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

• ChemBase ID: 170733
• Molecular Formular: C21H26O3
• Molecular Mass: 326.42934
• Monoisotopic Mass: 326.18819469
• SMILES: c1cc(c(c2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)O)OC
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)OC
• InChI: InChI=1S/C21H26O3/c1-4-21(23)12-10-17-15-5-6-16-13(7-8-18(24-3)19(16)22)14(15)9-11-20(17,21)2/h1,7-8,14-15,17,22-23H,5-6,9-12H2,2-3H3/t14-,15-,17+,20+,21+/m1/s1
• InChIKey: SRAITNKTWXKYDH-QOGIMEQTSA-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-6,14-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-6,14-diol
• Synonyms: (17α)-3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yne-4,17-diol; 4-Hydroxy Mestranol

Database IDs

• CAS Number: 65694-22-6
• PubChem SID: 164226643
• PubChem CID: 24840634

CALCULATED PROPERTIES

• Acid pKa: 10.325383
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.7396753
• LogD (pH = 7.4): 3.7391696
• Log P: 3.7396817
• Molar Refractivity: 93.8377 cm^3
• Polarizability: 36.411736 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H945855

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)