ChemSpider 2D Image | citrafungin B | C28H38O13

citrafungin B

  • Molecular FormulaC28H38O13
  • Average mass582.594 Da
  • Monoisotopic mass582.231262 Da
  • ChemSpider ID9961258

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres

More details:

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

3-Carboxy-2-O-[(3R)-3-carboxy-3-hydroxy-3-{(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-1,5,8-tetradecatrien-1-yl]tetrahydro-3-furanyl}propanoyl]-3,4-dideoxy-L-threo-pentaric acid [ACD/IUPAC Name]
3-Carboxy-2-O-[(3R)-3-carboxy-3-hydroxy-3-{(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-1,5,8-tetradecatrien-1-yl]tetrahydro-3-furanyl}propanoyl]-3,4-didesoxy-L-threo-pentarsäure [German] [ACD/IUPAC Name]
Acide 3-carboxy-2-O-[(3R)-3-carboxy-3-hydroxy-3-{(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-1,5,8-tétradécatrién-1-yl]tétrahydro-3-furanyl}propanoyl]-3,4-didésoxy-L-thréo-pentarique [French] [ACD/IUPAC Name]
citrafungin B
L-threo-Pentaric acid, 3-carboxy-2-O-[(3R)-3-carboxy-3-hydroxy-1-oxo-3-[(3R,5R)-tetrahydro-2-oxo-5-[(1E,5Z,8Z)-1,5,8-tetradecatrien-1-yl]-3-furanyl]propyl]-3,4-dideoxy- [ACD/Index Name]
3-carboxy-2-O-[(3R)-3-carboxy-3-hydroxy-3-{(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-1-yl]tetrahydrofuran-3-yl}propanoyl]-3,4-dideoxy-L-threo-pentaric acid
  • Miscellaneous

    • Chemical Class:

      A carboxylic ester obtained by the formal condensation of the 4-carboxy group of (2<stereo>R</stereo>)-2-hydroxy-2-{(3<stereo>R</stereo>,5<stereo>R</stereo>)-2-oxo-5-[(1<stereo>E</stereo>,5<stereo>Z</ stereo>,8<stereo>Z</stereo>)-tetradeca-1,5,8-trien-1-yl]tetrahydrofuran-3-yl}butanedioic acid with the hydroxy group of 3-carboxy-2,3-dideoxy-<stereo>L</stereo>-<stereo>threo</stereo>-pentaric acid. I t is a fungal metabolite that acts as an inhibitor of geranylgeranyltransferase type I(GGTase I) of pathogenic fungal species. ChEBI CHEBI:65636
      A carboxylic ester obtained by the formal condensation of the 4-carboxy group of (2R)-2-hydroxy-2-{(3R,5R)-2-oxo-5-[(1E,5Z,8Z)-tetradeca-1,5,8-trien-1-yl]tetrahydrofuran-3-yl}butanedioic acid with the hydroxy group of 3-carboxy-2,3-dideoxy-L-threo-pentaric acid. It is a fungal metabolite that acts as an inhibitor of geranylgeranyltransferase type I(GGTase I) of pathogenic fungal species. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:65636, CHEBI:65636

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.4±0.1 g/cm3
Boiling Point: 792.3±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±6.3 mmHg at 25°C
Enthalpy of Vaporization: 131.3±6.0 kJ/mol
Flash Point: 253.9±26.4 °C
Index of Refraction: 1.583
Molar Refractivity: 142.5±0.3 cm3
#H bond acceptors: 13
#H bond donors: 5
#Freely Rotating Bonds: 21
#Rule of 5 Violations: 3
ACD/LogP: 4.90
ACD/LogD (pH 5.5): -2.39
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.00
ACD/LogD (pH 7.4): -3.09
ACD/BCF (pH 7.4): 1.00
ACD/KOC (pH 7.4): 1.00
Polar Surface Area: 222 Å2
Polarizability: 56.5±0.5 10-24cm3
Surface Tension: 69.2±3.0 dyne/cm
Molar Volume: 426.5±3.0 cm3

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