Calpeptin
Basic information
- CAS
117591-20-5- Standard SMILES
CCCC[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)OCc1ccccc1- InChIKey
PGGUOGKHUUUWAF-ROUUACIJSA-N- Molecular formula
- C20H30N2O4
- Average molar mass
- 362.5 g/mol
- Monoisotopic mass
- 362.22055744
Overview
Calpeptin is an amino acid amide.
Names & identifiers
- Preferred name
- Calpeptin
- IUPAC
- benzyl N-[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxohexan-2-yl]amino]pentan-2-yl]carbamate
- English name
- CALPEPTIN
- Molecular formula
- C20H30N2O4
- Molecular weight
- 362.46
Names & synonyms
calpeptin117591-20-5Benzylcarbonyl-leu-nleu-HN-Cbz-leu-nleu-al18X9FR245WDTXSID90922464benzyl N-[(2S)-4-methyl-1-oxo-1-[[(2S)-1-oxohexan-2-yl]amino]pentan-2-yl]carbamatecarbamic acid, N-((1S)-1-((((1S)-1-formylpentyl)amino)carbonyl)-3-methylbutyl)-, phenylmethyl esterbenzyl N-[(1S)-1-[[(1S)-1-formylpentyl]carbamoyl]-3-methyl-butyl]carbamatebenzyl N-((1S)-1-(((1S)-1-formylpentyl)carbamoyl)-3-methyl-butyl)carbamatebenzyl N-((2S)-4-methyl-1-oxo-1-(((2S)-1-oxohexan-2-yl)amino)pentan-2-yl)carbamateSR914
Show more names
CS-1747Z-LEU-NLE-OHZ-LEU-NLE-CHOCalpeptin,95%Z-LEU-NORLEUCINALCalpeptin, 10 mM in DMSON-CBZ-L-LEUCYL-NORLEUCINALCalpain Inhibitor：CalpeptinBENZYLOXYCARBONYLLEUCYL-NORLEUCINAL
SR 914RefChem:123050DTXCID101351348benzyl ((S)-4-methyl-1-oxo-1-(((S)-1-oxohexan-2-yl)amino)pentan-2-yl)carbamateMFCD00155623CHEMBL92708KBio3_000476HMS3675M09
Database identifiers
- CAS
117591-20-5- PubChem CID
- 73364
- DTXSID
DTXSID90922464- ChEMBL
CHEMBL92708- ChEBI
CHEBI:3330- UNII
- 18X9FR245W
- Nikkaji
- J739.130G
Properties
Computed structural properties
- XLogP
- 3.9
- Topological polar surface area
- 84.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 12
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 434
Physicochemical properties
- Melting point
- 60 · 60-75 °C
- Boiling point
- 494.07 °C · 494.07°C (rough estimate)
- Density
- 1.1667 · 1.1667 (rough estimate)
- refractive index
- 1.68 · 1.6800 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 15 mg/ml · Soluble in DMSO at 15mg/ml
- form
- White to off-white solid
- pka
- 11.14 · 11.14±0.46(Predicted)
- color
- white to beige
- InChI
- 1S/C20H30N2O4/c1-4-5-11-17(13-23)21-19(24)18(12-15(2)3)22-20(25)26-14-16-9-7-6-8-10-16/h6-10,13,15,17-18H,4-5,11-12,14H2,1-3H3,(H,21,24)(H,22,25)/t17-,18-/m0/s1
- InChIKey
- PGGUOGKHUUUWAF-ROUUACIJSA-N
- SMILES
- C(OCC1=CC=CC=C1)(=O)N[C@H](C(N[C@H](C=O)CCCC)=O)CC(C)C
- CAS DataBase Reference
- 117591 · 117591-20-5(CAS DataBase Reference)
- FDA UNII
- 18 X9FR245W · 18X9FR245W
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- hs_code
- 29242990
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationExogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES.
Applications
UsesCalpeptin is used to to inhibit the activities of cathepsin L and calpain-1. Calpeptin blocked the expression of aspartyl protease cathepsin D, amyloid precursor protein, and calparin. It acts as an inhibitor of the Ca2+-dependent protease, calpain. Prevents collagen- and thrombin-induced platelet aggregation, probably by blocking calpain induced phospholipase C and thromboxane synthase activation. Potent cathepsin L inhibitor. It is shown to preferentially inhibit a subset of protein-tyrosine phosphatases.
General DescriptionCalpeptin (Z-Leu-nLeu-H) is a cell permeable, peptide aldehyde inhibitor. It is more sensitive to calpain I compared to other inhibitors, such as Z-Leu-Met-H and leupeptin. Calpeptin stimulates neurite elongation in differentiating pheochromocytoma (PC12) cells. Calpeptin decreases microgliosis, astrogliosis, axonal damage and neuron and oligodendrocyte death in experimental autoimmune encephalomyelitis (EAE) spinal cord. Therefore, it can be considered as a potent therapeutic for treating EAE and multiple sclerosis (MS).
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Calpeptin is an amino acid amide.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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