Guanosine-5',3'-Tetraphosphate

Identification

Name
Guanosine-5',3'-Tetraphosphate
Accession Number
DB04022  (EXPT01534)
Type
Small Molecule
Groups
Experimental
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
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 603.1603
Monoisotopic: 602.956990191
Chemical Formula
C10H17N5O17P4
InChI Key
BUFLLCUFNHESEH-UUOKFMHZSA-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-/m1/s1
IUPAC Name
{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})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@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UXanthine phosphoribosyltransferaseNot AvailableBacillus subtilis (strain 168)
UGTPase ObgENot AvailableBacillus subtilis (strain 168)
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
Human Metabolome Database
HMDB0059638
KEGG Compound
C01228
PubChem Compound
439450
PubChem Substance
46508997
ChemSpider
388557
ChEBI
17633
HET
G4P
PDB Entries
1lnz / 1smy / 1y0b / 2j4r / 3n75 / 3vr1 / 4edt / 4hnx / 4jk1 / 4jkr
show 9 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 Solubility10.3 mg/mLALOGPS
logP-0.5ALOGPS
logP-3.9ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)7.15ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area342.33 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity118.69 m3·mol-1ChemAxon
Polarizability44.68 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5479
Blood Brain Barrier+0.9175
Caco-2 permeable-0.7609
P-glycoprotein substrateNon-substrate0.662
P-glycoprotein inhibitor INon-inhibitor0.9067
P-glycoprotein inhibitor IINon-inhibitor0.9334
Renal organic cation transporterNon-inhibitor0.9421
CYP450 2C9 substrateNon-substrate0.8433
CYP450 2D6 substrateNon-substrate0.84
CYP450 3A4 substrateNon-substrate0.5579
CYP450 1A2 substrateNon-inhibitor0.8603
CYP450 2C9 inhibitorNon-inhibitor0.9182
CYP450 2D6 inhibitorNon-inhibitor0.8987
CYP450 2C19 inhibitorNon-inhibitor0.9229
CYP450 3A4 inhibitorNon-inhibitor0.9382
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9737
Ames testNon AMES toxic0.8765
CarcinogenicityNon-carcinogens0.9014
BiodegradationNot ready biodegradable0.964
Rat acute toxicity2.4724 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9768
hERG inhibition (predictor II)Non-inhibitor0.8504
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900251000-bee48e0fb5019193ebb1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0900110000-1afec092079feefa49a9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-1900000000-a38786c52bb589355d91
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0900026000-a8f89e925338c7ff167d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ke9-4900000000-9b838d812b5a59d56595
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9400000000-7ec14f477759ced2651f

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
Purine ribonucleoside 3',5'-bisphosphates / Pentose phosphates / Ribonucleoside 3'-phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Organic pyrophosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives
show 12 more
Substituents
Purine ribonucleoside 3',5'-bisphosphate / Purine ribonucleoside bisphosphate / Purine ribonucleoside diphosphate / Ribonucleoside 3'-phosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
guanosine bisphosphate (CHEBI:17633)

Targets

Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Xanthine phosphoribosyltransferase activity
Specific Function
Converts the preformed base xanthine, a product of nucleic acid breakdown, to xanthosine 5'-monophosphate (XMP), so that it can be reused for RNA or DNA synthesis.
Gene Name
xpt
Uniprot ID
P42085
Uniprot Name
Xanthine phosphoribosyltransferase
Molecular Weight
21038.005 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
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Magnesium ion binding
Specific Function
Necessary for the transition from vegetative growth to stage 0 or stage II of sporulation, but sporulation subsequent to these stages is unaffected at 45 degrees Celsius. This ts effect is probably...
Gene Name
obg
Uniprot ID
P20964
Uniprot Name
GTPase Obg
Molecular Weight
47688.635 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 October 01, 2018 13:44