Identification
- Generic Name
- 5'-Guanosine-Diphosphate-Monothiophosphate
- DrugBank Accession Number
- DB01864
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 5'-Guanosine-Diphosphate-Monothiophosphate (DB01864)
- Weight
- Average: 539.246
Monoisotopic: 538.967815849 - Chemical Formula
- C10H16N5O13P3S
- Synonyms
- gamma-Thio-GTP
- GTP gamma S
- Guanosine 5'-(gamma-S)triphosphate
- guanosine 5'-[gamma-thio]triphosphate
- Guanosine 5'-O-(3-thiotriphosphate)
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UADP-ribosylation factor 6 Not Available Humans UProtein-glutamine gamma-glutamyltransferase E Not Available Humans UCell division protein FtsZ Not Available Mycobacterium tuberculosis URas-related protein Rab-11A Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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 monophosphates / Pentose phosphates / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives / Pyrimidones / Monoalkyl phosphates show 13 more
- Substituents
- 1,2-diol / 6-oxopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound show 34 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- nucleoside triphosphate analogue (CHEBI:43000)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- EJ7Q9D2M9D
- CAS number
- 37589-80-3
- 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)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonothioic acid
- SMILES
- NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]2O)C(=O)N1
References
- General References
- Not Available
- External Links
- KEGG Compound
- C01806
- PubChem Compound
- 37792
- PubChem Substance
- 46507592
- ChemSpider
- 34654
- BindingDB
- 35866
- ChEBI
- 43000
- ChEMBL
- CHEMBL1204628
- ZINC
- ZINC000008217391
- PDBe Ligand
- GSP
- PDB Entries
- 1a2b / 1as0 / 1azs / 1azt / 1bh2 / 1cjk / 1cjt / 1cju / 1cjv / 1cs4 … show 120 more
Clinical Trials
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
Property Value Source logP -2.9 Chemaxon pKa (Strongest Acidic) 1.04 Chemaxon pKa (Strongest Basic) -0.37 Chemaxon Physiological Charge -4 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 8 Chemaxon Polar Surface Area 277.74 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 105.23 m3·mol-1 Chemaxon Polarizability 42.12 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5322 Blood Brain Barrier + 0.8002 Caco-2 permeable - 0.7021 P-glycoprotein substrate Non-substrate 0.6952 P-glycoprotein inhibitor I Non-inhibitor 0.8948 P-glycoprotein inhibitor II Non-inhibitor 0.9937 Renal organic cation transporter Non-inhibitor 0.9535 CYP450 2C9 substrate Non-substrate 0.7936 CYP450 2D6 substrate Non-substrate 0.8199 CYP450 3A4 substrate Non-substrate 0.5631 CYP450 1A2 substrate Non-inhibitor 0.8116 CYP450 2C9 inhibitor Non-inhibitor 0.8633 CYP450 2D6 inhibitor Non-inhibitor 0.8887 CYP450 2C19 inhibitor Non-inhibitor 0.8808 CYP450 3A4 inhibitor Non-inhibitor 0.9025 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9807 Ames test Non AMES toxic 0.8109 Carcinogenicity Non-carcinogens 0.8284 Biodegradation Not ready biodegradable 0.9811 Rat acute toxicity 2.5412 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9823 hERG inhibition (predictor II) Non-inhibitor 0.7467
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 174.01384 predictedDeepCCS 1.0 (2019) [M+H]+ 176.28593 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.05807 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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
- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52