15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,13,14-triol

• ChemBase ID: 103238
• Molecular Formular: C18H24O3
• Molecular Mass: 288.38136
• Monoisotopic Mass: 288.17254463
• SMILES: CC12CCC3C(CCc4c3ccc(O)c4)C1CC(O)C2O
• Canonical SMILES: Oc1ccc2c(c1)CCC1C2CCC2(C1CC(C2O)O)C
• InChI: InChI=1S/C18H24O3/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/h3,5,8,13-17,19-21H,2,4,6-7,9H2,1H3
• InChIKey: PROQIPRRNZUXQM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,13,14-triol; 15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol; 15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,13,14-triol
• IUPAC Traditional name: 15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,13,14-triol; 15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-5,13,14-triol; estriol
• Synonyms: (16β,17β)-Estra-1,3,5(10)-triene-3,16,17-triol; Estra-1,3,5(10)-triene-3,16β,17β-triol; 16-Epiestratriol; 16β,17β-Estriol; 16β-Hydroxyestradiol; Actriol; Epiestriol; NSC 26646; 16-Epiestriol; 16α-Hydroxyestradiol; 3,16α,17β-Trihydroxy-1,3,5(10)-estratriene; 1,3,5(10)-Estratriene-3,16α,17β-triol; ESTRIOL; 1,3,5(10)-Estratriene-3,16β,17β-triol; 16β-Hydroxy-17β-estradiol; 3,16β,17β-Trihydroxy-1,3,5(10)-estratriene; 16-Epiestriol

Database IDs

• CAS Number: 547-81-9; 50-27-1
• EC Number: 200-022-2; 208-937-9
• MDL Number: MFCD00067609
• PubChem SID: 24894522; 162090417
• PubChem CID: 3269

CALCULATED PROPERTIES

• Acid pKa: 10.326835
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 2.6705914
• LogD (pH = 7.4): 2.6700869
• Log P: 2.6705978
• Molar Refractivity: 81.2662 cm^3
• Polarizability: 31.925823 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 265-268°C; 282 °C

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• RTECS: KG8225000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: R:22
• Safety Statements: S:36/37/39
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ~97% (HPLC); 97%

DETAILS

MP Biomedicals - 02151076

Crystalline
Purity: 97%+.

Sigma Aldrich - E3625

Biochem/physiol Actions
16-Epiestriol is an estradiol metabolite that exhibits significant anti-inflammatory activity without glycogenic activity.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E3625.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - E586500

A metabolite of Estradiol.

REFERENCES

• Marrian, B., et al.: Biochem. J., 59, 136 (1955)
• Dietel, M., et al.: Cancer Res., 50, 6100 (1955)
• Schumacher, G., et al.: Clin. Cancer Res., 5, 493 (1955)
• Robert, J., et al.: J. Med. Chem., 46, 4805 (1955)