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

• ChemBase ID: 170089
• Molecular Formular: C20H26O3
• Molecular Mass: 314.41864
• Monoisotopic Mass: 314.18819469
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[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]2CCC2=CC(=O)CC[C@]12O
• InChI: InChI=1S/C20H26O3/c1-3-19(22)10-8-16-15-5-4-13-12-14(21)6-11-20(13,23)17(15)7-9-18(16,19)2/h1,12,15-17,22-23H,4-11H2,2H3/t15-,16-,17-,18-,19-,20+/m0/s1
• InChIKey: GYRPICHNIDQFOD-RPZLJYRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,10S,11S,14R,15S)-14-ethynyl-2,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: 10β-hydroxynorethindrone
• Synonyms: (17α)-10,17-Dihydroxy-19-norpregn-4-en-20-yn-3-one; 10,17-Dihydroxy-19-nor-17α-pregn-4-en-20-yn-3-one; 10β,17-Dihydroxy-19-nor-17α-pregn-4-en-20-yn-3-one; 10β,17β-Dihydroxy-17α-ethynylestr-4-en-3-one; 10β-Hydroxy-19-norethisterone; 10β-Hydroxynorethindrone; 10β-Hydroxynorethisterone; 17α-Ethinyl-10β,17β-dihydroxyestr-4-en-3-one; 17α-Ethynyl-10β,17β-dihydroxy-4-estren-3-one; NSC 63012; 10β-Hydroxy Norethindrone

Database IDs

• CAS Number: 1236-00-6
• PubChem SID: 164225999
• PubChem CID: 247747

CALCULATED PROPERTIES

• Acid pKa: 13.935828
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.135882
• LogD (pH = 7.4): 2.1358817
• Log P: 2.135882
• Molar Refractivity: 88.8756 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 - H750050

10β-Hydroxynorethindrone is the 6β-hydroxy analogue and a by-product of Norethindrone (N676000) synthesis. 10β-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)
• Gorog, S. et al.: Chem. Anal., 17, 263 (2010)