ChemSpider 2D Image | Eribulin | C40H59NO11

Eribulin

  • Molecular FormulaC40H59NO11
  • Average mass729.897 Da
  • Monoisotopic mass729.408813 Da
  • ChemSpider ID24721813
  • defined stereocentres - 19 of 19 defined stereocentres


More details:






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

(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33S,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-bis(methylene)-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32. 13,33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-one [ACD/IUPAC Name]
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33S,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-methoxy-14-methyl-8,15-dimethylen-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13, 33.16,9.112,16.018,22.029,36.031,35]hentetracontan-24-on [German] [ACD/IUPAC Name]
(1S,3S,6S,9S,12S,14R,16R,18S,20R,21R,22S,26R,29S,31R,32S,33S,35R,36S)-20-[(2S)-3-Amino-2-hydroxypropyl]-21-méthoxy-14-méthyl-8,15-diméthylène-2,19,30,34,37,39,40,41-octaoxanonacyclo[24.9.2.13,32.13 ,33.16,9.112,16.018,22.029,36.031,35]héntétracontan-24-one [French] [ACD/IUPAC Name]
2-(3-Amino-2-hydroxypropyl)hexacosahydro-3-methoxy- 26-methyl-20,27-bis(methylene)11,15-18,21-24,28-triepoxy- 7,9-ethano-12,15-methano-9H,15H-furo(3,2-i)furo(2',3'-5,6) pyrano(4,3-b)(1,4)dioxacyclopentacosin-5-(4H)-one
253128-41-5 [RN]
8854
ER-086526
eribulina [Spanish] [INN]
éribuline [French] [INN]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

CHEBI:63587 [DBID]
E7389 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A fully synthetic macrocyclic ketone analogue of marine sponge natural products. Inhibits growth phase of microtubules via tubulin-based antimitotic mechanism, which leads to G2/M cell-cycle block, di sruption of mitotic spindles, and, ultimately, apoptotic cell death after prolonged mitotic blockage ChEBI CHEBI:63587
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-13442
      Cell Cycle/DNA Damage; MedChem Express HY-13442
      Eribulin (E7389; ER-086526), a synthetic analogue of halichondrin B in phase III clinical trials for breast cancer, binds to tubulin and microtubules.; Target: Microtubule/Tubulin; Eribulin suppressed centromere dynamics at concentrations that arrest mitosis. MedChem Express HY-13442
      Eribulin (E7389; ER-086526), a synthetic analogue of halichondrin B in phase III clinical trials for breast cancer, binds to tubulin and microtubules.;Target: Microtubule/TubulinEribulin suppressed centromere dynamics at concentrations that arrest mitosis. At 60 nmol/L eribulin (2 x mitotic IC(50)), the relaxation rate was suppressed 21%, the time spent paused increased 67%, and dynamicity decreased 35% (but without reduction in mean centromere separation), indicating that eribulin decreased normal microtubule-dependent spindle tension at the kinetochores, preventing the signal for mitotic checkpoint passage [1]. [(3)H]eribulin binds soluble tubulin at a single site; however, this binding is complex with an overall K(d) of 46 microM, but also showing a real or apparent very high affinity (K(d) = 0.4 microM) for a subset of 25% of the tubulin. Eribulin also binds microtubules with a maximum stoichiometry of 14.7 +/- 1.3 molecules per microtubule (K(d) = 3.5 microM), strongly suggest MedChem Express HY-13442
      Microtubule/Tubulin MedChem Express HY-13442

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

Density: 1.3±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.584
Molar Refractivity: 188.5±0.4 cm3
#H bond acceptors: 12
#H bond donors: 3
#Freely Rotating Bonds: 4
#Rule of 5 Violations: 2
ACD/LogP: 3.88
ACD/LogD (pH 5.5): 0.50
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.83
ACD/LogD (pH 7.4): 1.54
ACD/BCF (pH 7.4): 2.90
ACD/KOC (pH 7.4): 20.21
Polar Surface Area: 146 Å2
Polarizability: 74.7±0.5 10-24cm3
Surface Tension: 54.8±5.0 dyne/cm
Molar Volume: 563.2±5.0 cm3

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