(1S,10R,11S,15S)-5,6-dihydroxy-15-methyl(3,4,13,13-2H4)tetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-one

• ChemBase ID: 170533
• Molecular Formular: C18H22O3
• Molecular Mass: 286.36548
• Monoisotopic Mass: 286.15689456
• SMILES: c1c(c(c2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)O)O
• Canonical SMILES: O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2O)O
• InChI: InChI=1S/C18H22O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11-,12-,14+,18+/m1/s1
• InChIKey: XQZVQQZZOVBNLU-QDTBLXIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,15S)-5,6-dihydroxy-15-methyl(3,4,13,13-^2H₄)tetracyclo[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)-5,6-dihydroxy-15-methyl(3,4,13,13-^2H₄)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• Synonyms: 3,4-Dihydroxyestra-1,3,5(10)-trien-17-one-d4; 3,4-Dihydroxy-1,3,5(10)-estratrien-17-one-d4; 4-Hydroxyestrone-1,2,16,16-d4; 4-Hydroxy Estrone-d4

Database IDs

• CAS Number: 81586-98-3
• PubChem SID: 164226443
• PubChem CID: 71749017

CALCULATED PROPERTIES

• Acid pKa: 9.694703
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.005436
• LogD (pH = 7.4): 4.003279
• Log P: 4.0054636
• Molar Refractivity: 81.0633 cm^3
• Polarizability: 31.3771 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941952

A labelled metabolite of Estradiol.

REFERENCES

• Fishman, H.G, et al.: Biochemistry, 8, 4304 (1969)
• Ryan, Sugar, J., et al.: J. Clin. Endocrinol. Metab., 50, 137 (1969)
• Numazawa, M., et al.: Steroids, 38, 149 (1969)
• Travis, R., et al.: Breast Cancer Res., 5, 239 (1969)