4-{[(1S,10R,11S,13R,14R,15S)-13,14-dihydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2,4,6-trien-5-yl]oxy}-4-oxobutanoic acid

• ChemBase ID: 168197
• Molecular Formular: C22H28O6
• Molecular Mass: 388.45412
• Monoisotopic Mass: 388.18858862
• SMILES: c1c(cc2c(c1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@H]([C@@H](C2)O)O)C)OC(=O)CCC(=O)O
• Canonical SMILES: OC(=O)CCC(=O)Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1C[C@H]([C@@H]2O)O)C
• InChI: InChI=1S/C22H28O6/c1-22-9-8-15-14-5-3-13(28-20(26)7-6-19(24)25)10-12(14)2-4-16(15)17(22)11-18(23)21(22)27/h3,5,10,15-18,21,23,27H,2,4,6-9,11H2,1H3,(H,24,25)/t15-,16-,17+,18-,21+,22+/m1/s1
• InChIKey: RRGGODVYWMYRLA-TZVXGSHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(1S,10R,11S,13R,14R,15S)-13,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}-4-oxobutanoic acid
• IUPAC Traditional name: 4-{[(1S,10R,11S,13R,14R,15S)-13,14-dihydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2,4,6-trien-5-yl]oxy}-4-oxobutanoic acid
• Synonyms: (16α,17β)-Estra-1,3,5(10)-triene-3,16,17-triol 1-(Hydrogen Butanedioate); Estriol 3-Succinate

Database IDs

• CAS Number: 47575-61-1
• PubChem SID: 162262329
• PubChem CID: 54281737

CALCULATED PROPERTIES

• Acid pKa: 3.852846
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.75511247
• LogD (pH = 7.4): -0.83102745
• Log P: 2.4062867
• Molar Refractivity: 101.311 cm^3
• Polarizability: 39.995186 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E668900

Conjugated Estriol analog, used in hormone replacement therapy for postmenopausal women.

REFERENCES

• Clarke, R., et al.: Biol., 48, 21 (2001)
• Casper, J., et al.: J. Biol. Chem., 280, 13071 (2001)