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

• ChemBase ID: 170732
• Molecular Formular: C21H26O3
• Molecular Mass: 326.42934
• Monoisotopic Mass: 326.18819469
• SMILES: c1c(c(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)OC)O
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1cc(O)c(c2)OC
• InChI: InChI=1S/C21H26O3/c1-4-21(23)10-8-17-15-6-5-13-11-19(24-3)18(22)12-16(13)14(15)7-9-20(17,21)2/h1,11-12,14-15,17,22-23H,5-10H2,2-3H3/t14-,15+,17-,20-,21-/m0/s1
• InChIKey: SKJZENPUQVKMJH-PVHGPHFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-4,14-diol
• IUPAC Traditional name: (1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-4,14-diol
• Synonyms: (17α)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yne-2,17-diol; 17α-Ethynyl-2-hydroxyestradiol 3-Methyl Ether; 2-Hydroxy Mestranol

Database IDs

• CAS Number: 26011-40-5
• PubChem SID: 164226642
• PubChem CID: 29981663

CALCULATED PROPERTIES

• Acid pKa: 10.32312
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.7396753
• LogD (pH = 7.4): 3.739167
• Log P: 3.7396817
• Molar Refractivity: 93.8377 cm^3
• Polarizability: 36.410294 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H945850

A metabolite of Mestranol.

REFERENCES

• Marks, F., et al.: Biochem. Biophys. Acta., 144, 690 (1967)
• Hahn, D.W., et al.: Contraception, 9, 393 (1967)
• Williams, J.G., et al.: Steroids, 26, 707 (1967)