ChemSpider 2D Image | (-)-Epothilone D | C27H41NO5S

(-)-Epothilone D

  • Molecular FormulaC27H41NO5S
  • Average mass491.683 Da
  • Monoisotopic mass491.270538 Da
  • ChemSpider ID9400674
  • Double-bond stereo - Double-bond stereo

    defined stereocentres - 5 of 5 defined stereocentres


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(-)-Epothilone D
(4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]oxacyclohexadec-13-en-2,6-dion [German] [ACD/IUPAC Name]
(4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)-1-propen-2-yl]oxacyclohexadec-13-ene-2,6-dione [ACD/IUPAC Name]
(4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentaméthyl-16-[(1E)-1-(2-méthyl-1,3-thiazol-4-yl)-1-propén-2-yl]oxacyclohexadéc-13-ène-2,6-dione [French] [ACD/IUPAC Name]
(4S,7R,8S,9S,13Z,16S)-4,8-Dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]oxacyclohexadec-13-ene-2,6-dione
189453-10-9 [RN]
EPOTHILONE D
Oxacyclohexadec-13-ene-2,6-dione, 4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)- [ACD/Index Name]
T0358E0YUF
(-)-Desoxyepothilone B
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

C12039 [DBID]
KOS 862 [DBID]
KOS-862 [DBID]
LMPK03000001 [DBID]
NCI60_036875 [DBID]
NSC 703147 [DBID]
NSC703147 [DBID]
NSC-703147 [DBID]
NSC721085 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      An epithilone that is epithilone C in which the hydrogen at position 13 of the oxacyclohexadec-13-ene-2,6-dione macrocycle has been replaced by a methyl group. ChEBI CHEBI:29579
    • Bio Activity:

      Cell Cycle/DNA Damage MedChem Express HY-15278
      Cell Cycle/DNA Damage; MedChem Express HY-15278
      Epothilone D(Desoxyepothilone B; KOS 862) is a natural polyketide compound isolated from the myxobacterium Sorangium cellulosum. MedChem Express HY-15278
      Epothilone D(Desoxyepothilone B; KOS 862) is a natural polyketide compound isolated from the myxobacterium Sorangium cellulosum. ;IC50 Value: ;Target: Microtubule/TubulinEpothilone D binds to tubulin and inhibits the disassembly of microtubules, resulting in the inhibition of mitosis, cellular proliferation, and cell motility. Intermediary obtained in the synthesis of members of the Epothilone family, polyketide natural products that inhibit cancer cells via a mechanism similar to Paclitaxel. Epothilone D also found to be effective against Paclitaxel-resistant tumors. Epothilone D currently in Phase I of clinical testing. MedChem Express HY-15278
      Microtubule/Tubulin MedChem Express HY-15278

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

Density: 1.1±0.1 g/cm3
Boiling Point: 663.7±55.0 °C at 760 mmHg
Vapour Pressure: 0.0±2.1 mmHg at 25°C
Enthalpy of Vaporization: 102.6±3.0 kJ/mol
Flash Point: 355.2±31.5 °C
Index of Refraction: 1.523
Molar Refractivity: 138.4±0.3 cm3
#H bond acceptors: 6
#H bond donors: 2
#Freely Rotating Bonds: 2
#Rule of 5 Violations: 0
ACD/LogP: 4.28
ACD/LogD (pH 5.5): 4.57
ACD/BCF (pH 5.5): 1733.70
ACD/KOC (pH 5.5): 7242.88
ACD/LogD (pH 7.4): 4.57
ACD/BCF (pH 7.4): 1735.68
ACD/KOC (pH 7.4): 7251.16
Polar Surface Area: 125 Å2
Polarizability: 54.9±0.5 10-24cm3
Surface Tension: 39.0±3.0 dyne/cm
Molar Volume: 453.3±3.0 cm3

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