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Gliotoxin

AlkaPlorer ID: AK002974

Synonym: None

IUPAC Name: (1R,7S,8S,11R)-7-hydroxy-11-(hydroxymethyl)-15-methyl-12,13-dithia-9,15-diazatetracyclo[9.2.2.01,9.03,8]pentadeca-3,5-diene-10,14-dione

Structure

SMILES: CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SS3

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InChI: InChI=1S/C13H14N2O4S2/c1-14-10(18)12-5-7-3-2-4-8(17)9(7)15(12)11(19)13(14,6-16)21-20-12/h2-4,8-9,16-17H,5-6H2,1H3/t8-,9-,12+,13+/m0/s1

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InChIKey: FIVPIPIDMRVLAY-RBJBARPLSA-N

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Properties Information

Molecule Weight: 326.399

TPSA？: 81.08000000000001

MolLogP？: -0.3036999999999995

Number of H-Donors: 2

Number of H-Acceptors: 6

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Athelia rolfsii Athelia rolfsii ED50 6.47 uM 10.1016/j.bmc.2010.02.034
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 2511.9 nM None
Candida albicans Candida albicans IC50 3100.0 nM 10.1021/np050141k
Candida albicans Candida albicans MIC 4.0 ug.mL-1 10.1021/np2001573
Cryptococcus gattii Cryptococcus bacillisporus Activity nan None 10.1128/aac.00153-10
Electrophorus electricus Acetylcholinesterase Inhibition -11.27 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 10.3 % 10.1016/j.bmc.2012.09.040
Giardia intestinalis Putative fructose-1,6-bisphosphate aldolase Potency 22334.2 nM None
Globisporangium debaryanum Globisporangium debaryanum ED50 90.12 uM 10.1016/j.bmc.2010.02.034
Homo sapiens A549 IC50 3.0 nM 10.1016/j.bmc.2010.02.034
Homo sapiens CCRF-CEM IC50 150.0 nM 10.1021/np050141k
Homo sapiens Creatine kinase M Activity 32.0 % 10.1016/S0960-894X(97)10052-X
Homo sapiens DU-145 Activity nan None 10.1021/np200563x
Homo sapiens Geranylgeranyl transferase type I IC50 17000.0 nM 10.1016/j.bmcl.2003.08.022
Homo sapiens HeLa IC50 2450.0 nM 10.1016/j.bmc.2010.02.034
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 IC50 530.0 nM 10.1016/j.ejmech.2012.08.010
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 IC50 6400.0 nM 10.1021/np200740e
Homo sapiens Histone-lysine N-methyltransferase SETD7 Inhibition nan % 10.1021/np200740e
Homo sapiens Histone-lysine N-methyltransferase SUV39H1 IC50 260.0 nM 10.1016/j.ejmech.2012.08.010
Homo sapiens HUVEC IC50 123.0 nM 10.1016/j.bmc.2010.02.034
Homo sapiens Hypoxia-inducible factor 1 alpha Inhibition nan % 10.1021/acs.jnatprod.5b00846
Homo sapiens Jurkat IC50 1000.0 nM 10.1016/j.bmc.2010.02.034
Homo sapiens Protein farnesyltransferase IC50 1100.0 nM 10.1021/jm970226l
Homo sapiens Protein farnesyltransferase IC50 80000.0 nM 10.1016/j.bmcl.2003.08.022
Homo sapiens Pyruvate kinase isozymes M1/M2 IC50 22640.0 nM 10.1021/acs.jmedchem.1c00981
Homo sapiens Sharpin/RBCK1/RNF31 IC50 510.0 nM 10.1021/acs.jmedchem.6b01817
Homo sapiens SH-SY5Y Activity nan None 10.1016/j.ejmech.2015.12.003
Homo sapiens Vitamin D receptor Potency 3981.1 nM None
