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name Structure Reference Source Properties Activities Metabolism

Oleoylethanolamide

AlkaPlorer ID: AK321746

Synonym: None

IUPAC Name: (Z)-N-(2-hydroxyethyl)octadec-9-enamide

Structure

SMILES: CCCCCCCC/C=C\CCCCCCCC(O)=NCCO

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InChI: InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

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InChIKey: BOWVQLFMWHZBEF-KTKRTIGZSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Homo sapiens Homo Hominidae Primates Mammalia Chordata Metazoa Eukaryota

Properties Information

Molecule Weight: 325.537

TPSA？: 52.82000000000001

MolLogP？: 5.972700000000008

Number of H-Donors: 2

Number of H-Acceptors: 2

RingCount: 0

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Bacillus anthracis Anthrax lethal factor Potency 10000.0 nM None
Bacillus subtilis 4'-phosphopantetheinyl transferase ffp Potency 89125.1 nM None
Equus caballus Ferritin light chain Potency 17782.8 nM None
Escherichia coli K-12 Beta-lactamase AmpC Potency 50118.7 nM None
Escherichia coli K-12 Endonuclease 4 Potency 17782.8 nM None
Homo sapiens 786-0 GI50 35.4 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens 786-0 TGI 64.6 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens Acid ceramidase IC50 500000.0 nM 10.1021/acs.jmedchem.0c01561
Homo sapiens Acid ceramidase Ki 500000.0 nM 10.1021/jm301879g
Homo sapiens Alpha-galactosidase A Potency 50118.7 nM None
Homo sapiens ATPase family AAA domain-containing protein 5 Potency 11577.4 nM None
Homo sapiens Bloom syndrome protein Potency 19952.6 nM None
Homo sapiens Bromodomain-containing protein 4 Delta TM -1.73 C 10.6019/CHEMBL5308504
Homo sapiens Cannabinoid CB1 receptor Ki 1100.0 nM 10.1021/jm051240y
Homo sapiens Cannabinoid CB1 receptor Ki 1100.0 nM 10.1021/jm900130m
Homo sapiens Cannabinoid CB2 receptor Ki 10000.0 nM 10.1021/jm051240y
Homo sapiens Cannabinoid CB2 receptor Ki 10000.0 nM 10.1021/jm900130m
Homo sapiens Casein kinase I delta Delta TM -0.85 C 10.6019/CHEMBL5308504
Homo sapiens Cerebroside-sulfatase Potency 1069.1 nM None
Homo sapiens Chromobox protein homolog 1 Potency 50118.7 nM None
Homo sapiens Cyclin-dependent kinase 2 Delta TM -0.92 C 10.6019/CHEMBL5308504
Homo sapiens Cytochrome P450 1A2 AC50 15848.93 nM None
Homo sapiens Cytochrome P450 2C19 AC50 nan None None
Homo sapiens Cytochrome P450 2C19 Potency 19952.6 nM None
Homo sapiens Cytochrome P450 2C9 AC50 nan None None
Homo sapiens Cytochrome P450 2C9 Potency 31622.8 nM None
Homo sapiens Cytochrome P450 2D6 AC50 nan None None
Homo sapiens Cytochrome P450 3A4 AC50 31622.78 nM None
Homo sapiens Cytochrome P450 3A4 Potency 31622.8 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 35481.3 nM None
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 39810.7 nM None
Homo sapiens DNA polymerase beta Potency 31622.8 nM None
Homo sapiens DNA polymerase eta Potency 44668.4 nM None
Homo sapiens DNA polymerase iota Potency 15848.9 nM None
Homo sapiens DNA polymerase kappa Potency 14125.4 nM None
Homo sapiens DNA polymerase kappa Potency 21192.3 nM None
Homo sapiens Dopamine D1 receptor Potency 31622.8 nM None
Homo sapiens Fibroblast Growth Rate 0.19 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.35 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.64 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.78 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.96 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast Growth Rate 0.98 None 10.6019/CHEMBL5303304
Homo sapiens Fibroblast growth factor receptor 3 Delta TM 1.23 C 10.6019/CHEMBL5308504
Homo sapiens Flap endonuclease 1 Potency 8436.8 nM None
Homo sapiens Geminin Potency 12589.3 nM None
Homo sapiens Geminin Potency 35481.3 nM None
Homo sapiens Glucose-dependent insulinotropic receptor EC50 930.0 nM 10.1016/j.bmcl.2019.126855
Homo sapiens Glucose-dependent insulinotropic receptor EC50 2200.0 nM 10.1016/j.bmc.2012.12.013
Homo sapiens Glucose-dependent insulinotropic receptor EC50 2200.0 nM 10.1016/j.bmc.2016.10.030
Homo sapiens Glucose-dependent insulinotropic receptor EC50 2200.0 nM 10.1016/j.bmcl.2012.12.011
Homo sapiens Glucose-dependent insulinotropic receptor EC50 2200.0 nM 10.1016/j.bmcl.2017.03.092
Homo sapiens Glucose-dependent insulinotropic receptor EC50 3200.0 nM 10.1016/j.bmc.2018.06.035
Homo sapiens Glucose-dependent insulinotropic receptor EC50 3200.0 nM 10.1021/jm300484d
Homo sapiens Glucose-dependent insulinotropic receptor Emax 100.0 % 10.1016/j.bmcl.2012.12.011
Homo sapiens Glucose-dependent insulinotropic receptor Emax 100.0 % 10.1016/j.bmcl.2019.126855
Homo sapiens Glucose-dependent insulinotropic receptor %max 100.0 % 10.1016/j.bmcl.2017.03.092
Homo sapiens Glycogen synthase kinase-3 beta Delta TM -2.08 C 10.6019/CHEMBL5308504
