Detailed information for compound 415236

Basic information

Technical information
  • TDR Targets ID: 415236
  • Name: 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nit robenzoic acid
  • MW: 361.657 | Formula: C14H7ClF3NO5
  • H donors: 1 H acceptors: 4 LogP: 4.32 Rotable bonds: 5
    Rule of 5 violations (Lipinski): 1
  • SMILES: Clc1cc(ccc1Oc1ccc(c(c1)C(=O)O)[N+](=O)[O-])C(F)(F)F
  • InChi: 1S/C14H7ClF3NO5/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21/h1-6H,(H,20,21)
  • InChiKey: NUFNQYOELLVIPL-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-benzoic acid
  • acifluorfen
  • 94128-04-8
  • 50594-66-6
  • 34311_RIEDEL
  • 5-{[2-chloro-4-(trifluoromethyl)phenyl]oxy}-2-nitrobenzoic acid
  • ACJ
  • MLS001066351
  • SMR000471865
  • 5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoic acid
  • PS1016_SUPELCO
  • 2-Nitro-5-(2-chloro-4-(trifluoromethyl)phenoxy)benzoic acid
  • 5-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoic acid
  • 5-(2-Chloro-alapha,alpha,alpha-trifluoro-p-tolyloxy)-2-nitrobenzoic acid
  • 5-(2-Chloro-alpha,alpha,alpha-trifluoro-p-tolyloxy)-2-nitrobenzoic acid (IUPAC)
  • Acifluorfen [BSI:ISO]
  • Acifluorfene
  • Acifluorfene [ISO-French]
  • BRN 2953865
  • Benzoic acid, 5-(2-chloro-4-(trifluoromethyl)phenoxy)-2-nitro-
  • CCRIS 3491
  • EINECS 256-634-5
  • Tackle
  • Benzoic acid, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-
  • NCGC00163887-01
  • NCGC00163887-02

