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

• ChemBase ID: 170532
• Molecular Formular: C18H22O3
• Molecular Mass: 286.36548
• Monoisotopic Mass: 286.15689456
• SMILES: c1(c(cc2c(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]2CCc2c1cc(O)c(c2)O
• InChI: InChI=1S/C18H22O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,19-20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1
• InChIKey: SWINWPBPEKHUOD-JPVZDGGYSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 81586-97-2
• PubChem SID: 164226442
• PubChem CID: 71749016

CALCULATED PROPERTIES

• Acid pKa: 9.670288
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.0054345
• LogD (pH = 7.4): 4.0031533
• Log P: 4.0054636
• Molar Refractivity: 81.0633 cm^3
• Polarizability: 31.378582 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H941947

A labelled metabolite of Estradiol (E888000).

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)