(1S,10R,11S,14R,15S)-14-ethynyl-5,14-dihydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-8-one

• ChemBase ID: 172067
• Molecular Formular: C20H22O3
• Molecular Mass: 310.38688
• Monoisotopic Mass: 310.15689456
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2=O)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)O
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC(=O)c2c1ccc(c2)O
• InChI: InChI=1S/C20H22O3/c1-3-20(23)9-7-17-15-11-18(22)16-10-12(21)4-5-13(16)14(15)6-8-19(17,20)2/h1,4-5,10,14-15,17,21,23H,6-9,11H2,2H3/t14-,15-,17+,19+,20+/m1/s1
• InChIKey: QHTAUDUBRNENFJ-VCNAKFCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-14-ethynyl-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-8-one
• IUPAC Traditional name: (1S,10R,11S,14R,15S)-14-ethynyl-5,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-8-one
• Synonyms: 3,17β-Dihydroxy-17α-ethynylestra-1,3,5(10)-trien-6-one; (17α)-3,17-Dihydroxy-19-norpregna-1,3,5(10)-trien-20-yn-6-one; 6-Keto Ethynyl Estradiol

Database IDs

• CAS Number: 38002-18-5
• PubChem SID: 164227977
• PubChem CID: 11209099

CALCULATED PROPERTIES

• Acid pKa: 8.882315
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.7527988
• LogD (pH = 7.4): 2.7389956
• Log P: 2.7529778
• Molar Refractivity: 88.161 cm^3
• Polarizability: 34.09763 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - K188770

An oxidative tranformation product of Norethindrone Acetate (N675990) and Ethynyl Estradiol (E685100).

REFERENCES

• Ekhato, I.V. et al.: Steroids, 67, 165 (2002)
• Lane. P.A. et al.: J. Pharmac. Sci., 76, 44 (2002)