(1S,8S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-triene-5,8,14-triol

• ChemBase ID: 170545
• Molecular Formular: C20H24O3
• Molecular Mass: 312.40276
• Monoisotopic Mass: 312.17254463
• SMILES: [C@H]12[C@H]3[C@@]([C@](C#C)(CC3)O)(CC[C@@H]1c1c([C@H](C2)O)cc(cc1)O)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C[C@@H](c2c1ccc(c2)O)O
• InChI: InChI=1S/C20H24O3/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/h1,4-5,10,14-15,17-18,21-23H,6-9,11H2,2H3/t14-,15-,17+,18+,19+,20+/m1/s1
• InChIKey: XFBUZQAUNLRYCT-VTPPTGSRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,8S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,8,14-triol
• IUPAC Traditional name: (1S,8S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,8,14-triol
• Synonyms: (6α,17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,6,17-triol; 19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,6α,17-triol; 6α-Hydroxy-17α-ethynylestradiol; 6α-Hydroxy Ethynyl Estradiol

Database IDs

• CAS Number: 27521-34-2
• PubChem SID: 164226455
• PubChem CID: 13991348

CALCULATED PROPERTIES

• Acid pKa: 9.622353
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.6665094
• LogD (pH = 7.4): 2.663962
• Log P: 2.666542
• Molar Refractivity: 88.89 cm^3
• Polarizability: 34.582775 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H942005

Ethynyl Estradiol (E685100) impurity E.

REFERENCES

• Leese, M., et al.: J. Med. Chem., 49, 7683 (2006)
• Saxena, H., et al.: Steroids, 2007, 72, 892 (2006)