Guanosine 5'-Diphosphate 2':3'-Cyclic Monophosphate

Identification

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Name
Guanosine 5'-Diphosphate 2':3'-Cyclic Monophosphate
Accession Number
DB02836  (EXPT01643)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 505.1651
Monoisotopic: 504.980095095
Chemical Formula
C10H14N5O13P3
InChI Key
NGYWTCOGOZELRS-UUOKFMHZSA-N
InChI
InChI=1S/C10H14N5O13P3/c11-10-13-7-4(8(16)14-10)12-2-15(7)9-6-5(26-31(22,23)27-6)3(25-9)1-24-30(20,21)28-29(17,18)19/h2-3,5-6,9H,1H2,(H,20,21)(H,22,23)(H2,17,18,19)(H3,11,13,14,16)/t3-,5-,6-,9-/m1/s1
IUPAC Name
[({[(3aR,4R,6R,6aR)-2-hydroxy-6-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
SMILES
[H][C@]1(COP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]2([H])OP(O)(=O)O[C@]12[H]

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAdenylosuccinate synthetaseNot AvailableEscherichia coli (strain K12)
UBifunctional (p)ppGpp synthase/hydrolase RelANot AvailableStreptococcus dysgalactiae subsp. equisimilis
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
PubChem Compound
444825
PubChem Substance
46508518
ChemSpider
392639
HET
GPX
PDB Entries
1ch8 / 1vj7

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 Solubility6.67 mg/mLALOGPS
logP-0.86ALOGPS
logP-2.5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.48ChemAxon
pKa (Strongest Basic)4.94ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area264.57 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity104.04 m3·mol-1ChemAxon
Polarizability38.22 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.6564
Blood Brain Barrier+0.9474
Caco-2 permeable-0.7399
P-glycoprotein substrateNon-substrate0.6835
P-glycoprotein inhibitor INon-inhibitor0.9321
P-glycoprotein inhibitor IINon-inhibitor0.9611
Renal organic cation transporterNon-inhibitor0.9467
CYP450 2C9 substrateNon-substrate0.8647
CYP450 2D6 substrateNon-substrate0.8343
CYP450 3A4 substrateNon-substrate0.5882
CYP450 1A2 substrateNon-inhibitor0.8589
CYP450 2C9 inhibitorNon-inhibitor0.8915
CYP450 2D6 inhibitorNon-inhibitor0.8847
CYP450 2C19 inhibitorNon-inhibitor0.8991
CYP450 3A4 inhibitorNon-inhibitor0.9154
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9748
Ames testNon AMES toxic0.8391
CarcinogenicityNon-carcinogens0.886
BiodegradationNot ready biodegradable0.9577
Rat acute toxicity2.4828 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9814
hERG inhibition (predictor II)Non-inhibitor0.8653
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside diphosphates
Alternative Parents
2',3'-cyclic purine nucleotides / Ribonucleoside 3'-phosphates / Pentose phosphates / 6-oxopurines / Hypoxanthines / Organic pyrophosphates / Monosaccharide phosphates / Pyrimidones / Aminopyrimidines and derivatives / Monoalkyl phosphates
show 11 more
Substituents
Purine ribonucleoside diphosphate / 2',3'-cyclic purine ribonucleotide / Ribonucleoside 3'-phosphate / Pentose phosphate / Pentose-5-phosphate / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Organic pyrophosphate / Imidazopyrimidine
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Plays an important role in the de novo pathway of purine nucleotide biosynthesis. Catalyzes the first committed step in the biosynthesis of AMP from IMP.
Gene Name
purA
Uniprot ID
P0A7D4
Uniprot Name
Adenylosuccinate synthetase
Molecular Weight
47344.585 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]
Kind
Protein
Organism
Streptococcus dysgalactiae subsp. equisimilis
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
In eubacteria ppGpp (guanosine 3'-diphosphate 5-' diphosphate) is a mediator of the stringent response that coordinates a variety of cellular activities in response to changes in nutritional abunda...
Gene Name
relA
Uniprot ID
Q54089
Uniprot Name
Bifunctional (p)ppGpp synthase/hydrolase RelA
Molecular Weight
83912.61 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]

Drug created on June 13, 2005 07:24 / Updated on August 02, 2019 07:10