2-[(1S,2S,5R,6S,7S,10S,11S,13S,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

• ChemBase ID: 2427
• Molecular Formular: C31H48O6
• Molecular Mass: 516.70922
• Monoisotopic Mass: 516.34508926
• SMILES: O[C@H]1[C@@H]2[C@@]([C@@]3([C@@H](C1)/C(=C(\CCC=C(C)C)/C(=O)O)/[C@@H](OC(=O)C)C3)C)(CC[C@@H]1[C@@]2(CC[C@@H](O)[C@H]1C)C)C
• Canonical SMILES: CC(=O)O[C@H]1C[C@]2([C@H](/C/1=C(/C(=O)O)\CCC=C(C)C)C[C@H]([C@@H]1[C@]2(C)CC[C@@H]2[C@]1(C)CC[C@H]([C@H]2C)O)O)C
• InChI: InChI=1S/C31H48O6/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1
• InChIKey: IECPWNUMDGFDKC-MZJAQBGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,5R,6S,7S,10S,11S,13S,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]-6-methylhept-5-enoic acid; 2-[(1S,2S,5R,6S,7S,10S,11S,13S,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid
• IUPAC Traditional name: discoid; ramycin
• Brand Name: Fucidin Cream 2%; Fucithalmic; Fusidine; Ramycin; Fucidin; Fucidin acid; Fucidine
• Synonyms: Fusidic acid; Diethanolamine fusidate; Fucidic acid; Fusidate; Fusidate Sodium; Fucidate Sodium; Fucidate; Fusidic Acid

Database IDs

• CAS Number: 6990-06-3
• EC Number: 230-256-0
• MDL Number: MFCD00865135
• PubChem SID: 160965878; 24894729; 46505364
• PubChem CID: 3000226

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.664285
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.5278952
• LogD (pH = 7.4): 1.7501483
• Log P: 4.4219136
• Molar Refractivity: 144.1233 cm^3
• Polarizability: 56.94671 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.97
• LOG S: -5.0
• Solubility (Water): 5.21e-03 g/l

PROPERTIES

Safety Information

• RTECS: RC1350000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

DETAILS

DrugBank - DB02703

• Drug Groups: approved
• Description: An antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed) It acts by inhibiting translocation during protein synthesis.
• Indication: For the treatment of bacterial infections.
• Pharmacology: Fusidic acid is a bacteriostatic antibiotic that is often used topically in creams and eyedrops, but may also be given systemically as tablets or injections.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Metabolites include dicarboxylic ester/acid, 3-keto fusidic acid, hydroxy fusidic acid, glucuronide fusidic acid and a glycol metabolite.
• Absorption: Sodium fusidic acid tablets have a 91% oral bioavailability. Absorption of the film-coated tablets is complete when compared to a solution, however oral absorption is variable. Oral fusidic acid hemihydrate (suspension) achieved a 22.5% bioavailability in pediatric patients following a 20 milligram/kilogram dose.
• Half Life: Approximately 5 to 6 hours in adults.
• Protein Binding: 97 to 99%
• External Links: Wikipedia

Sigma Aldrich - F0756

Biochem/physiol Actions
Suppresses nitric oxide lysis of pancreatic islet cells. Inhibits protein synthesis in prokaryotes by inhibiting the ribosome-dependent activity of G factor and translocation of peptidyl-tRNA.