Identification
Name5'-Guanosine-Diphosphate-Monothiophosphate
Accession NumberDB01864  (EXPT01651)
TypeSmall Molecule
GroupsExperimental
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
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: 539.246
Monoisotopic: 538.967815849
Chemical FormulaC10H16N5O13P3S
InChI KeyXOFLBQFBSOEHOG-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
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
ADP-ribosylation factor 6ProteinunknownNot AvailableHumanP62330 details
Protein-glutamine gamma-glutamyltransferase EProteinunknownNot AvailableHumanQ08188 details
Cell division protein FtsZProteinunknownNot AvailableMycobacterium tuberculosisP9WN95 details
Ras-related protein Rab-11AProteinunknownNot AvailableHumanP62491 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 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside diphosphates
Alternative ParentsPurine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Organic pyrophosphates / Monosaccharide phosphates / Aminopyrimidines and derivatives / Pyrimidones / Monoalkyl phosphates
SubstituentsPurine ribonucleoside diphosphate / Purine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / Glycosyl compound / N-glycosyl compound / 6-oxopurine / Hypoxanthine / Monosaccharide phosphate / Organic pyrophosphate
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsnucleoside 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 reorganization of the actin cytoskeleton and the formation of stress fibers. May also modulate vesicle budding and uncoating within the Golgi apparatus. Involved in the regulation of dendritic spine develop...
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 formation of the cornified envelope (CE), a specialized component consisting of covalent cross-links of proteins beneath the plasma membrane of terminally differentiated keratinocytes. Catalyzes small...
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 form and an active GTP-bound form that is able to recruit to membranes different set of downstream effectors directly responsible for vesicle formation, movement, tethering and fusion. That Rab regulates...
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 July 18, 2017 17:03