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Lactacystin

AlkaPlorer ID: AK005138

Synonym: None

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

Structure

SMILES: CC(=O)N[C@@H](CSC(=O)[C@]1([C@@H](O)C(C)C)NC(=O)[C@H](C)[C@@H]1O)C(=O)O

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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

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InChIKey: DAQAKHDKYAWHCG-RWTHQLGUSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Streptomyces sp. Streptomyces Streptomycetaceae Kitasatosporales Actinomycetes Actinomycetota None Bacteria

Properties Information

Molecule Weight: 376.43100000000015

TPSA？: 153.03

MolLogP？: -1.281999999999998

Number of H-Donors: 5

Number of H-Acceptors: 7

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Candida albicans Candida albicans Activity nan None 10.1021/np2001573
Homo sapiens 20S proteasome IC50 259.0 nM 10.1021/np060162u
Homo sapiens NCI-H23 IC50 5230.0 nM 10.1021/acs.jmedchem.8b01943
Homo sapiens NCI-H727 IC50 100000.0 nM 10.1021/acs.jmedchem.8b01943
Homo sapiens Proteasome component C5 IC50 8000.0 nM 10.1016/j.ejmech.2018.01.045
Homo sapiens Proteasome component C5 IC50 40000.0 nM 10.1016/j.ejmech.2018.01.045
Homo sapiens Proteasome Macropain subunit IC50 3250.0 nM 10.1016/j.ejmech.2018.01.045
Homo sapiens Proteasome Macropain subunit IC50 40000.0 nM 10.1016/j.ejmech.2018.01.045
Homo sapiens Proteasome Macropain subunit MB1 IC50 160.0 nM 10.1016/j.ejmech.2018.01.045
Homo sapiens Proteasome Macropain subunit MB1 IC50 370.0 nM 10.1021/jm400221d
Homo sapiens Proteasome Macropain subunit MB1 IC50 500.0 nM 10.1021/jm500045x
Homo sapiens Proteasome Macropain subunit MB1 IC50 4960.0 nM 10.1016/j.ejmech.2018.01.045
Homo sapiens Proteasome Macropain subunit MB1 IC50 10090.0 nM 10.1016/j.ejmech.2015.05.023
Homo sapiens Proteasome Macropain subunit MB1 Inhibition nan % 10.1021/jm4002296
Homo sapiens Proteasome subunit beta type-8 IC50 3000.0 nM 10.1021/jm500045x
Homo sapiens Proteasome subunit beta type-8 Inhibition nan % 10.1021/jm4002296
Homo sapiens Splicing factor 3B subunit 3 Activity 50.0 % 10.1038/nchembio.2007.16
Homo sapiens Splicing factor 3B subunit 3 Activity 80.03 % 10.1038/nchembio.2007.16
Homo sapiens Splicing factor 3B subunit 3 Activity 81.29 % 10.1038/nchembio.2007.16
Homo sapiens Splicing factor 3B subunit 3 IC50 3481.0 nM 10.1038/nchembio.2007.16
Homo sapiens Splicing factor 3B subunit 3 IC50 10000.0 nM 10.1038/nchembio.2007.16
Mus musculus Nuclear receptor ROR-gamma Potency 281.8 nM None
Rattus norvegicus PC-12 Activity 98.3 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 133.5 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 150.0 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 190.5 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 216.8 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 220.0 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 234.0 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 248.7 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 320.5 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 341.4 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity 354.0 nmol/mg 10.1074/jbc.m603712200
Rattus norvegicus PC-12 Activity nan None 10.1074/jbc.m603712200
None Unchecked Activity 49.7 % 10.1074/jbc.m603712200
None Unchecked Activity 70.3 % 10.1074/jbc.m603712200
None Unchecked Activity 77.2 % 10.1074/jbc.m603712200
None Unchecked Activity 84.9 % 10.1074/jbc.m603712200
None Unchecked Activity 94.3 % 10.1074/jbc.m603712200
None Unchecked Activity 98.0 % 10.1074/jbc.m603712200
None Unchecked Activity nan None 10.1021/jm400221d
None Unchecked Activity nan None 10.1074/jbc.m703902200
None Unchecked FC 6.2 None 10.1016/j.bmc.2011.11.066
None Unchecked FC 72.0 None 10.1016/j.bmc.2011.11.066
None Unchecked FC 93.0 None 10.1016/j.bmc.2011.11.066
None Unchecked FC 106.0 None 10.1016/j.bmc.2011.11.066
None Unchecked IC50 70.0 nM 10.1016/j.bmc.2011.11.066
None Unchecked IC50 300.0 nM 10.1016/j.bmc.2011.11.066
None Unchecked IC50 5600.0 nM 10.1016/j.bmc.2008.05.078
None Unchecked IC50 5600.0 nM 10.1016/j.bmcl.2011.02.041
None Unchecked IC50 5600.0 nM 10.1016/j.bmcl.2011.07.072
None Unchecked IC50 10090.0 nM 10.1016/j.bmcl.2012.02.086
None Unchecked IC50 11400.0 nM 10.1016/j.bmcl.2012.10.041
None Unchecked IC50 30000.0 nM 10.1016/j.bmc.2008.05.078
None Unchecked Inhibition nan % 10.1016/j.bmcl.2012.10.041
None Unchecked Inhibition nan % 10.1021/jm400221d
None Unchecked Potency 177.8 nM None
None Unchecked Potency 2511.9 nM None
None Unchecked Potency 3162.3 nM None
None Unchecked Potency 3548.1 nM None
None Unchecked Potency 14125.4 nM None
None Unchecked Potency 25118.9 nM None
None Unchecked Ratio IC50 19.0 None 10.1021/acs.jmedchem.8b01943

Metabolism Information