Epoxomicin

Mfr.No.	SIH-388
Alternative Names	N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-L-threoninamide
Appearance	White solid
Function	Proteasome Inhibitor
Inchi	InChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1
Inchikey	DOGIDQKFVLKmlQ-JTHVHQAWSA-N
Mode Of Action	Inhibitor
Molecular Formula	C28H50N4O7
Pubchem Cid	11226684
Sd File	C30H53N5O8 APtclcactv02131419112D 0 0.00000 0.00000 96 96 0 0 1 0 0 0 0 0999 V2000 13.8660 1.2990 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 13.3660 2.1651 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8660 1.2990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8660 -0.4330 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3660 -1.2990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8660 1.2990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3660 2.1651 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.3660 -1.2990 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 14.8660 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3660 0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8660 3.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -2.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3660 0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 2.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.3660 0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3660 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3660 2.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3660 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.3660 3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8660 -2.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 -3.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1760 0.7621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0560 0.9699 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6760 -1.8360 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5560 -0.9699 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6760 -1.8360 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8660 3.0311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8660 -0.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 0.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 0.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 -0.4330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.3660 2.1651 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 0.7990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3660 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3660 2.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3660 0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8660 -0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8660 -0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3660 0.4330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8660 3.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3660 -3.0311 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.7990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8660 1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 9.3660 0.4330 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 -1.2990 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8660 -0.4330 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 13.8660 3.0311 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 15.4486 1.5111 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7584 1.9096 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2460 1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0560 2.7020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1760 0.7621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5560 0.1039 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6760 -0.7621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9486 0.6451 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2584 1.0436 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3894 0.6914 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2121 0.2164 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8291 0.7430 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0560 -0.1039 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9030 0.1230 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9030 1.8551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6760 2.7020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8291 2.4751 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8291 0.1230 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6760 -0.1039 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.9030 0.7430 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0560 2.7020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3410 2.6326 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3410 3.4296 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9030 4.2071 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0560 4.4341 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8291 3.5871 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3660 2.7851 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7460 