(1S,2R,8R,10R,11S,14R,15S)-14-ethynyl-8,14-dihydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 170082
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](C[C@H]2O)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@H](C2=CC(=O)CC[C@H]12)O
• InChI: InChI=1S/C20H26O3/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/h1,10,13-15,17-18,22-23H,4-9,11H2,2H3/t13-,14-,15-,17+,18-,19+,20+/m1/s1
• InChIKey: RONQVEAZNZIVHW-BHJGDWCPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8R,10R,11S,14R,15S)-14-ethynyl-8,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,8R,10R,11S,14R,15S)-14-ethynyl-8,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (6β,17α)-6,17-Dihydroxy-19-norpregn-4-en-20-yn-3-one; 6β,17β-Dihydroxy-17α-ethynylestr-4-en-3-one; 6β,17β-Dihydroxy-19-nor-17α-pregn-4-en-20-yn-3-one; 6β-Hydroxynorethindrone; 6β-Hydroxynorethisterone; 6β-Hydroxy Norethindrone

Database IDs

• CAS Number: 51724-44-8
• PubChem SID: 164225992
• PubChem CID: 71748798

CALCULATED PROPERTIES

• Acid pKa: 14.553155
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.9864168
• LogD (pH = 7.4): 1.9864168
• Log P: 1.9864168
• Molar Refractivity: 88.94 cm^3
• Polarizability: 34.623283 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H750025

6β-Hydroxynorethindrone is the 6β-hydroxy analogue of Norethindrone (N676000). 6β-Hydroxynorethindrone is also a metabolite of the progestagen hormone, Lynestrenol.

REFERENCES

• Choudhary, M.I. et al.: Nat. Prod. Res., 24, 1 (2010)
• Bagocsi, B. et al.: J. Plan. Chrom. Mod. TLC, 16, 359 (2010)