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Lactacystin

CAT: 0931-T15702-02Size: 100 µgDry Ice: NoHazardous: No
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CAT#:0931-T15702-02Size:100 µg
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CAS Number
133343-34-7
Target
Protease, Apoptosis, cAMP
Related Pathways
GPCR/G Protein, Proteases/Proteasome, Apoptosis
Bioactivity
Lactacystin is an orally active, irreversible, and cell-permeable proteasome inhibitor (IC50 = 4.8 μM) that also inhibits the lysosomal enzyme cathepsin A. It induces apoptosis and cell cycle arrest, possesses anticancer, antiviral, and antioxidant activities, can penetrate the blood-brain barrier, and is commonly used in the construction of Parkinson’s disease and dementia models.
Smiles
C(SC[C@H](NC(C)=O)C(O)=O)(=O)[C@@]1([C@H](C(C)C)O)[C@@H](O)[C@@H](C)C(=O)N1
Molecular Formula
C15H24N2O7S
Molecular Weight
376.43
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Lactacystin

Lactacystin is L-Cysteine substituted at nitrogen by an acetyl group and at sulfur by a substituted-lactam carbonyl group. It is a lactam and a S-substituted L-cysteine.

CAS Number133343-34-7
PubChem CID6610292
IUPAC Name(2R)-2-acetamido-3-[(2R,3S,4R)-3-hydroxy-2-[(1S)-1-hydroxy-2-methylpropyl]-4-methyl-5-oxopyrrolidine-2-carbonyl]sulfanylpropanoic acid
Molecular FormulaC15H24N2O7S
Molecular Weight376.4
XLogP-0.3
Topological Polar Surface Area178
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Heavy Atom Count25
Formal Charge0
Complexity568
SMILES
C[C@@H]1[C@@H]([C@](NC1=O)([C@H](C(C)C)O)C(=O)SC[C@@H](C(=O)O)NC(=O)C)O
InChI
InChI=1S/C15H24N2O7S/c1-6(2)10(19)15(11(20)7(3)12(21)17-15)14(24)25-5-9(13(22)23)16-8(4)18/h6-7,9-11,19-20H,5H2,1-4H3,(H,16,18)(H,17,21)(H,22,23)/t7-,9+,10+,11+,15-/m1/s1
InChIKey
DAQAKHDKYAWHCG-RWTHQLGUSA-N
Chemical Structure
2D Structure
2D structure of Lactacystin
CAS: 133343-34-7
CID: 6610292
Formula: C15H24N2O7S
MW: 376.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight376.4
XLogP3-0.3
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count8
Rotatable Bond Count8
Exact Mass376.13042228
Monoisotopic Mass376.13042228
Topological Polar Surface Area178 Ų
Heavy Atom Count25
Formal Charge0
Complexity568
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
L0900-01(+) -Lactacystin (Lactacystin)
MBS6103528-01(+)-Lactacystin (Lactacystin)
ILC-4368-VLactacystin
281185-01(+) -Lactacystin
TRC-L101000-0.25MG(+)-Lactacystin

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