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

• ChemBase ID: 172073
• Molecular Formular: C31H46O6
• Molecular Mass: 514.69334
• Monoisotopic Mass: 514.32943919
• SMILES: C1[C@H]([C@H]([C@H]2[C@](C1)([C@H]1[C@](CC2)([C@@]2([C@@H](CC1=O)/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)CC(=O)[C@@H]1[C@]2(C)CC[C@@H]2[C@]1(C)CC[C@H]([C@H]2C)O)C
• InChI: InChI=1S/C31H46O6/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/h9,18,21-23,25,27,33H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,23+,25+,27-,29-,30-,31-/m0/s1
• InChIKey: RLYFYROONDDGHK-IETRILBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,5R,6S,7S,10S,11S,13R,14Z,15R)-13-(acetyloxy)-5-hydroxy-2,6,10,11-tetramethyl-17-oxotetracyclo[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)-13-(acetyloxy)-5-hydroxy-2,6,10,11-tetramethyl-17-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]-6-methylhept-5-enoic acid
• Synonyms: (3α,4α,8α,9β,13α,14β,16β,17Z)-16-(Acetyloxy)-3-hydroxy-11-oxo-29-nordammara-17(20),24-dien-21-oic Acid; 11-Oxofusidic Acid; 11-Keto Fusidic Acid

Database IDs

• CAS Number: 16711-91-4
• PubChem SID: 164227983
• PubChem CID: 71749682

CALCULATED PROPERTIES

• Acid pKa: 4.6067715
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.862942
• LogD (pH = 7.4): 2.086688
• Log P: 4.807428
• Molar Refractivity: 143.1981 cm^3
• Polarizability: 56.401592 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - K188990

A metabolite of Fusidic Acid.

REFERENCES

• Godtfredsen, W.O., et al.: J. Med. Chem., 9, 15 (1966)
• Perry, M.J., et al.: J. Antibiot., 36, 1659 (1966)