5-[(1S,2R,5S,7S,10R,11S,14S,15R)-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2H-pyran-2-one

• ChemBase ID: 178127
• Molecular Formular: C24H34O5
• Molecular Mass: 402.52376
• Monoisotopic Mass: 402.24062419
• SMILES: C1[C@@H](C[C@@]2([C@](C1)([C@@H]1[C@@H](CC2)[C@@]2([C@](CC1)([C@H](CC2)c1coc(=O)cc1)C)O)C)O)O
• Canonical SMILES: O[C@H]1CC[C@]2([C@](C1)(O)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2c1ccc(=O)oc1)C)C
• InChI: InChI=1S/C24H34O5/c1-21-9-5-16(25)13-23(21,27)11-7-19-18(21)6-10-22(2)17(8-12-24(19,22)28)15-3-4-20(26)29-14-15/h3-4,14,16-19,25,27-28H,5-13H2,1-2H3/t16-,17+,18-,19+,21+,22+,23-,24-/m0/s1
• InChIKey: PBSOJKPTQWWJJD-ZBDZJSKLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(1S,2R,5S,7S,10R,11S,14S,15R)-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2H-pyran-2-one
• IUPAC Traditional name: 5-[(1S,2R,5S,7S,10R,11S,14S,15R)-5,7,11-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pyran-2-one
• Synonyms: (3β,5β)-3,5,14-Trihydroxybufa-20,22-dienolide; 3β,5,14-Trihydroxy- 5β-bufa-20,22-dienolide; Telocinobufagin; NSC 119989; NSC 90782; Telobufotoxin; Telocinobufogenin

Database IDs

• CAS Number: 472-26-4
• PubChem SID: 164234037
• PubChem CID: 259991

CALCULATED PROPERTIES

• Acid pKa: 14.223752
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.0446658
• LogD (pH = 7.4): 2.0446677
• Log P: 2.0446677
• Molar Refractivity: 109.9732 cm^3
• Polarizability: 43.44222 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T017060

Telocinobufagin is isolated as a major component from skin secretion of the toad Bufo rubescens. Telocinobufogenin is a novel antibiotic cardiotonic.

REFERENCES

• Akizawa, T., et al.: Chem. Pharm. Bull., 42, 754 (1994)
• Hancock, R., et al.: Antimicrob. Agents Chemother., 1999, 43, 1317 (1994)
• Jing, Y., et al.: J. Cancer Res., 85, 645 (1994)
• Kamano, Y., et al.: J. Med. Chem., 45, 5440 (1994)
• Schoner, W., et al.: