2-[(1S,2S,5R,6S,7S,10S,11S,13R,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: 169526
• Molecular Formular: C31H48O6
• Molecular Mass: 516.70922
• Monoisotopic Mass: 516.34508926
• SMILES: C1[C@H]([C@H]([C@H]2[C@](C1)([C@H]1[C@](CC2)([C@@]2([C@@H](C[C@H]1O)/C(=C(\CCC=C(C)C)/C(=O)O)/[C@@H](C2)OC(=O)C)C)C)C)C)O
• 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-SMSBSRTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,5R,6S,7S,10S,11S,13R,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
• IUPAC Traditional name: 2-[(1S,2S,5R,6S,7S,10S,11S,13R,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
• Synonyms: (3α,4α,8α,9β,11α,13α,147β,167β,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic Acid; Flucidin; Fucithalmic; Fusidinic Acid; NSC 56192; Ramycin; SQ 16603; Fusidic Acid

Database IDs

• CAS Number: 6990-06-3
• PubChem SID: 162263658
• PubChem CID: 71317019

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 190-192°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F865500

Fusidic acid is a bacteriostatic antibiotic. Fusidic Acid 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.

REFERENCES

• Collignon, P., et al.: Int. J. Antimicrob. Agents, 12, S45 (1999)
• Di Marco, R., et al.: J. Autoimmun., 13, 187 (1999)
• Price, C.T., et al.: J. Antimicrob., Chemother., 44, 57 (1999)