Identification
NamePhosphoaminophosphonic Acid Guanylate Ester
Accession NumberDB02082  (EXPT01658)
TypeSmall Molecule
GroupsExperimental
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. [PubChem]

Structure
Thumb
SynonymsNot Available
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
UNIINot Available
CAS numberNot Available
WeightAverage: 522.1957
Monoisotopic: 522.006644196
Chemical FormulaC10H17N6O13P3
InChI KeyUQABYHGXWYXDTK-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
[H][[email protected]]1(COP(O)(=O)OP(O)(=O)NP(O)(O)=O)O[[email protected]@]([H])(N2C=NC3=C2NC(=N)N=C3O)[[email protected]]([H])(O)[[email protected]]1([H])O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Ras-related protein Rab-8BProteinunknownNot AvailableHumanQ92930 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 Solubility7.0 mg/mLALOGPS
logP-1ALOGPS
logP-4.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.34ChemAxon
pKa (Strongest Basic)3.58ChemAxon
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
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside monophosphates
Alternative ParentsPentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Aminopyrimidines and derivatives / Pyrimidones / Monoalkyl phosphates / Primary aromatic amines / N-substituted imidazoles
SubstituentsPurine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Pentose monosaccharide / Imidazopyrimidine
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsnucleoside triphosphate analogue (CHEBI:78408 )

Targets

Kind
Protein
Organism
Human
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 form and an active GTP-bound form that is able to recruit to membranes different sets of downstream effectors directly responsible for vesicle formation, movement, tethering and fusion. That Rab may be i...
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 September 01, 2017 10:47