sodium 9-{[(2E)-4-[(2S,3aS,6S,7S,7aR)-2-[(2S,3S)-1,3-dihydroxy-2-methylbutyl]-7-hydroxy-hexahydro-2H-furo[3,2-c]pyran-6-yl]-3-methylbut-2-enoyl]oxy}nonanoate

• ChemBase ID: 169521
• Molecular Formular: C26H43NaO9
• Molecular Mass: 522.60399
• Monoisotopic Mass: 522.28047724
• SMILES: O1[C@@H](C[C@@H]2[C@@H]1[C@H]([C@@H](OC2)C/C(=C/C(=O)OCCCCCCCCC(=O)[O-])/C)O)C([C@H]([C@@H](O)C)C)O.[Na+]
• Canonical SMILES: [O-]C(=O)CCCCCCCCOC(=O)/C=C(/C[C@@H]1OC[C@H]2[C@H]([C@H]1O)O[C@@H](C2)C([C@H]([C@@H](O)C)C)O)\C.[Na+]
• InChI: InChI=1S/C26H44O9.Na/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)26-19(15-34-20)14-21(35-26)24(31)17(2)18(3)27;/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29);/q;+1/p-1/b16-13+;/t17-,18-,19-,20-,21-,24?,25-,26+;/m0./s1
• InChIKey: WGWNMOGICRTCLI-VPEGRPEISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 9-{[(2E)-4-[(2S,3aS,6S,7S,7aR)-2-[(2S,3S)-1,3-dihydroxy-2-methylbutyl]-7-hydroxy-hexahydro-2H-furo[3,2-c]pyran-6-yl]-3-methylbut-2-enoyl]oxy}nonanoate
• IUPAC Traditional name: sodium 9-{[(2E)-4-[(2S,3aS,6S,7S,7aR)-2-[(2S,3S)-1,3-dihydroxy-2-methylbutyl]-7-hydroxy-hexahydro-2H-furo[3,2-c]pyran-6-yl]-3-methylbut-2-enoyl]oxy}nonanoate
• Synonyms: [2R-[2α(1S*,2S*,3S*),3aβ,6α(E),7β,7aα]]-9-[[4-[2-(1,3-Dihydroxy-2-methylbutyl)hexahydro-7-hydroxy-4H-furo[3,2-c]pyran-6-yl]-3-methyl-1-oxo-2-butenyl]oxy]nonanoic Acid Monosodium Salt; 4H-Furo[2,3-c]pyranyl Mupirocin Sodium Impurity

Database IDs

• CAS Number: 116182-43-5
• PubChem SID: 162263653
• PubChem CID: 71317016

CALCULATED PROPERTIES

• Acid pKa: 4.8340716
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.7011259
• LogD (pH = 7.4): -0.070945084
• Log P: 2.4513257
• Molar Refractivity: 140.2312 cm^3
• Polarizability: 51.421883 Å^3
• Polar Surface Area: 145.58 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F864850

Mupirocin (M794000) impurity. The rearrangement isomer of Mupirocin is prepared using an enzyme-catalyzed, selective deesterification.

REFERENCES

• Sime, J.T., et al.: Tetrahedron Lett., 28, 5169 (1987)