Detailed information for compound 15424

Basic information

Technical information
  • TDR Targets ID: 15424
  • Name: (Z)-N-phenyloctadec-9-enamide
  • MW: 357.573 | Formula: C24H39NO
  • H donors: 1 H acceptors: 1 LogP: 8.58 Rotable bonds: 17
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)Nc1ccccc1
  • InChi: 1S/C24H39NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19-22-24(26)25-23-20-17-16-18-21-23/h9-10,16-18,20-21H,2-8,11-15,19,22H2,1H3,(H,25,26)/b10-9-
  • InChiKey: YPUOCYKJOLQYQS-KTKRTIGZSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (Z)-N-phenyl-9-octadecenamide
  • oleoylanilide
  • 5429-85-6
  • Oleanilide (7CI)
  • Oleic acid anilide
  • Oleyl anilide
  • Oleylanilide
  • NSC14233
  • Oleanilide
  • cis-9-Octadecenanilide
  • (Z)-N-Phenyl-9-octadeceneamide
  • 2-12-00-00150 (Beilstein Handbook Reference)
  • 9-Octadecenamide, N-phenyl-, (Z)-
  • BRN 3533033
  • EINECS 226-584-9
  • NSC 14233

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Acyl coenzyme A:cholesterol acyltransferase 1 Starlite/ChEMBL References
Homo sapiens sterol O-acyltransferase 2 Starlite/ChEMBL References
Homo sapiens sterol O-acyltransferase 1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma japonicum ko:K00637 sterol O-acyltransferase [EC2.3.1.26], putative Get druggable targets OG5_133487 All targets in OG5_133487
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133487 All targets in OG5_133487
Echinococcus multilocularis sterol O acyltransferase 1 Get druggable targets OG5_133487 All targets in OG5_133487
Schistosoma mansoni sterol O-acyltransferase 1 Get druggable targets OG5_133487 All targets in OG5_133487
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133487 All targets in OG5_133487
Echinococcus granulosus sterol O acyltransferase 1 Get druggable targets OG5_133487 All targets in OG5_133487
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Toxoplasma gondii acyl-CoA:cholesterol acyltransferase alpha ACAT1-alpha Acyl coenzyme A:cholesterol acyltransferase 1   545 aa 510 aa 24.1 %
Toxoplasma gondii acyl-CoA:diacylglycerol acyltransferase 1-related enzyme sterol O-acyltransferase 2 522 aa 531 aa 25.2 %
Toxoplasma gondii acyl-CoA:cholesterol acyltransferase alpha ACAT1-alpha sterol O-acyltransferase 1 492 aa 413 aa 25.9 %
Dictyostelium discoideum diacylglycerol O-acyltransferase 1 Acyl coenzyme A:cholesterol acyltransferase 1   545 aa 547 aa 22.3 %
Neospora caninum sterol O-acyltransferase, putative Acyl coenzyme A:cholesterol acyltransferase 1   545 aa 510 aa 21.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus Membrane bound O acyl transferase MBOAT 0.0077 0.0137 0.0137
Echinococcus multilocularis o acyltransferase (membrane bound) domain 0.0077 0.0137 0.0137
Trypanosoma brucei C-8 sterol isomerase, putative 0.0375 0.1595 0.1595
Trypanosoma brucei DNA repair and recombination helicase protein PIF6 0.209 1 1
Schistosoma mansoni diacylglycerol O-acyltransferase 1 0.0077 0.0137 0.0137
Giardia lamblia CAMP-specific 3,5-cyclic phosphodiesterase 4B 0.0387 0.1656 0.1656
Echinococcus multilocularis cAMP specific 3',5' cyclic phosphodiesterase 0.034 0.1425 0.1425
Leishmania major glycerol uptake protein, putative 0.0077 0.0137 0.0137
Schistosoma mansoni hypothetical protein 0.0077 0.0137 0.0137
Loa Loa (eye worm) hhat protein 0.0077 0.0137 0.0556
Toxoplasma gondii acyl-CoA:cholesterol acyltransferase alpha ACAT1-alpha 0.0077 0.0137 0.0821
Loa Loa (eye worm) hypothetical protein 0.0077 0.0137 0.0556
Leishmania major PIF1 helicase-like protein, putative,DNA repair and recombination protein, mitochondrial precursor, putative 0.209 1 1
Onchocerca volvulus 0.0077 0.0137 0.5
