Navigation

name Structure Reference Source Properties Activities Metabolism

N-(3-oxododecanoyl)-L-homoserine lactone

AlkaPlorer ID: AK049923

Synonym: '3-oxo-C12-HSL', 'N-(3-ketododecanoyl)-L-homoserine lactone', '3-oxo-C12-AHL'

IUPAC Name: 3-oxo-N-[(3S)-2-oxooxolan-3-yl]dodecanamide

Structure

SMILES: CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O

copy

InChI: InChI=1S/C16H27NO4/c1-2-3-4-5-6-7-8-9-13(18)12-15(19)17-14-10-11-21-16(14)20/h14H,2-12H2,1H3,(H,17,19)/t14-/m0/s1

copy

InChIKey: PHSRRHGYXQCRPU-AWEZNQCLSA-N

copy

Properties Information

Molecule Weight: 297.39500000000004

TPSA？: 72.47

MolLogP？: 2.5180000000000007

Number of H-Donors: 1

Number of H-Acceptors: 4

RingCount: 1

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Agrobacterium tumefaciens Transcriptional activator protein traR EC50 nan None 10.1016/j.bmcl.2008.07.089
Chromobacterium violaceum CviR transcriptional regulator Inhibition nan % 10.1039/C5MD00015G
Clostridioides difficile Clostridioides difficile Activity nan None 10.1128/aac.00702-09
Clostridioides difficile Clostridioides difficile Inhibition nan % 10.1128/aac.00702-09
Homo sapiens Blood Activity nan None 10.1126/science.1156499
Homo sapiens DU-145 Activity 0.2 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity 0.5 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity 1.1 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity 9.2 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity 9.7 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity 12.2 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity 77.9 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity 89.2 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Activity nan None 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 FC 2.0 None 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 GI 20.0 % 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 GI nan None 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 IC50 19330.0 nM 10.1016/j.ejmech.2018.12.014
Homo sapiens DU-145 Inhibition nan % 10.1016/j.ejmech.2018.12.014
Homo sapiens Inhibitor of nuclear factor kappa B kinase alpha subunit Activity nan None 10.1126/science.1156499
Homo sapiens Jurkat EC50 250000.0 nM 10.1021/jm2001019
Homo sapiens MAP kinase p38 Activity nan None 10.1126/science.1156499
Homo sapiens MCF7 IC50 26240.0 nM 10.1016/j.ejmech.2018.12.014
Homo sapiens MCF7 IC50 37310.0 nM 10.1016/j.ejmech.2015.02.026
Homo sapiens MDA-MB-231 Activity -0.07 None 10.1021/acs.jnatprod.0c01003
Homo sapiens MDA-MB-231 Activity 0.05 None 10.1021/acs.jnatprod.0c01003
Homo sapiens MGC-803 IC50 29530.0 nM 10.1016/j.ejmech.2018.12.014
Homo sapiens MGC-803 IC50 101830.0 nM 10.1016/j.ejmech.2015.02.026
Homo sapiens NCI-H630 IC50 12000.0 nM 10.1021/jm8015377
Homo sapiens NCI-H630 IC50 34000.0 nM 10.1021/jm8015377
Homo sapiens Nuclear factor NF-kappa-B p65 subunit Activity nan None 10.1126/science.1156499
Homo sapiens PBMC Activity nan None 10.1126/science.1156499
Homo sapiens PC-3 IC50 5000.0 nM 10.1021/jm8015377
Homo sapiens PC-3 IC50 22510.0 nM 10.1016/j.ejmech.2018.12.014
Homo sapiens SMMC-7721 IC50 128000.0 nM 10.1016/j.ejmech.2015.02.026
Homo sapiens THP-1 Activity nan None 10.1126/science.1156499
Homo sapiens WI-38 Activity nan None 10.1126/science.1156499
Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 10000.0 nM 10.1021/jm020909n
Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 15000.0 nM 10.1021/jm020909n
Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 35000.0 nM 10.1021/jm020909n
Human immunodeficiency virus 1 Human immunodeficiency virus 1 IC50 60000.0 nM 10.1021/jm020909n
Mus musculus Eukaryotic translation initiation factor 2 subunit 1 Activity nan None 10.1016/j.bmcl.2010.11.122
