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

• ChemBase ID: 160665
• Molecular Formular: C31H46O5
• Molecular Mass: 498.69394
• Monoisotopic Mass: 498.33452457
• SMILES: C1[C@H]([C@H]([C@H]2[C@](C1)(C1=CC[C@@H]3[C@@]([C@]1(CC2)C)(C[C@H](/C/3=C(/CCC=C(C)C)\C(=O)O)OC(=O)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=C1[C@]2(C)CC[C@@H]2[C@]1(C)CC[C@H]([C@H]2C)O)C
• InChI: InChI=1S/C31H46O5/c1-18(2)9-8-10-21(28(34)35)27-23-11-12-26-29(5)15-14-24(33)19(3)22(29)13-16-30(26,6)31(23,7)17-25(27)36-20(4)32/h9,12,19,22-25,33H,8,10-11,13-17H2,1-7H3,(H,34,35)/b27-21-/t19-,22-,23-,24+,25+,29-,30-,31-/m0/s1
• InChIKey: XLGDRQJDRPAHDF-AGJDMTFUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,5R,6S,7S,10R,11S,13R,14Z,15R)-13-(acetyloxy)-5-hydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-1(17)-en-14-ylidene]-6-methylhept-5-enoic acid
• IUPAC Traditional name: 2-[(2S,5R,6S,7S,10R,11S,13R,14Z,15R)-13-(acetyloxy)-5-hydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-1(17)-en-14-ylidene]-6-methylhept-5-enoic acid
• Synonyms: (3α,4α,8α,13α,14β,16β,17Z)-16-(Acetyloxy)-3-hydroxy-29-nordammara-9(11),17(20),24-trien-21-oic Acid; 9,11-Anhydrofusidic Acid; 9,11-Anhydro Fusidic Acid

Database IDs

• CAS Number: 74048-41-2
• PubChem SID: 162254800
• PubChem CID: 71313418

CALCULATED PROPERTIES

• Acid pKa: 4.7227745
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.481561
• LogD (pH = 7.4): 2.704066
• Log P: 5.325099
• Molar Refractivity: 143.3808 cm^3
• Polarizability: 56.07808 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A639500

9,11-Anhydro Fusidic Acid is a co-metabolite of Fusidic Acid (F865500).

REFERENCES

• Godtfredsen, W.O. et al.: Tetrahedron, 35, 2419 (1979)