{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({hydroxy[1-(2-nitrophenyl)ethoxy]phosphoryl}oxy)phosphoryl]oxy})phosphinic acid

• ChemBase ID: 163535
• Molecular Formular: C18H23N6O16P3
• Molecular Mass: 672.327103
• Monoisotopic Mass: 672.03833858
• SMILES: [C@@H]1(O)[C@@H](COP(=O)(OP(=O)(OP(=O)(OC(c2ccccc2[N+](=O)[O-])C)O)O)O)O[C@H]([C@@H]1O)n1c2[nH]c(nc(=O)c2nc1)N
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(OC(c2ccccc2[N+](=O)[O-])C)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C18H23N6O16P3/c1-8(9-4-2-3-5-10(9)24(28)29)38-42(32,33)40-43(34,35)39-41(30,31)36-6-11-13(25)14(26)17(37-11)23-7-20-12-15(23)21-18(19)22-16(12)27/h2-5,7-8,11,13-14,17,25-26H,6H2,1H3,(H,30,31)(H,32,33)(H,34,35)(H3,19,21,22,27)/t8?,11-,13-,14-,17-/m1/s1
• InChIKey: NYWDUFBXCCSYMK-JQJVVODZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({hydroxy[1-(2-nitrophenyl)ethoxy]phosphoryl}oxy)phosphoryl]oxy})phosphinic acid
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[hydroxy(1-(2-nitrophenyl)ethoxy)phosphoryl]oxyphosphoryl}oxy)phosphinic acid
• Synonyms: Caged GTP; Guanosine 5'-Triphosphate P3-[1-(2-Nitrophenyl)ethyl]ester; Guanosine 5'-(Tetrahydrogen Triphosphate) P''-[1-(2-Nitrophenyl)ethyl]ester

Database IDs

• CAS Number: 124830-99-5
• PubChem SID: 162257670
• PubChem CID: 3081724

CALCULATED PROPERTIES

• Acid pKa: 0.8905675
• H Acceptors: 16
• H Donor: 7
• LogD (pH = 5.5): -7.3351836
• LogD (pH = 7.4): -7.9126654
• Log P: -2.3877075
• Molar Refractivity: 137.6448 cm^3
• Polarizability: 53.85094 Å^3
• Polar Surface Area: 329.63 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C084900

A caged phosphate. Fourier transform IR photolysis is studied of cages phosphate, caged GTP, caged ATP, and caged calcium.

REFERENCES

• John, J., et al.: J. Biol. Chem., 264, 13086 (1989)
• Dantzig, J., et al.: J. Physiol., 451, 247 (1989)
• Georg, H., et al.: Biochim. Biophys. Acta, 1188, 139 (1989)