PAC-1
2-(4-benzylpiperazin-1-yl)-N-[(E)-(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]acetamide
Molecular Identity
PAC-1
2-(4-benzylpiperazin-1-yl)-N-[(E)-(2-hydroxy-3-prop-2-enylphenyl)methylideneamino]acetamide
PubChem CID: 135421197
Pac-1 is procaspase Activating Compound-1 VO-100 is an orally bioavailable procaspase activating compound-1 (PAC-1), with potential proapoptotic and antineoplastic activities. Upon administration, VO-100 binds to and forms a chelating complex with zinc (Zn) ions inside cells, which prevents the binding of Zn ions to procaspase-3 (PC3) and abrogates the Zn-mediated inhibition of PC3. This allows for the proteolytic autoactivation of PC3 into the active form caspase-3. This results in the selective caspase-3-mediated induction of apoptosis and cell death in cancer cells. In addition, VO-100 is able to cross the blood-brain-barrier (BBB). PC3, a Zn-inhibited proenzyme, is upregulated in a variety of cancer cell types, while its expression is minimal in normal healthy cells.
2D Structure
Properties
C23H28N4O2
Molecular Formula
392.50
Molecular Weight
g/mol
392.2212
Exact Mass
Da
3.3
XLogP
Drug-like (Lipinski: < 5)
68.2
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
5
H-Bond Acceptors
539
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
PAC-1315183-21-2UNII-9LIS8N0B2CProcaspase-activating compound 12-(4-Benzylpiperazin-1-yl)-N-((2-hydroxy-3-prop-2-enyl-phenyl)methylideneamino)acetamide1-Piperazineacetic acid, 4-(phenylmethyl)-, ((2-hydroxy-3-(2-propenyl)phenyl)methylene)hydrazide1-Piperazineacetic acid, 4-(phenylmethyl)-, 2-((2-hydroxy-3-(2-propen-1-yl)phenyl)methylene)hydrazideDTXSID308974252-(4-benzylpiperazin-1-yl)-N'-[(1E)-[2-hydroxy-3-(prop-2-en-1-yl)phenyl]methylidene]acetohydrazide2-(4-benzylpiperazin-1-yl)-N'-((1E)-(2-hydroxy-3-(prop-2-en-1-yl)phenyl)methylidene)acetohydrazideRefChem:169429PAC-1 VO-100DTXCID401326768VO-100Procaspase Activating Compound-1 VO-100
Data from PubChem (NCBI)
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