(1S,2R,10S,11S,15S,17R)-17-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase ID: 170194
• Molecular Formular: C18H24O3
• Molecular Mass: 288.38136
• Monoisotopic Mass: 288.17254463
• SMILES: C1CC(=O)C=C2[C@H]1[C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@H]1O)(C(=O)CC2)C
• Canonical SMILES: O=C1CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2[C@H](O)C[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C18H24O3/c1-18-9-15(20)17-12-5-3-11(19)8-10(12)2-4-13(17)14(18)6-7-16(18)21/h8,12-15,17,20H,2-7,9H2,1H3/t12-,13-,14-,15+,17+,18-/m0/s1
• InChIKey: VDCOSJPGDDQNJH-JVSYPLCOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,15S,17R)-17-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione
• IUPAC Traditional name: (1S,2R,10S,11S,15S,17R)-17-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione
• Synonyms: (11α)-11-Hydroxyestr-4-ene-3,17-dione; 11α-Hydroxyestr-4-ene-3,17-dione

Database IDs

• CAS Number: 6615-00-5
• PubChem SID: 164226104
• PubChem CID: 10902298

CALCULATED PROPERTIES

• Acid pKa: 14.887338
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.3201392
• LogD (pH = 7.4): 2.3201392
• Log P: 2.3201392
• Molar Refractivity: 80.7249 cm^3
• Polarizability: 31.492874 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H825250

An intermediate for 18-demethyl Etonogestrel. Etonogestrel is the active metabolite of Desogestrel.

REFERENCES

• Kim, I., et al.: J. Biol. Chem., 248, 2134 (1973)