ChemSpider 2D Image | Cucurbitacin E | C32H44O8

Cucurbitacin E

  • Molecular FormulaC32H44O8
  • Average mass556.687 Da
  • Monoisotopic mass556.303589 Da
  • ChemSpider ID4444696

  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 8 of 8 defined stereocentres

More details:

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

(3E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxo-3-hepten-2-yl acetate
(3E,6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-Dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-4,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxo-3-hepten-2-ylacetat
(4R,9β,16α,23E)-2,16,20-Trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl acetate [ACD/IUPAC Name]
(4R,9β,16α,23E)-2,16,20-Trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-ylacetat
(4R,9β,16α,23E)-2,16,20-Trihydroxy-9,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholesta-2,5,23-trien-25-yl-acetat [German] [ACD/IUPAC Name]
(9b,10a,16a,23E)-25-(Acetyloxy)-2,16,20-trihydroxy-9-methyl-19-norlanosta-1,5,23-triene-3,11,22-trione
18444-66-1 [RN]
19-Nor-9β,10α-lanosta-1,5,23-triene-3,11,22-trione, 2,16α,20,25-tetrahydroxy-9-methyl-, 25-acetate (8CI)
19-Norlanosta-1,5,23-triene-3,11,22-trione, 25-(acetyloxy)-2,16,20-trihydroxy-9-methyl-, (9β,10α,16α,23E)-
25-(Acetyloxy)-2b,16a,20-trihydroxy-9b-methyl-19-nor-10a-lanosta-1,5,23E-triene-3,11,22-trione
More...

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

2343323 [DBID]
C08797 [DBID]
NCI60_000150 [DBID]
NSC106399 [DBID]
NSC521775 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      A cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 1, 5 and 23. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3944, CHEBI:3944

    • Bio Activity:

      Cucurbitacin E is a widely available plant-derived natural product, making it a useful tool to study actin dynamics in cells and actin-based processes such as cytokinesis. MedChem Express
      Cucurbitacin E is a widely available plant-derived natural product, making it a useful tool to study actin dynamics in cells and actin-based processes such as cytokinesis.; IC50 value: 7?50 nM in 2- t o 6-day exposures; Target:; In vitro: In assays using pure fluorescently labeled actin, cucurbitacin E specifically affects depolymerization without affecting polymerization. MedChem Express HY-N0417
      Cucurbitacin E is a widely available plant-derived natural product, making it a useful tool to study actin dynamics in cells and actin-based processes such as cytokinesis.;IC50 value: 7?50 nM in 2- to 6-day exposures;Target:;In vitro: In assays using pure fluorescently labeled actin, cucurbitacin E specifically affects depolymerization without affecting polymerization. In assays using pure fluorescently labeled actin, cucurbitacin E specifically affects depolymerization without affecting polymerization. It inhibits actin depolymerization at substoichiometric concentrations up to 1:6 cucurbitacin E:actin. Cucurbitacin E specifically binds to filamentous actin (F-actin) forming a covalent bond at residue Cys257, but not to monomeric actin (G-actin) [1]. Cucurbitacin E at low concentrations (3-50 nmol/l) inhibited the growth of HL-60 cells, which was associated with G2/M cell-cycle arrest, decrease in the levels of cyclin-dependent kinase1, and increase in the levels of p21. Cucurbita MedChem Express HY-N0417
      Others MedChem Express HY-N0417

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

Density: 1.2±0.1 g/cm3
Boiling Point: 712.6±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±5.2 mmHg at 25°C
Enthalpy of Vaporization: 119.0±6.0 kJ/mol
Flash Point: 224.4±26.4 °C
Index of Refraction: 1.579
Molar Refractivity: 148.1±0.4 cm3
#H bond acceptors: 8
#H bond donors: 3
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 1
ACD/LogP: 3.15
ACD/LogD (pH 5.5): 3.46
ACD/BCF (pH 5.5): 249.00
ACD/KOC (pH 5.5): 1805.85
ACD/LogD (pH 7.4): 3.42
ACD/BCF (pH 7.4): 231.49
ACD/KOC (pH 7.4): 1678.88
Polar Surface Area: 138 Å2
Polarizability: 58.7±0.5 10-24cm3
Surface Tension: 54.4±5.0 dyne/cm
Molar Volume: 445.9±5.0 cm3

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