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]-5,6-dihydroxy-6-methylheptanoic acid

• ChemBase ID: 167820
• Molecular Formular: C31H50O8
• Molecular Mass: 550.7239
• Monoisotopic Mass: 550.35056856
• 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(O)(C)C)O)/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(O)(C)C)O)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/C31H50O8/c1-16-19-10-13-30(6)26(29(19,5)12-11-21(16)33)22(34)14-20-25(23(39-17(2)32)15-31(20,30)7)18(27(36)37)8-9-24(35)28(3,4)38/h16,19-24,26,33-35,38H,8-15H2,1-7H3,(H,36,37)/b25-18-/t16-,19-,20-,21+,22+,23+,24?,26-,29-,30-,31-/m0/s1
• InChIKey: PGLFLDPZTHZNCH-UBMISKSXSA-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]-5,6-dihydroxy-6-methylheptanoic 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]-5,6-dihydroxy-6-methylheptanoic acid
• Synonyms: (3α,4α,8α,9β,11α,13α,14β,16β,17Z)-16-(Acetyloxy)-3,11,24,25-tetrahydroxy-29-nordammar-17(20)-en-21-oic Acid; 24,25-Dihydroxyfusidic Acid; 24,25-Dihydroxy Fusidic Acid

Database IDs

• CAS Number: 80445-74-5
• PubChem SID: 162261953
• PubChem CID: 71316244

CALCULATED PROPERTIES

• Acid pKa: 4.5395365
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.277034
• LogD (pH = 7.4): -0.49527246
• Log P: 2.281475
• Molar Refractivity: 146.4709 cm^3
• Polarizability: 58.47138 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D452840

24,25-Dihydroxy Fusidic Acid is a hydrolysis product of Fusidic Acid (F865500).

REFERENCES

• Suchkova, G.S. et al.: Antibiotiki, 26, 731 (1981)