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name Structure Reference Source Properties Activities Metabolism

cerulenin

AlkaPlorer ID: AK002901

Synonym: '(2R,3S)-3-((4E,7E)-nona-4,7-dienoyl)oxirane-2-carboxamide', 'SMR000058786', 'Helicocerin', '(2R,3S)-3-((4E,7E)-Nona-4,7-dienoyl)-oxirane-2-carboxylic acid amide', 'MLS006010821', '(+)-Cerulenin', 'Cerulenin'

IUPAC Name: (2R,3S)-3-[(4E,7E)-nona-4,7-dienoyl]oxirane-2-carboxamide

Structure

SMILES: C/C=C/C/C=C/CCC(=O)[C@H]1O[C@H]1C(N)=O

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InChI: InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1

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InChIKey: GVEZIHKRYBHEFX-NQQPLRFYSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Cephalosporium caerulens Cephalosporium None Hypocreales Sordariomycetes Ascomycota Fungi Eukaryota

Properties Information

Molecule Weight: 223.272

TPSA？: 72.69

MolLogP？: 1.1107999999999998

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus subtilis Bacillus subtilis Inhibition nan % 10.1021/acs.jmedchem.7b00355
Candida albicans Candida albicans IC50 0.4 ug.mL-1 10.1021/np020289t
Candida albicans Candida albicans IZ 20.0 mm 10.1021/np030046g
Candida albicans Candida albicans MFC 5.0 ug ml-1 10.1021/np030046g
Candida albicans Candida albicans MIC 0.2 ug.mL-1 10.1128/aac.00740-08
Candida albicans Candida albicans MIC 2.0 ug.mL-1 10.1128/aac.00182-07
Candida albicans Candida albicans MIC 4.0 ug.mL-1 10.1128/aac.00182-07
Candida albicans Candida albicans MIC 5.0 ug.mL-1 10.1021/np030046g
Candida albicans Candida albicans MIC 6.25 ug.mL-1 10.1128/aac.00740-08
Candida albicans Candida albicans MIC 8.0 ug.mL-1 10.1128/aac.00182-07
Candida albicans Candida albicans MIC 1000.0 ug.mL-1 10.1021/np030046g
Candida dubliniensis Candida dubliniensis MIC 0.2 ug.mL-1 10.1128/aac.00740-08
Candida dubliniensis Candida dubliniensis MIC 0.78 ug.mL-1 10.1128/aac.00740-08
Candida dubliniensis Candida dubliniensis MIC 3.13 ug.mL-1 10.1128/aac.00740-08
Cryptococcus neoformans Cryptococcus neoformans IC50 0.15 ug.mL-1 10.1021/np020289t
Drosophila melanogaster 3-oxoacyl-[acyl-carrier-protein] reductase Inhibition nan % None
Electrophorus electricus Acetylcholinesterase Inhibition -4.02 % 10.1016/j.bmc.2012.09.040
Equus caballus Cholinesterase Inhibition 3.38 % 10.1016/j.bmc.2012.09.040
Homo sapiens Acetylcholinesterase AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Adenosine A3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Aldehyde dehydrogenase 1A1 Potency 39810.7 nM None
Homo sapiens Alpha-1a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Alpha-2a adrenergic receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Androgen Receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Beta-glucocerebrosidase Potency 39810.7 nM None
Homo sapiens Coagulation factor XIII IC50 4000.0 nM 10.1016/j.ejmech.2015.05.019
Homo sapiens Coagulation factor XIII IC50 18000.0 nM 10.1016/j.ejmech.2015.05.019
Homo sapiens Cyclooxygenase-1 AC50 15450.1 nM 10.1038/s41467-023-40064-9
Homo sapiens Cyclooxygenase-1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D1 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine D3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Dopamine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Estrogen receptor alpha AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Fatty acid synthase IC50 0.19 ug.mL-1 10.1021/np020429z
Homo sapiens Fatty acid synthase IC50 0.5 ug.mL-1 10.1021/np030046g
Homo sapiens Fatty acid synthase IC50 5800.0 nM 10.1016/j.bmcl.2011.07.083
Homo sapiens Fatty acid synthase IC50 13000.0 nM 10.1016/j.bmcl.2006.07.018
Homo sapiens Fatty acid synthase IC50 21860.0 nM 10.1021/jm2005805
Homo sapiens Fatty acid synthase Inhibition 96.0 % 10.1021/jm980591s
Homo sapiens Fatty acid synthase Inhibition nan % None
Homo sapiens HERG AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histamine H3 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Histone deacetylase 6 Inhibition -19.77 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition -7.37 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 19952.6 nM None
Homo sapiens Microtubule-associated protein tau Potency 17782.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 31622.8 nM None
