(1S,10R,11S,15S)-5-hydroxy-6-methoxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-one

• ChemBase ID: 172738
• Molecular Formular: C19H24O3
• Molecular Mass: 300.39206
• Monoisotopic Mass: 300.17254463
• SMILES: c1c(c(c2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)OC)O
• Canonical SMILES: COc1c(O)ccc2c1CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C
• InChI: InChI=1S/C19H24O3/c1-19-10-9-12-11-5-7-16(20)18(22-2)14(11)4-3-13(12)15(19)6-8-17(19)21/h5,7,12-13,15,20H,3-4,6,8-10H2,1-2H3/t12-,13-,15+,19+/m1/s1
• InChIKey: PUEXVLNGOBYUEW-BFDPJXHCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,15S)-5-hydroxy-6-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• IUPAC Traditional name: (1S,10R,11S,15S)-5-hydroxy-6-methoxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• Synonyms: 3-Hydroxy-4-methoxyestra-1,3,5(10)-trien-17-one; 4-Methoxy Estrone

Database IDs

• CAS Number: 58562-33-7
• PubChem SID: 164228648
• PubChem CID: 194066

CALCULATED PROPERTIES

• Acid pKa: 10.337582
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.1513515
• LogD (pH = 7.4): 4.15086
• Log P: 4.1513577
• Molar Refractivity: 85.5456 cm^3
• Polarizability: 33.27913 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M226135

An endogenous estrogen metabolite, risk-factor for development of breast cancer.

REFERENCES

• Beral, V., et al.: Lancet, 362, 419 (2003)
• Nelson, R., et al.: Clin. Chem., 50, 373 (2003)
• Malekinejad, H., et al.: J. Agric. Food Chem., 54, 9785 (2003)