ChemSpider 2D Image | Epoxomicin | C28H50N4O7

Epoxomicin

  • Molecular FormulaC28H50N4O7
  • Average mass554.719 Da
  • Monoisotopic mass554.367920 Da
  • ChemSpider ID9401737
  • defined stereocentres - 8 of 8 defined stereocentres


More details:



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134381-21-8 [RN]
Epoxomicin
L-Threoninamide, N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]- [ACD/Index Name]
MFCD03791061
N-acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-L-threoninamide
N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-{(2S)-4-methyl-1-[(2R)-2-methyl-2-oxiranyl]-1-oxo-2-pentanyl}-L-threoninamid [German] [ACD/IUPAC Name]
N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-{(2S)-4-methyl-1-[(2R)-2-methyl-2-oxiranyl]-1-oxo-2-pentanyl}-L-threoninamide [ACD/IUPAC Name]
N-Acétyl-N-méthyl-L-isoleucyl-L-isoleucyl-N-{(2S)-4-méthyl-1-[(2R)-2-méthyl-2-oxiranyl]-1-oxo-2-pentanyl}-L-thréoninamide [French] [ACD/IUPAC Name]
Y0900I3U8U
(2R,3S)-2-[acetyl(methyl)amino]-N-[(2S,3S)-1-{[(2S,3R)-3-hydroxy-1-({(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl}amino)-1-oxobutan-2-yl]amino}-3-methyl-1-oxopentan-2-yl]-3-methylpentanamide
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  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Chemical Class:

      A tripeptide consisting of an Ile-Ile-Thr-NH<smallsub>2</smallsub> sequence N-substituted on the threonamide amidic nitrogen with a (2<stereo>S</stereo>)-4-methyl-1-[(2<stereo>R</stereo>)-2-methyloxir an-2-yl]-1-oxopentan-2-yl group and with acetyl and methyl groups on the nitrogen of the isoleucine residue distal to the threonamide; a naturally occurring selective proteasome inhibitor with anti-in flammatory activity. ChEBI CHEBI:42265
      A tripeptide consisting of an Ile-Ile-Thr-NH2 sequence N-substituted on the threonamide amidic nitrogen with a (2S)-4-methyl-1-[(2R)-2-methyloxir; an-2-yl]-1-oxopentan-2-yl group and with acetyl and m ethyl groups on the nitrogen of the isoleucine residue distal to the threonamide; a naturally occurring selective proteasome inhibitor with anti-inflammatory activity. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:42265
    • Bio Activity:

      Epoxomicin(BU-4061T) is a potent anti-tumor agent isolated from Actinomycetes that is used as a selective and irreversible inhibitor of the 20S proteasome. MedChem Express
      Epoxomicin(BU-4061T) is a potent anti-tumor agent isolated from Actinomycetes that is used as a selective and irreversible inhibitor of the 20S proteasome.; IC50 value:; Target: 20S proteasome; in vitro: Epoxomicin inhibits proteasome activity in cell growth assays with an IC50 value of 4 nM and demonstrates potent cytotoxicity against B16-F10, HCT116, and Moser solid tumor cells, as well as P388 and K562 leukemia cells with IC50 values ranging from 2-44 nM [1] [2]. MedChem Express HY-13821
      Epoxomicin(BU-4061T) is a potent anti-tumor agent isolated from Actinomycetes that is used as a selective and irreversible inhibitor of the 20S proteasome.;IC50 value:;Target: 20S proteasome;In vitro: Epoxomicin inhibits proteasome activity in cell growth assays with an IC50 value of 4 nM and demonstrates potent cytotoxicity against B16-F10, HCT116, and Moser solid tumor cells, as well as P388 and K562 leukemia cells with IC50 values ranging from 2-44 nM [1] [2]. By inhibiting osteoblast proteasome activity, epoxomicin stimulates bone formation at concentrations as low as 10 nM [3].;In vivo: Intraperitoneal injection of 1.5 mg/kg epoxomicin given daily for two weeks induces Parkinson?s-like symptoms in rats and addition of 100 nM epoxomicin to rat ventral midbrain cultures results in apoptosis specific to dopaminergic neurons [4]. MedChem Express HY-13821
      Metabolism/Protease MedChem Express HY-13821
      Metabolism/Protease; MedChem Express HY-13821
      Proteasome MedChem Express HY-13821

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

Density: 1.1±0.1 g/cm3
Boiling Point: 795.7±60.0 °C at 760 mmHg
Vapour Pressure: 0.0±6.3 mmHg at 25°C
Enthalpy of Vaporization: 131.8±6.0 kJ/mol
Flash Point: 435.0±32.9 °C
Index of Refraction: 1.504
Molar Refractivity: 147.0±0.3 cm3
#H bond acceptors: 11
#H bond donors: 4
#Freely Rotating Bonds: 16
#Rule of 5 Violations: 2
ACD/LogP: 3.32
ACD/LogD (pH 5.5): 2.18
ACD/BCF (pH 5.5): 26.76
ACD/KOC (pH 5.5): 365.98
ACD/LogD (pH 7.4): 2.18
ACD/BCF (pH 7.4): 26.76
ACD/KOC (pH 7.4): 365.97
Polar Surface Area: 157 Å2
Polarizability: 58.3±0.5 10-24cm3
Surface Tension: 43.8±3.0 dyne/cm
Molar Volume: 496.3±3.0 cm3

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