sodium 6-methyl-2-[(1S,2S,6S,7S,10S,11S,13S,14Z,15R)-5,13,17-trihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-ylidene]hept-5-enoate

• ChemBase ID: 165454
• Molecular Formular: C29H45NaO5
• Molecular Mass: 496.65437
• Monoisotopic Mass: 496.31646882
• SMILES: C1C([C@H]([C@H]2[C@](C1)([C@H]1[C@](CC2)([C@@]2([C@@H](CC1O)/C(=C(\CCC=C(C)C)/C(=O)[O-])/[C@H](C2)O)C)C)C)C)O.[Na+]
• Canonical SMILES: CC(=CCC/C(=C\1/[C@@H](O)C[C@]2([C@H]1CC(O)[C@@H]1[C@]2(C)CC[C@@H]2[C@]1(C)CCC([C@H]2C)O)C)/C(=O)[O-])C.[Na+]
• InChI: InChI=1S/C29H46O5.Na/c1-16(2)8-7-9-18(26(33)34)24-20-14-22(31)25-27(4)12-11-21(30)17(3)19(27)10-13-28(25,5)29(20,6)15-23(24)32;/h8,17,19-23,25,30-32H,7,9-15H2,1-6H3,(H,33,34);/q;+1/p-1/b24-18-;/t17-,19-,20-,21?,22?,23-,25-,27-,28-,29-;/m0./s1
• InChIKey: JEYUBRGRWBRNNN-GFFQJFARSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 6-methyl-2-[(1S,2S,6S,7S,10S,11S,13S,14Z,15R)-5,13,17-trihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]hept-5-enoate
• IUPAC Traditional name: sodium 6-methyl-2-[(1S,2S,6S,7S,10S,11S,13S,14Z,15R)-5,13,17-trihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-ylidene]hept-5-enoate
• Synonyms: (3.α,4α,8α,9α,11α,13α,14β,16β,17Z)-3,11,16-Trihydroxy-29-nordammara-17(20),24-dien-21-oic Acid Monosodium Salt; 16-Desacetylfusidic Acid Sodium Salt; 16-O-Deacetylfusidic Acid Sodium Salt; 16-Deacetyl Fusidic Acid Sodium Salt

Database IDs

• CAS Number: 55601-53-1
• PubChem SID: 162259587
• PubChem CID: 71315211

CALCULATED PROPERTIES

• Acid pKa: 4.7528744
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 3.1628568
• LogD (pH = 7.4): 1.3861879
• Log P: 3.9807885
• Molar Refractivity: 145.8089 cm^3
• Polarizability: 53.001556 Å^3
• Polar Surface Area: 100.82 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D198950

An impurity of Fusidic acid.

REFERENCES

• Godtfredsen, W.O., et al.: Antimicrob. Agents Chemother.,132, 1965 (1961)