(13R,14S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-triene-5,13,14-triol

• ChemBase ID: 155196
• Molecular Formular: C18H24O3
• Molecular Mass: 288.38136
• Monoisotopic Mass: 288.17254463
• SMILES: CC12CCC3c4ccc(cc4CCC3C1C[C@H]([C@H]2O)O)O
• Canonical SMILES: Oc1ccc2c(c1)CCC1C2CCC2(C1C[C@H]([C@H]2O)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/t13?,14?,15?,16-,17-,18?/m1/s1
• InChIKey: PROQIPRRNZUXQM-CKMBUZLOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (13R,14S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,13,14-triol; (13R,14S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,13,14-triol
• IUPAC Traditional name: (13R,14S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,13,14-triol; (13R,14S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,13,14-triol
• Synonyms: 1,3,5(10)-Estratriene-3,16α,17α-triol; 16α-Hydroxy-17α-estradiol; 3,16α,17α-Trihydroxy-1,3,5(10)-estratriene; 17-Epiestriol; (16α,17α)-Estra-1,3,5(10)-triene-3,16,17-triol; 16α,17α-Estriol; 17α-Estriol; NSC 84051; 17-Epiestriol

Database IDs

• CAS Number: 1228-72-4
• MDL Number: MFCD00069500
• PubChem SID: 24894525; 162249334
• PubChem CID: 16219315

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: Ethanol; Methanol
• Apperance: Off-White Solid; off-white to yellow
• Melting Point: 239-241°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C18H24O3

DETAILS

Sigma Aldrich - E3750

Biochem/physiol Actions
17-epiestriol is an estradiol metabolite and a selective estrogen receptor (ER) beta agonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. E3750.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - E586510

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)