(1S,2R,8S,10R,11S,14R,15S)-14-ethynyl-8-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 170083
• Molecular Formular: C22H28O4
• Molecular Mass: 356.45532
• Monoisotopic Mass: 356.19875938
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](C[C@@H]2O)[C@H]2[C@](CC1)([C@@](CC2)(C#C)OC(=O)C)C
• Canonical SMILES: C#C[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H](C2=CC(=O)CC[C@H]12)O)OC(=O)C
• InChI: InChI=1S/C22H28O4/c1-4-22(26-13(2)23)10-8-19-17-12-20(25)18-11-14(24)5-6-15(18)16(17)7-9-21(19,22)3/h1,11,15-17,19-20,25H,5-10,12H2,2-3H3/t15-,16-,17-,19+,20+,21+,22+/m1/s1
• InChIKey: NVEXGWVOAPQSMX-OARMXLMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10R,11S,14R,15S)-14-ethynyl-8-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,8S,10R,11S,14R,15S)-14-ethynyl-8-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: (6α,17α)-17-(Acetyloxy)-6-hydroxy-19-norpregn-4-en-20-yn-3-one; 6α-Hydroxy Norethindrone Acetate

Database IDs

• CAS Number: 6856-28-6
• PubChem SID: 164225993
• PubChem CID: 71748799

CALCULATED PROPERTIES

• Acid pKa: 14.553155
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.4275422
• LogD (pH = 7.4): 2.4275422
• Log P: 2.4275422
• Molar Refractivity: 98.0915 cm^3
• Polarizability: 38.45994 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H750030

An oxidative product of the drug Norethindrone (N676000). Norethindrone impurity.

REFERENCES

• Reif, V., et al.: Pharmaceutical Res., 4, 54 (1987)
• Rao, P., et al.: Steroids, 59, 621 (1987)