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

• ChemBase ID: 161564
• Molecular Formular: C25H28O3
• Molecular Mass: 376.48802
• Monoisotopic Mass: 376.20384476
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)[C@@H](C2)O)C)OCc1ccccc1
• Canonical SMILES: O[C@@H]1C[C@@H]2[C@](C1=O)(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OCc1ccccc1
• InChI: InChI=1S/C25H28O3/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/h2-6,8,10,13,20-23,26H,7,9,11-12,14-15H2,1H3/t20-,21-,22+,23-,25+/m1/s1
• InChIKey: SUPOXPOBSXUHRG-ABMICEGHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,13R,15S)-5-(benzyloxy)-13-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• IUPAC Traditional name: (1S,10R,11S,13R,15S)-5-(benzyloxy)-13-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• Synonyms: 3-(Benzyloxy)-16α-hydroxy-estra-1,3,5(10)-trien-17-one; 3-O-Benzyl 16α-Hydroxy Estrone

Database IDs

• CAS Number: 14982-20-8
• PubChem SID: 162255699
• PubChem CID: 71313825

CALCULATED PROPERTIES

• Acid pKa: 13.382196
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.30833
• LogD (pH = 7.4): 5.30833
• Log P: 5.30833
• Molar Refractivity: 109.6695 cm^3
• Polarizability: 42.889893 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B279035

Protected Estradiol metabolite.

REFERENCES

• Nambara, T., et al.: Chem. Pharm. Bull., 15, 1232 (1967)