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

• ChemBase ID: 172072
• Molecular Formular: C31H46O6
• Molecular Mass: 514.69334
• Monoisotopic Mass: 514.32943919
• SMILES: C1C(=O)[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
• 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)CCC(=O)[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/h9,18,21-22,24-25,27,34H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,24+,25+,27-,29-,30-,31-/m0/s1
• InChIKey: DEKASDKLVVYODQ-XDSXGCCMSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 4680-37-9
• PubChem SID: 164227982
• PubChem CID: 71749681

CALCULATED PROPERTIES

• Acid pKa: 4.664284
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.9134097
• LogD (pH = 7.4): 2.1356626
• 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

DETAILS

Toronto Research Chemicals - K188980

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)