(1S,10R,11S,13S,14R,15S)-5-(benzyloxy)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-triene-13,14-diol

• ChemBase ID: 161442
• Molecular Formular: C25H30O3
• Molecular Mass: 378.5039
• Monoisotopic Mass: 378.21949482
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H]([C@H](C2)O)O)C)OCc1ccccc1
• Canonical SMILES: O[C@H]1C[C@@H]2[C@]([C@H]1O)(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OCc1ccccc1
• InChI: InChI=1S/C25H30O3/c1-25-12-11-20-19-10-8-18(28-15-16-5-3-2-4-6-16)13-17(19)7-9-21(20)22(25)14-23(26)24(25)27/h2-6,8,10,13,20-24,26-27H,7,9,11-12,14-15H2,1H3/t20-,21-,22+,23+,24+,25+/m1/s1
• InChIKey: GDUPBUZZJUIEDX-FLEOUKIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,13S,14R,15S)-5-(benzyloxy)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-13,14-diol
• IUPAC Traditional name: (1S,10R,11S,13S,14R,15S)-5-(benzyloxy)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-13,14-diol
• Synonyms: 3-(Benzyloxy)-estra-1,3,5(10)-triene-16β,17β-diol; (16β,17β)-3-(Phenylmethoxy)-estra-1,3,5(10)-triene-16,17-diol; 3-O-Benzyl 16-Epiestriol

Database IDs

• CAS Number: 33116-58-4
• PubChem SID: 162255577
• PubChem CID: 70632387

CALCULATED PROPERTIES

• Acid pKa: 13.623882
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.540965
• LogD (pH = 7.4): 4.5409646
• Log P: 4.540965
• Molar Refractivity: 110.3611 cm^3
• Polarizability: 43.438515 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 194-196°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B276455

Protected 16-Epiestriol.

REFERENCES

• Kuduk, S., et al.: Bioorg. Med. Chem. Lett., 9, 1233 (1999)
• Matsumoto, T., et al.: Steroids, 68, 751 (1999)