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens geminin, DNA replication inhibitor Starlite/ChEMBL No references
Zea mays Protoporphyrinogen IX oxidase Starlite/ChEMBL No references
Homo sapiens protoporphyrinogen oxidase Starlite/ChEMBL References
Homo sapiens androgen receptor Starlite/ChEMBL No references
Nicotiana tabacum Protoporphyrinogen oxidase, mitochondrial Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma mansoni Protoporphyrinogen oxidase chloroplast/mitochondrial precursor Get druggable targets OG5_129066 All targets in OG5_129066
Candida albicans protoporphyrinogen oxidase, heme biosynthesis Get druggable targets OG5_129066 All targets in OG5_129066
Schistosoma japonicum ko:K00231 protoporphyrinogen oxidase [EC1.3.3.4B], putative Get druggable targets OG5_129066 All targets in OG5_129066
Chlamydia trachomatis protoporphyrinogen oxidase Get druggable targets OG5_129066 All targets in OG5_129066
Mycobacterium leprae PROBABLE PROTOPORPHYRINOGEN OXIDASE HEMY (PROTOPORPHYRINOGEN-IX OXIDASE) (PROTOPORPHYRINOGENASE) (PPO) Get druggable targets OG5_129066 All targets in OG5_129066
Mycobacterium tuberculosis Probable protoporphyrinogen oxidase HemY (protoporphyrinogen-IX oxidase) (protoporphyrinogenase) (PPO) Get druggable targets OG5_129066 All targets in OG5_129066
Echinococcus granulosus protoporphyrinogen oxidase Get druggable targets OG5_129066 All targets in OG5_129066
Mycobacterium ulcerans protoporphyrinogen oxidase Get druggable targets OG5_129066 All targets in OG5_129066
Candida albicans protoporphyrinogen oxidase Get druggable targets OG5_129066 All targets in OG5_129066
Echinococcus multilocularis protoporphyrinogen oxidase Get druggable targets OG5_129066 All targets in OG5_129066
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Brugia malayi Hypothetical 65.5 kDa Trp-Asp repeats containing protein F02E8.5 inchromosome X geminin, DNA replication inhibitor 209 aa 176 aa 27.8 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus multilocularis lysine specific histone demethylase 1A 0.0076 0.0707 0.0691
Mycobacterium ulcerans protoporphyrinogen oxidase 0.0576 1 1
Echinococcus granulosus X box binding protein 1 0.0333 0.5491 0.6383
Plasmodium falciparum conserved Plasmodium protein, unknown function 0.0076 0.0707 1
Mycobacterium leprae PROBABLE PROTOPORPHYRINOGEN OXIDASE HEMY (PROTOPORPHYRINOGEN-IX OXIDASE) (PROTOPORPHYRINOGENASE) (PPO) 0.0576 1 0.5
Trichomonas vaginalis bromodomain-containing protein, putative 0.0049 0.0215 0.0444
Loa Loa (eye worm) hypothetical protein 0.0076 0.0707 0.1428
Schistosoma mansoni hypothetical protein 0.0333 0.5491 0.5483
Trichomonas vaginalis glucosylceramidase, putative 0.0299 0.4849 1
Trichomonas vaginalis glucosylceramidase, putative 0.0196 0.2941 0.6064
Loa Loa (eye worm) O-glycosyl hydrolase family 30 protein 0.0299 0.4849 1
Brugia malayi beta-NAC-like protein 0.004 0.005 0.0069
Loa Loa (eye worm) hypothetical protein 0.0076 0.0707 0.1428
Echinococcus granulosus histone acetyltransferase KAT2B 0.0163 0.2327 0.2694
Trichomonas vaginalis conserved hypothetical protein 0.0039 0.0017 0.0035
Mycobacterium tuberculosis Probable protoporphyrinogen oxidase HemY (protoporphyrinogen-IX oxidase) (protoporphyrinogenase) (PPO) 0.05 0.8592 1
Schistosoma mansoni hypothetical protein 0.0109 0.1333 0.1318
Schistosoma mansoni amine oxidase 0.0076 0.0707 0.0691
Trichomonas vaginalis glucosylceramidase, putative 0.0196 0.2941 0.6064
Loa Loa (eye worm) ICD-1 protein 0.004 0.005 0.0069
Trichomonas vaginalis cat eye syndrome critical region protein 2, cscr2, putative 0.0049 0.0215 0.0444
Toxoplasma gondii histone lysine-specific demethylase 0.0076 0.0707 1
Schistosoma mansoni transcription factor btf3 0.004 0.005 0.0034
Trypanosoma cruzi UDP-galactopyranose mutase 0.0076 0.0707 1
Echinococcus multilocularis protoporphyrinogen oxidase 0.0576 1 1
Loa Loa (eye worm) acetyltransferase 0.0168 0.2414 0.4961
Trypanosoma cruzi transcription factor btf3, putative 0.004 0.005 0.0714
Onchocerca volvulus Glucosylceramidase homolog 0.0196 0.2941 1
Toxoplasma gondii histone lysine-specific demethylase LSD1/BHC110/KDMA1A 0.0076 0.0707 1
Entamoeba histolytica hypothetical protein 0.004 0.005 0.3637
Plasmodium falciparum histone acetyltransferase GCN5 0.0045 0.0139 0.1345
