(1S,10R,11S,13R,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,13,14-triol

• ChemBase ID: 168078
• Molecular Formular: C20H24O3
• Molecular Mass: 312.40276
• Monoisotopic Mass: 312.17254463
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@]([C@@H](C2)O)(C#C)O)C)O
• Canonical SMILES: C#C[C@]1(O)[C@H](O)C[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
• InChI: InChI=1S/C20H24O3/c1-3-20(23)18(22)11-17-16-6-4-12-10-13(21)5-7-14(12)15(16)8-9-19(17,20)2/h1,5,7,10,15-18,21-23H,4,6,8-9,11H2,2H3/t15-,16-,17+,18-,19+,20+/m1/s1
• InChIKey: VSODIPLKPBLGCC-NADOGSGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,13R,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,13,14-triol
• IUPAC Traditional name: (1S,10R,11S,13R,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,13,14-triol
• Synonyms: (16α,17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,16,17-triol; 19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,16α,17-triol; 17α-Ethynylestriol; 17-Ethynylestriol

Database IDs

• CAS Number: 4717-40-2
• PubChem SID: 162262210
• PubChem CID: 11723045

CALCULATED PROPERTIES

• Acid pKa: 10.31818
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.822443
• LogD (pH = 7.4): 2.8219283
• Log P: 2.8224494
• Molar Refractivity: 88.736 cm^3
• Polarizability: 34.511497 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E686500

A metabolite of 17α-Ethynylestradiol.

REFERENCES

• Napolitano, E., et al.: J. Med. Chem., 38, 429 (1995)
• Katzenellenbogen, J., et al.: Chem. Biol., 3, 529 (1995)
• Waller, C., et al.: Chem. Res. Toxicol., 9, 1240 (1995)