2.1651 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3660 1.5451 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9030 4.2071 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0560 4.4341 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8291 3.5871 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.9030 3.5871 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.6760 4.4341 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8291 4.2071 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6760 -0.7621 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3291 -1.8551 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5560 -2.7020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4030 -2.4751 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3911 -1.7665 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3911 -2.5636 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6760 -2.4942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3291 -3.5871 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5560 -4.4341 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4030 -4.2071 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 -3.6511 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9860 -3.0311 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3660 -2.4111 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 30 38 2 0 0 0 0 3 44 1 6 0 0 0 31 39 2 0 0 0 0 5 46 1 1 0 0 0 32 40 2 0 0 0 0 1 9 1 0 0 0 0 6 14 1 6 0 0 0 5 39 1 0 0 0 0 6 43 1 0 0 0 0 34 43 1 0 0 0 0 3 37 1 0 0 0 0 9 15 1 0 0 0 0 39 47 1 0 0 0 0 3 7 1 0 0 0 0 2 36 1 0 0 0 0 7 11 1 0 0 0 0 10 47 1 0 0 0 0 11 16 1 0 0 0 0 37 45 1 0 0 0 0 7 17 1 1 0 0 0 10 40 1 0 0 0 0 2 48 1 1 0 0 0 18 48 1 0 0 0 0 6 40 1 0 0 0 0 41 48 1 0 0 0 0 4 45 1 1 0 0 0 33 41 2 0 0 0 0 6 34 1 0 0 0 0 19 41 1 0 0 0 0 36 44 1 0 0 0 0 4 8 1 0 0 0 0 1 13 1 6 0 0 0 8 20 1 0 0 0 0 4 38 1 0 0 0 0 8 35 1 6 0 0 0 28 36 2 0 0 0 0 5 12 1 0 0 0 0 1 2 1 0 0 0 0 12 42 1 0 0 0 0 29 37 2 0 0 0 0 21 42 1 0 0 0 0 38 46 1 0 0 0 0 22 42 1 0 0 0 0 9 49 1 0 0 0 0 9 50 1 0 0 0 0 1 51 1 0 0 0 0 2 52 1 0 0 0 0 23 44 1 0 0 0 0 3 53 1 0 0 0 0 24 45 1 0 0 0 0 4 54 1 0 0 0 0 25 46 1 0 0 0 0 5 55 1 0 0 0 0 26 47 1 0 0 0 0 10 56 1 0 0 0 0 10 57 1 0 0 0 0 34 58 1 0 0 0 0 34 59 1 0 0 0 0 13 60 1 0 0 0 0 13 61 1 0 0 0 0 13 62 1 0 0 0 0 14 63 1 0 0 0 0 14 64 1 0 0 0 0 14 65 1 0 0 0 0 15 66 1 0 0 0 0 15 67 1 0 0 0 0 15 68 1 0 0 0 0 7 69 1 0 0 0 0 11 70 1 0 0 0 0 11 71 1 0 0 0 0 16 72 1 0 0 0 0 16 73 1 0 0 0 0 16 74 1 0 0 0 0 17 75 1 0 0 0 0 17 76 1 0 0 0 0 17 77 1 0 0 0 0 18 78 1 0 0 0 0 18 79 1 0 0 0 0 18 80 1 0 0 0 0 19 81 1 0 0 0 0 19 82 1 0 0 0 0 19 83 1 0 0 0 0 8 84 1 0 0 0 0 20 85 1 0 0 0 0 20 86 1 0 0 0 0 20 87 1 0 0 0 0 27 35 1 0 0 0 0 12 88 1 0 0 0 0 12 89 1 0 0 0 0 42 90 1 0 0 0 0 21 91 1 0 0 0 0 21 92 1 0 0 0 0 21 93 1 0 0 0 0 22 94 1 0 0 0 0 22 95 1 0 0 0 0 22 96 1 0 0 0 0 M END $$$$
Research Area	Cell Signaling
Safety Phrases	Classification: Caution. Substance not yet fully tested. Safety Phrases: S22 - Do not breathe dust S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection S24/25 - Avoid contact with skin and eyes
Smiles	[C@@H](CC)(C)[C@@H](C(N[C@H](C(N[C@@H]([C@@H](C)O)C(=O)N[C@H](C(=O)NCC(=O)[C@]1(C)OC1)CC(C)C)=O)[C@H](CC)C)=O)N(C)C
Field Of Use	Not for use in humans. Not for use in diagnostics or therapeutics. For in vitro research use only.
Cas Number	134381-21-8
Molecular Weight	554.7
Scientific Background	Epoxomicin is a cell permeable, potent and selective proteasome inhibitor originally isolated from Actinomycetes strain based on its potent in vivo antitumor activity. It is a more potent inhibitor of the chymotrypsin-like activity of the proteasome than lactacystin. Epoxomicin also blocks trypsin-like and PGPH activities of the proteasome and regulates antigen presentation at non-toxic doses. It effectively inhibits NF-κB activation in vitro and potently blocks inflammation in vivo in the mouse ear edema assay. The ubiquitin-proteasome system (UPS) and autophagy serve as two complementary, reciprocally regulated protein degradation systems, thus inhibition of UPS by Epoxomicin activates autophagy.
Solubility	Soluble in DMSO (15 mg/ml) or dichloromethane:methanol (9:1); insoluble in water.
Source	Synthetic
Adr Code	Non-hazardous
Country Of Origin	Canada
Tarriff Code	3822.00.1090

Shipping Temperature	Shipped Ambient
Gross Weight (kg)	0.25
Net Weight (g)	0.0001
Purity	>95%
Storage Temperature	-20ºC
Stock Product	Y

Reference	1. F. Yang, et al. (2009) Neurosci. Lett. 454: 203. 2. K. Ohkawa, et al. (2004) Int. J. Oncol. 24: 425. 3. K. Schwarz, et al. (2000) J. Immunol. 164: 6147. 4. L. Meng, et al. (1999) PNAS. 96: 10403. 5. K.B. Kim, et al. (1999) Bioorg. Med. Chem. Lett. 9: 3335. 6. N. Sin, et al. (1999) Bioorg. Med. Chem. Lett. 9: 2283. 7. M. Hanada, et al. (1992) J. Antibiot. (Tokyo) 45: 1746.

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Combination SKU	Supplier No.	Size	Your price	Quantity
BHB11900176-1	SIH-388-100UG	100 ug	$219		Add to Cart

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