Detailed information for compound 114077

Basic information

Technical information
  • TDR Targets ID: 114077
  • Name: 2-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl] phenyl]acetic acid
  • MW: 353.821 | Formula: C16H16ClNO4S
  • H donors: 2 H acceptors: 4 LogP: 2.93 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: OC(=O)Cc1ccc(cc1)CCNS(=O)(=O)c1ccc(cc1)Cl
  • InChi: 1S/C16H16ClNO4S/c17-14-5-7-15(8-6-14)23(21,22)18-10-9-12-1-3-13(4-2-12)11-16(19)20/h1-8,18H,9-11H2,(H,19,20)
  • InChiKey: IULOBWFWYDMECP-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[4-[2-[(4-chlorophenyl)sulfonylamino]ethyl]phenyl]ethanoic acid
  • daltroban
  • 93-32-3
  • 105218-03-9
  • 79094-20-5
  • 4-(2-(4-Chlorobenzenesulfonylamino)ethyl)benzeneacetic acid
  • (p-(2-(p-Chlorobenzenesulfonamido)ethyl)phenyl)acetic acid
  • BM 13,505
  • BM 13505
  • Benzeneacetic acid, 4-(2-(((4-chlorophenyl)sulfonyl)amino)ethyl)-
  • Daltroban [USAN:INN]
  • Daltrobanum [Latin]
  • SK&F 96148
  • SKF 96148
  • BM 13.505
  • BM-13505
  • SK&F-96148
  • NCGC00165787-01
  • 4-[2-[(4-Chlorophenylsulfonyl)amino]ethyl]benzeneacetic acid
  • D7441_SIGMA
  • SKF-96148
  • 4-(2-(4-Chlorophenylsulfonylamino)ethyl)phenylacetic acid
  • D03642
  • Daltroban (USAN)

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Peripheral myelin protein 22 Starlite/ChEMBL No references
Homo sapiens thromboxane A2 receptor Starlite/ChEMBL References
Rattus norvegicus Thromboxane A2 receptor Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Schistosoma mansoni opsin-like receptor Thromboxane A2 receptor   341 aa 313 aa 22.4 %
Brugia malayi hypothetical protein Peripheral myelin protein 22   160 aa 129 aa 25.6 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Mycobacterium ulcerans dihydrofolate reductase DfrA 0.0864 1 1
Trypanosoma brucei dihydrofolate reductase-thymidylate synthase 0.0463 0.5 0.5
Mycobacterium tuberculosis Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) 0.0864 1 1
Plasmodium vivax bifunctional dihydrofolate reductase-thymidylate synthase, putative 0.0463 0.5 0.5
Echinococcus granulosus dihydrofolate reductase 0.0864 1 1
Onchocerca volvulus 0.0106 0.0545 0.5
Leishmania major dihydrofolate reductase-thymidylate synthase 0.0463 0.5 0.5
Plasmodium falciparum bifunctional dihydrofolate reductase-thymidylate synthase 0.0463 0.5 0.5
Echinococcus multilocularis dihydrofolate reductase 0.0864 1 1
Schistosoma mansoni dihydrofolate reductase 0.0864 1 1
Mycobacterium leprae DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) 0.0864 1 1
Loa Loa (eye worm) dihydrofolate reductase 0.0864 1 1
Brugia malayi Dihydrofolate reductase 0.0864 1 1
Schistosoma mansoni bifunctional dihydrofolate reductase-thymidylate synthase 0.0106 0.0545 0.0545
Chlamydia trachomatis dihydrofolate reductase 0.0864 1 0.5
Toxoplasma gondii bifunctional dihydrofolate reductase-thymidylate synthase 0.0463 0.5 0.5
Trypanosoma cruzi dihydrofolate reductase-thymidylate synthase 0.0463 0.5 0.5

