Basic information
- CAS
154226-60-5- Standard SMILES
CC(C)C(O)C12NC(=O)C(C)C1OC2=O- InChIKey
FWPWHHUJACGNMZ-UHFFFAOYSA-N- Molecular formula
- C10H15NO4
- Average molar mass
- 213.23 g/mol
- Monoisotopic mass
- 213.10010796
Overview
Clasto-Lactacystin beta-lactone is an organonitrogen compound and an organooxygen compound. It is functionally related to an alpha-amino acid.
Names & identifiers
- Preferred name
- 1-(1-Hydroxy-2-methylpropyl)-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
- IUPAC
- 1-(1-hydroxy-2-methylpropyl)-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
- English name
- Clasto-Lactacystin ?-lactone
- Molecular formula
- C10H15NO4
- Molecular weight
- 213.23
Names & synonyms
1-(1-hydroxy-2-methylpropyl)-4-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione154226-60-5SCHEMBL8269976CHEBI:201486AKOS025294594clasto-lactacystin β-lactoneOMURALIDEBETA-CLASTOLACTACYSTINClasto-lactacystin (OMuralide)CLASTO-LACTACYSTIN BETA-LACTONELACTACYSTIN, CLASTO-, BETA-LACTONEclasto-Lactacystin β-Lactone
Show more names
clasto-Lactacystin beta-lactone, 20S proteasome inhibitor1R-[1S-1HYDROXY-2-METHYLPROPYL]-4R-METHYL-6-OXA-2-AZABICYCLO[3.2.0]HEPTANE-3,7-DIONE(1R,4R,5S)-1-[(1S)-1-Hydroxy-2-Methylpropyl]-4-Methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
Database identifiers
- CAS
154226-60-5- PubChem CID
- 2779
- ChEBI
CHEBI:201486- EC Number
- 664-305-6
Properties
Computed structural properties
- XLogP
- 0.7
- Topological polar surface area
- 75.6 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 327
Physicochemical properties
- Melting point
- 186 · 186-187°C
- Boiling point
- 440.815 · 440.815±40.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.28 · 1.280±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- DMF, Ethanol, Hot Ethyl Acetate, Methanol, Pyridine
- form
- White solid
- pka
- 13.332 · 13.332±0.20(predicted)
- color
- White
- InChI
- 1S/C10H15NO4/c1-4(2)6(12)10-7(15-9(10)14)5(3)8(13)11-10/h4-7,12H,1-3H3,(H,11,13)/t5-,6+,7+,10-/m1/s1
- InChIKey
- FWPWHHUJACGNMZ-NBBQQVJHSA-N
- SMILES
- [H][C@@]12OC(=O)[C@@]1(NC(=O)[C@@H]2C)[C@@H](O)C(C)C
- UNSPSC Code
- 12352202 · 12352202
- 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.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- wgk
- 2
- ridadr
- UN 2811 6.1 / PGIII
- risk_code
- 20/21/22-37/38-41-36/37/38-25
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- T
- safety_code
- 16-26-36/37/39-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Applications
UsesA cell permeable, irreversible proteasome inhibitor. It is 20-fold more potent than Lactacystin. Lactacytstin spontaneously converts to clasto-lactacystin in biological systems. Clasto-lactacystin is the only cell permeable form of lactacystin. Induces neurite growth and inhibits cell cycle progression similar to lactacytin.
UsesClasto-Lactacystin β-lactone has been used as a proteasomal inhibitor.
Usesclasto-Lactacystin beta-lactone is a 20S proteasome and cathepsin A inhibitor.
Upstream & downstream products
Upstream raw materials
Suppliers12 total
MedBio脉铂医药021-69568360 18916172912 · [email protected]
AdooQ BioScience, LLC+1 (866) 930-6790 · [email protected]
ApexBio Technology LLC+1-832-696-8203 · [email protected]
凯试（上海）科技有限公司021-50135380 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
安耐吉化学&3A（安徽泽升科技股份有限公司）400-0056266 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…