| Identification | Back Directory | [Name]
EMBELIN | [CAS]
550-24-3 | [Synonyms]
EMBELIN
emberine
NSC 91874
embelicacid
EMbeliaquinone
XIAP INHIBITOR
TIMTEC-BB SBB005949
Embelin (Embelic acid)
APOPTOSIS ACTIVATOR III
embelin from embelia seeds
Apoptosis Activator III, Embelin
2,5-dihydroxy-3-undecyl-p-benzoquinon
2,5-DIHYDROXY-3-UNDECYL-P-BENZOQUINONE
2,5-DIHYDROXY-3-UNDECYL-1,4-BENZOQUINONE
2,5-DIHYDROXY-3-UNDECYL-P-BENZOQUINONE, EMBELIN
4-dione,2,5-dihydroxy-3-undecyl-5-cyclohexadiene-1
2,5-DIHYDROXY-3-UNDECYL-2,5-CYCLOHEXADIENE-1,4-DIONE
2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
2,5-dihydroxy-3-undecyl-cyclohexa-2,5-diene-1,4-dione
2,5-Cyclohexadiene-1,4-dione, 2,5-dihydroxy-3-undecyl- free base | [EINECS(EC#)]
208-979-8 | [Molecular Formula]
C17H26O4 | [MDL Number]
MFCD00016369 | [MOL File]
550-24-3.mol | [Molecular Weight]
294.39 |
| Chemical Properties | Back Directory | [Melting point ]
142-143°C | [Boiling point ]
356.15°C (rough estimate) | [density ]
1.131 | [refractive index ]
1.4230 (estimate) | [storage temp. ]
Store at +4°C | [solubility ]
DMSO: >10 mg/mL
| [form ]
solid
| [pka]
2.84±0.50(Predicted) | [color ]
Dark orange | [Sensitive ]
Light Sensitive | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month. | [InChI]
1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3 | [InChIKey]
IRSFLDGTOHBADP-UHFFFAOYSA-N | [SMILES]
CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O | [LogP]
5.024 (est) |
| Hazard Information | Back Directory | [Chemical Properties]
Orange Solid | [Uses]
Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embel
in also displays contraceptive and pro-apoptotic properties. | [Definition]
ChEBI: A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, an
ineoplastic and inhibitory activity towards hepatitis C protease. | [Biological Activity]
Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC 50 = 4.1 μ M in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC 50 4-6 μ M), but has a weaker effect on normal prostate cells (IC 50 = 19-20 μ M). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo . | [Description]
Embelin (550-24-3) inhibits?the lysine acetyl transferase PCAF?in vitro and in vivo?(in vitro?IC50=7.2 mM). Inhibits H3K9 acetylation in mouse liver tissue while leaving levels of H3K14, H4K8, H4K12 unchanged.1? Also inhibits X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 μM, competing with Smac peptide). Binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Induces apoptosis and alters gene expression profiles in breast cancer cells.3?Possesses anti-inflammatory and analgesic activity?in vivo.4?Cell-permeable. | [References]
1) Modak?et al. (2013),?Probing p300/CBP associated factor (PCAF)-dependent pathways with a small molecule inhibitor; ACS Chem. Biol.,?8?1311
2) Nikolovska-Coleska?et al. (2004),?Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database; J. Med. Chem.,?47?2430
3) Shah?et al.?(2016),?Embelin inhibits proliferation, induces apoptosis and alters gene expression profiles in breast cancer cells; Pharmacol. Rep.,?68?638
4) Chitra?et al. (1994),?Antitumor, anti-inflammatory and analgesic property of embelin, a plant product.; Chemotherapy,?40?109 |
| Safety Data | Back Directory | [WGK Germany ]
3
| [RTECS ]
DK4230000
| [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Repr. 2 |
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