(1S,10R,11S,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,6,14-triol

• ChemBase ID: 170536
• Molecular Formular: C20H24O3
• Molecular Mass: 312.40276
• Monoisotopic Mass: 312.17254463
• SMILES: c1cc(c(c2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(CC2)(O)C#C)C)O)O
• Canonical SMILES: C#CC1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)O
• InChI: InChI=1S/C20H24O3/c1-3-20(23)11-9-16-14-4-5-15-12(6-7-17(21)18(15)22)13(14)8-10-19(16,20)2/h1,6-7,13-14,16,21-23H,4-5,8-11H2,2H3/t13-,14-,16+,19+,20?/m1/s1
• InChIKey: SYFHJXSYRPNSOI-DFJNYNKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,6,14-triol
• IUPAC Traditional name: (1S,10R,11S,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,6,14-triol
• Synonyms: (17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,4,17-triol; 17α-Ethynylestra-1,3,5(10)-triene-3,4,17β-triol; 19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,4,17-triol; 4-Hydroxy Ethynyl Estradiol

Database IDs

• CAS Number: 50394-90-6
• PubChem SID: 164226446
• PubChem CID: 66396

CALCULATED PROPERTIES

• Acid pKa: 9.694768
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.5937603
• LogD (pH = 7.4): 3.5916038
• Log P: 3.5937877
• Molar Refractivity: 89.3554 cm^3
• Polarizability: 34.498493 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941965

A metabolite of 17α-Ethynylestradiol.

REFERENCES

• Buchthal, J., et al.: Eur. J. Clin. Pharmacol., 47, 431 (1995)
• Krausz, K., et al.: Drug Metab. Dispos., 29, 1410 (1995)
• Hall, S., et al.: Clin. Pharmacol. Ther., 74, 525 (1995)
• Chen, Y., et al.: J. Pharmacol. Exp. Ther., 308, 495 (2004)