Echinococcus multilocularis geminin 0.0205 0.3102 0.3091
Loa Loa (eye worm) hypothetical protein 0.0076 0.0707 0.1428
Entamoeba histolytica transcription factor BTF3, putative 0.004 0.005 0.3637
Trichomonas vaginalis glucosylceramidase, putative 0.0196 0.2941 0.6064
Trichomonas vaginalis glucosylceramidase, putative 0.0299 0.4849 1
Trichomonas vaginalis rotamase, putative 0.0039 0.0017 0.0035
Trichomonas vaginalis conserved hypothetical protein 0.004 0.005 0.0104
Trichomonas vaginalis glucosylceramidase, putative 0.0206 0.3137 0.6469
Trichomonas vaginalis glucosylceramidase, putative 0.0196 0.2941 0.6064
Echinococcus multilocularis X box binding protein 1 0.0333 0.5491 0.5483
Trichomonas vaginalis glucosylceramidase, putative 0.0299 0.4849 1
Brugia malayi SWIRM domain containing protein 0.0076 0.0707 0.1428
Echinococcus multilocularis 0.0076 0.0707 0.0691
Schistosoma mansoni gcn5proteinral control of amino-acid synthesis 5-like 2 gcnl2 0.0168 0.2414 0.2401
Trichomonas vaginalis conserved hypothetical protein 0.004 0.005 0.0104
Plasmodium falciparum protoporphyrinogen oxidase 0.0076 0.0707 1
Echinococcus granulosus histone acetyltransferase KAT2B 0.0049 0.0215 0.0231
Leishmania major UDP-galactopyranose mutase 0.0076 0.0707 1
Trichomonas vaginalis conserved hypothetical protein 0.004 0.005 0.0104
Echinococcus granulosus protoporphyrinogen oxidase 0.05 0.8592 1
Brugia malayi O-Glycosyl hydrolase family 30 protein 0.0299 0.4849 1
Plasmodium vivax protoporphyrinogen oxidase, putative 0.0076 0.0707 1
Echinococcus granulosus lysine specific histone demethylase 1A 0.0076 0.0707 0.0805
Trypanosoma cruzi UDP-galactopyranose mutase 0.0076 0.0707 1
Plasmodium vivax hypothetical protein, conserved 0.0076 0.0707 1
Schistosoma mansoni amine oxidase 0.0076 0.0707 0.0691
Plasmodium vivax hypothetical protein, conserved 0.0076 0.0707 1
Loa Loa (eye worm) hypothetical protein 0.0076 0.0707 0.1428
Trichomonas vaginalis glucosylceramidase, putative 0.0206 0.3137 0.6469
Loa Loa (eye worm) hypothetical protein 0.0076 0.0707 0.1428
Toxoplasma gondii histone lysine acetyltransferase GCN5-A 0.0049 0.0215 0.3042
Echinococcus granulosus geminin 0.0205 0.3102 0.3598
Trichomonas vaginalis glucosylceramidase, putative 0.0299 0.4849 1
Schistosoma mansoni Protoporphyrinogen oxidase chloroplast/mitochondrial precursor 0.0576 1 1
Trypanosoma brucei RNA helicase, putative 0.0109 0.1333 1
Echinococcus granulosus lysine specific histone demethylase 1A 0.0076 0.0707 0.0805
Toxoplasma gondii NAC domain-containing protein 0.004 0.005 0.0714
Trichomonas vaginalis glucosylceramidase, putative 0.0196 0.2941 0.6064
Schistosoma mansoni hypothetical protein 0.0205 0.3102 0.3091
Schistosoma mansoni hypothetical protein 0.0205 0.3102 0.3091
Brugia malayi hypothetical protein 0.0076 0.0707 0.1428
Loa Loa (eye worm) hypothetical protein 0.0076 0.0707 0.1428
Plasmodium falciparum lysine-specific histone demethylase 1, putative 0.0076 0.0707 1
Leishmania major basic transcription factor 3a, putative 0.004 0.005 0.0714
Plasmodium vivax histone acetyltransferase GCN5, putative 0.0049 0.0215 0.2507
Echinococcus multilocularis transcription factor btf3 0.004 0.005 0.0034
Trichomonas vaginalis glucosylceramidase, putative 0.0196 0.2941 0.6064
Brugia malayi amine oxidase, flavin-containing family protein 0.0076 0.0707 0.1428
Giardia lamblia Histone acetyltransferase GCN5 0.0045 0.0139 0.5
Entamoeba histolytica acetyltransferase, GNAT family 0.0045 0.0139 1
Plasmodium vivax lysine-specific histone demethylase 1, putative 0.0076 0.0707 1
Toxoplasma gondii histone lysine acetyltransferase GCN5-B 0.0049 0.0215 0.3042
Echinococcus multilocularis gcn5proteinral control of amino acid synthesis 0.0168 0.2414 0.2401
Echinococcus granulosus transcription factor btf3 0.004 0.005 0.0039
Trichomonas vaginalis glucosylceramidase, putative 0.0299 0.4849 1
Trichomonas vaginalis glucosylceramidase, putative 0.0196 0.2941 0.6064
Trypanosoma cruzi transcription factor btf3, putative 0.004 0.005 0.0714
Trichomonas vaginalis glucosylceramidase, putative 0.0299 0.4849 1
Trypanosoma brucei transcription factor BTF3, putative 0.004 0.005 0.0379
Brugia malayi acetyltransferase, GNAT family protein 0.0168 0.2414 0.4961
Schistosoma mansoni Lysine-specific histone demethylase 1 0.0076 0.0707 0.0691

