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

• ChemBase ID: 178325
• Molecular Formular: C25H36O7
• Molecular Mass: 448.54914
• Monoisotopic Mass: 448.24610349
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=O)([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)CC(=O)[C@H]1[C@H]2CC[C@H]2[C@]1(C)CC[C@H](C2)OC(=O)C
• InChI: InChI=1S/C25H36O7/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/h16-19,22,30H,5-13H2,1-4H3/t16-,17-,18+,19+,22-,23+,24+,25+/m1/s1
• InChIKey: PXQRJZNDFRAFTF-BQCMLFGMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,5R,7R,10S,11S,14R,15S)-5-(acetyloxy)-14-hydroxy-2,15-dimethyl-17-oxotetracyclo[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)-5-(acetyloxy)-14-hydroxy-2,15-dimethyl-17-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2-oxoethyl acetate
• Synonyms: 3β,17,21-Trihydroxy-5β-pregnane-11,20-dione 3,21-Diacetate; 3β,5β-Tetrahydro Cortisone 3,21-Diacetate

Database IDs

• CAS Number: 4003-93-4
• PubChem SID: 164234235
• PubChem CID: 21119912

CALCULATED PROPERTIES

• Acid pKa: 12.60116
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.381265
• LogD (pH = 7.4): 2.3812623
• Log P: 2.381265
• Molar Refractivity: 114.9792 cm^3
• Polarizability: 46.226734 Å^3
• Polar Surface Area: 106.97 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 - T293325

Cortisone (C696500) derivative. Intermediate in the synthesis of steroid metabolites.

REFERENCES

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