2-[(1S,2R,10S,11S,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate

• ChemBase ID: 176876
• Molecular Formular: C27H36O8
• Molecular Mass: 488.56994
• Monoisotopic Mass: 488.24101811
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1CC[C@@]2(C(=O)COC(=O)CC)OC(=O)OCC)C)O)C
• Canonical SMILES: CCOC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2CCC2=CC(=O)C=C[C@]12C)C(=O)COC(=O)CC
• InChI: InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3/t18-,19-,20-,23+,25-,26-,27-/m0/s1
• InChIKey: FNPXMHRZILFCKX-KAJVQRHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,10S,11S,14R,15S,17S)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• IUPAC Traditional name: batmen
• Synonyms: (11β)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-21-(1-oxopropoxy)pregna-1,4-diene-3,20-dione; Dermatop; EsCort; HOE 777; Prednisolone 17-(Ethyl Carbonate) 21-Propionate; Prednitop; Regenit; S 77-0777; Prednicarbate

Database IDs

• CAS Number: 73771-04-7
• PubChem SID: 164232786
• PubChem CID: 6714002

CALCULATED PROPERTIES

• Acid pKa: 14.829222
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.8318758
• LogD (pH = 7.4): 3.8318756
• Log P: 3.8318758
• Molar Refractivity: 127.7954 cm^3
• Polarizability: 50.123066 Å^3
• Polar Surface Area: 116.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P703700

Topical anti-inflammatory agent. Glucocorticoid.

REFERENCES

• Stache, U., et al.: Arzneim.-Forsch., 35, 1753 (1985)