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Epoxomicin

AlkaPlorer ID: AK004285

Synonym: None

IUPAC Name: (2S,3S)-2-[[(2S,3S)-2-[acetyl(methyl)amino]-3-methylpentanoyl]amino]-N-[(2S,3R)-3-hydroxy-1-[[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]amino]-1-oxobutan-2-yl]-3-methylpentanamide

Structure

SMILES: CC[C@H](C)[C@H](N=C(O)[C@H]([C@@H](C)CC)N(C)C(C)=O)C(O)=N[C@H](C(O)=N[C@@H](CC(C)C)C(=O)[C@@]1(C)CO1)[C@@H](C)O

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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

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InChIKey: DOGIDQKFVLKMLQ-JTHVHQAWSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
bacterium None None None None None None Bacteria

Properties Information

Molecule Weight: 554.7290000000004

TPSA？: 167.91

MolLogP？: 3.685700000000003

Number of H-Donors: 4

Number of H-Acceptors: 7

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bos taurus Alpha-chymotrypsin k obs / 1 nan None 10.1016/s0960-894x(99)00376-5
Carica papaya Papain k obs / 1 nan None 10.1016/s0960-894x(99)00376-5
Homo sapiens A549 Activity 80.0 % 10.1128/aac.00088-09
Homo sapiens Calpain 1 k obs / 1 nan None 10.1016/s0960-894x(99)00376-5
Homo sapiens Cathepsin B IC50 120000.0 nM 10.1021/jm058289o
Homo sapiens Cathepsin S IC50 25000.0 nM 10.1021/jm058289o
Homo sapiens Cathepsin S k obs / 1 nan None 10.1016/s0960-894x(99)00376-5
Homo sapiens HEK293 IC50 33.6 nM 10.6019/CHEMBL2113921
Homo sapiens PC-3 IC50 1.0 nM 10.1021/jm058289o
Homo sapiens Proteasome component C5 IC50 300.0 nM 10.1021/jm4002007
Homo sapiens Proteasome component C5 IC50 2200.0 nM 10.1021/jm058289o
Homo sapiens Proteasome Macropain subunit IC50 160.0 nM 10.1021/jm058289o
Homo sapiens Proteasome Macropain subunit IC50 980.0 nM 10.1016/j.bmcl.2006.03.070
Homo sapiens Proteasome Macropain subunit MB1 IC50 3.7 nM 10.1021/jm058289o
Homo sapiens Proteasome Macropain subunit MB1 IC50 26.0 nM 10.1021/jm4002007
Homo sapiens Proteasome Macropain subunit MB1 IC50 47.0 nM 10.1016/j.bmcl.2006.03.070
Homo sapiens Proteasome Macropain subunit MB1 Ratio 0.27 None 10.1021/jm058289o
Homo sapiens RPMI-8226 IC50 11.0 nM 10.1021/acs.jmedchem.8b01943
Homo sapiens Trypsin I k obs / 1 nan None 10.1016/s0960-894x(99)00376-5
Mus musculus NIH3T3 Activity 80.0 % 10.1128/aac.00088-09
Plasmodium falciparum Plasmodium falciparum Activity 77.0 % 10.1128/aac.00088-09
Plasmodium falciparum Plasmodium falciparum Activity 86.0 % 10.1128/aac.00088-09
Plasmodium falciparum Plasmodium falciparum IC50 0.3 nM 10.6019/CHEMBL2113921
Plasmodium falciparum Plasmodium falciparum IC50 0.7 nM 10.1016/j.ejmech.2018.03.024
Plasmodium falciparum Plasmodium falciparum IC50 0.7 nM 10.1021/jm4004279
Plasmodium falciparum Plasmodium falciparum IC50 2.0 nM 10.1021/jm3005898
Plasmodium falciparum Plasmodium falciparum IC50 2.2 nM 10.1021/jm4004279
Plasmodium falciparum Plasmodium falciparum IC50 4.2 nM 10.6019/CHEMBL2113921
Plasmodium falciparum Plasmodium falciparum IC50 7.0 nM 10.1016/j.ejmech.2018.03.024
