5-[(1S,2R,5S,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]-2H-pyran-2-one

• ChemBase ID: 177715
• Molecular Formular: C24H32O4
• Molecular Mass: 384.50848
• Monoisotopic Mass: 384.2300595
• SMILES: C1[C@@H](C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@@]2([C@](CC1)([C@H](CC2)c1coc(=O)cc1)C)O)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@]1(O)CC[C@@H]2c1ccc(=O)oc1)C)C
• InChI: InChI=1S/C24H32O4/c1-22-10-7-17(25)13-16(22)4-5-20-19(22)8-11-23(2)18(9-12-24(20,23)27)15-3-6-21(26)28-14-15/h3,6,13-14,17-20,25,27H,4-5,7-12H2,1-2H3/t17-,18+,19-,20+,22-,23+,24-/m0/s1
• InChIKey: OVUOVMIMOCJILI-KFZANIOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(1S,2R,5S,10R,11S,14S,15R)-5,11-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2H-pyran-2-one
• IUPAC Traditional name: scillarenin
• Synonyms: (3β)-3,14-Dihydroxybufa-4,20,22-trienolide; 3β,14-Dihydroxybufa-4,20,22-trienolide; 3β-Scillarenin; Cardiogenin; NSC 234669; Scillarenin A; Scillarenine; β-Scillarenin; Scillarenin

Database IDs

• CAS Number: 465-22-5
• PubChem SID: 164233625
• PubChem CID: 12315393

CALCULATED PROPERTIES

• Acid pKa: 17.504416
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.0270877
• LogD (pH = 7.4): 3.0270894
• Log P: 3.0270896
• Molar Refractivity: 109.1847 cm^3
• Polarizability: 42.56758 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S199960

A bufadienolide derivative that acts as a cardiotonic agent. A metabolite of Meproscillarin.

REFERENCES

• Rietbrock, N. et al.: Eur. J. Clin. Pharmacol., 8, 427 (1975)
• Shamovskii, I.L. et al.: Bioorg. Khim., 9, 1112 (1975)
• Hammarstroem, L. et al.: Mol. Immunol., 17, 463 (1975)