disodium 2-amino-9-[(2R,3R,4S,5R)-5-({[(hydrogen phosphonatooxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-7-methyl-9H-purin-7-ium-6-olate

• ChemBase ID: 132379
• Molecular Formular: C11H15N5Na2O11P2
• Molecular Mass: 501.190762
• Monoisotopic Mass: 501.00386815
• SMILES: C[n+]1cn(c2c1c(nc(n2)N)[O-])[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)(O)[O-])O)O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(O)[O-])[O-])O[C@H]([C@@H]1O)n1c[n+](c2c1nc(N)nc2[O-])C.[Na+].[Na+]
• InChI: InChI=1S/C11H17N5O11P2.2Na/c1-15-3-16(8-5(15)9(19)14-11(12)13-8)10-7(18)6(17)4(26-10)2-25-29(23,24)27-28(20,21)22;;/h3-4,6-7,10,17-18H,2H2,1H3,(H5-,12,13,14,19,20,21,22,23,24);;/q;2*+1/p-2/t4-,6-,7-,10-;;/m1../s1
• InChIKey: VSMXIKIFPKDZJA-IDIVVRGQSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 2-amino-9-[(2R,3R,4S,5R)-5-({[(hydrogen phosphonatooxy)phosphinato]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]-7-methyl-9H-purin-7-ium-6-olate
• IUPAC Traditional name: disodium 2-amino-9-[(2R,3R,4S,5R)-5-{[(hydrogen phosphonatooxyphosphinato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-7-methylpurin-7-ium-6-olate
• Synonyms: m7GDP; 7-Methylguanosine 5′-diphosphate sodium salt

Database IDs

• CAS Number: 104809-16-7
• MDL Number: MFCD00057869
• PubChem SID: 162226656
• PubChem CID: 71308552

CALCULATED PROPERTIES

• Acid pKa: 1.826851
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -9.378793
• LogD (pH = 7.4): -10.001703
• Log P: -6.488964
• Molar Refractivity: 100.3679 cm^3
• Polarizability: 36.038223 Å^3
• Polar Surface Area: 252.31 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥92.5%

DETAILS

Sigma Aldrich - M5883

Application
7-Methylguanosine 5′-diphosphate (m7GDP) may be used to study the structure, functions and metabolism of mRNA 5′-cap structures. M7GDP is used in the synthesis of mRNA cap analogues.