Phosphoaminophosphonic acid guanylate ester

Identification

Name
Phosphoaminophosphonic acid guanylate ester
Accession Number
DB02082  (EXPT01658)
Type
Small Molecule
Groups
Experimental
Description

A non-hydrolyzable analog of GTP, in which the oxygen atom bridging the beta to the gamma phosphate is replaced by a nitrogen atom. It binds tightly to G-protein in the presence of Mg2+. The nucleotide is a potent stimulator of adenylate cyclase.

Structure
Thumb
Synonyms
  • 5'-guanylylimidodiphosphate
  • GMP-PNP
  • Gpp(NH)p
  • Guanosine 5'-[beta,gamma-imido]triphosphate
  • Guanylyl imidodiphosphate
Categories
UNII
Not Available
CAS number
34273-04-6
Weight
Average: 522.1957
Monoisotopic: 522.006644196
Chemical Formula
C10H17N6O13P3
InChI Key
UQABYHGXWYXDTK-UUOKFMHZSA-N
InChI
InChI=1S/C10H17N6O13P3/c11-10-13-7-4(8(19)14-10)12-2-16(7)9-6(18)5(17)3(28-9)1-27-32(25,26)29-31(23,24)15-30(20,21)22/h2-3,5-6,9,17-18H,1H2,(H,25,26)(H3,11,13,14,19)(H4,15,20,21,22,23,24)/t3-,5-,6-,9-/m1/s1
IUPAC Name
({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}amino)phosphonic acid
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)NP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
URas-related protein Rab-8BNot AvailableHumans
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
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

References

General References
Not Available
External Links
PubChem Compound
36735
PubChem Substance
46506592
ChemSpider
33738
BindingDB
81791
ChEBI
78408
ChEMBL
CHEMBL1233085
ZINC
ZINC000037868676
PDBe Ligand
GNP
PDB Entries
1agp / 1am4 / 1b23 / 1cf4 / 1cip / 1ctq / 1day / 1e0a / 1eft / 1ek0
show 467 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 Solubility8.9 mg/mLALOGPS
logP-0.88ALOGPS
logP-5.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)-1.9ChemAxon
pKa (Strongest Basic)20.4ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area298.6 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity109.77 m3·mol-1ChemAxon
Polarizability40.6 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5813
Blood Brain Barrier+0.8498
Caco-2 permeable-0.7304
P-glycoprotein substrateNon-substrate0.5987
P-glycoprotein inhibitor INon-inhibitor0.9079
P-glycoprotein inhibitor IINon-inhibitor0.9777
Renal organic cation transporterNon-inhibitor0.9568
CYP450 2C9 substrateNon-substrate0.8639
CYP450 2D6 substrateNon-substrate0.8329
CYP450 3A4 substrateNon-substrate0.5467
CYP450 1A2 substrateNon-inhibitor0.8485
CYP450 2C9 inhibitorNon-inhibitor0.905
CYP450 2D6 inhibitorNon-inhibitor0.9001
CYP450 2C19 inhibitorNon-inhibitor0.8995
CYP450 3A4 inhibitorNon-inhibitor0.9138
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9774
Ames testNon AMES toxic0.8162
CarcinogenicityNon-carcinogens0.9001
BiodegradationNot ready biodegradable0.9422
Rat acute toxicity2.4914 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9625
hERG inhibition (predictor II)Non-inhibitor0.8407
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 monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Pyrimidones / Monoalkyl phosphates / N-substituted imidazoles / Vinylogous amides
show 10 more
Substituents
Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Pentose monosaccharide / Imidazopyrimidine
show 31 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
nucleoside triphosphate analogue (CHEBI:78408)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Receptor binding
Specific Function
The small GTPases Rab are key regulators of intracellular membrane trafficking, from the formation of transport vesicles to their fusion with membranes. Rabs cycle between an inactive GDP-bound for...
Gene Name
RAB8B
Uniprot ID
Q92930
Uniprot Name
Ras-related protein Rab-8B
Molecular Weight
23583.84 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]

Drug created on June 13, 2005 07:24 / Updated on May 02, 2020 03:38

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