2-[(1S,2S,10S,11S,13S,14R,15S,17S)-14-hydroxy-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-14-yl]-2-oxoethyl propanoate

• ChemBase ID: 162009
• Molecular Formular: C25H32O6
• Molecular Mass: 428.51798
• Monoisotopic Mass: 428.21988874
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@]32[C@H](C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)COC(=O)CC)O)C)C)O3)C
• Canonical SMILES: CCC(=O)OCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)C[C@@H]1O[C@@]31[C@H]2CCC1=CC(=O)C=C[C@]31C
• InChI: InChI=1S/C25H32O6/c1-5-21(28)30-13-19(27)24(29)14(2)10-18-17-7-6-15-11-16(26)8-9-22(15,3)25(17)20(31-25)12-23(18,24)4/h8-9,11,14,17-18,20,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,20-,22-,23-,24-,25+/m0/s1
• InChIKey: VHNLZHWRYPLCSE-QYIVYLGBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,10S,11S,13S,14R,15S,17S)-14-hydroxy-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• IUPAC Traditional name: 2-[(1S,2S,10S,11S,13S,14R,15S,17S)-14-hydroxy-2,13,15-trimethyl-5-oxo-18-oxapentacyclo[8.8.0.0^1,^1^7.0^2,^7.0^1^1,^1^5]octadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• Synonyms: Beclomethasone 9,11-Epoxide 21-Propionate; Betamethasone 9,11-Epoxide 21-Propionate; (9β,11β,16β)-9,11-Epoxy-17-hydroxy-16-methyl-21-(1-oxopropoxy)pregna-1,4-diene-3,20-dione

Database IDs

• CAS Number: 205105-83-5
• PubChem SID: 162256144
• PubChem CID: 71313954

CALCULATED PROPERTIES

• Acid pKa: 12.469114
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.0938427
• LogD (pH = 7.4): 3.093839
• Log P: 3.0938427
• Molar Refractivity: 114.4533 cm^3
• Polarizability: 44.905437 Å^3
• Polar Surface Area: 93.2 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 215-219°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B327045

Betamethasone (B327000) impurity, as antiinflammatory agent.

REFERENCES

• Foe, K., et al.: Drug Metab. Disposition, 26, 132, (1998)