Detailed information for compound 301731

Basic information

Technical information
  • TDR Targets ID: 301731
  • Name: (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-(methylamin o)but-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)me thylidene]-1H-indol-2-one
  • MW: 355.363 | Formula: C19H18FN3O3
  • H donors: 4 H acceptors: 2 LogP: 0.91 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: CN[C@H](C#Cc1c(F)ccc2c1/C(=C/c1[nH]ccc1OC)/C(=O)N2)CO
  • InChi: 1S/C19H18FN3O3/c1-21-11(10-24)3-4-12-14(20)5-6-15-18(12)13(19(25)23-15)9-16-17(26-2)7-8-22-16/h5-9,11,21-22,24H,10H2,1-2H3,(H,23,25)/b13-9-/t11-/m1/s1
  • InChiKey: ZSPQUICTVOBVJJ-NASPGAHYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-(methylamino)but-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]indolin-2-one
  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-(methylamino)but-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-indolinone
  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-(methylamino)but-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]oxindole
  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-methylaminobut-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-methylamino-but-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]indolin-2-one
  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-methylaminobut-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2-indolinone
  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-methylamino-but-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]oxindole
  • (3Z)-5-fluoro-4-[(3R)-4-hydroxy-3-methylamino-but-1-ynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens cyclin E2 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
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trichomonas vaginalis Esterase, putative 0.0202 0.0152 1
Echinococcus granulosus acetylcholinesterase 0.0069 0.004 0.004
Loa Loa (eye worm) hypothetical protein 0.0069 0.004 0.004
Brugia malayi Carboxylesterase family protein 0.0069 0.004 0.2642
Entamoeba histolytica cyclin, putative 0.0021 0 0.5
Mycobacterium tuberculosis Probable carboxylesterase LipQ 0.0202 0.0152 0.5
Mycobacterium tuberculosis Probable lipase/esterase LipN 0.0202 0.0152 0.5
Trypanosoma cruzi Isoprenylcysteine alpha-carbonyl methylesterase, putative 0.0202 0.0152 1
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0202 0.0152 0.0152
Trichomonas vaginalis Esterase, putative 0.0202 0.0152 1
Mycobacterium tuberculosis Probable esterase LipM 0.0202 0.0152 0.5
Mycobacterium tuberculosis Probable lipase LipH 0.0202 0.0152 0.5
Mycobacterium leprae Possible lipase LipU 0.0202 0.0152 0.5
Loa Loa (eye worm) hypothetical protein 0.0069 0.004 0.004
Mycobacterium ulcerans lipase/esterase LipN 0.0202 0.0152 0.5
Loa Loa (eye worm) aryl-acylamidase 0.0202 0.0152 0.0152
Trypanosoma cruzi Isoprenylcysteine alpha-carbonyl methylesterase, putative 0.0202 0.0152 1
Giardia lamblia Hypothetical protein 0.0021 0 0.5
Mycobacterium tuberculosis Putative acetyl hydrolase MbtJ 0.0202 0.0152 0.5
Mycobacterium ulcerans carboxylesterase LipQ 0.0202 0.0152 0.5
Echinococcus multilocularis hormone sensitive lipase 1.1937 1 1
Entamoeba histolytica cyclin family protein 0.0021 0 0.5
Echinococcus granulosus acetylcholinesterase 0.0069 0.004 0.004
Schistosoma mansoni hormone-sensitive lipase (S09 family) 1.1937 1 1
Echinococcus multilocularis acetylcholinesterase 0.0069 0.004 0.004
Onchocerca volvulus 0.0202 0.0152 1
Trichomonas vaginalis conserved hypothetical protein 0.0202 0.0152 1
Mycobacterium ulcerans membrane-bound esterase LipM 0.0202 0.0152 0.5
Mycobacterium ulcerans acetyl hydrolase MbtJ 0.0202 0.0152 0.5
