5'-Guanosine-Diphosphate-Monothiophosphate

Identification

Name
5'-Guanosine-Diphosphate-Monothiophosphate
Accession Number
DB01864  (EXPT01651)
Type
Small Molecule
Groups
Experimental
Description

Guanosine 5'-(trihydrogen diphosphate), monoanhydride with phosphorothioic acid. A stable GTP analog which enjoys a variety of physiological actions such as stimulation of guanine nucleotide-binding proteins, phosphoinositide hydrolysis, cyclic AMP accumulation, and activation of specific proto-oncogenes. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 539.246
Monoisotopic: 538.967815849
Chemical Formula
C10H16N5O13P3S
InChI Key
XOFLBQFBSOEHOG-UUOKFMHZSA-N
InChI
InChI=1S/C10H16N5O13P3S/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(26-9)1-25-29(19,20)27-30(21,22)28-31(23,24)32/h2-3,5-6,9,16-17H,1H2,(H,19,20)(H,21,22)(H2,23,24,32)(H3,11,13,14,18)/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}oxy)phosphonothioic acid
SMILES
[H][C@]1(COP(O)(=O)OP(O)(=O)OP(O)(O)=S)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UADP-ribosylation factor 6Not AvailableHuman
UProtein-glutamine gamma-glutamyltransferase ENot AvailableHuman
UCell division protein FtsZNot AvailableMycobacterium tuberculosis
URas-related protein Rab-11ANot AvailableHuman
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
KEGG Compound
C01806
PubChem Compound
37792
PubChem Substance
46507592
ChemSpider
34654
BindingDB
35866
ChEBI
43000
ChEMBL
CHEMBL1204628
HET
GSP
PDB Entries
1a2b / 1as0 / 1azs / 1azt / 1bh2 / 1cjk / 1cjt / 1cju / 1cjv / 1cs4
show 79 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 Solubility5.15 mg/mLALOGPS
logP-0.58ALOGPS
logP-2.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.08ChemAxon
pKa (Strongest Basic)4.91ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area278.73 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity115.81 m3·mol-1ChemAxon
Polarizability41.98 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5322
Blood Brain Barrier+0.8002
Caco-2 permeable-0.7021
P-glycoprotein substrateNon-substrate0.6952
P-glycoprotein inhibitor INon-inhibitor0.8948
P-glycoprotein inhibitor IINon-inhibitor0.9937
Renal organic cation transporterNon-inhibitor0.9535
CYP450 2C9 substrateNon-substrate0.7936
CYP450 2D6 substrateNon-substrate0.8199
CYP450 3A4 substrateNon-substrate0.5631
CYP450 1A2 substrateNon-inhibitor0.8116
CYP450 2C9 inhibitorNon-inhibitor0.8633
CYP450 2D6 inhibitorNon-inhibitor0.8887
CYP450 2C19 inhibitorNon-inhibitor0.8808
CYP450 3A4 inhibitorNon-inhibitor0.9025
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9807
Ames testNon AMES toxic0.8109
CarcinogenicityNon-carcinogens0.8284
BiodegradationNot ready biodegradable0.9811
Rat acute toxicity2.5412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9823
hERG inhibition (predictor II)Non-inhibitor0.7467
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 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 monophosphates / Pentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives / Pyrimidones / Monoalkyl phosphates
show 13 more
Substituents
Purine ribonucleoside diphosphate / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Organic pyrophosphate
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
nucleoside triphosphate analogue (CHEBI:43000)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Thioesterase binding
Specific Function
GTP-binding protein involved in protein trafficking that regulates endocytic recycling and cytoskeleton remodeling. Required for normal completion of mitotic cytokinesis. Plays a role in the reorga...
Gene Name
ARF6
Uniprot ID
P62330
Uniprot Name
ADP-ribosylation factor 6
Molecular Weight
20082.01 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transferase activity, transferring acyl groups
Specific Function
Catalyzes the calcium-dependent formation of isopeptide cross-links between glutamine and lysine residues in various proteins, as well as the conjugation of polyamines to proteins. Involved in the ...
Gene Name
TGM3
Uniprot ID
Q08188
Uniprot Name
Protein-glutamine gamma-glutamyltransferase E
Molecular Weight
76631.26 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
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
Essential cell division protein that forms a contractile ring structure (Z ring) at the future cell division site. The regulation of the ring assembly controls the timing and the location of cell division. One of the functions of the FtsZ ring is to recruit other cell division proteins to the septum to produce a new cell wall between the dividing cells. Binds GTP and shows GTPase activity.
Specific Function
Gtp binding
Gene Name
ftsZ
Uniprot ID
P9WN95
Uniprot Name
Cell division protein FtsZ
Molecular Weight
38755.52 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
Human
Pharmacological action
Unknown
General Function
Syntaxin 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
RAB11A
Uniprot ID
P62491
Uniprot Name
Ras-related protein Rab-11A
Molecular Weight
24393.305 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 November 02, 2018 05:07