trisodium hydrogen {[({[(2R,3S,4R,5R)-5-(2-amino-6-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]amino}phosphonate

• ChemBase ID: 155143
• Molecular Formular: C10H14N6Na3O13P3
• Molecular Mass: 588.141153
• Monoisotopic Mass: 587.95247727
• SMILES: c1nc2c(n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(NP(=O)(O)[O-])[O-])O)O)nc(nc2O)N.[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(NP(=O)(O)[O-])[O-])[O-])O[C@H]([C@@H]1O)n1cnc2c1nc(N)nc2O.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C10H17N6O13P3.3Na/c11-10-13-7-4(8(19)14-10)12-2-16(7)9-6(18)5(17)3(28-9)1-27-32(25,26)29-31(23,24)15-30(20,21)22;;;/h2-3,5-6,9,17-18H,1H2,(H,25,26)(H3,11,13,14,19)(H4,15,20,21,22,23,24);;;/q;3*+1/p-3/t3-,5-,6-,9-;;;/m1.../s1
• InChIKey: QGJNRMUNXAROIT-CYCLDIHTSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium hydrogen {[({[(2R,3S,4R,5R)-5-(2-amino-6-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]amino}phosphonate
• IUPAC Traditional name: trisodium hydrogen ({[(2R,3S,4R,5R)-5-(2-amino-6-hydroxypurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphinato)aminophosphonate
• Synonyms: β:γ-Imidoguanosine 5′-triphosphate trisodium salt hydrate; 5′-Guanylyl-imidodiphosphate trisodium salt hydrate; GMP-PNP; Gpp(NH)p; Guanosine 5′-[β,γ-imido]triphosphate trisodium salt hydrate

Database IDs

• CAS Number: 148892-91-5
• MDL Number: MFCD00084770
• PubChem SID: 162249281; 24895020
• PubChem CID: 16219382

CALCULATED PROPERTIES

• Acid pKa: 0.23122565
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -9.807186
• LogD (pH = 7.4): -10.796439
• Log P: -4.2329125
• Molar Refractivity: 96.3259 cm^3
• Polarizability: 39.54993 Å^3
• Polar Surface Area: 310.65 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37
• 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: ≥85% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C10H14N6Na3O13P3 · xH2O

DETAILS

Sigma Aldrich - G0635

Application
Non-hydrolyzable analog of GTP; the preferred GTP analog to activate ADP-ribosylation factor.
Guanosine 5′-[β,γ-imido]triphosphate (GMP-PNP, Gpp(NH)p) is a non-hydrolyzable analog of GTP that binds and irreversibly activates G proteins. Gpp(NH)p is used in a variety of applications that involve GTP binding, including GTP-activation, GTP-inhibition, GTP transport, GTP hydrolysis, and GTP structure stabilization. Since a cycle of GTP binding, hydrolysis, and release is required for the initiation of protein translocation across the endoplasmic reticulum, guanosine 5′-[β,γ-imido]triphosphate is often used in studies of protein synthesis. Gpp(NH)p is used to activate ADP-ribosylation factors and to modulate G proteins involved in cell signaling, protein synthesis and other metabolic processes.
Biochem/physiol Actions
Binds and irreversibly activates G proteins.1 Since a cycle of GTP binding, hydrolysis, and release is required for the initiation of protein translocation across the endoplasmic reticulum, this non-hydrolyzable GTP analog is often used in studies of protein synthesis.2,3