Echinococcus granulosus membrane bound acyltransferase:hhat 0.0077 0.0137 0.0137
Toxoplasma gondii 3'5'-cyclic nucleotide phosphodiesterase domain-containing protein 0.0051 0.0007 0.004
Trypanosoma brucei DNA repair and recombination helicase protein PIF7 0.209 1 1
Loa Loa (eye worm) hypothetical protein 0.0057 0.0039 0.0159
Schistosoma mansoni membrane-bound acyltransferase/hhat 0.0077 0.0137 0.0137
Schistosoma mansoni o-acyltransferase (membrane bound) domain containing protein 0.0077 0.0137 0.0137
Brugia malayi Hhat protein 0.0077 0.0137 0.0862
Echinococcus multilocularis cAMP specific 3',5' cyclic phosphodiesterase 0.0387 0.1656 0.1656
Echinococcus granulosus protein cysteine N palmitoyltransferase 0.0077 0.0137 0.0137
Toxoplasma gondii acyl-CoA:diacylglycerol acyltransferase 1-related enzyme 0.0077 0.0137 0.0821
Brugia malayi ERG2 and Sigma1 receptor like protein 0.0375 0.1595 1
Brugia malayi Cytochrome P450 family protein 0.0104 0.0266 0.1669
Schistosoma mansoni o-acyltransferase (membrane bound) domain containing protein 0.0077 0.0137 0.0137
Trypanosoma cruzi glycerol uptake protein, putative 0.0077 0.0137 0.0137
Brugia malayi MBOAT family protein 0.0077 0.0137 0.0862
Leishmania major glycerol uptake protein, putative 0.0077 0.0137 0.0137
Echinococcus multilocularis sterol O acyltransferase 1 0.0554 0.2471 0.2471
Loa Loa (eye worm) hypothetical protein 0.0375 0.1595 0.6453
Echinococcus granulosus lysophospholipid acyltransferase 7 0.0077 0.0137 0.0137
Leishmania major C-8 sterol isomerase-like protein 0.0375 0.1595 0.1595
Trypanosoma cruzi GUP1, putative 0.0077 0.0137 0.0137
Schistosoma mansoni camp-specific 35-cyclic phosphodiesterase 0.0387 0.1656 0.1656
Echinococcus multilocularis protein cysteine N palmitoyltransferase 0.0077 0.0137 0.0137
Echinococcus granulosus o acyltransferase membrane bound domain 0.0077 0.0137 0.0137
Brugia malayi diacylglycerol acyltransferase 0.0077 0.0137 0.0862
Brugia malayi MBOAT family protein 0.0077 0.0137 0.0862
Trichomonas vaginalis porcupine, putative 0.0077 0.0137 0.0137
Plasmodium vivax diacylglycerol O-acyltransferase, putative 0.0077 0.0137 0.5
Echinococcus multilocularis diacylglycerol O acyltransferase 1 0.0077 0.0137 0.0137
Leishmania major PIF1 helicase-like protein, putative,DNA repair and recombination protein, mitochondrial precursor, putative 0.209 1 1
Brugia malayi Probable 3',5'-cyclic phosphodiesterase R153.1, putative 0.034 0.1425 0.8937
Toxoplasma gondii 3'5'-cyclic nucleotide phosphodiesterase domain-containing protein 0.0391 0.1673 1
Trichomonas vaginalis conserved hypothetical protein 0.0077 0.0137 0.0137
Loa Loa (eye worm) membrane bound O-acyltransferase domain containing 1 0.0077 0.0137 0.0556
Trichomonas vaginalis conserved hypothetical protein 0.0077 0.0137 0.0137
Loa Loa (eye worm) MBOAT family protein 0.0077 0.0137 0.0556
Brugia malayi MBOAT family protein 0.0077 0.0137 0.0862
Trypanosoma brucei cytochrome P450, putative 0.0104 0.0266 0.0266
Trypanosoma brucei glycerol uptake protein, putative 0.0077 0.0137 0.0137
Trypanosoma cruzi DNA repair and recombination helicase protein PIF6, putative 0.209 1 1
Echinococcus granulosus cAMP specific 3'5' cyclic phosphodiesterase 0.034 0.1425 0.1425
Echinococcus granulosus sterol O acyltransferase 1 0.0554 0.2471 0.2471
Echinococcus multilocularis o acyltransferase (membrane bound) domain 0.0077 0.0137 0.0137
Echinococcus granulosus o acyltransferase membrane bound domain 0.0077 0.0137 0.0137
Leishmania major glycerol uptake protein, putative 0.0077 0.0137 0.0137
Loa Loa (eye worm) cytochrome P450 family protein 0.0104 0.0266 0.1077
Loa Loa (eye worm) hypothetical protein 0.0077 0.0137 0.0556
Schistosoma mansoni sterol O-acyltransferase 1 0.0554 0.2471 0.2471
