E-64 - 10mM in DMSO , CAS No.66701-25-5

CAS: 66701-25-5 Cat. No.: E425359 Molecular Weight: 357.41 Beilstein Registry Number: 1405664 EC Number: 613-978-4

GRADE & PURITY 10mM in DMSO

Synonyms

SCHEMBL4740187 | BDBM50157741 | (2S,3S)-3-(N-{(S)-1-[N-(4-guanidinobutyl)carbamoyl]3-methylbutyl}carbamoyl)oxirane-2-carboxylic acid | AKOS016007415 | (2S,3S)-3-[[(2S)-1-[4-(diaminomethylideneamino)butylamino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

protease inhibitor ，E-64 is an effective ligand for affinity purification of cysteine proteases. When coupled to a thiolated affinity matrix, binding is no longer irreversible, but specificity is retained

E-64 is a cysteine protease inhibitor that was isolated from the mold Aspergillus japonicus TPR-64. E-64 is also known as N-[N-(L-3-trans-carboxyoxiran-2-carbonyl)-L-leucyl]-agmatine. E-64 effectively inhibits various cysteine proteases, in particular:

• cathepsin K

• cathepsin L

• cathepsin S

E-64 also acts against other enzymes, such as:

• calpain

• cathepsin B

• cathepsin H

• papain

application：

It is used as a broad spectrum cysteine proteinase and calpain activation inhibitor. Additionally, Prevotella intermediate studies report that E-64 blocks the breakdown of methaemoglobin and the oxidation of oxyhaemoglobin by InpA. E-64 has also been used to study excystation in Giardia lamblia. E-64 is an inhibitor of Calpain, cathepsin K and cathepsin S. E-64 is an effective ligand for affinity purification of cysteine proteases. When coupled to a thiolated affinity matrix, binding is no longer irreversible, but specificity is retained

Specifications

Synonyms

SCHEMBL4740187 | BDBM50157741 | (2S, 3S)-3-(N-{(S)-1-[N-(4-guanidinobutyl)carbamoyl]3-methylbutyl}carbamoyl)oxirane-2-carboxylic acid | AKOS016007415 | (2S, 3S)-3-[[(2S)-1-[4-(diaminomethylideneamino)butylamino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

E-64 is an irreversible, potent, and highly selective cysteine protease inhibitor. E-64 does not react with the functional thiol group of non-protease enzymes, such as L-lactate dehydrogenase or creatine kinase. E-64 will not inhibit serine proteases (exc

Storage

Protected from light, Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CC(C)C[C@H](NC(=O)[C@@H]1O[C@H]1C(O)=O)C(=O)NCCCCNC(N)=N
• IUPAC Name: (2S,3S)-3-[[(2S)-1-[4-(diaminomethylideneamino)butylamino]-4-methyl-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylic acid
• InChIKey: LTLYEAJONXGNFG-DCAQKATOSA-N
• INCHI: 1S/C15H27N5O5/c1-8(2)7-9(20-13(22)10-11(25-10)14(23)24)12(21)18-5-3-4-6-19-15(16)17/h8-11H,3-7H2,1-2H3,(H,18,21)(H,20,22)(H,23,24)(H4,16,17,19)/t9-,10-,11-/m0/s1
• Isomeric SMILES: CC(C)C[C@@H](C(=O)NCCCCN=C(N)N)NC(=O)[C@@H]1[C@H](O1)C(=O)O
• WGK Germany: 3
• RTECS: RR0390000
• Molecular Weight: 357.41
• Beilstein: 1405664

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Epoxides
      • Subclass Oxirane carboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Epoxides
• Subclass: Oxirane carboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Oxirane carboxylic acids
• Alternative Parents: Guanidines Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Monocarboxylic acids and derivatives Dialkyl ethers Carboxylic acids Carboximidic acids Carboximidamides Organopnictogen compounds Organic oxides Imines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Oxirane carboxylic acid - Guanidine - Carboximidic acid - Carboximidic acid derivative - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Ether - Monocarboxylic acid or derivatives - Carboximidamide - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Oxacycle - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Imine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as oxirane carboxylic acids. These are compounds containing an oxirane ring bearing a carboxylic acid group.
• External Descriptors: guanidines - epoxy monocarboxylic acid - dicarboxylic acid monoamide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP3A4 Tclin Cytochrome P450 3A4 (0 Activities)

Discover Target: CYP3A4

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CTSL Tclin Cathepsin L1 (6 Activities)

Discover Target: CTSL

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CTSS Tchem Cathepsin S (1 Activities)