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 6.7 Inhibition of protoporphyrinogen IX oxidase in Zea mays cv. Anjou (maize) seedlings homogenates assessed as protoporphyrinogen IX formation by spectrophotometry ChEMBL. No reference
IC50 (functional) = 457.1 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 96 hrs ChEMBL. 17060533
IC50 (functional) = 457.1 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 96 hrs ChEMBL. 17060533
IC50 (functional) = 524.8 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 48 hrs ChEMBL. 17060533
IC50 (functional) = 524.8 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 48 hrs ChEMBL. 17060533
Ki (binding) = 0.07 uM Inhibition of Nicotiana tobacum PPO ChEMBL. 22130420
Ki (binding) = 1.71 uM Inhibition of human PPO expressed in Escherichia coli BL21(DE3) by continuous fluorometric method ChEMBL. 22130420
MIC90 (functional) = 691.8 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 96 hrs ChEMBL. 17060533
MIC90 (functional) = 691.8 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 96 hrs ChEMBL. 17060533
MIC90 (functional) = 871 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 48 hrs ChEMBL. 17060533
MIC90 (functional) = 871 uM Inhibition of Plasmodium falciparum FCK2 growth assessed as [3H]hypoxanthine uptake after 48 hrs ChEMBL. 17060533
Potency (functional) 0.0517 uM PubChem BioAssay. A quantitative high throughput screen for small molecules that induce DNA re-replication in SW480 colon adenocarcinoma cells. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 0.1836 uM PubChem BioAssay. A quantitative high throughput screen for small molecules that induce DNA re-replication in MCF 10a normal breast cells. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 19.5916 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 21.8617 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 21.9822 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 26.6795 uM PUBCHEM_BIOASSAY: qHTS for Inhibitors of Polymerase Kappa. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID588638] ChEMBL. No reference
Potency (functional) 27.2783 uM PubChem BioAssay: Tox21. qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) = 28.1838 um PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors Targeting the Menin-MLL Interaction in MLL Related Leukemias: Competition With Fluorescein Labeled MLL-derived Peptide. (Class of assay: confirmatory) ChEMBL. No reference
Potency (binding) = 28.1838 um PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Tyrosyl-DNA Phosphodiesterase (TDP1). (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 28.1838 uM PUBCHEM_BIOASSAY: qHTS assay for small molecule agonists of glucocorticoid receptor signaling. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 31.0506 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 31.6228 uM PUBCHEM_BIOASSAY: qHTS assay for small molecule antagonists of peroxisome proliferator-activated receptor delta signaling. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 34.8394 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the NFkB signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 35.4813 uM PUBCHEM_BIOASSAY: qHTS assay for small molecule agonists of peroxisome proliferator-activated receptor delta signaling. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 55.2167 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 61.6146 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 63.0957 uM PUBCHEM_BIOASSAY: HTS for Inhibitors of HP1-beta Chromodomain Interactions with Methylated Histone Tails. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID488962] ChEMBL. No reference
Potency (functional) 89.1251 uM PUBCHEM_BIOASSAY: Inhibitors of the vitamin D receptor (VDR): qHTS. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID504855] ChEMBL. No reference
Potency (functional) 100 uM PUBCHEM_BIOASSAY: qHTS Assay for Inhibitors of Rango (Ran-regulated importin-beta cargo) - Importin beta complex formation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID540273] ChEMBL. No reference

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

2 literature references were collected for this gene.

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