{[({[(5-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-7-yl}-3-hydroxyoxolan-2-yl)methoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid

• ChemBase ID: 132324
• Molecular Formular: C11H17N4O13P3
• Molecular Mass: 506.192963
• Monoisotopic Mass: 506.00049651
• SMILES: c1cn(c2c1c(=O)nc([nH]2)N)C1CC(C(O1)COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O
• Canonical SMILES: OC1CC(OC1COP(=O)(OP(=O)(OP(=O)(O)O)O)O)n1ccc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C11H17N4O13P3/c12-11-13-9-5(10(17)14-11)1-2-15(9)8-3-6(16)7(26-8)4-25-30(21,22)28-31(23,24)27-29(18,19)20/h1-2,6-8,16H,3-4H2,(H,21,22)(H,23,24)(H2,18,19,20)(H3,12,13,14,17)
• InChIKey: DLLXAZJTLIUPAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[({[(5-{2-amino-4-oxo-1H,4H,7H-pyrrolo[2,3-d]pyrimidin-7-yl}-3-hydroxyoxolan-2-yl)methoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid
• IUPAC Traditional name: {[(5-{2-amino-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-7-yl}-3-hydroxyoxolan-2-yl)methoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxyphosphonic acid
• Synonyms: -N7-dGTP; 7-Deaza-dGTP; 7-Deaza-2′-deoxyguanosine 5′-triphosphate lithium salt

Database IDs

• CAS Number: 101515-08-6
• MDL Number: MFCD00171614
• PubChem SID: 162226601; 24894227
• PubChem CID: 4169155

CALCULATED PROPERTIES

• Acid pKa: 0.9788977
• H Acceptors: 13
• H Donor: 7
• LogD (pH = 5.5): -8.119415
• LogD (pH = 7.4): -8.859265
• Log P: -1.8618969
• Molar Refractivity: 97.4717 cm^3
• Polarizability: 38.71373 Å^3
• Polar Surface Area: 261.69 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 2
• Storage Temperature: -20°C

Product Information

• Concentration: 10 mM in H2O
• Shipped in: dry ice

DETAILS

Sigma Aldrich - D8783

Application
G residues can form secondary structures which are not fully denatured during electrophoresis. This can lead to sequence ambiguities. 7-Deaza-G doesn′t form these secondary structures, so avoids sequence ambiguities.
Biochem/physiol Actions
This dGTP analog pairs weakly with conventional bases to minimize DNA secondary structures, while being a good substrate for DNA ploymerases.