Compound: 66701-25-5
SMILES: O=C(O)[C@H]1O[C@@H]1C(=O)N[C@H](C(=O)NCCCCNC(=N)N)CC(C)C
InChIKey: LTLYEAJONXGNFG-DCAQKATOSA-N
Synonyms: 66701-25-5, Proteinase inhibitor E 64, R76F7856MV, trans-epoxysuccinyl-l-leucylamido-(4-guanidino)butane, DTXSID90985271, RefChem:898897, DTXCID501412467, e-64, (2S,3S)-3-(((S)-1-((4-Guanidinobutyl)amino)-4-methyl-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxylic acid, MFCD00080261, CHEMBL374508, E 64, E64, (2S,3S)-3-[[(2S)-1-[4-(diaminomethylideneamino)butylamino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylic acid, C15H27N5O5, Thiol protease inhibitor, (2S,3S)-3-[[(1S)-1-(4-guanidinobutylcarbamoyl)-3-methyl-butyl]carbamoyl]oxirane-2-carboxylic acid, E 64 (proteinase inhibitor), BRN 1405664, UNII-R76F7856MV, (2S,3S)-3-[[(S)-1-[(4-Guanidinobutyl)amino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylic Acid, 2-OXIRANECARBOXYLIC ACID, 3-((((1S)-1-(((4-((AMINOIMINOMETHYL)AMINO)BUTYL)AMINO)CARBONYL)-3-METHYLBUTYL)AMINO)CARBONYL)-, (2S,3S)-, 2-Oxiranecarboxylic acid, 3-[[[(1S)-1-[[[4-[(aminoiminomethyl)amino]butyl]amino]carbonyl]-3-methylbutyl]amino]carbonyl]-, (2S,3S)-, Proteinase inhibitor E64, 5-18-07-00006 (Beilstein Handbook Reference), SCHEMBL4740187, SCHEMBL29440579, CHEBI:30270, PROTEINASE INHIBITOR E-64, GLXC-07974, 3-[[1-[4-(diaminomethylideneamino)butylamino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylic acid, 80408-29-3, EX-A2284, IES-4096, BDBM50157741, AKOS016007415, CCG-207844, CCG-208198, CS-4140, FD21944, FE29621, NCGC00163544-01, NCGC00163544-09, 3-[[[(1S)-1-[[[4-[(aminoiminomethyl)amino]butyl]amino]carbonyl]-3-methylbutyl]amino]carbonyl]-(2S,3S)-oxiranecarboxylic acid, AC-36011, DA-52771, HY-15282, Oxiranecarboxylic acid, 3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbonyl)-3-methylbutyl)amino)carbonyl)-, (2S-(2-alpha,3-beta(R*)))-, Oxiranecarboxylic acid, 3-(((1-(((4-((aminoiminomethyl)amino)butyl)amino)carbonyl)-3-methylbutyl)amino)carbonyl)-, (2S-(2alpha,3beta(R*)))-, SY076761, C01341, H51107, Q5321373, (L-3-trans-Carboxyoxiran-2-carbonyl)-L-leucyl-admat, (2S,3S)-3-((S)-1-(4-Guanidinobutylamino)-4-methyl-1-oxopentan-2-ylcarbamoyl)oxirane-2-carboxylic acid, (2S,3S)-3-(N-{(S)-1-[N-(4-guanidinobutyl)carbamoyl]3-methylbutyl}carbamoyl)oxirane-2-carboxylic acid
Theoretical properties:
molecular_formula: C15H27N5O5
molecular_weight: 357.41 g/mol
exact_mass: 357.20121898 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 11
heavy_atom_count: 25
topological_polar_surface_area: 172 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: E64 is an epoxy monocarboxylic acid, a member of guanidines, a L-leucine derivative and a dicarboxylic acid monoamide. It has a role as an antiparasitic agent, a protease inhibitor and an antimalarial. It is a tautomer of an E64 zwitterion.
chebi: Zwitterionic form of E64, a compound isolated from Aspergillus japonicus, resulting from transfer of a proton from the carboxy to the guanidino group; major species at pH 7.3.
chembl: E-64 is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: E-64 is an epoxide which can irreversibly inhibit a wide range of cysteine peptidases.
The compound was first isolated and identified from Aspergillus japonicus in 1978.  It has since been shown to inhibit many cysteine peptidases such as papain, cathepsin B, cathepsin L, calpain and staphopain.
The low toxic effects of the inhibitor, in addition to its effective mechanism of action, makes E-64 a potential template for drugs to treat diseases where high levels of a cysteine proteases are the primary cause.