MARIZOMIB

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Synonyms
Status
Molecule Category Free-form
UNII 703P9YDP7F

Structure

InChI Key NGWSFRIPKNWYAO-SHTIJGAHSA-N
Smiles C[C@@]12OC(=O)[C@]1([C@@H](O)[C@@H]1C=CCCC1)NC(=O)[C@@H]2CCCl
InChI
InChI=1S/C15H20ClNO4/c1-14-10(7-8-16)12(19)17-15(14,13(20)21-14)11(18)9-5-3-2-4-6-9/h3,5,9-11,18H,2,4,6-8H2,1H3,(H,17,19)/t9-,10+,11+,14+,15+/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H20ClNO4
Molecular Weight 313.78
AlogP 1.13
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 75.63
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 21.0

Bioactivity

Mechanism of Action Action Reference
20S proteosome inhibitor INHIBITOR PubMed
Protein: 20S proteasome
Description: Proteasome subunit beta type-11
Organism : Homo sapiens
A5LHX3 ENSG00000222028
Protein: 20S proteasome
Description: Proteasome subunit alpha type-7
Organism : Homo sapiens
O14818 ENSG00000101182
Protein: 20S proteasome
Description: Proteasome subunit beta type-1
Organism : Homo sapiens
P20618 ENSG00000008018
Protein: 20S proteasome
Description: Proteasome subunit alpha type-1
Organism : Homo sapiens
P25786 ENSG00000129084
Protein: 20S proteasome
Description: Proteasome subunit alpha type-2
Organism : Homo sapiens
P25787 ENSG00000106588
Protein: 20S proteasome
Description: Proteasome subunit alpha type-3
Organism : Homo sapiens
P25788 ENSG00000100567
Protein: 20S proteasome
Description: Proteasome subunit alpha type-4
Organism : Homo sapiens
P25789 ENSG00000041357
Protein: 20S proteasome
Description: Proteasome subunit beta type-8
Organism : Homo sapiens
P28062 ENSG00000204264
Protein: 20S proteasome
Description: Proteasome subunit beta type-9
Organism : Homo sapiens
P28065 ENSG00000240065
Protein: 20S proteasome
Description: Proteasome subunit alpha type-5
Organism : Homo sapiens
P28066 ENSG00000143106
Protein: 20S proteasome
Description: Proteasome subunit beta type-4
Organism : Homo sapiens
P28070 ENSG00000159377
Protein: 20S proteasome
Description: Proteasome subunit beta type-6
Organism : Homo sapiens
P28072 ENSG00000142507
Protein: 20S proteasome
Description: Proteasome subunit beta type-5
Organism : Homo sapiens
P28074 ENSG00000100804
Protein: 20S proteasome
Description: Proteasome subunit beta type-10
Organism : Homo sapiens
P40306 ENSG00000205220
Protein: 20S proteasome
Description: Proteasome subunit beta type-3
Organism : Homo sapiens
P49720 ENSG00000277791
Protein: 20S proteasome
Description: Proteasome subunit beta type-2
Organism : Homo sapiens
P49721 ENSG00000126067
Protein: 20S proteasome
Description: Proteasome subunit alpha type-6
Organism : Homo sapiens
P60900 ENSG00000100902
Protein: 20S proteasome
Description: Proteasome subunit alpha-type 8
Organism : Homo sapiens
Q8TAA3 ENSG00000154611
Protein: 20S proteasome
Description: Proteasome subunit beta type-7
Organism : Homo sapiens
Q99436 ENSG00000136930
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Protease Threonine protease Threonine protease PBT clan Threonine protease T1A subfamily
- 4-22 - - -
Assay Description Organism Bioactivity Reference
Inhibition of NF-kB activation in HEK293 cells Homo sapiens 11.0 nM
Inhibition of trypsin-like (T-L) activity of rabbit 20S proteasome Oryctolagus cuniculus 21.0 nM
Inhibition of caspase-like (CA-L) activity of rabbit 20S proteasome Oryctolagus cuniculus 430.0 nM
Inhibition of chymotrypsin-like (CT-L) activity of rabbit 20S proteasome Oryctolagus cuniculus 2.6 nM
Cytotoxic activity against RPMI 8226 cells Homo sapiens 8.2 nM
Inhibition of chymotrypsin-like activity of rabbit 20S proteasome Oryctolagus cuniculus 2.5 nM
Inhibition of trypsin-like activity of rabbit 20S proteasome Oryctolagus cuniculus 26.0 nM
Inhibition of caspase-like activity of rabbit 20S proteasome Oryctolagus cuniculus 330.0 nM
Inhibition of chymotrypsin-like activity of yeast 20S proteasome Saccharomyces cerevisiae 2.0 nM
Inhibition of trypsin-like activity of yeast 20S proteasome Saccharomyces cerevisiae 59.0 nM
