2-[(1S,2S,4R,8S,9S,11S,12R,13S)-16-(2-chloroethoxy)-12-fluoro-19-formyl-11-hydroxy-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-16,18-dien-8-yl]-2-oxoethyl acetate

• ChemBase ID: 169357
• Molecular Formular: C29H38ClFO8
• Molecular Mass: 569.0586232
• Monoisotopic Mass: 568.22392408
• SMILES: C1C(=CC2=C(C[C@@H]3[C@@]([C@]2(C1)C)([C@H](C[C@]1([C@H]3C[C@@H]2[C@]1(OC(O2)(C)C)C(=O)COC(=O)C)C)O)F)C=O)OCCCl
• Canonical SMILES: ClCCOC1=CC2=C(C=O)C[C@@H]3[C@]([C@]2(CC1)C)(F)[C@@H](O)C[C@]1([C@H]3C[C@@H]2[C@]1(OC(O2)(C)C)C(=O)COC(=O)C)C
• InChI: InChI=1S/C29H38ClFO8/c1-16(33)37-15-23(35)29-24(38-25(2,3)39-29)12-20-21-10-17(14-32)19-11-18(36-9-8-30)6-7-26(19,4)28(21,31)22(34)13-27(20,29)5/h11,14,20-22,24,34H,6-10,12-13,15H2,1-5H3/t20-,21-,22-,24+,26-,27-,28-,29+/m0/s1
• InChIKey: QNXUUBBKHBYRFW-QWAPGEGQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-16-(2-chloroethoxy)-12-fluoro-19-formyl-11-hydroxy-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-16,18-dien-8-yl]-2-oxoethyl acetate
• IUPAC Traditional name: dermacort
• Synonyms: (11β,16α)-21-(acetyloxy)-3-(2-chloroethoxy)-9-fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-20-oxopregna-3,5-diene-6-carboxaldehyde; NSC 150527; 3-(2-Chloroethoxy)-6-formyl-9α-fluoropregna-3,5-diene-11β,16α,17,21-tetrol-20-one 21-Acetate 16α,17α-Acetonide; Cortocin F; Cutisterol; Deflamene; Deflamin; Dermacort; FI 6341; Fluderma; Fluoformylon; Fluoroformylon; Fluoroformylone; Formocortal

Database IDs

• CAS Number: 2825-60-7
• PubChem SID: 162263489
• PubChem CID: 289085

CALCULATED PROPERTIES

• Acid pKa: 13.643156
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 2.0719712
• LogD (pH = 7.4): 2.071971
• Log P: 2.0719712
• Molar Refractivity: 141.3611 cm^3
• Polarizability: 55.328007 Å^3
• Polar Surface Area: 108.36 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F693100

A corticosteroid with antiinflammatory activity used in ophthalmology.

REFERENCES

• Tajima, T. et al.: Nip. Yakur. Zas., 62, 115 (1966)
• Marchese, A. et al.: Chemotherapy, 47, 304 (1966)
• Bertazzoli, C. et al.: J. Eur. Toxicol., 3, 88 (1966)