| Identification | Back Directory | [Name]
dihydroeponemycin | [CAS]
126463-64-7 | [Synonyms]
dihydroeponemycin
Dihydroeponemycin >=98% (HPLC)
Heptanamide, N-[(1S)-1-(hydroxymethyl)-2-[[(1S)-1-[[(2R)-2-(hydroxymethyl)-2-oxiranyl]carbonyl]-3-methylbutyl]amino]-2-oxoethyl]-6-methyl- | [Molecular Formula]
C20H36N2O6 | [MDL Number]
MFCD17215971 | [MOL File]
126463-64-7.mol | [Molecular Weight]
400.51 |
| Chemical Properties | Back Directory | [storage temp. ]
2-8°C | [solubility ]
DMSO: ≥1mg/mL | [form ]
powder | [color ]
off-white to light tan | [Optical Rotation]
[α]/D ±35.7° | [InChI]
1S/C20H36N2O6/c1-13(2)7-5-6-8-17(25)21-16(10-23)19(27)22-15(9-14(3)4)18(26)20(11-24)12-28-20/h13-16,23-24H,5-12H2,1-4H3,(H,21,25)(H,22,27)/t15-,16-,20+/m0/s1 | [InChIKey]
IUDBVFIQSSOIDB-TWOQFEAHSA-N | [SMILES]
CC(C)CCCCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)[C@@]1(CO)CO1 |
| Hazard Information | Back Directory | [Description]
Dihydroeponemycin is a natural, irreversible inhibitor of proteasomal degradation of proteins that acts by binding the IFN-γ-inducible proteins LMP2 and LMP7, as well as the constitutive proteasome subunit X. It potently inhibits both the chymotrypsin-like and PGPH activity, with 10-fold less inhibition of trypsin-like activity. Dihydroeponemycin does not inhibit calpain or trypsin and has minor effects on cathepsin B and chymotrypsin at higher concentrations. It is cell-permeable and induces apoptosis in bovine aortic endothelial cells. | [Uses]
Dihydroeponemycin, an analogue of the antitumor and antiangiogenic natural product eponemycin, selectively targets the 20S proteasome. Dihydroeponemycin covalently modifies a subset of catalytic proteasomal subunits, binding preferentially to the IFN-gamma-inducible subunits LMP2 and LMP7. Dihydroeponemycin-mediated proteasome inhibition induces a spindle-like cellular morphological change and apoptosis[1]. | [target]
Proteasome | [References]
[1] Meng L, et al. Eponemycin exerts its antitumor effect through the inhibition of proteasome function. Cancer Res. 1999;59(12):2798-2801. PMID:10383134 |
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BOC Sciences
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Energy Chemical
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Merck KGaA
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