(2S,3S,4R,5R)-2-{[(2-aminoethyl)sulfanyl]methyl}-5-(6-{[(4-nitrophenyl)methyl]amino}-9H-purin-9-yl)oxolane-3,4-diol

• ChemBase ID: 177673
• Molecular Formular: C19H23N7O5S
• Molecular Mass: 461.49482
• Monoisotopic Mass: 461.14813787
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1c2c(nc1)c(ncn2)NCc1ccc(cc1)[N+](=O)[O-])CSCCN)O)O
• Canonical SMILES: NCCSC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C19H23N7O5S/c20-5-6-32-8-13-15(27)16(28)19(31-13)25-10-24-14-17(22-9-23-18(14)25)21-7-11-1-3-12(4-2-11)26(29)30/h1-4,9-10,13,15-16,19,27-28H,5-8,20H2,(H,21,22,23)/t13-,15-,16-,19-/m1/s1
• InChIKey: OAFPVFZXWPVEBS-NVQRDWNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-2-{[(2-aminoethyl)sulfanyl]methyl}-5-(6-{[(4-nitrophenyl)methyl]amino}-9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: (2S,3S,4R,5R)-2-{[(2-aminoethyl)sulfanyl]methyl}-5-(6-{[(4-nitrophenyl)methyl]amino}purin-9-yl)oxolane-3,4-diol
• Synonyms: 5’-S-(2-Aminoethyl)-N6-[(4-nitrobenzyl)-5’-thioadenosine; 5'-S-(2-Aminoethyl)-N-[(4-nitrophenyl)methyl]-5'-thio-adenosine; SAENTA

Database IDs

• CAS Number: 130117-76-9
• PubChem SID: 164233583
• PubChem CID: 164293

CALCULATED PROPERTIES

• Acid pKa: 12.472476
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -2.7894535
• LogD (pH = 7.4): -1.9382162
• Log P: 0.30099943
• Molar Refractivity: 119.6129 cm^3
• Polarizability: 45.41833 Å^3
• Polar Surface Area: 177.16 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S081000

A novel ligand with high affinity for polypeptides associated with nucleoside transport.

REFERENCES

• Agbanyo, F.R., et al.: Biochem. J., 270, 605 (1990)