({[({[(2R,3S,4R,5R)-5-(2-amino-8-hydroxy-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

• ChemBase ID: 170631
• Molecular Formular: C10H16N5O15P3
• Molecular Mass: 539.179823
• Monoisotopic Mass: 538.98557473
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1c2c(nc1O)c(=O)[nH]c(n2)N)COP(=O)(OP(=O)(O)OP(=O)(O)O)O)O)O
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)(OP(=O)(O)O)O)O)O[C@H]([C@@H]1O)n1c(O)nc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H16N5O15P3/c11-9-13-6-3(7(18)14-9)12-10(19)15(6)8-5(17)4(16)2(28-8)1-27-32(23,24)30-33(25,26)29-31(20,21)22/h2,4-5,8,16-17H,1H2,(H,12,19)(H,23,24)(H,25,26)(H2,20,21,22)(H3,11,13,14,18)/t2-,4-,5-,8-/m1/s1
• InChIKey: JCHLKIQZUXYLPW-UMMCILCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[({[(2R,3S,4R,5R)-5-(2-amino-8-hydroxy-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
• IUPAC Traditional name: ({[(2R,3S,4R,5R)-5-(2-amino-8-hydroxy-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: 7,8-Dihydro-8-oxoguanosine 5'-(Tetrahydrogen Triphosphate) Triethylammonium Salt; 2-Amino-9-β-D-ribofuranosylpurine-6,8(1H,9H)-dione 5'-(Tetrahydrogen Triphosphate) Triethylammonium Salt; 8-Ketoguanosine 5'-Triphosphate Bis(triethylammonium) Triethylammonium Salt; 8-OH-GTP Di-TEA Triethylammonium Salt; 8-Hydroxy Guanosine 5'-Triphosphate Triethylammonium Salt

Database IDs

• PubChem SID: 164226541
• PubChem CID: 167974

CALCULATED PROPERTIES

• Acid pKa: 0.75593835
• H Acceptors: 15
• H Donor: 9
• LogD (pH = 5.5): -9.953689
• LogD (pH = 7.4): -10.703523
• Log P: -3.2852812
• Molar Refractivity: 98.694 cm^3
• Polarizability: 39.275795 Å^3
• Polar Surface Area: 315.04 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H942780

8-Hydroxy Guanosine 5’-Triphosphate is an oxidized ribonucleotide induced mutations in cDNA, suggesting disturbance of genetic information during transcription and/or reverse transcription. It is a potential antiviral drug that cause mutations in genomic

REFERENCES

• Taddei, F., et al.: Science, 278, 128 (1997)
• Kasai, H., et al.: Mutat. Res., 387, 147 (1997)
• Kamiya, H., et al.: Nucleic Acids Res., 231, 517 (1997)