({[({[5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}methyl)phosphonic acid sodium

• ChemBase ID: 132368
• Molecular Formular: C11H18N5NaO13P3
• Molecular Mass: 544.197373
• Monoisotopic Mass: 544.00116483
• SMILES: c1nc2c(n1C1C(C(C(O1)COP(=O)(O)OP(=O)(CP(=O)(O)O)O)O)O)[nH]c(nc2=O)N.[Na]
• Canonical SMILES: OC1C(COP(=O)(OP(=O)(CP(=O)(O)O)O)O)OC(C1O)n1cnc2c1[nH]c(N)nc2=O.[Na]
• InChI: InChI=1S/C11H18N5O13P3.Na/c12-11-14-8-5(9(19)15-11)13-2-16(8)10-7(18)6(17)4(28-10)1-27-32(25,26)29-31(23,24)3-30(20,21)22;/h2,4,6-7,10,17-18H,1,3H2,(H,23,24)(H,25,26)(H2,20,21,22)(H3,12,14,15,19)
• InChIKey: BOCIJVWLZVQKJK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}methyl)phosphonic acid sodium
• IUPAC Traditional name: ({[5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)methylphosphonic acid sodium
• Synonyms: GMPPCP; GppCp; Guanosine-5′-[(β,γ)-methyleno]triphosphate sodium salt; β,γ-Methyleneguanosine 5′-triphosphate sodium salt

Database IDs

• CAS Number: 10470-57-2
• MDL Number: MFCD00070117
• PubChem SID: 162226645; 24896847
• PubChem CID: 16219647

CALCULATED PROPERTIES

• Acid pKa: 1.3501971
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): -10.163931
• LogD (pH = 7.4): -10.705364
• Log P: -5.1423225
• Molar Refractivity: 99.1601 cm^3
• Polarizability: 39.67486 Å^3
• Polar Surface Area: 285.58 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: -
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - M3509

Application
βγ-Methyleneguanosine 5′-triphosphate (GMPPCP, GppCp) is a non-hydrolyzable analog of GTP used in a variety of applications that involve GTP binding including GTP-activation, GTP-inhibition, GTP transport, GTP hydrolysis and GTP structure stabilization. GMPPCP (GuoPP[CH2MP) is used to modulate and study G proteins involved in cell signaling, protein synthesis and other metabolic processes.