ChemSpider 2D Image | Mupirocin | C26H44O9


  • Molecular FormulaC26H44O9
  • Average mass500.622 Da
  • Monoisotopic mass500.298523 Da
  • ChemSpider ID393914
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 8 of 8 defined stereocentres

More details:

Featured data source

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

[2S-[2a(E),3b,4b,5a[2R*,3R*(1R*,2R*)]]]-9-[[3-Methyl-1-oxo-4-[tetrahydro-3,4-dihydroxy-5-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-2H-pyran-2-yl]-2-butenyl]oxy]nonanoic Acid
12650-69-0 [RN]
5,9-Anhydro-2,3,4,8-tetradeoxy-8-[[3-(2-hydroxy-1-methylpropyl)oxiranyl]methyl]-3-methyl-[2E,8[2S,3S(1S,2S)]]-L-talonon-2-enonic acid 8-carboxyoctyl ester
9-({(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-({(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid
9-({(2E)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-({(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl}oxy)nonanoic acid (non-preferred name)
9-({(2E)-4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-({(2S,3S)-3-[(1S,2S)-2-hydroxy-1-methylpropyl]oxiran-2-yl}methyl)tetrahydro-2H-pyran-2-yl]-3-methylbut-2-enoyl}oxy)nonansäure [German]
9-({(2E)-4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-({(2S,3S)-3-[(2S,3S)-3-hydroxy-2-butanyl]-2-oxiranyl}methyl)tetrahydro-2H-pyran-2-yl]-3-methyl-2-butenoyl}oxy)nonanoic acid [ACD/IUPAC Name]
9-({(2E)-4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-({(2S,3S)-3-[(2S,3S)-3-hydroxy-2-butanyl]-2-oxiranyl}methyl)tetrahydro-2H-pyran-2-yl]-3-methyl-2-butenoyl}oxy)nonansäure [German] [ACD/IUPAC Name]

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C11758 [DBID]
D01076 [DBID]
MFCD00006068 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Appearance:

      WHITE FINE CRYSTALS NIH Clinical Collection [SMR000471888]
    • Safety:

      D06AX09 Wikidata Q413578
      R01AX06 Wikidata Q413578
    • Target Organs:

      DNA Synthesis inhibitor TargetMol T1465
    • Chemical Class:

      An <locant>alpha</locant>,<locant>beta</locant>-unsaturated ester resulting from the formal condensation of the alcoholic hydroxy group of 9-hydroxynonanoic acid with the carboxy group of (2<stereo>E< /stereo>)-4-[(2<stereo>S</stereo>)-tetrahydro-2<element>H</element>-pyran-2-yl]-3-methylbut-2-enoic acid in which the tetrahydropyranyl ring is substituted at positions 3 and 4 by hydroxy groups and a t position 5 by a {(2<stereo>S</stereo>,3<stereo>S</stereo>)-3-[(2<stereo>S</stereo>,3<stereo>S</stereo>)-3-hydroxybutan-2-yl]oxiran-2-yl}methyl group. Originally isolated from the Gram-negative bacte rium <ital>Pseudomonas fluorescens</ital>, it is used as a topical antibiotic for the treatment of Gram-positive bacterial infections. ChEBI CHEBI:7025
    • Therapeutical Effect:

      antibacterial, isoleucyl-tRNA synthetase inhibitor Microsource [01505706]
    • Drug Status:

      USP, INN, BAN Microsource [01505706]
    • Compound Source:

      Pseudomonas fluorescens; BRL-4910A Microsource [01505706]
    • Bio Activity:

      Antibacterial MedChem Express HY-B0958
      Anti-infection MedChem Express HY-B0958
      Anti-infection; MedChem Express HY-B0958
      DNA Damage/DNA Repair TargetMol T1465
      DNA Synthesis TargetMol T1465
      Mupirocin(BRL-4910A) is an antibiotic of the monoxycarbolic acid class; effective against Gram-positive bacteria, including MRSA. MedChem Express, HY-B0958

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.2±0.1 g/cm3
Boiling Point: 672.3±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±4.7 mmHg at 25°C
Enthalpy of Vaporization: 113.0±6.0 kJ/mol
Flash Point: 216.5±25.0 °C
Index of Refraction: 1.524
Molar Refractivity: 129.5±0.3 cm3
#H bond acceptors: 9
#H bond donors: 4
#Freely Rotating Bonds: 17
#Rule of 5 Violations: 1
ACD/LogP: 3.44
ACD/LogD (pH 5.5): 2.11
ACD/BCF (pH 5.5): 15.28
ACD/KOC (pH 5.5): 145.25
ACD/LogD (pH 7.4): 0.32
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 2.33
Polar Surface Area: 146 Å2
Polarizability: 51.3±0.5 10-24cm3
Surface Tension: 49.1±3.0 dyne/cm
Molar Volume: 423.1±3.0 cm3

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