(1S,2R,10S,11S,14R,15S,17S)-14-[2-(acetyloxy)acetyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl propanoate

• ChemBase ID: 170048
• Molecular Formular: C26H36O7
• Molecular Mass: 460.55984
• Monoisotopic Mass: 460.24610349
• SMILES: C1CC(=O)C=C2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)COC(=O)C)OC(=O)CC)C)C
• Canonical SMILES: CCC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)C(=O)COC(=O)C
• InChI: InChI=1S/C26H36O7/c1-5-22(31)33-26(21(30)14-32-15(2)27)11-9-19-18-7-6-16-12-17(28)8-10-24(16,3)23(18)20(29)13-25(19,26)4/h12,18-20,23,29H,5-11,13-14H2,1-4H3/t18-,19-,20-,23+,24-,25-,26-/m0/s1
• InChIKey: MFBMYAOAMQLLPK-FZNHGJLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-14-[2-(acetyloxy)acetyl]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl propanoate
• IUPAC Traditional name: hydrocortisone aceponate
• Synonyms: (11β)-21-(Acetyloxy)-11-hydroxy-17-(1-oxopropoxy)pregn-4-ene-3,20-dione; Cortisol 17-Propionate 21-Acetate; Hydrocortisone Aceponate; Hydrocortisone 17-Propionate 21-Acetate

Database IDs

• CAS Number: 74050-20-7
• PubChem SID: 164225958
• PubChem CID: 68921

CALCULATED PROPERTIES

• Acid pKa: 14.812671
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.857953
• LogD (pH = 7.4): 2.857953
• Log P: 2.857953
• Molar Refractivity: 120.3299 cm^3
• Polarizability: 47.81237 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 144-146°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H714628

A new topical hydrocortisone derivative with esterification in positions 17 and 21, inhibit the incorporation of [3H]thymidine in DNA in human skin fibroblasts less strongly than the halogenated glucocorticosteroids betamethasone 17-valerate and clobetaso

REFERENCES

• Dooms-Goossens, A., et al.: Eur. J. Dermatol., 3, 713 (1993)
• Isaksson, M., et al.: Contact Dermatitis, 43, 41 (1993)
• Matura, M., et al.: Allergy, 55, 698 (1993)