tetralithium(1+) ion [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[dioxido(sulfanylidene)-λ5-phosphanyl phosphonato]oxy}phosphonate

• ChemBase ID: 133362
• Molecular Formular: C10H12Li4N5O13P3S
• Molecular Mass: 562.978263
• Monoisotopic Mass: 563.00053456
• SMILES: [Li+].[Li+].[Li+].[Li+].c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])OP(=S)([O-])[O-])O)O)N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=S)([O-])[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1nc(N)[nH]c2=O.[Li+].[Li+].[Li+].[Li+]
• InChI: InChI=1S/C10H16N5O13P3S.4Li/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);;;;/q;4*+1/p-4/t3-,5-,6-,9-;;;;/m1..../s1
• InChIKey: AMQXJFWJOAWCPV-ZVQJTLEUSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetralithium(1+) ion [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[dioxido(sulfanylidene)-λ^5-phosphanyl phosphonato]oxy}phosphonate
• IUPAC Traditional name: tetralithium(1+) ion [(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [dioxido(sulfanylidene)-λ^5-phosphanyl phosphonato]oxyphosphonate
• Synonyms: GTPγS tetralithium salt; GTP-γ-S-Li4; Guanosine 5′-O-(3-thiotriphosphate) tetralithium salt; Guanosine 5′-[γ-thio]triphosphate tetralithium salt

Database IDs

• CAS Number: 94825-44-2
• EC Number: 305-606-1
• MDL Number: MFCD00135151
• Beilstein Number: 8182249
• PubChem SID: 162227639; 24895344
• PubChem CID: 16219452

CALCULATED PROPERTIES

• Acid pKa: 0.9068175
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): -9.706276
• LogD (pH = 7.4): -11.171074
• Log P: -2.8171282
• Molar Refractivity: 100.7439 cm^3
• Polarizability: 41.085682 Å^3
• Polar Surface Area: 289.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥75 mg/mL (Solutions are very unstable; prepare immediately prior to use.)
• Apperance: off-white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥75% (HPLC)
• Shipped in: dry ice

DETAILS

Sigma Aldrich - G8634

Biochem/physiol Actions
GTP-γ-S is a non-hydrolyzable GTP analog, known for its role as a G-protein activator. It has recently been shown to protect proteins from proteolytic degradation, stimulate GLUT4 translocation in a tyrosine kinase-dependent manner, stimulate phospholipases and induce actin polymerization in vitro.