Inhibition of chymotrypsin-like activity of human 20S proteasome Homo sapiens 3.5 nM
Inhibition of trypsin-like activity of human 20S proteasome Homo sapiens 28.0 nM
Inhibition of caspase-like activity of human 20S proteasome Homo sapiens 430.0 nM
Inhibition of chymotrypsin-like activity of human 20S proteasome assessed as release of free AMC substrate by fluorimetry based kinetic assay Homo sapiens 23.0 nM
Inhibition of trypsin-like activity of human 20S proteasome assessed as release of free AMC substrate by fluorimetry based kinetic assay Homo sapiens 97.0 nM
Cytotoxicity against human HCT116 cells Homo sapiens 0.002 ug.mL-1
Inhibition of chymotrypsin-like activity of rabbit 20S proteasome Oryctolagus cuniculus 4.0 nM
Inhibition of trypsin-like activity of rabbit 20S proteasome Oryctolagus cuniculus 34.0 nM
Inhibition of caspase-like activity of rabbit 20S proteasome Oryctolagus cuniculus 364.0 nM
Cytotoxicity against human RPMI8226 cells after 48 hrs by resazurin assay Homo sapiens 11.0 nM
Inhibition of chymotrypsin like activity of yeast 20S proteasome beta 5 subunit after 30 mins by fluorescence assay Saccharomyces cerevisiae 1.9 nM
Cytotoxicity against human HCT116 cells after 72 hrs by MTS/PMS assay Homo sapiens 16.0 nM
Irreversible inhibition of 20S proteasome None 1.3 nM
Cytotoxicity against human HCT116 cells Homo sapiens 35.0 nM
Reversible inhibition of human erythrocyte derived 20S proteasome subunit beta1 after 30 mins by fluorogenic assay Homo sapiens 430.0 nM
Reversible inhibition of human erythrocyte derived 20S proteasome subunit beta2 after 30 mins by fluorogenic assay Homo sapiens 28.0 nM
Reversible inhibition of human erythrocyte derived 20S proteasome subunit beta5 after 30 mins by fluorogenic assay Homo sapiens 3.5 nM
Inhibition of caspase-like activity of 20S proteasome in rabbit erythrocytes using Z-LLE-betaNA as substrate preincubated for 15 mins measured after 45 mins by fluorescence assay Oryctolagus cuniculus 460.0 nM
Inhibition of trypsin-like activity of 20S proteasome in rabbit erythrocytes using Boc-LRR-AMC as substrate preincubated for 15 mins measured after 45 mins by fluorescence assay Oryctolagus cuniculus 21.0 nM
Inhibition of chymotrypsin-like activity of 20S proteasome in rabbit erythrocytes using Suc-LLVY-AMC as substrate preincubated for 15 mins measured after 45 mins by fluorescence assay Oryctolagus cuniculus 2.6 nM
Antiplasmodial activity against Plasmodium falciparum by SYBR Green staining-based fluorescence assay Plasmodium falciparum 11.0 nM
Inhibition of chymotrypsin like activity of human 20S proteasome after 1 hr by luminescence assay Homo sapiens 22.0 nM
Inhibition of 20s constitutive proteasome beta 1 subunit caspase-like activity in rabbit erythrocytes using Z-LLE-betaNA as substrate incubated for 15 mins prior to substrate addition measured after 45 mins by fluorescence assay Oryctolagus cuniculus 460.0 nM
Inhibition of 20s constitutive proteasome beta 2 subunit trypsin-like activity in rabbit erythrocytes using Boc-LRR-AMC as substrate incubated for 15 mins prior to substrate addition measured after 45 mins by fluorescence assay Oryctolagus cuniculus 21.0 nM
Inhibition of 20s constitutive proteasome beta 5 subunit chymotrypsin-like activity in rabbit erythrocytes using Suc-LLVY-AMC as substrate incubated for 15 mins prior to substrate addition measured after 45 mins by fluorescence assay Oryctolagus cuniculus 2.6 nM
Inhibition of 20S proteasome beta 1c (unknown origin) after 1 hr by fluorescence based assay Homo sapiens 0.604 nM
Inhibition of 20S proteasome beta 2c (unknown origin) after 1 hr by fluorescence based assay Homo sapiens 10.6 nM
Inhibition of 20S proteasome beta 5c (unknown origin) after 1 hr by fluorescence based assay Homo sapiens 3.5 nM

Cross References

Resources Reference
ChEBI 48045
ChEMBL CHEMBL371405
DrugBank DB11762
FDA SRS 703P9YDP7F
PubChem 11347535
SureChEMBL SCHEMBL151667
ZINC ZINC000003990364
CONTENTS