2-[(1S,2S,5R,7R,10S,11S,14R,15S,17S)-5-(acetyloxy)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2-oxoethyl acetate

• ChemBase ID: 178327
• Molecular Formular: C25H38O7
• Molecular Mass: 450.56502
• Monoisotopic Mass: 450.26175356
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)COC(=O)C)O)C)C)OC(=O)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H](C2)OC(=O)C
• InChI: InChI=1S/C25H38O7/c1-14(26)31-13-21(29)25(30)10-8-19-18-6-5-16-11-17(32-15(2)27)7-9-23(16,3)22(18)20(28)12-24(19,25)4/h16-20,22,28,30H,5-13H2,1-4H3/t16-,17-,18+,19+,20+,22-,23+,24+,25+/m1/s1
• InChIKey: QGAODEALOJFHBD-NHOVEWACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,5R,7R,10S,11S,14R,15S,17S)-5-(acetyloxy)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2S,5R,7R,10S,11S,14R,15S,17S)-5-(acetyloxy)-14,17-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2-oxoethyl acetate
• Synonyms: 3β,11β,17,21-tetrahydroxy-5β-pregnan-20-one 3,21-Diacetate; 3β-Tetrahydrocortisol 3,21-Diacetate

Database IDs

• CAS Number: 6820-57-1
• PubChem SID: 164234237
• PubChem CID: 71752442

CALCULATED PROPERTIES

• Acid pKa: 12.610285
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.9957508
• LogD (pH = 7.4): 1.9957482
• Log P: 1.9957508
• Molar Refractivity: 115.9044 cm^3
• Polarizability: 46.7679 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T293355

Cortisol derivative. Intermediate in the synthesis of steroid metabolites.

REFERENCES

• Harnik, M.; J. Org. Chem. 28, 3386 (1963)