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

• ChemBase ID: 170050
• Molecular Formular: C24H34O6
• Molecular Mass: 418.52316
• Monoisotopic Mass: 418.23553881
• 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)CO)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)CO
• InChI: InChI=1S/C24H34O6/c1-4-20(29)30-24(19(28)13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)21(16)18(27)12-23(17,24)3/h11,16-18,21,25,27H,4-10,12-13H2,1-3H3/t16-,17-,18-,21+,22-,23-,24-/m0/s1
• InChIKey: JZUOTTDVXIVTTR-RPPPWEFESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-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: (1S,2R,10S,11S,14R,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl propanoate
• Synonyms: Hydrocortisone 17-Propionate

Database IDs

• CAS Number: 65980-97-4
• PubChem SID: 164225960
• PubChem CID: 13502224

CALCULATED PROPERTIES

• Acid pKa: 13.748229
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.4168277
• LogD (pH = 7.4): 2.4168274
• Log P: 2.4168277
• Molar Refractivity: 111.1784 cm^3
• Polarizability: 43.965054 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 183-186°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H714635

A topical hydrocortisone derivative used to treat inflammation and skin diseases.

REFERENCES

• Mitsukuchi, M., et al.: Chem. Pharm. Bull., 38, 786 (1990)
• Buchwald, P., et al.: Steroids, 73, 193 (1990)