Identification

Generic Name
Guanosine tetraphosphate
DrugBank Accession Number
DB04022
Background

Guanosine tetraphosphate is 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.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 603.1603
Monoisotopic: 602.956990191
Chemical Formula
C10H17N5O17P4
Synonyms
  • Guanosine-5',3'-tetraphosphate

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

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
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
Purine ribonucleoside 3',5'-bisphosphates / Pentose phosphates / Ribonucleoside 3'-phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Organic pyrophosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives
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Substituents
6-oxopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound
show 33 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
guanosine bisphosphate (CHEBI:17633)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
33503-72-9
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-3-{[hydroxy(phosphonooxy)phosphoryl]oxy}-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}phosphonic acid
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](OP(O)(=O)OP(O)(O)=O)[C@H]2O)C(=O)N1

References

General References
Not Available
Human Metabolome Database
HMDB0059638
KEGG Compound
C01228
PubChem Compound
439450
PubChem Substance
46508997
ChemSpider
388557
ChEBI
17633
ZINC
ZINC000008217069
PDBe Ligand
G4P
Wikipedia
Guanosine_pentaphosphate
PDB Entries
1lnz / 1smy / 1y0b / 2j4r / 3n75 / 3vr1 / 4edt / 4hnx / 4jk1 / 4jkr
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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
logP-4.8ChemAxon
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)15ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area342.33 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity118.69 m3·mol-1ChemAxon
Polarizability44.69 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

Targets

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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. [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]
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. [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