UCH-L1 Inhibitor
Basic information
- CAS
668467-91-2- Standard SMILES
CC(=O)ON=C1C(=O)N(Cc2cc(Cl)ccc2Cl)c2ccc(Cl)cc21- InChIKey
OPQRFPHLZZPCCH-UHFFFAOYSA-N- Molecular formula
- C17H11Cl3N2O3
- Average molar mass
- 397.6 g/mol
- Monoisotopic mass
- 395.983525
Names & identifiers
- Preferred name
- UCH-L1 Inhibitor
- IUPAC
- [[5-chloro-1-[(2,5-dichlorophenyl)methyl]-2-oxoindol-3-ylidene]amino] acetate
- English name
- LDN-57444
- Molecular formula
- C17H11Cl3N2O3
- Molecular weight
- 397.64
Names & synonyms
UCH-L1 Inhibitor3-(acetoxyimino)-5-chloro-1-(2,5-dichlorobenzyl)indolin-2-one5-Chloro-1-[(2,5-dichlorophenyl)methyl]-1H-indole-2,3-dione 3-(O-acetyloxime)orb1307095HMS3653K09TBB46791s7135AKOS024457921F870120[[5-chloro-1-[(2,5-dichlorophenyl)methyl]-2-oxo-indolin-3-ylidene]amino] acetate[[5-chloro-1-[(2,5-dichlorophenyl)methyl]-2-oxoindol-3-ylidene]amino] acetateCS-988
Show more names
LDN-57444LDN 57444, >=98%LDN-57444 ，S7135LDN-57444/LDN57444LDN-57444 USP/EP/BPLDN-57444, 10 mM in DMSOLDN57444LDN-57444, UCH-L1 inhibitor
Database identifiers
- CAS
668467-91-2- PubChem CID
- 24906255
- EC Number
- 687-399-0
Properties
Computed structural properties
- XLogP
- 4.6
- Topological polar surface area
- 59 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 571
Physicochemical properties
- Boiling point
- 534.4 · 534.4±60.0 °C(Predicted)
- Density
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 16 mg/mL · DMSO: soluble16mg/mL
- form
- solid
- pka
- -2.57 · -2.57±0.20(Predicted)
- color
- Yellow
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 week.
- InChI
- 1S/C17H11Cl3N2O3/c1-9(23)25-21-16-13-7-12(19)3-5-15(13)22(17(16)24)8-10-6-11(18)2-4-14(10)20/h2-7H,8H2,1H3/b21-16-
- InChIKey
- OPQRFPHLZZPCCH-PGMHBOJBSA-N
- SMILES
- CC(=O)O\N=C1/C(=O)N(Cc2cc(Cl)ccc2Cl)c3ccc(Cl)cc13
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
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
- ridadr
- UN 3077 9 / PGIII
- risk_code
- 50/53
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- N
- safety_code
- 60-61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionThe ubiquitin C-terminal hydrolase L1 (UCH-L1) is a member of a family of de-ubiquitinating enzymes that can generate free ubiquitin from ubiquitin precursors via its ubiquitin ligase activity. By associating with free ubiquitin, it also prevents its degradation. Neuronal UCH-L1 has been linked to Parkinson’s disease, the development of tumors, and neuropathic pain. LDN-57444 is an inhibitor of UCH-L1 activity (IC50 = 0.88, Ki = 0.4 μM) that demonstrates selectivity for UCH-L1 compared to UCH-L3 (IC50 = 25 μM). Loss of UCH-L1 activity causes cell death through the apoptosis pathway due to an impaired ubiquitin-proteasome pathway. LDN-57444-induced reduction of free ubiquitin has been shown to create dramatic alterations in synaptic structure and function, increasing spine size while decreasing spine density in hippocampal neurons.
UsesLDN 57444 is an inhibitor of UCH-L1, an enzyme expressed by certain lung tumor-derived cell lines, suggesting that this enzyme plays a role in tumor progression.
Related reactions
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Compound notes
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