Homo sapiens HaCaT Activity nan None 10.1016/j.bmc.2010.12.046
Homo sapiens HaCaT LC50 14.4 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens HaCaT TGI 53.5 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens Heat shock protein HSP 90-alpha AC50 7666.0 nM None
Homo sapiens HEK-293T Growth Rate -0.38 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate 0.43 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate 0.62 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate 0.75 None 10.6019/CHEMBL5303304
Homo sapiens HEK-293T Growth Rate 0.83 None 10.6019/CHEMBL5303304
Homo sapiens HERG Potency 35481.3 nM None
Homo sapiens Histone deacetylase 6 Inhibition -6.96 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 0.02 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 2238.7 nM None
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 44668.4 nM None
Homo sapiens LNCaP Control nan None 10.1016/s0960-894x(00)00370-x
Homo sapiens MAP kinase ERK2 Delta TM -1.79 C 10.6019/CHEMBL5308504
Homo sapiens MAP kinase ERK2 Potency 3981.1 nM None
Homo sapiens MCF7 GI50 25.9 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens MCF7 TGI 66.7 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens Menin/Histone-lysine N-methyltransferase MLL Potency 22387.2 nM None
Homo sapiens Microtubule-associated protein tau Potency 25118.9 nM None
Homo sapiens Microtubule-associated protein tau Potency 28183.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 31622.8 nM None
Homo sapiens Microtubule-associated protein tau Potency 35481.3 nM None
Homo sapiens Microtubule-associated protein tau Potency 39810.7 nM None
Homo sapiens M-phase phosphoprotein 8 Potency 63095.7 nM None
Homo sapiens NAD-dependent protein deacetylase sirtuin-6 EC50 3100.0 nM 10.1021/acs.jmedchem.1c00601
Homo sapiens NAD-dependent protein deacetylase sirtuin-6 FC 2.1 None 10.1021/acs.jmedchem.1c00601
Homo sapiens NAD-dependent protein deacetylase sirtuin-6 FC 3.7 None 10.1021/acs.jmedchem.1c00601
Homo sapiens NCI/ADR-RES GI50 9.1 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens NCI/ADR-RES TGI 39.5 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens NCI-H460 GI50 36.5 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens NCI-H460 TGI 81.0 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens Nuclear factor erythroid 2-related factor 2 Potency 32642.7 nM None
Homo sapiens Nuclear factor NF-kappa-B p105 subunit Potency 112.2 nM None
Homo sapiens Peregrin Delta TM -0.91 C 10.6019/CHEMBL5308504
Homo sapiens Peroxisome proliferator-activated receptor alpha Activity nan None 10.1016/j.bmcl.2015.05.045
Homo sapiens Peroxisome proliferator-activated receptor alpha Activity nan None 10.1021/jm0601102
Homo sapiens Peroxisome proliferator-activated receptor alpha EC50 110.0 nM 10.1021/jm0601102
Homo sapiens Peroxisome proliferator-activated receptor alpha EC50 120.0 nM 10.1016/j.bmc.2016.08.067
Homo sapiens Peroxisome proliferator-activated receptor alpha EC50 152.0 nM 10.1021/acs.jmedchem.5b00849
Homo sapiens Peroxisome proliferator-activated receptor alpha EC50 152.0 nM 10.1021/ml200091q
Homo sapiens Peroxisome proliferator-activated receptor alpha EC50 185.0 nM 10.1021/ml200091q
Homo sapiens Peroxisome proliferator-activated receptor delta EC50 1100.0 nM 10.1016/j.bmc.2016.08.067
Homo sapiens Prelamin-A/C Potency 11220.2 nM None
Homo sapiens Prelamin-A/C Potency 12589.3 nM None
Homo sapiens Rap guanine nucleotide exchange factor 4 Potency 89125.1 nM None
Homo sapiens Serine/threonine-protein kinase Aurora-A Delta TM -2.91 C 10.6019/CHEMBL5308504
Homo sapiens Thyroid stimulating hormone receptor Potency 5011.9 nM None
Homo sapiens Thyroid stimulating hormone receptor Potency 39810.7 nM None
Homo sapiens Transcription intermediary factor 1-alpha Delta TM -2.56 C 10.6019/CHEMBL5308504
Homo sapiens Tumor susceptibility gene 101 protein Potency 19952.6 nM None
Homo sapiens Tyrosine-protein kinase ABL Delta TM -1.47 C 10.6019/CHEMBL5308504
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 2909.3 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 25929.0 nM None
Homo sapiens Tyrosyl-DNA phosphodiesterase 1 Potency 29855.4 nM None
Homo sapiens U-251 GI50 27.3 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens U-251 TGI 51.3 ug.mL-1 10.1016/j.bmc.2014.11.019
Homo sapiens U2OS Growth Rate -0.18 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.54 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.62 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.68 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.74 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.76 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.79 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.81 None 10.6019/CHEMBL5303304
