trisodium {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl (phosphonatooxy)phosphonate

• ChemBase ID: 132652
• Molecular Formular: C10H13N5Na3O14P3
• Molecular Mass: 589.125913
• Monoisotopic Mass: 588.93649285
• SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)(O)OP(=O)([O-])OP(=O)([O-])[O-])O)O)N.[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)([O-])[O-])[O-])O)O[C@H]([C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C10H16N5O14P3.3Na/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(27-9)1-26-31(22,23)29-32(24,25)28-30(19,20)21;;;/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H,24,25)(H2,19,20,21)(H3,11,13,14,18);;;/q;3*+1/p-3/t3-,5-,6-,9-;;;/m1.../s1
• InChIKey: KZRMTEVIDYXWQW-CYCLDIHTSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl (phosphonatooxy)phosphonate
• IUPAC Traditional name: trisodium [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonatooxyphosphonate
• Synonyms: GTP; Guanosine 5′-triphosphate sodium salt solution; Guanosine 5′-triphosphate sodium salt hydrate

Database IDs

• CAS Number: 36051-31-7
• MDL Number: MFCD00077781
• Beilstein Number: 3585677
• PubChem SID: 24895138; 24895354; 162226929
• PubChem CID: 16219405

CALCULATED PROPERTIES

• Acid pKa: 0.802243
• H Acceptors: 14
• H Donor: 5
• LogD (pH = 5.5): -10.325367
• LogD (pH = 7.4): -11.083946
• Log P: -3.633383
• Molar Refractivity: 93.8747 cm^3
• Polarizability: 38.17548 Å^3
• Polar Surface Area: 303.3 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL; H2O: soluble50 mg/mL, clear, colorless
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; -70°C

Pharmacology Properties

• Gene Information: human ... HRAS(3265)

Product Information

• Purity: ≥95% (HPLC); ≥95.0% (HPLC)
• Concentration: 100 mM in H2O (adjusted to pH 7)
• Impurities: ≤10% water; ≤4% Solvent
• Foreign Activity: DNase, RNase and Nickase, none detected
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C10H16N5O14P3 · xNa+

DETAILS

Sigma Aldrich - G3776

Application
For use in DNA-dependent RNA polymerase transcription

Sigma Aldrich - G8877

Preparation Note
Prepared by enzymatic phosphorylation of 5′-GMP.
Biochem/physiol Actions
GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.

Sigma Aldrich - 51123

Biochem/physiol Actions
GTP functions as a carrier of phosphates and pyrophosphates involved in channeling chemical energy into specific biosynthetic pathways. GTP activates the signal transducing G proteins which are involved in various cellular processes including proliferation, differentiation, and activation of several intracellular kinase cascades. Proliferation and apoptosis are regulated in part by the hydrolysis of GTP by small GTPases Ras and Rho. Another type of small GTPase, Rab, plays a role in the docking and fusion of vesicles and may also be involved in vesicle formation. In addition to its role in signal transduction, GTP also serves as an energy-rich precursor of mononucleotide units in the enzymatic biosynthesis of DNA and RNA.