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Identification
NameGuanosine-5',3'-Tetraphosphate
Accession NumberDB04022  (EXPT01534)
Typesmall molecule
Groupsexperimental
Description

Guanosine 5'-diphosphate 2'(3')-diphosphate. A guanine nucleotide containing four phosphate groups. Two phosphate groups are esterified to the sugar moiety in the 5' position and the other two in the 2' or 3' position. This nucleotide serves as a messenger to turn off the synthesis of ribosomal RNA when amino acids are not available for protein synthesis. Synonym: magic spot I. [PubChem]

Structure
Thumb
SynonymsNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 603.1603
Monoisotopic: 602.956990191
Chemical FormulaC10H17N5O17P4
InChI KeyBUFLLCUFNHESEH-FULWYAMNSA-N
InChI
InChI=1S/C10H17N5O17P4/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(30-36(26,27)32-34(21,22)23)3(29-9)1-28-35(24,25)31-33(18,19)20/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5+,6-,9+/m0/s1
IUPAC Name
[({[(2S,3R,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-4-hydroxy-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@@H](CO[P@](O)(=O)OP(O)(O)=O)[C@H](O[P@](O)(=O)OP(O)(O)=O)[C@H]2O)C(=O)N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassGlycosyl Compounds
Direct parentPurine Ribonucleoside Diphosphates
Alternative parentsPurine Ribonucleoside 3',5'-Bisphosphates; Hypoxanthines; Organic Pyrophosphates; Pyrimidones; Primary Aromatic Amines; N-substituted Imidazoles; Organic Phosphoric Acids; Organophosphate Esters; Tetrahydrofurans; Oxolanes; Secondary Alcohols; Polyamines; Ethers
Substituentsorganic pyrophosphate; hypoxanthine; imidazopyrimidine; purine; pyrimidone; organic phosphate; phosphoric acid ester; n-substituted imidazole; primary aromatic amine; pyrimidine; tetrahydrofuran; imidazole; azole; oxolane; secondary alcohol; polyamine; ether; alcohol; primary amine; organonitrogen compound; amine
Classification descriptionThis compound belongs to the purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.5479
Blood Brain Barrier + 0.9175
Caco-2 permeable - 0.7609
P-glycoprotein substrate Non-substrate 0.662
P-glycoprotein inhibitor I Non-inhibitor 0.9067
P-glycoprotein inhibitor II Non-inhibitor 0.9334
Renal organic cation transporter Non-inhibitor 0.9421
CYP450 2C9 substrate Non-substrate 0.8433
CYP450 2D6 substrate Non-substrate 0.84
CYP450 3A4 substrate Non-substrate 0.5579
CYP450 1A2 substrate Non-inhibitor 0.8603
CYP450 2C9 substrate Non-inhibitor 0.9182
CYP450 2D6 substrate Non-inhibitor 0.8987
CYP450 2C19 substrate Non-inhibitor 0.9229
CYP450 3A4 substrate Non-inhibitor 0.9382
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9737
Ames test Non AMES toxic 0.8765
Carcinogenicity Non-carcinogens 0.9014
Biodegradation Not ready biodegradable 0.964
Rat acute toxicity 2.4724 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9768
hERG inhibition (predictor II) Non-inhibitor 0.8504
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility8.42e+00 g/lALOGPS
logP-0.29ALOGPS
logP-4ChemAxon
logS-1.9ALOGPS
pKa (strongest acidic)1.1ChemAxon
pKa (strongest basic)1.63ChemAxon
physiological charge-5ChemAxon
hydrogen acceptor count16ChemAxon
hydrogen donor count9ChemAxon
polar surface area341.34ChemAxon
rotatable bond count10ChemAxon
refractivity108.11ChemAxon
polarizability44.27ChemAxon
number of rings3ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound46936862
PubChem Substance46508997
ChEBI17633
ChEMBL
HETG4P
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Xanthine phosphoribosyltransferase

Kind: protein

Organism: Bacillus subtilis (strain 168)

Pharmacological action: unknown

Components

Name UniProt ID Details
Xanthine phosphoribosyltransferase P42085 Details

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
  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

2. GTPase ObgE

Kind: protein

Organism: Bacillus subtilis (strain 168)

Pharmacological action: unknown

Components

Name UniProt ID Details
GTPase ObgE P20964 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:23