(1S,10R,11S,12R,13R,14R,15S)-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-triene-5,12,13,14-tetrol

• ChemBase ID: 127303
• Molecular Formular: C18H24O4
• Molecular Mass: 304.38076
• Monoisotopic Mass: 304.16745925
• SMILES: Oc1cc2c(cc1)[C@H]1CC[C@@]3([C@@H](O)[C@H](O)[C@H](O)[C@H]3[C@@H]1CC2)C
• Canonical SMILES: Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H](O)[C@H]([C@@H]2O)O)C
• InChI: InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1
• InChIKey: AJIPIJNNOJSSQC-NYLIRDPKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,12R,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-triene-5,12,13,14-tetrol; (1S,10R,11S,12R,13R,14R,15S)-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-triene-5,12,13,14-tetrol
• IUPAC Traditional name: estetrol
• Synonyms: Estetrol; (15α,16α,17β)-Estra-1,3,5(10)-triene-3,15,16,17-tetrol; Estra-1,3,5(10)-triene-3,15α,16α,17β-tetrol; 15α-Hydroxyestriol; 3,15α,16α,17β-Tetrahydroxyestra-1,3,5(10)-triene

Database IDs

• CAS Number: 15183-37-6
• PubChem SID: 162221624
• PubChem CID: 27125
• Chemspider ID: 25245
• Wikipedia Title: Estetrol

CALCULATED PROPERTIES

• Acid pKa: 10.325741
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 1.6736414
• LogD (pH = 7.4): 1.6731356
• Log P: 1.6736479
• Molar Refractivity: 82.5507 cm^3
• Polarizability: 32.558163 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Off-White Solid
• Melting Point: 233-236°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E668450

A metabolite of Estradiol. It is an estrogenic steroid synthesized exclusively by the fetal liver during human pregnancy and reaching the maternal circulation through the placenta.

REFERENCES

• Gurpide, E., et al.: J. Clin. Endocrinol., 26, 1355 (1966)
• Hagen, A., et al.: J. Clin. Endocrinol., 30, 763 (1966)
• Schollberg, K., et al.: Exp. Clin. Endocrinol., 85, 204 (1966)
• Coelingh Bennink, H., et al.: Contraception, 77, 186 (1966)