Mus musculus Inhibitor of nuclear factor kappa-B kinase subunit alpha Activity nan None 10.1126/science.1156499
Mus musculus MAP kinase p38 Activity nan None 10.1016/j.bmcl.2010.11.122
Mus musculus MAP kinase p38 Activity nan None 10.1126/science.1156499
Mus musculus MEF Activity nan None 10.1126/science.1156499
Mus musculus Mus musculus Activity nan None 10.1126/science.1156499
Mus musculus Mus musculus IC50 4000.0 nM 10.1021/jm020909n
Mus musculus P388 Activity 31.9 % 10.1016/j.bmcl.2006.01.054
Mus musculus Transcription factor p65 Activity nan None 10.1126/science.1156499
Pseudomonas aeruginosa PhzR Activity 109.0 % 10.1016/j.bmcl.2007.11.095
Pseudomonas aeruginosa PhzR EC50 14.74 nM 10.1016/j.bmc.2018.05.018
Pseudomonas aeruginosa PhzR EC50 22.0 nM 10.1016/j.bmcl.2007.11.095
Pseudomonas aeruginosa Pseudomonas aeruginosa Activity nan None 10.1021/jm8015377
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Acyl-homoserine-lactone synthase Activity 100.0 % 10.1016/j.bmc.2011.07.044
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Transcriptional activator protein lasR EC50 1.507 nM 10.1016/j.bmc.2018.05.018
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Transcriptional activator protein lasR EC50 7.0 nM 10.1021/jm901742e
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Transcriptional activator protein lasR EC50 31.0 nM 10.1021/ml500459f
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Transcriptional activator protein lasR EC50 139.0 nM 10.1016/j.bmc.2019.115282
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228) Transcriptional activator protein lasR Ratio 12.3 None 10.1021/jm2001019
Staphylococcus aureus Accessory gene regulator protein A IC50 6000.0 nM 10.1021/jm3014635
Staphylococcus aureus Staphylococcus aureus MIC 100000.0 nM 10.1021/jm500215s
Vibrio fischeri (strain ATCC 700601 / ES114) Transcriptional activator protein luxR EC50 nan None 10.1016/j.bmcl.2008.07.089
None Epithelial cell Activity nan None 10.1126/science.1156499
None Macrophage Activity nan None 10.1126/science.1156499
None NON-PROTEIN TARGET IC50 128000.0 nM 10.1016/j.ejmech.2015.02.026
None No relevant target Stability nan % 10.1039/C5MD00015G
None No relevant target T1/2 48.2 hr 10.1016/j.bmc.2011.06.071
None Unchecked Activity nan None 10.1016/j.bmcl.2010.11.122
None Unchecked Activity nan None 10.1126/science.1156499
None Unchecked EC50 1.5 nM 10.1039/C5MD00015G
None Unchecked EC50 1.8 nM 10.1016/j.bmc.2019.115282
None Unchecked EC50 10000.0 nM 10.1016/j.bmcl.2008.07.089
None Unchecked EC50 21000.0 nM 10.1021/jm2001019
None Unchecked EC50 64700.0 nM 10.1016/j.bmc.2016.10.021
None Unchecked IC50 22000.0 nM 10.1021/jm500215s
None Unchecked Inhibition nan % 10.1016/j.bmcl.2017.05.012
None Unchecked Inhibition nan % 10.1021/jm500215s
None Unchecked Ratio EC50 10.0 None 10.1016/j.bmc.2018.05.018

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000063 *C(=O)CC(=O)CCCCCCCCC.C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O RXN-10023
AKRT008455 CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O.CSC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O>>C[S@@+](CC[C@H](N)C(=O)O)C[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1O RXN-10023
AKRT008456 CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O>>*C(=O)CC(=O)CCCCCCCCC RXN-10023
AKRT008457 CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O>>CCCCCCCCCC(=O)CC(=O)N[C@@H](CCO)C(=O)O RXN-10049
AKRT008458 CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O>>CCCCCCCCCC(=O)CC(=O)O RXN-10042
AKRT008459 CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O>>CCCCCCCCCC(=O)CC(=O)O.N[C@H]1CCOC1=O None
AKRT008460 CCCCCCCCCC(=O)CC(=O)N[C@H]1CCOC1=O>>N[C@H]1CCOC1=O RXN-10042