Homo sapiens U2OS Growth Rate 0.87 None 10.6019/CHEMBL5303304
Homo sapiens Ubiquitin carboxyl-terminal hydrolase 1 Potency 44668.4 nM None
Homo sapiens Vanilloid receptor EC50 40.0 nM 10.1021/jm300484d
Homo sapiens Vanilloid receptor EC50 890.0 nM 10.1021/jm051240y
Homo sapiens Vanilloid receptor EC50 3650.0 nM 10.1021/jm900130m
Homo sapiens Vanilloid receptor Emax 50.1 % 10.1021/jm051240y
Influenza A virus Nonstructural protein 1 Potency 7079.5 nM None
Mus musculus Cannabinoid CB2 receptor Ki 31000.0 nM 10.1021/jm970257g
Mus musculus Glucose-dependent insulinotropic receptor EC50 2900.0 nM 10.1021/acs.jmedchem.5b01198
Mus musculus Mus musculus Activity -3.42 % 10.1021/jm300484d
Mus musculus Mus musculus Activity -2.57 % 10.1021/jm300484d
Mus musculus Mus musculus Activity -1.17 % 10.1021/jm300484d
Mus musculus Mus musculus Activity -0.23 % 10.1021/jm300484d
Mus musculus Mus musculus Activity -0.2 % 10.1021/jm300484d
Mus musculus Mus musculus Activity -0.18 % 10.1021/jm300484d
Mus musculus Mus musculus Activity -0.15 % 10.1021/jm300484d
Mus musculus Mus musculus Activity 1.43 % 10.1021/jm300484d
Mus musculus RAW264.7 Activity 117.0 % 10.1016/j.bmc.2008.10.015
Mycobacterium tuberculosis Acyl-CoA synthase AC50 100000.0 nM None
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 12.5 ug.mL-1 10.1016/j.bmcl.2010.06.149
Mycobacterium tuberculosis Mycobacterium tuberculosis MIC 25.0 ug.mL-1 10.1016/j.bmcl.2010.06.149
Plasmodium falciparum Plasmodium falciparum IC50 1995.26 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 3162.28 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 3981.07 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 5011.87 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 6309.57 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum IC50 7943.28 nM 10.1038/nchembio.215
Plasmodium falciparum Plasmodium falciparum Potency 2616.9 nM None
Plasmodium falciparum Plasmodium falciparum Potency 2936.2 nM None
Plasmodium falciparum 3D7 HSP90 AC50 9250.0 nM None
Rattus norvegicus Anandamide amidohydrolase Rate of hydrolysis 0.79 nM min-1 mg-1 10.1021/jm980461j
Rattus norvegicus Anandamide amidohydrolase Relative rate of hydrolysis 61.1 % 10.1021/jm980461j
Rattus norvegicus Cannabinoid CB1 receptor Ki 10000.0 nM 10.1021/jm980461j
Rattus norvegicus Cannabinoid CB1 receptor Ki 20000.0 nM 10.1021/jm970257g
Rattus norvegicus Cannabinoid CB1 receptor Ki 44000.0 nM 10.1021/jm970257g
Rattus norvegicus Rattus norvegicus IC50 23000.0 nM 10.1021/jm051240y
Rattus norvegicus Rattus norvegicus Inhibition 0.0 % 10.1016/s0960-894x(99)00148-1
Rattus norvegicus Rattus norvegicus Inhibition 100.0 % 10.1016/s0960-894x(99)00148-1
Rattus norvegicus RBL-2H3 IC50 20000.0 nM 10.1021/jm051240y
Rattus norvegicus RBL-2H3 IC50 50000.0 nM 10.1021/acs.jmedchem.9b00994
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 25118.9 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 26679.5 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 28183.8 nM None
Rattus norvegicus Thioredoxin reductase 1, cytoplasmic Potency 37685.8 nM None
Rattus norvegicus Transient receptor potential cation channel subfamily V member 2 IC50 1800.0 nM 10.1021/acs.jmedchem.8b00734
Rattus norvegicus Transient receptor potential cation channel subfamily V member 2 IC50 5400.0 nM 10.1021/acs.jmedchem.8b00734
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 9.15 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 13.83 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 0.42 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 3.39 % 10.6019/CHEMBL4495565
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition 35.38 % 10.21203/rs.3.rs-23951/v1
Trypanosoma cruzi Cruzipain Potency 19952.6 nM None
None ADMET Activity 140.0 % 10.1016/j.bmc.2008.10.015
None NON-PROTEIN TARGET GI50 16.9 ug.mL-1 10.1016/j.bmc.2014.11.019
None NON-PROTEIN TARGET GI50 35.4 ug.mL-1 10.1016/j.bmc.2014.11.019
None NON-PROTEIN TARGET Potency 2511.9 nM None
None NON-PROTEIN TARGET Potency 3548.1 nM None
None NON-PROTEIN TARGET Potency 3981.1 nM None
None NON-PROTEIN TARGET Potency 4466.8 nM None
None NON-PROTEIN TARGET Potency 7943.3 nM None
None NON-PROTEIN TARGET Potency 8912.5 nM None
None NON-PROTEIN TARGET TGI 44.2 ug.mL-1 10.1016/j.bmc.2014.11.019
None NON-PROTEIN TARGET TGI 71.7 ug.mL-1 10.1016/j.bmc.2014.11.019
None Unchecked IC50 24000.0 nM 10.1016/j.bmc.2009.12.071
None Unchecked IC50 28000.0 nM 10.1016/j.bmc.2009.12.071
None Unchecked IC50 71000.0 nM 10.1016/j.bmc.2009.12.071
None Unchecked IC50 76000.0 nM 10.1016/j.bmc.2009.12.071
None Unchecked IC50 nan None 10.1016/j.bmc.2009.12.071
None Unchecked Inhibition nan % 10.1038/nchembio873
None Unchecked Potency 10000.0 nM None
None Unchecked Potency 22387.2 nM None
None Unchecked Potency 39810.7 nM None