Homo sapiens Monoamine oxidase A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Mu opioid receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M1 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Muscarinic acetylcholine receptor M2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Norepinephrine transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 3A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Phosphodiesterase 4A AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Progesterone receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 1a (5-HT1a) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin 2b (5-HT2b) receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Serotonin transporter AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Survival motor neuron protein Potency 31622.8 nM None
Homo sapiens T-24 IC50 17000.0 nM 10.1021/jm980591s
Homo sapiens Thrombin AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thromboxane A2 receptor AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Thyroid hormone receptor beta-1 Potency 31622.8 nM None
Homo sapiens Vascular endothelial growth factor receptor 2 AC50 30000.0 nM 10.1038/s41467-023-40064-9
Homo sapiens Vitamin D receptor Potency 44668.4 nM None
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 protease IC50 2500.0 nM 10.1021/jm00112a001
Human rhinovirus sp. Human rhinovirus A protease IC50 2500000.0 nM 10.1021/jm00112a001
Issatchenkia orientalis ATP binding cassette transporter Abc1p Activity nan None 10.1128/aac.01095-08
Moloney murine leukemia virus Moloney murine leukemia virus IC50 2700.0 nM 10.1016/S0960-894X(00)80049-9
Mus musculus Fatty acid synthase Activity 73.3 % None
Mus musculus Fatty acid synthase Inhibition nan % None
Mus musculus Mus musculus Control 170.0 % 10.1016/S0960-894X(00)80049-9
Mus musculus NIH3T3 Activity nan None 10.1016/j.bmc.2018.09.013
Mus musculus NIH3T3 Inhibition nan % 10.1016/j.bmc.2018.09.013
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 0.5 ug.mL-1 10.1016/j.bmc.2019.04.032
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 1.5 ug.mL-1 10.1021/jm000149l
Plasmodium falciparum Plasmodium falciparum Activity nan None 10.1128/aac.00808-06
Plasmodium falciparum Plasmodium falciparum IC50 10100.0 nM 10.1016/j.bmc.2009.02.050
Plasmodium falciparum Plasmodium falciparum IC50 15100.0 nM 10.1128/aac.00808-06
Plasmodium falciparum Plasmodium falciparum IC50 16900.0 nM 10.1128/aac.00808-06
Plasmodium falciparum Plasmodium falciparum IC50 20000.0 nM 10.1128/aac.00124-07
Plasmodium falciparum Plasmodium falciparum MIC90 52300.0 nM 10.1128/aac.00808-06
Plasmodium falciparum Plasmodium falciparum MIC90 64900.0 nM 10.1128/aac.00808-06
Rattus norvegicus GABA receptor alpha-1 subunit AC50 30000.0 nM 10.1038/s41467-023-40064-9
Rotavirus Rotavirus ED50 28.5 uM 10.1016/j.ejmech.2012.02.010
Saccharomyces cerevisiae Saccharomyces cerevisiae MIC 0.5 ug.mL-1 10.1126/science.1142189
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 13.06 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 19952.62 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 IC50 20000.0 nM 10.6019/CHEMBL4651402
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.03 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.15 % 10.21203/rs.3.rs-23951/v1
Staphylococcus aureus Staphylococcus aureus Activity 32.0 ug ml-1 10.1021/np050416w
Staphylococcus aureus Staphylococcus aureus Activity 50.0 % 10.1128/aac.01293-08
Staphylococcus aureus Staphylococcus aureus Activity 235.1 % 10.1128/aac.01293-08
Staphylococcus aureus Staphylococcus aureus Activity nan None 10.1021/jm900519b
Staphylococcus aureus Staphylococcus aureus Inhibition 8.4 % 10.1128/aac.01293-08
Staphylococcus aureus Staphylococcus aureus Inhibition 10.7 % 10.1128/aac.01293-08
Staphylococcus aureus Staphylococcus aureus Inhibition 71.9 % 10.1016/j.ejmech.2021.113402
Staphylococcus aureus Staphylococcus aureus Inhibition 71.9 % 10.1039/D1MD00230A
Staphylococcus aureus Staphylococcus aureus MIC 64.0 ug.mL-1 10.1021/np050416w
None ADMET TD50 56.7 uM 10.1016/j.ejmech.2012.02.010
None No relevant target AbsAC35 14.03 uM None
None No relevant target AbsAC35 18.26 uM None
None No relevant target AbsAC35 60.07 uM None
None Unchecked AbsAC35 7.67 uM None
None Unchecked AbsAC35 13.2 uM None
None Unchecked Activity nan None 10.1016/j.bmcl.2011.06.055
None Unchecked Activity nan None 10.1128/aac.00124-07
None Unchecked Activity nan None 10.1128/aac.01458-06
None Unchecked IC50 0.1 ug.mL-1 10.1021/acs.jmedchem.0c02185
None Unchecked IC50 0.15 ug.mL-1 10.1021/np020289t
None Unchecked IC50 0.19 ug.mL-1 10.1021/np020442j
None Unchecked IC50 0.5 ug.mL-1 10.1021/np030046g
None Unchecked IC50 1.5 ug.mL-1 10.1021/np050416w
None Unchecked IC50 150.0 ug.mL-1 10.1021/acs.jmedchem.0c02185
None Unchecked Inhibition 48.0 % 10.1021/jm980591s
None Unchecked Inhibition 62.0 % 10.1128/aac.01458-06
None Unchecked Potency 15848.9 nM None

Metabolism Information