sodium 9-{[(2E)-4-[(2R,3S,4aS,7S,8S,8aR)-3,8-dihydroxy-2-[(2S,3S)-3-hydroxybutan-2-yl]-octahydropyrano[4,3-b]pyran-7-yl]-3-methylbut-2-enoyl]oxy}nonanoate

• ChemBase ID: 177113
• Molecular Formular: C26H43NaO9
• Molecular Mass: 522.60399
• Monoisotopic Mass: 522.28047724
• SMILES: [C@@H]12[C@H]([C@H]([C@@H](OC1)C/C(=C/C(=O)OCCCCCCCCC(=O)[O-])/C)O)O[C@@H]([C@H](C2)O)[C@H]([C@@H](O)C)C.[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]([C@H](C2)O)[C@H]([C@@H](O)C)C)\C.[Na+]
• InChI: InChI=1S/C26H44O9.Na/c1-16(13-23(31)33-11-9-7-5-4-6-8-10-22(29)30)12-21-24(32)26-19(15-34-21)14-20(28)25(35-26)17(2)18(3)27;/h13,17-21,24-28,32H,4-12,14-15H2,1-3H3,(H,29,30);/q;+1/p-1/b16-13+;/t17-,18-,19-,20-,21-,24-,25+,26+;/m0./s1
• InChIKey: XZMQVUOWANJXDT-WENNQWSDSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 9-{[(2E)-4-[(2R,3S,4aS,7S,8S,8aR)-3,8-dihydroxy-2-[(2S,3S)-3-hydroxybutan-2-yl]-octahydropyrano[4,3-b]pyran-7-yl]-3-methylbut-2-enoyl]oxy}nonanoate
• IUPAC Traditional name: sodium 9-{[(2E)-4-[(2R,3S,4aS,7S,8S,8aR)-3,8-dihydroxy-2-[(2S,3S)-3-hydroxybutan-2-yl]-octahydropyrano[4,3-b]pyran-7-yl]-3-methylbut-2-enoyl]oxy}nonanoate
• Synonyms: [2R-[2α(1S*,2S*),3β,4aα,7β(E),8α,8aβ]]-9-[[4-[hexahydro-3,8-dihydroxy-2-(2-hydroxy-1-methylpropyl)-2H,5H-pyrano[4,3-b]pyran-7-yl]-3-methyl-1-oxo-2-butenyl]oxy]nonanoic Acid Monosodium Salt; 2H,5H-Pyrano[4,3-b]pyranyl Mupirocin Sodium Impurity

Database IDs

• CAS Number: 116182-44-6
• PubChem SID: 164233023
• PubChem CID: 23662788

CALCULATED PROPERTIES

• Acid pKa: 4.8340716
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.7011259
• LogD (pH = 7.4): -0.07094501
• Log P: 2.4513257
• Molar Refractivity: 140.2312 cm^3
• Polarizability: 51.421883 Å^3
• Polar Surface Area: 145.58 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P840550

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)