Activities

Activity type Activity value Assay description Source Reference
Aggregation (functional) = 0 % Inhibitory effect of the compound on the U-46619 induced platelet aggregation was determined ex vivo in the guinea pig ChEMBL. 1388208
EC50 (functional) = 0.53 mg Extra vivo inhibitory activity of the compound for the aggregation of guinea pig platelets induced by U-46,619 (4 uM) was determined ChEMBL. 10091692
I50 (functional) = 0.63 uM Ability to inhibit platelet aggregation of human platelet-rich plasma (PRP) induced by 800 uM of AA-IPA (arachidonic acid) ChEMBL. 2391688
IC50 (binding) = 0.000000062 M Inhibition of specific binding of [3H]-U-46,619 to TXA2/PGH2 receptor in guinea pig platelet membrane ChEMBL. 1535377
IC50 (functional) = 0.00000012 M Concentration of the compound required to reduced U-46619-induced contraction of the rabbit aorta by 50%. ChEMBL. 1535377
IC50 (functional) = 0.00000064 M Concentration of the compound required to reduced U-46619-induced aggregation of human platelet by 50%. ChEMBL. 1535377
IC50 (functional) = 0.00000064 M Concentration of the compound required to reduced U-46619-induced aggregation of human platelet by 50%. ChEMBL. 1535377
IC50 (functional) = 37.1 nM In vitro thromboxane A2 antagonistic activity of the compound on U-46619 (0.1 uM) induced contraction of rat aorta ChEMBL. 10091692
IC50 (functional) = 37.1 nM In vitro thromboxane A2 antagonistic activity of the compound on U-46619 (0.1 uM) induced contraction of rat aorta ChEMBL. 10091692
IC50 (binding) = 0.15 uM In vitro thromboxane-A2 receptor binding affinity to displace by 50% [3H]-SQ 29548 binding from washed human platelets ChEMBL. 7932586
IC50 (binding) = 0.15 uM In vitro thromboxane-A2 receptor binding affinity to displace by 50% [3H]-SQ 29548 binding from washed human platelets ChEMBL. 7932586
IC50 (functional) = 0.37 uM In vitro inhibitory activity of the compound for the aggregation of human platelets induced by U-46,619 (1 uM) was determined ChEMBL. 10091692
IC50 (functional) = 0.37 uM In vitro inhibitory activity of the compound for the aggregation of human platelets induced by U-46,619 (1 uM) was determined ChEMBL. 10091692
IC50 (functional) = 0.46 uM In vitro thromboxane A2 antagonistic activity on aggregation of rabbit platelets induced by U-46,619 (4 uM) ChEMBL. 10091692
IC50 (functional) = 0.46 uM In vitro thromboxane A2 antagonistic activity on aggregation of rabbit platelets induced by U-46,619 (4 uM) ChEMBL. 10091692
IC50 (functional) = 0.5 uM In vitro inhibitory activity of the compound for the aggregation of guinea pig platelets induced by U-46,619 (4 uM) was determined ChEMBL. 10091692
IC50 (functional) = 0.63 uM Ability to inhibit platelet aggregation of human platelet-rich plasma (PRP) induced by 800 uM of AA-IPA (arachidonic acid) ChEMBL. 2391688
IC50 (binding) > 100 uM In vitro inhibition of thromboxane-A2 synthase in rat whole blood during clotting at 37 degrees centigrade ChEMBL. 7932586
IC50 (binding) > 100 uM In vitro inhibition of thromboxane-A2 synthase in rat whole blood during clotting at 37 degrees centigrade ChEMBL. 7932586
Inhibition (functional) = 25 % Ex vivo inhibitory activity of the compound (0.3 mg/kg p.o.) on the aggregation of guinea pig platelets induced by arachidonic acid (100 uM) ChEMBL. 10091692
Inhibition (functional) < 36 % The compound was tested in vivo for the inhibition of U-46619-induced bronchoconstriction in guinea pig, 1 hr after oral administration of the compound at a dose of 1.25 mg/Kg. ChEMBL. 1535377
Inhibition (functional) = 55 % Extra vivo inhibitory activity of compound (0.3 mg/kg p.o.) on the aggregation of guinea pig platelets induced by U-46619 (1 uM) ChEMBL. 10091692
Inhibition (functional) < 73 % The compound was tested in vivo for the inhibition of U-46619-induced bronchoconstriction in rat, 1 hr after oral administration of the compound at a dose of 5 mg/Kg. ChEMBL. 1535377
Inhibition (functional) < 84 % The compound was tested in vivo for the inhibition of U-46619-induced bronchoconstriction in guinea pig, 1 hr after oral administration of the compound at a dose of 5 mg/Kg. ChEMBL. 1535377
Ki (binding) = 63 nM Compound was tested for its binding affinity at Thromboxane A2/ Prostaglandin H2 receptor by measuring its ability to displace [3H]-U-46,619 from guinea pig platelets ChEMBL. 1388208
Ki (binding) = 63 nM Compound was tested for its binding affinity at Thromboxane A2/ Prostaglandin H2 receptor by measuring its ability to displace [3H]-U-46,619 from guinea pig platelets ChEMBL. 1388208
Potency (functional) 12.8178 uM PUBCHEM_BIOASSAY: S16 Schwann cell PMP22 intronic element firefly luciferase assay. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 13.4591 uM PUBCHEM_BIOASSAY: Primary qHTS for delayed death inhibitors of the malarial parasite plastid, 96 hour incubation. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID488745, AID488752, AID488774, AID504848, AID504850] ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23
Homo sapiens ChEMBL23 10091692

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.
 
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External resources for this compound

Bibliographic References

5 literature references were collected for this gene.

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