ChemSpider 2D Image | (−)-Epothilone B | C27H41NO6S

(−)-Epothilone B

  • Molecular FormulaC27H41NO6S
  • Average mass507.682 Da
  • Monoisotopic mass507.265472 Da
  • ChemSpider ID10213816
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 7 of 7 defined stereocentres


More details:



Featured data source



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

(−)-Epothilone B
(-)-Epothilone B
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecan-5,9-dion [German] [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentaméthyl-3-[(1E)-1-(2-méthyl-1,3-thiazol-4-yl)-1-propén-2-yl]-4,17-dioxabicyclo[14.1.0]heptadécane-5,9-dione [French] [ACD/IUPAC Name]
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
(1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
[1R*,3R*(E),7R*,10S*,11R*,12R*,16S*]-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
152044-54-7 [RN]
4,17-Dioxabicyclo[14.1.0]heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (1S,3S,7S,10R,11S,12S,16R)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C12154 [DBID]
DXA [DBID]
E2656_SIGMA [DBID]
EPO 906 [DBID]
EPO-906 [DBID]
nchembio853-comp4 [DBID]
NCI60_030305 [DBID]
NSC684363 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the <stereo>S</stereo>,<stereo>S</stereo> stereoisomer). ChEBI CHEBI:31550
    • Bio Activity:

      Cell Biology Tocris Bioscience 3502
      Cell Cycle/DNA Damage MedChem Express HY-17029
      Cell Cycle/DNA Damage; MedChem Express HY-17029
      Cytoskeleton and Motor Proteins Tocris Bioscience 3502
      Epothilone B (EPO906, Patupilone) is a Taxol-like microtubule-stabilizing agent with EC0.01 of 1.8 ?M. MedChem Express HY-17029
      Microtubule stabilization agent that promotes tubulin polymerization and induces G2-M cell cycle arrest (EC50 = 32 nM in HeLa cells). Inhibits proliferation of human carcinoma cell lines in vitro, inc luding MDR cells overexpressing the P-glycoprotein efflux pump. Exhibits potent cytotoxicity in MCF-7 and A549 cells (EC50 values are 0.3 and 2.7 nM respectively). Inhibits growth of HCT-15 tumors in mice in vivo. Tocris Bioscience 3502
      Microtubule stabilization agent that promotes tubulin polymerization and induces G2-M cell cycle arrest (EC50 = 32 nM in HeLa cells). Inhibits proliferation of human carcinoma cell lines in vitro, including MDR cells overexpressing the P-glycoprotein efflux pump. Exhibits potent cytotoxicity in MCF-7 and A549 cells (EC50 values are 0.3 and 2.7 nM respectively). Inhibits growth of HCT-15 tumors in mice in vivo. Tocris Bioscience 3502
      Microtubule stabilization agent; promotes tubulin polymerization Tocris Bioscience 3502
      Microtubule/Tubulin MedChem Express HY-17029
      Microtubules Tocris Bioscience 3502

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

Density: 1.1±0.1 g/cm3
Boiling Point: 680.2±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.2 mmHg at 25°C
Enthalpy of Vaporization: 104.8±3.0 kJ/mol
Flash Point: 365.2±31.5 °C
Index of Refraction: 1.532
Molar Refractivity: 138.4±0.3 cm3
#H bond acceptors: 7
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 1
ACD/LogP: 2.29
ACD/LogD (pH 5.5): 3.02
ACD/BCF (pH 5.5): 116.37
ACD/KOC (pH 5.5): 1047.58
ACD/LogD (pH 7.4): 3.02
ACD/BCF (pH 7.4): 116.50
ACD/KOC (pH 7.4): 1048.78
Polar Surface Area: 137 Å2
Polarizability: 54.9±0.5 10-24cm3
Surface Tension: 41.6±3.0 dyne/cm
Molar Volume: 446.6±3.0 cm3

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