplash10-0udl-3904000000-051a745d5db4f607a935
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0udi-0901000000-a2a6721a5a98c3d3e945
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udj-0907000000-ae3d3b4dfb6aefdd34c3
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udj-0904000000-fd635f17953dbbff039b
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0902000000-36d8b1a240f9f6471886
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0009000000-4c75be42ba8dbd671bbf
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0009000000-06ee1dc93418cde4fe39
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-db6612a4a4b92db51507
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-8455683aa1bc0141dd38
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0udi-0900000000-196c267f58b468d3a8f5
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0009000000-7637808812023bf3fb33
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0009000000-34c09019debbbd2ef2a6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0002-0009000000-db049b28da12291887ce
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-0900000000-c1eb6327e06d564ab1ae

Taxonomy

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 / Pentose phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Purinone / Imidazopyrimidine / Purine
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
3',5'-cyclic purine nucleotide, guanyl ribonucleotide (CHEBI:16356) / 3',5'-Cyclic nuclcleotides (C00942)

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 Mit...
Gene Name
PDE2A
Uniprot ID
O00408
Uniprot Name
cGMP-dependent 3',5'-cyclic phosphodiesterase
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 transpor...
Gene Name
HCN2
Uniprot ID
Q9UL51
Uniprot Name
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2
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
Uniprot Name
cAMP-dependent protein kinase type I-alpha regulatory subunit
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 ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
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 November 02, 2018 05:15