Treponema pallidum alginate O-acetylation protein (algI) 0.0077 0.0137 0.5
Schistosoma mansoni o-acyltransferase (membrane bound) domain containing protein 0.0077 0.0137 0.0137
Trichomonas vaginalis conserved hypothetical protein 0.209 1 1
Trypanosoma cruzi DNA repair and recombination helicase protein PIF7, putative 0.209 1 1
Loa Loa (eye worm) MBOAT family protein 0.0077 0.0137 0.0556
Trypanosoma cruzi glycerol uptake protein, putative 0.0077 0.0137 0.0137
Giardia lamblia Rrm3p helicase 0.209 1 1
Echinococcus granulosus cAMP specific 3'5' cyclic phosphodiesterase 0.0387 0.1656 0.1656
Toxoplasma gondii hypothetical protein 0.0077 0.0137 0.0821
Trichomonas vaginalis conserved hypothetical protein 0.0077 0.0137 0.0137
Echinococcus multilocularis lysophospholipid acyltransferase 7 0.0077 0.0137 0.0137
Echinococcus multilocularis membrane bound acyltransferase:hhat 0.0077 0.0137 0.0137
Echinococcus multilocularis ATP dependent DNA helicase PIF1 0.209 1 1
Trypanosoma cruzi GUP1, putative 0.0077 0.0137 0.0137
Echinococcus multilocularis o acyltransferase (membrane bound) domain 0.0077 0.0137 0.0137
Leishmania major glycerol uptake protein, putative 0.0077 0.0137 0.0137
Trypanosoma brucei glycerol uptake protein, putative 0.0077 0.0137 0.0137
Loa Loa (eye worm) diacylglycerol acyltransferase 0.0077 0.0137 0.0556
Mycobacterium ulcerans cytochrome P450 185A4 Cyp185A4 0.0104 0.0266 0.5
Trypanosoma cruzi cytochrome P450, putative 0.0104 0.0266 0.0266
Brugia malayi MBOAT family protein 0.0077 0.0137 0.0862
Echinococcus multilocularis cAMP specific 3',5' cyclic phosphodiesterase 0.0387 0.1656 0.1656
Loa Loa (eye worm) hypothetical protein 0.0077 0.0137 0.0556
Loa Loa (eye worm) cytochrome P450 family protein 0.0104 0.0266 0.1077
Schistosoma mansoni zinc finger protein 0.0077 0.0137 0.0137
Loa Loa (eye worm) MBOAT family protein 0.0077 0.0137 0.0556
Loa Loa (eye worm) hypothetical protein 0.0476 0.2092 0.8467
Echinococcus granulosus o acyltransferase membrane bound domain 0.0077 0.0137 0.0137
Schistosoma mansoni hypothetical protein 0.209 1 1
Trichomonas vaginalis transmembrane protein nessy, putative 0.0077 0.0137 0.0137
Trypanosoma cruzi DNA repair and recombination helicase protein PIF7, putative 0.209 1 1
Loa Loa (eye worm) hypothetical protein 0.0554 0.2471 1
Loa Loa (eye worm) cyclic AMP specific phosphodiesterase PDE4D5A 0.034 0.1425 0.5767
Entamoeba histolytica hypothetical protein, conserved 0.209 1 1
Leishmania major glycerol uptake protein, putative 0.0077 0.0137 0.0137
Leishmania major hypothetical protein, conserved 0.0077 0.0137 0.0137
Trypanosoma cruzi glycerol uptake protein, putative 0.0077 0.0137 0.0137
Echinococcus granulosus cAMP specific 3'5' cyclic phosphodiesterase 0.0387 0.1656 0.1656
Schistosoma mansoni leukocyte receptor cluster (lrc) member 4 protein 0.0077 0.0137 0.0137
Brugia malayi MBOAT family protein 0.0077 0.0137 0.0862
Entamoeba histolytica DNA repair and recombination protein, putative 0.209 1 1
Loa Loa (eye worm) hhat protein 0.0077 0.0137 0.0556
Trypanosoma cruzi C-8 sterol isomerase, putative 0.0375 0.1595 0.1595
Loa Loa (eye worm) CYP4Cod1 0.0104 0.0266 0.1077
Loa Loa (eye worm) hypothetical protein 0.0387 0.1656 0.6702
Brugia malayi Cytochrome P450 family protein 0.0104 0.0266 0.1669
Echinococcus multilocularis Membrane bound O acyl transferase, MBOAT 0.0077 0.0137 0.0137
Plasmodium falciparum diacylglycerol O-acyltransferase 0.0077 0.0137 0.5
Trypanosoma cruzi cytochrome P450, putative 0.0104 0.0266 0.0266
Echinococcus granulosus diacylglycerol O acyltransferase 1 0.0077 0.0137 0.0137
Leishmania major cytochrome p450-like protein 0.0104 0.0266 0.0266
Loa Loa (eye worm) hypothetical protein 0.0191 0.0697 0.2821