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000340 *C(=O)OC[C@H](COP(=O)(O)OCCNC(=O)CCCCCCC/C=C\CCCCCCCC)OC(*)=O>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCO RXN-20517
AKRT008158 CCCCCCCC/C=C\CCCCCCCC(=O)NCCO>>CCCCCCCC/C=C\CCCCCCCC(=O)O 45060
AKRT008159 CCCCCCCC/C=C\CCCCCCCC(=O)NCCO>>CCCCCCCC/C=C\CCCCCCCC(=O)O.NCCO None
AKRT008160 CCCCCCCC/C=C\CCCCCCCC(=O)NCCO>>NCCO 45060
AKRT008161 CCCCCCCC/C=C\CCCCCCCC(=O)NCCOP(=O)(O)O>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCO 62160
AKRT008162 CCCCCCCC/C=C\CCCCCCCC(=O)NCCOP(=O)(O)OC[C@@H](COC(=O)CCCCCCC/C=C\CCCCCCCC)OC(=O)CCCCCCC/C=C\CCCCCCCC>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCO 45532
AKRT008163 CCCCCCCC/C=C\CCCCCCCC(=O)NCCOP(=O)(O)OC[C@H](O)CO/C=C\CCCCCCCCCCCCCCCC>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCO 53188
AKRT008164 CCCCCCCC/C=C\CCCCCCCC(=O)NCCOP(=O)(O)OC[C@H](O)CO>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCO 45432
AKRT008165 CCCCCCCC/C=C\CCCCCCCC(=O)NCCOP(=O)(O)OC[C@H](O)COC(=O)CCCCCCC/C=C\CCCCCCCC>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCO 56460
AKRT008189 CCCCCCCC/C=C\CCCCCCCC(=O)O.NCCO>>CCCCCCCC/C=C\CCCCCCCC(=O)NCCO enzymemap_77717