Discover Target: CTSS

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CTSK Tchem Cathepsin K (1 Activities)

Discover Target: CTSK

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CTSH Tchem Pro-cathepsin H (1 Activities)

Discover Target: CTSH

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CTSC Tchem Dipeptidyl peptidase 1 (1 Activities)

Discover Target: CTSC

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CTSB Tchem Cathepsin B (4 Activities)

Discover Target: CTSB

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

CAPN1 Tchem Calpain-1 catalytic subunit (1 Activities)

Discover Target: CAPN1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ACHE Tclin Acetylcholinesterase (18204 Activities)

Discover Target: ACHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ELANE Tclin Leukocyte elastase (8173 Activities)

Discover Target: ELANE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSD Tchem Cathepsin D (3201 Activities)

Discover Target: CTSD

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSB Tchem Cathepsin B (3822 Activities)

Discover Target: CTSB

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSK Tchem Cathepsin K (3011 Activities)

Discover Target: CTSK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSS Tchem Cathepsin S (3285 Activities)

Discover Target: CTSS

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSH Tchem Cathepsin H (179 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSC Tchem Dipeptidyl peptidase I (1385 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HUVEC (11049 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

Discover Target: POLK

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSA Tchem Lysosomal protective protein (919 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RUNX1 Tbio Runt-related transcription factor 1/Core-binding factor subunit beta (7867 Activities)

Discover Target: RUNX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEK-293T (167025 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAPN9 Tbio Calpain-9 (15 Activities)

Discover Target: CAPN9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Papain (844 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cruzipain (33337 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CTSL Cathepsin L (58 Activities)

Discover Target: CTSL

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CAPN1 Calpain 1 (219 Activities)

Discover Target: CAPN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Carboxylesterase (379 Activities)

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Trypanosoma brucei brucei (13300 Activities)

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Plasmodium falciparum (966862 Activities)

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Leishmania amazonensis (3813 Activities)

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Toxoplasma gondii (4585 Activities)

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Rattus norvegicus (775804 Activities)

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NIH3T3 (5395 Activities)

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rhodesain Rhodesain (1463 Activities)

Discover Target: rhodesain

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cysteine protease falcipain-3 (47 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BCHE Cholinesterase (8742 Activities)

Discover Target: BCHE

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Falcipain 2 (539 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive；Moisture sensitive
• Melt Point(°C): >170°C
• Molecular Weight: 357.410 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 357.201 Da
• Monoisotopic Mass: 357.201 Da
• Topological Polar Surface Area: 172.000 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 518.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Limei Cai, Xiaoming Liu, Zhiqiang Tian, J.P. Michaud, Zhongjian Shen, Zhen Li, Songdou Zhang, Xiaoxia Liu.  (2022)  Safety of Bacillus thuringiensis Cry1Ah and Vip3Aa toxins for the predatory stink bug Arma custos (Hemiptera: Pentatomidae).  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:35987246] [10.1016/j.scitotenv.2022.158120]

2. Yunhua Zhang, Jinyun Ji, Xiao Zhao, Ruoheng Jin, Jianhong Li, Hu Wan.  (2017)  Expression, purification and enzymatic properties of a β-N-acetylhexosaminidase from brown planthopper, Nilaparvata lugens.  JOURNAL OF ASIA-PACIFIC ENTOMOLOGY,      [PMID:] [10.1016/j.aspen.2017.10.005]

3. Jiandong Shen, Bijiang Zhong, Wenshui Xia, Yanshun Xu.  (2024)  Action of structural proteins in textural deterioration of grass carp (Ctenopharyngodon idellus) fillets during refrigerated storage.  INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY,  59  (4): (2659-2666).  [PMID:] [10.1111/ijfs.17010]

4. Xia Gao, Meng Gui, Shengjun Chen, Xiao Hu, Juan You, Tao Yin, Yang Hu, Shanbai Xiong, Ru Liu.  (2025)  Insights into HIU enhancement of salt-reduced surimi gelation properties: Dual regulation of endogenous transglutaminase activation and protease inhibition.  ULTRASONICS SONOCHEMISTRY,      [PMID:40834706] [10.1016/j.ultsonch.2025.107516]

5. Jiandong Shen, Wei Zhang, Qixing Jiang, Pei Gao, Yanshun Xu, Wenshui Xia.  (2022)  The role of cathepsin L on structural changes of collagen fibers involved in textural deterioration of chilled grass carp (Ctenopharyngodon idella) fillets.  JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE,  102  (13): (5858-5866).  [PMID:35426126] [10.1002/jsfa.11935]