9-{[(2E)-4-[(2S,3R,4R)-3,4-dihydroxy-5-{[(2R,3R)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid

• ChemBase ID: 179703
• Molecular Formular: C26H44O9
• Molecular Mass: 500.62216
• Monoisotopic Mass: 500.29853299
• SMILES: O1[C@@H]([C@H]1CC1[C@H]([C@H]([C@@H](OC1)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)O)O)[C@H]([C@@H](O)C)C
• Canonical SMILES: OC(=O)CCCCCCCCOC(=O)/C=C(/C[C@@H]1OCC([C@H]([C@H]1O)O)C[C@H]1O[C@@H]1[C@H]([C@@H](O)C)C)\C
• InChI: InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19?,20-,21+,24+,25-,26+/m0/s1
• InChIKey: MINDHVHHQZYEEK-CQLBTRCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-{[(2E)-4-[(2S,3R,4R)-3,4-dihydroxy-5-{[(2R,3R)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid
• IUPAC Traditional name: 9-{[(2E)-4-[(2S,3R,4R)-3,4-dihydroxy-5-{[(2R,3R)-3-[(2S,3S)-3-hydroxybutan-2-yl]oxiran-2-yl]methyl}oxan-2-yl]-3-methylbut-2-enoyl]oxy}nonanoic acid
• Synonyms: Bactroban; Eismycin; Mupirocin; Antibiotic BRL 4910A; Antibiotic Y 11633; Pseudomonic acid A; Mupirocin

Database IDs

• CAS Number: 12650-69-0
• PubChem SID: 164235613
• PubChem CID: 17571751

CALCULATED PROPERTIES

• Acid pKa: 4.8340716
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.7011259
• LogD (pH = 7.4): -0.07094509
• Log P: 2.4513257
• Molar Refractivity: 129.3941 cm^3
• Polarizability: 51.53534 Å^3
• Polar Surface Area: 146.05 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Binds to bacterial isoleucyl-tRNA synthetase, which halts the incorporation of isoleucine into bacterial proteins

Product Information

• Biological Source: Prod. by Pseudomonas fluorescens
• Application(s): Broad spectrum antibiotic effective against gram-positive organisms

REFERENCES

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