(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carboxylic acid

• ChemBase ID: 163726
• Molecular Formular: C21H27FO4
• Molecular Mass: 362.4350832
• Monoisotopic Mass: 362.18933756
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@H]2C(=O)O)C)C)O)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@H]2C(=O)O)C)C)C
• InChI: InChI=1S/C21H27FO4/c1-11-8-15-14-5-4-12-9-13(23)6-7-20(12,3)21(14,22)16(24)10-19(15,2)17(11)18(25)26/h6-7,9,11,14-17,24H,4-5,8,10H2,1-3H3,(H,25,26)/t11-,14+,15+,16+,17+,19+,20+,21+/m1/s1
• InChIKey: VNEWQJPVNZRHHG-XPSMQULISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• IUPAC Traditional name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• Synonyms: (11β,16α,17β)-9-Fluoro-11-hydroxy-16-methyl-3-oxoandrosta-1,4-diene-17-carboxylic Acid; 17β-Carboxy 17-Desoxymethasone; 17β-Carboxy-17-desoxy Dexamethasone

Database IDs

• CAS Number: 75262-69-0
• PubChem SID: 162257861
• PubChem CID: 71314532

CALCULATED PROPERTIES

• Acid pKa: 4.823652
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.0798898
• LogD (pH = 7.4): 0.30703473
• Log P: 2.8386636
• Molar Refractivity: 95.9166 cm^3
• Polarizability: 36.953304 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 294-296°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C177925

An impurity of Dexamethasone (D298800), Desoxymethasone, Fluocortolone (F500500) and Diflucortolone.

REFERENCES

• Dekker, D., et al.: 5, 195 (1980)