(2R,3R,4R,5S,6S)-6-{2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 162001
• Molecular Formular: C28H37FO11
• Molecular Mass: 568.5851832
• Monoisotopic Mass: 568.23199022
• SMILES: O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)OCC(=O)[C@@]1([C@@]2([C@H]([C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C2)O)F)C)C[C@@H]1C)C)O
• 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@]2(O)C(=O)CO[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)C)C)C
• InChI: InChI=1S/C28H37FO11/c1-12-8-16-15-5-4-13-9-14(30)6-7-25(13,2)27(15,29)17(31)10-26(16,3)28(12,38)18(32)11-39-24-21(35)19(33)20(34)22(40-24)23(36)37/h6-7,9,12,15-17,19-22,24,31,33-35,38H,4-5,8,10-11H2,1-3H3,(H,36,37)/t12-,15-,16-,17-,19+,20+,21-,22+,24-,25-,26-,27-,28-/m0/s1
• InChIKey: UBHXMSIBGRGDSX-SRABRGTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-6-{2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-6-{2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (11β,16β)-9-Fluoro-11,17-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-21-yl β-D-Glucopyranosiduronic Acid; Betamethasone β-D-Glucuronide

Database IDs

• CAS Number: 744161-79-3
• PubChem SID: 162256136
• PubChem CID: 71313952

CALCULATED PROPERTIES

• Acid pKa: 3.0697167
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.1676288
• LogD (pH = 7.4): -3.2347093
• Log P: 0.23100857
• Molar Refractivity: 134.7736 cm^3
• Polarizability: 53.34473 Å^3
• Polar Surface Area: 191.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B327010

Antiinflammatory steroid.