(1S,10R,11S,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-4,5,14-triol

• ChemBase ID: 170535
• Molecular Formular: C20H24O3
• Molecular Mass: 312.40276
• Monoisotopic Mass: 312.17254463
• SMILES: c1c(c(cc2c1[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]2CCc2c1cc(O)c(c2)O
• InChI: InChI=1S/C20H24O3/c1-3-20(23)9-7-16-14-5-4-12-10-17(21)18(22)11-15(12)13(14)6-8-19(16,20)2/h1,10-11,13-14,16,21-23H,4-9H2,2H3/t13-,14+,16-,19-,20?/m0/s1
• InChIKey: KQJCDKMHNQVWDV-CRWCAEIDSA-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-4,5,14-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-4,5,14-triol
• Synonyms: (17α)-19-Norpregna-1,3,5(10)-trien-20-yne-2,3,17-triol; 17α-Ethynyl-2-hydroxyestradiol; 19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-2,3,17-triol; 2-Hydroxy Ethynyl Estradiol

Database IDs

• CAS Number: 50394-89-3
• PubChem SID: 164226445
• PubChem CID: 66395

CALCULATED PROPERTIES

• Acid pKa: 9.670355
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 3.5937586
• LogD (pH = 7.4): 3.5914779
• Log P: 3.5937877
• Molar Refractivity: 89.3554 cm^3
• Polarizability: 34.497055 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Tan Solid
• Melting Point: 220-223°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H941960

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)