Basic information
- CAS
88321-09-9- Standard SMILES
CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C- InChIKey
SRVFFFJZQVENJC-IHRRRGAJSA-N- Molecular formula
- C17H30N2O5
- Average molar mass
- 342.4 g/mol
- Monoisotopic mass
- 342.21547206
Overview
Aloxistatin is an L-leucine derivative that is the amide obtained by formal condensation of the carboxy group of (2S,3S)-3-(ethoxycarbonyl)oxirane-2-carboxylic acid with the amino group of N-(3-methylbutyl)-L-leucinamide. It has a role as an anticoronaviral agent and a cathepsin B inhibitor. It is an ethyl ester, a L-leucine derivative, a monocarboxylic acid amide and an epoxide.
Names & identifiers
- Preferred name
- Aloxistatin
- IUPAC
- ethyl (2S,3S)-3-[[(2S)-4-methyl-1-(3-methylbutylamino)-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylate
- English name
- EST
- Molecular formula
- C17H30N2O5
- Molecular weight
- 342.43
Names & synonyms
Aloxistatin88321-09-9E-64DLoxistatinE 64dAloxistatinaAloxistatineAloxistatinumE 64c ethyl esterE64dL5W337AOURNSC-694281
Show more names
ESTep453EstateCS-1622oxistatinNSC694281E64d,E-64dLOXASTATIN
ethyl (2S,3S)-3-[[(2S)-4-methyl-1-(3-methylbutylamino)-1-oxopentan-2-yl]carbamoyl]oxirane-2-carboxylateEthyl (+)-(2S,3S)-2,3-epoxy-N-((S)-1-(isopentylcarbamoyl)-3-methylbutyl)succinamateCHEBI:101381DTXSID00904150ethyl (2S,3S)-3-(((2S)-4-methyl-1-(3-methylbutylamino)-1-oxopentan-2-yl)carbamoyl)oxirane-2-carboxylateEP-453protease inhibitor E64dRefChem:110983
Database identifiers
- CAS
88321-09-9- PubChem CID
- 65663
- DTXSID
DTXSID00904150- ChEMBL
CHEMBL63440- ChEBI
CHEBI:101381- UNII
- L5W337AOUR
- EC Number
- 635-831-3
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 97 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 11
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 450
Physicochemical properties
- Melting point
- 126.2 °C · 126.2°C
- Boiling point
- 477.88 °C · 477.88°C (rough estimate)
- Density
- 1.0657 · 1.0657 (rough estimate)
- refractive index
- 1.58 · 1.5800 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO, DMF or ethanol
- form
- White solid
- pka
- 13.32 · 13.32±0.40(Predicted)
- color
- Fine needles from EtOH
- biological source
- synthetic (organic)
- Stability
- 1 year · 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/C17H30N2O5/c1-6-23-17(22)14-13(24-14)16(21)19-12(9-11(4)5)15(20)18-8-7-10(2)3/h10-14H,6-9H2,1-5H3,(H,18,20)(H,19,21)/t12-,13-,14-/m0/s1
- InChIKey
- SRVFFFJZQVENJC-IHRRRGAJSA-N
- SMILES
- N([C@@H](CC(C)C)C(=O)NCCC(C)C)C(=O)[C@H]1O[C@@H]1C(=O)OCC
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 2
- rtecs
- RR0404300
- ridadr
- 3077
- hs_code
- 29242990
- Toxicity
- cyt-ham:lng 200 mg/L IYKEDH 17,815,86
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs or agents which antagonize or impair any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
Exogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES.
Applications
DescriptionE-64d is an irreversible, membrane-permeable inhibitor of lysosomal and cytosolic cysteine proteases and has diverse biological activities. It is a synthetic analog of E-64 and prodrug form of E-64c that inhibits calpain and the cysteine proteases cathepsins F, -K, -B, -H, and -L. E-64d (20-200 μM) induces cell cycle arrest at the G2/M phase in A431 human epidermoid carcinoma cells. It inhibits protease-resistant prion protein accumulation in scrapie-infected neuroblastoma cells with an IC50 value of 0.5 μM. E-46d also inhibits entry of vesicular stomatitis virus (VSV) particles pseudotyped with severe acute respiratory syndrome coronavirus (SARS-CoV) or SARS-CoV-2 spike glycoprotein into Vero cells, an effect that is reduced by expression of the serine protease TMPRSS2.
UsesE-64d is an inhibitor of cathepsins B and L as well as a potential inhibitor of calpain. E-64d has been shown to inhibit lysosomal proteases. E-64d has been used in combination with Prepstatin A to interfere with autolysosomal digestion. E-64d displays neurovascular and neuronal protective effects after focal cerebral ischemia in rats.
UsesE-64d has been used as a lysosomal inhibitor in human acute promyelocytic leukemia NB4 cells and Huh-7cells. It has also been used as a protease inhibitor in free calcium physiological tyrode solution for perfusion into the isolated heart samples.
Upstream & downstream products
Upstream raw materials
Related reactions
0 records
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Compound notes
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