Macrophomina phaseolina Macrophomina phaseolina ED50 0.9 uM 10.1016/j.bmc.2010.02.034
Macrophomina phaseolina Macrophomina phaseolina ED50 5.4 uM 10.1016/j.bmc.2010.02.034
Mus musculus Mus musculus Activity 59.0 % 10.1016/S0960-894X(97)10052-X
Mus musculus Mus musculus ED50 0.35 uM 10.1016/S0960-894X(97)10052-X
Mus musculus Mus musculus LD50 17.9 mg.kg-1 10.1016/j.bmc.2010.02.034
Mus musculus Nuclear receptor ROR-gamma Potency 44.7 nM None
Mus musculus P388 IC50 24.0 nM 10.1021/np200740e
Mus musculus P815 ED50 2.0 uM 10.1016/S0960-894X(97)10052-X
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 30.0 nM 10.1016/j.ejmech.2019.01.026
Mycobacterium tuberculosis Mycothiol S-conjugate amidase IC50 50000.0 nM 10.1016/j.bmc.2010.02.034
Plasmodium falciparum Plasmodium falciparum IC50 3600.0 nM 10.1016/j.bmc.2010.02.034
Pythium aphanidermatum Pythium aphanidermatum ED50 36.87 uM 10.1016/j.bmc.2010.02.034
Rhizoctonia solani Rhizoctonia solani ED50 9.75 uM 10.1016/j.bmc.2010.02.034
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 0.06 ug.mL-1 10.1128/aac.01393-07
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 0.125 ug.mL-1 10.1128/aac.01393-07
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 0.5 ug.mL-1 10.1128/aac.01393-07
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 2.0 ug.mL-1 10.1128/aac.01393-07
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 8.0 ug.mL-1 10.1128/aac.01393-07
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 16.0 ug.mL-1 10.1128/aac.01393-07
Saccharomyces cerevisiae S288c Acetolactate synthase catalytic subunit, mitochondrial IC50 200.0 nM 10.1016/j.bmc.2010.02.034
Tetrahymena pyriformis Tetrahymena pyriformis EC50 380.0 nM 10.1016/j.bmc.2010.02.034
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 10.0 nM 10.1016/j.bmc.2010.02.034
Trypanosoma brucei rhodesiense Rhodesain IC50 50000.0 nM 10.1016/j.bmc.2010.02.034
None ADMET EC50 1350.0 nM 10.1016/j.bmc.2010.02.034
None ADMET EC50 1650.0 nM 10.1016/j.bmc.2010.02.034
None ADMET EC50 2000.0 nM 10.1016/j.bmc.2010.02.034
None Macrophage ED50 0.104 uM 10.1016/j.bmc.2010.02.034
None Neutrophil Activity nan None 10.1016/j.bmc.2013.01.009
None Unchecked Activity 0.3 uM 10.1016/j.bmc.2010.02.034
None Unchecked Activity 6.1 % 10.1016/j.bmc.2019.07.047
None Unchecked Activity 30.7 uM 10.1016/j.bmc.2010.02.034
None Unchecked Activity 300.0 nM 10.1016/j.bmc.2010.02.034
None Unchecked Concentration 6.3 mg kg-1 10.1021/jm970226l
None Unchecked IC50 500.0 nM 10.1016/j.bmc.2010.02.034
None Unchecked IC50 9000.0 nM 10.1016/j.bmc.2010.02.034
None Unchecked IC50 10000.0 nM 10.1016/j.bmc.2010.02.034
None Unchecked IC50 93000.0 nM 10.1016/j.bmc.2010.02.034
None Unchecked Potency 1412.5 nM None
None Unchecked Potency 2511.9 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT010512 CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SS3>>CN1C(=O)[C@]2(S)CC3=CC=C[C@H](O)[C@H]3N2C(=O)[C@]1(S)CO RXN-16208
AKRT014730 C[SAH].O=C1N2[C@H]3C(=CC=C[C@@H]3O)C[C@]23SS[C@@]1(CO)NC3=O>>CN1C(=O)[C@]23CC4=CC=C[C@H](O)[C@H]4N2C(=O)[C@@]1(CO)SS3 RXN-15686