Plasmodium falciparum Plasmodium falciparum IC50 7.0 nM 10.1016/j.ejmech.2018.09.018
Plasmodium falciparum Plasmodium falciparum IC50 11.8 nM 10.1021/acs.jmedchem.5b01374
Plasmodium falciparum Plasmodium falciparum IC50 41.0 nM 10.1128/aac.00088-09
Plasmodium falciparum Plasmodium falciparum IC50 54.0 nM 10.1128/aac.00088-09
Plasmodium falciparum Plasmodium falciparum IC50 nan None 10.1021/jm4004279
Plasmodium falciparum K1 Plasmodium falciparum K1 IC50 2.8 nM 10.6019/CHEMBL2113921
Plasmodium yoelii yoelii Plasmodium yoelii yoelii IC50 3950.0 nM 10.1021/jm201095h
Plasmodium yoelii yoelii Plasmodium yoelii yoelii IC50 3950.0 nM 10.1128/aac.01043-07
Rattus norvegicus Plasma Stability nan % 10.1021/jm058289o
Schistosoma mansoni Schistosoma mansoni EC50 226.0 nM 10.6019/CHEMBL5096127
Schistosoma mansoni Schistosoma mansoni In vitro activity nan None 10.6019/CHEMBL5096127
Schistosoma mansoni Schistosoma mansoni Worm movement inhibition 97.15 % 10.6019/CHEMBL5096127
None Hepatocyte TC50 4.73 10'4nM 10.1128/aac.01043-07
None NON-PROTEIN TARGET IC50 4.0 nM 10.1016/s0960-894x(99)00612-5
None NON-PROTEIN TARGET IC50 4.8 nM 10.1016/j.bmc.2011.11.066
None No relevant target Solubility nan None 10.1021/jm058289o
None Proteasome IC50 261.0 nM 10.1016/j.ejmech.2021.114053
None Proteasome k obs / 1 37200.0 M-1 s-1 10.1016/s0960-894x(99)00376-5
None Unchecked FC 100.0 None 10.1016/j.bmc.2011.11.066
None Unchecked FC 112.0 None 10.1016/j.bmc.2011.11.066
None Unchecked IC50 5.0 nM 10.1016/j.bmc.2009.06.025
None Unchecked IC50 5.0 nM 10.1016/j.bmcl.2008.02.016
None Unchecked IC50 5.0 nM 10.1016/j.ejmech.2007.10.002
None Unchecked IC50 5.0 nM 10.1021/jm100122e
None Unchecked IC50 6.0 nM 10.1016/j.bmc.2011.11.066
None Unchecked IC50 9.0 nM 10.1016/j.bmc.2009.06.025
None Unchecked IC50 9.0 nM 10.1016/j.bmcl.2009.02.046
None Unchecked IC50 60.0 nM 10.1016/j.bmc.2011.11.066
None Unchecked IC50 261.0 nM 10.1021/jm301443r
None Unchecked IC50 284.0 nM 10.1016/j.bmc.2009.06.025
None Unchecked IC50 284.0 nM 10.1016/j.bmcl.2008.02.016
None Unchecked IC50 284.0 nM 10.1016/j.ejmech.2007.10.002
None Unchecked IC50 284.0 nM 10.1021/jm100122e
None Unchecked IC50 311.0 nM 10.1016/j.bmcl.2009.02.046
None Unchecked IC50 541.0 nM 10.1021/acs.jmedchem.8b01943
None Unchecked IC50 758.0 nM 10.1016/j.bmc.2009.06.025
None Unchecked IC50 4560.0 nM 10.1016/j.bmc.2009.06.025
None Unchecked IC50 4560.0 nM 10.1016/j.bmcl.2008.02.016
None Unchecked IC50 4560.0 nM 10.1016/j.ejmech.2007.10.002
None Unchecked IC50 4560.0 nM 10.1021/jm100122e
None Unchecked IC50 5640.0 nM 10.1016/j.bmcl.2009.02.046
None Unchecked IC50 10000.0 nM 10.1016/j.bmc.2009.06.025
None Unchecked Inhibition 100.0 % 10.1016/j.bmcl.2014.05.025
None Unchecked Inhibition nan % 10.1021/np300231f
None Unchecked k obs / 1 43.0 M-1 s-1 10.1016/s0960-894x(99)00612-5
None Unchecked k obs / 1 310.0 M-1 s-1 10.1016/s0960-894x(99)00612-5
None Unchecked k obs / 1 20000.0 M-1 s-1 10.1016/s0960-894x(99)00612-5
None Unchecked Ratio IC50 49.2 None 10.1021/acs.jmedchem.8b01943
None Unchecked Selectivity Index 11.97 None 10.1128/aac.01043-07

Metabolism Information