NAV

Guanosine 5'-diphosphate 2':3'-cyclic monophosphate

Identification

Generic Name
Guanosine 5'-diphosphate 2':3'-cyclic monophosphate
DrugBank Accession Number
DB02836
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 505.1651
Monoisotopic: 504.980095095
Chemical Formula
C10H14N5O13P3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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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
Not Available
Chemical TaxonomyProvided by Classyfire
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
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Substituents
1,3_dioxaphospholane / 2',3'-cyclic purine ribonucleotide / 6-oxopurine / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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)-6-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-2-hydroxy-2-oxo-tetrahydro-2H-2lambda5-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
SMILES
[H]N([H])C1=NC(=O)C2=C(N1[H])N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@]2([H])O[P@](O)(=O)O[C@@]12[H]

References

General References
Not Available
PubChem Compound
444825
PubChem Substance
46508518
ChemSpider
392639
ZINC
ZINC000016051591
PDBe Ligand
GPX
PDB Entries
1ch8 / 1vj7

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility6.92 mg/mLALOGPS
logP-0.42ALOGPS
logP-2.7Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)-0.2Chemaxon
pKa (Strongest Basic)2Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count13Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area263.58 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity93.03 m3·mol-1Chemaxon
Polarizability38.21 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/MSsplash10-0a4i-0000090000-cdfec987d3b5e86c22a9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0000190000-f08933796375b03474cf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0100910000-06bd65145f2763e637d1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pbi-0000920000-7ef24daf373b445f74b9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a7i-0401900000-a4677121a3167a89a51e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a6r-4900300000-3f8bb2c7d1e829ca33d9
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.40562
predicted
DeepCCS 1.0 (2019)
[M+H]+179.80142
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.71394
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Adenylosuccinate synthetase
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. [Article]
  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. [Article]
Details2. Bifunctional (p)ppGpp synthase/hydrolase RelA
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52