(1S,10S,11S,13R,15S)-5,13-dihydroxy-15-methyl(1,4,6,8,8-2H5)tetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-14-one

• ChemBase ID: 170523
• Molecular Formular: C18H22O3
• Molecular Mass: 286.36548
• Monoisotopic Mass: 286.15689456
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)[C@@H](C2)O)C)O
• Canonical SMILES: Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H](C2=O)O)C
• InChI: InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13?,14-,15+,16-,18+/m1/s1
• InChIKey: WPOCIZJTELRQMF-QZFBELJMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10S,11S,13R,15S)-5,13-dihydroxy-15-methyl(1,4,6,8,8-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• IUPAC Traditional name: (1S,10S,11S,13R,15S)-5,13-dihydroxy-15-methyl(1,4,6,8,8-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-14-one
• Synonyms: (16α)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-one-d5; 3,16α-Dihydroxy-1,3,5(10)-estratrien-17-one-d5; Estra-1,3,5(10)-triene-3,16α-diol-17-one-d5; 16α-Hydroxy Estrone-d5 (Major) (mixture of the 16 and 17 keto tautomers)

Database IDs

• PubChem SID: 164226433
• PubChem CID: 71749012

CALCULATED PROPERTIES

• Acid pKa: 10.326568
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.4379566
• LogD (pH = 7.4): 3.4374518
• Log P: 3.437963
• Molar Refractivity: 80.5746 cm^3
• Polarizability: 31.54694 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 212-222°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H941902

A major labelled metabolite of Estradiol.A representative lot was 80% d5, 16% d4, 3% d3 with no detectable d0 with 80% of the 17 keto tautomer.

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)