Leishmania major ecotin, putative 0.0202 0.0152 1
Mycobacterium ulcerans esterase LipW 0.0202 0.0152 0.5
Trypanosoma cruzi Alpha/beta hydrolase domain-containing protein 0.0202 0.0152 1
Plasmodium falciparum cyclin 0.0021 0 0.5
Mycobacterium tuberculosis Possible lipase LipU 0.0202 0.0152 0.5
Schistosoma mansoni hormone-sensitive lipase (S09 family) 1.1937 1 1
Giardia lamblia Cyclin A 0.0021 0 0.5
Schistosoma mansoni family S9 non-peptidase homologue (S09 family) 0.0069 0.004 0.004
Loa Loa (eye worm) acetylcholinesterase 1 0.0069 0.004 0.004
Echinococcus multilocularis acetylcholinesterase 0.0069 0.004 0.004
Trypanosoma cruzi serine peptidase, Clan SC, Family S9D 0.0202 0.0152 1
Trichomonas vaginalis Esterase, putative 0.0202 0.0152 1
Mycobacterium ulcerans hypothetical protein 0.0202 0.0152 0.5
Mycobacterium ulcerans esterase LipO 0.0202 0.0152 0.5
Entamoeba histolytica cyclin family protein 0.0021 0 0.5
Giardia lamblia G2/mitotic-specific cyclin B 0.0021 0 0.5
Mycobacterium tuberculosis Possible esterase LipW 0.0202 0.0152 0.5
Mycobacterium ulcerans esterase LipC 0.0202 0.0152 0.5
Brugia malayi Carboxylesterase family protein 0.0069 0.004 0.2642
Brugia malayi aryl-acylamidase 0.0202 0.0152 1
Leishmania major hypothetical protein, conserved 0.0202 0.0152 1
Echinococcus multilocularis carboxylesterase 5A 0.0069 0.004 0.004
Schistosoma mansoni hormone-sensitive lipase (S09 family) 1.1937 1 1
Mycobacterium ulcerans lipase LipU 0.0202 0.0152 0.5
Mycobacterium ulcerans lipase LipU 0.0202 0.0152 0.5
Mycobacterium ulcerans lipase LipH 0.0202 0.0152 0.5
Mycobacterium tuberculosis Probable esterase/lipase LipF 0.0202 0.0152 0.5
Mycobacterium tuberculosis Probable esterase LipC 0.0202 0.0152 0.5
Loa Loa (eye worm) hypothetical protein 1.1937 1 1
Toxoplasma gondii alpha/beta hydrolase fold domain-containing protein 0.0202 0.0152 0.5
Mycobacterium tuberculosis Probable esterase LipO 0.0202 0.0152 0.5
Echinococcus granulosus carboxylesterase 5A 0.0069 0.004 0.004
Entamoeba histolytica cyclin, putative 0.0021 0 0.5
Toxoplasma gondii alpha/beta hydrolase fold domain-containing protein 0.0202 0.0152 0.5
Trypanosoma brucei Isoprenylcysteine alpha-carbonyl methylesterase, putative 0.0202 0.0152 1
Loa Loa (eye worm) ammd protein 0.0202 0.0152 0.0152
Loa Loa (eye worm) carboxylesterase 0.0069 0.004 0.004
Mycobacterium ulcerans esterase/lipase 0.0202 0.0152 0.5
Mycobacterium ulcerans lipase LipI 0.0202 0.0152 0.5
Treponema pallidum N-acetylphosphinothricin-tripetide-deacetylase 0.0202 0.0152 0.5
Mycobacterium tuberculosis Probable non lipolytic carboxylesterase NlhH 0.0202 0.0152 0.5
Mycobacterium tuberculosis Probable acetyl-hydrolase/esterase LipR 0.0202 0.0152 0.5

Activities

Activity type Activity value Assay description Source Reference
IC50 (binding) = 8 nM In vitro inhibition of recombinant Cyclin Dependent Kinase-2/Cyclin E. ChEMBL. 15012993
IC50 (binding) = 8 nM In vitro inhibition of recombinant Cyclin Dependent Kinase-2/Cyclin E. ChEMBL. 15012993
IC50 (functional) = 100 nM In vitro inhibition of SW480 (human colon cancer) cell proliferation. ChEMBL. 15012993
IC50 (functional) = 100 nM In vitro inhibition of SW480 (human colon cancer) cell proliferation. ChEMBL. 15012993
IC50 (functional) = 349 nM In vitro inhibition of MDA MB 435 (human breast cancer) cell proliferation. ChEMBL. 15012993
IC50 (functional) = 349 nM In vitro inhibition of MDA MB 435 (human breast cancer) cell proliferation. ChEMBL. 15012993

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 15012993

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

1 literature reference was collected for this gene.

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