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 0.02 uM Inhibitory activity against rat liver microsomal Acyl coenzyme A:cholesterol acyltransferase ChEMBL. 15261286
IC50 (binding) = 0.14 uM Concentration of the compound required to inhibit Acyl coenzyme A:cholesterol acyltransferase 1 ChEMBL. 15149654
IC50 (binding) = 0.14 uM Inhibition of human ACAT1 expressed in Hi5 cells ChEMBL. 16919944
IC50 (binding) = 0.14 uM Concentration of the compound required to inhibit Acyl coenzyme A:cholesterol acyltransferase 1 ChEMBL. 15149654
IC50 (binding) = 0.14 uM Inhibitory activity against human Acyl coenzyme A:cholesterol acyltransferase 1 ChEMBL. 15261286
IC50 (binding) = 0.14 uM Inhibition of human ACAT1 expressed in Hi5 cells ChEMBL. 16919944
IC50 (binding) = 0.17 uM Concentration of the compound required to inhibit Acyl coenzyme A:cholesterol acyltransferase 2 ChEMBL. 15149654
IC50 (binding) = 0.17 uM Inhibition of human ACAT2 expressed in Hi5 cells ChEMBL. 16919944
IC50 (binding) = 0.17 uM Concentration of the compound required to inhibit Acyl coenzyme A:cholesterol acyltransferase 2 ChEMBL. 15149654
IC50 (binding) = 0.17 uM Inhibitory activity against human Acyl coenzyme A:cholesterol acyltransferase 2 ChEMBL. 15261286
IC50 (binding) = 0.17 uM Inhibition of human ACAT2 expressed in Hi5 cells ChEMBL. 16919944
IC50 (binding) = 26 uM In vitro inhibition of acyl coenzyme A:cholesterol acyltransferase, in intestinal microsomes isolated from cholesterol-fed rabbits ChEMBL. 1578488
Inhibition (functional) = 0 % Inhibition of rat glial cell gap junction at the concentration of 50 microM ChEMBL. 10328303
Inhibition (binding) = 57 % Inhibition of human ACAT1 at 0.3 mM ChEMBL. 16724860

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

We have no manually annotated phenotypes for this drug. What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

5 literature references were collected for this gene.

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