Detailed information for compound 335627

Basic information

Technical information
  • TDR Targets ID: 335627
  • Name: (2S)-N-[[2-(aminomethyl)-5-chlorophenyl]methy l]-1-(5-hydroxyindeno[1,2-b]pyridine-5-carbon yl)pyrrolidine-2-carboxamide
  • MW: 476.955 | Formula: C26H25ClN4O3
  • H donors: 3 H acceptors: 4 LogP: 1.77 Rotable bonds: 7
    Rule of 5 violations (Lipinski): 1
  • SMILES: NCc1ccc(cc1CNC(=O)[C@@H]1CCCN1C(=O)C1(O)c2ccccc2c2c1cccn2)Cl
  • InChi: 1S/C26H25ClN4O3/c27-18-10-9-16(14-28)17(13-18)15-30-24(32)22-8-4-12-31(22)25(33)26(34)20-6-2-1-5-19(20)23-21(26)7-3-11-29-23/h1-3,5-7,9-11,13,22,34H,4,8,12,14-15,28H2,(H,30,32)/t22-,26?/m0/s1
  • InChiKey: VUAPYCRJLHPJMB-CHQVSRGASA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2S)-N-[[2-(aminomethyl)-5-chloro-phenyl]methyl]-1-(5-hydroxyindeno[1,2-b]pyridine-5-carbonyl)pyrrolidine-2-carboxamide
  • (2S)-N-[[2-(aminomethyl)-5-chlorophenyl]methyl]-1-[(5-hydroxy-5-indeno[1,2-b]pyridinyl)-oxomethyl]-2-pyrrolidinecarboxamide
  • (2S)-N-[[2-(aminomethyl)-5-chloro-phenyl]methyl]-1-(5-hydroxyindeno[1,2-b]pyridin-5-yl)carbonyl-pyrrolidine-2-carboxamide
  • (2S)-N-[2-(aminomethyl)-5-chloro-benzyl]-1-(5-hydroxyindeno[1,2-b]pyridine-5-carbonyl)pyrrolidine-2-carboxamide
  • (2S)-N-[[2-(aminomethyl)-5-chlorophenyl]methyl]-1-(5-hydroxyindeno[3,2-b]pyridine-5-carbonyl)pyrrolidine-2-carboxamide
  • (2S)-N-[[2-(aminomethyl)-5-chloro-phenyl]methyl]-1-(5-hydroxyindeno[3,2-b]pyridine-5-carbonyl)pyrrolidine-2-carboxamide
  • (2S)-N-[[2-(aminomethyl)-5-chlorophenyl]methyl]-1-[(5-hydroxy-5-indeno[3,2-b]pyridinyl)-oxomethyl]-2-pyrrolidinecarboxamide
  • (2S)-N-[2-(aminomethyl)-5-chloro-benzyl]-1-(5-hydroxyindeno[3,2-b]pyridine-5-carbonyl)pyrrolidine-2-carboxamide
  • (2S)-N-[[2-(aminomethyl)-5-chloro-phenyl]methyl]-1-(5-hydroxyindeno[3,2-b]pyridin-5-yl)carbonyl-pyrrolidine-2-carboxamide

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens coagulation factor II (thrombin) 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
Onchocerca volvulus 0.0431 1 1
Echinococcus granulosus snurportin 1 0.0354 0.8056 1
Brugia malayi hypothetical protein 0.0035 0.0047 0.0047
Mycobacterium leprae PROBABLE BIFUNCTIONAL PENICILLIN-BINDING PROTEIN 1A/1B PONA1 (MUREIN POLYMERASE) (PBP1): PENICILLIN-INSENSITIVE TRANSGLYCOSYLASE 0.007 0.0913 0.2923
Toxoplasma gondii orotate phosphoribosyltransferase 0.0042 0.0217 0.0594
Loa Loa (eye worm) hypothetical protein 0.0431 1 1
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0042 0.0217 0.0269
Plasmodium vivax basic transcription factor 3b, putative 0.0034 0.0022 0.0062
Echinococcus granulosus adenine phosphoribosyltransferase 0.0042 0.0217 0.0269
Loa Loa (eye worm) runx1 0.0054 0.0526 0.0526
Treponema pallidum penicillin-binding protein (pbp-2) 0.007 0.0913 1
Toxoplasma gondii NAC domain-containing protein 0.0034 0.0022 0.0062
Loa Loa (eye worm) adenine phosphoribosyltransferase 0.0042 0.0217 0.0217
Mycobacterium tuberculosis Hypoxanthine-guanine phosphoribosyltransferase Hpt (HGPRT) (HGPRTase) (hypoxanthine phosphoribosyltransferase) (imp pyrophosphor 0.0137 0.26 1
Schistosoma mansoni Adenine phosphoribosyltransferase 0.0042 0.0217 0.0269
Toxoplasma gondii hypoxanthine-xanthine-guanine phosphoribosyl transferase HXGPRT 0.0178 0.3649 1
Echinococcus granulosus hypoxanthine guanine phosphoribosyltransferase 0.0178 0.3649 0.453
Brugia malayi latrophilin 2 splice variant baaae 0.0034 0.0013 0.0013
Brugia malayi orotate phosphoribosyltransferase family protein 0.0042 0.0217 0.0217
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0178 0.3649 1
Trichomonas vaginalis conserved hypothetical protein 0.007 0.0913 0.2456
Mycobacterium leprae Probable hypoxanthine-guanine phosphoribosyltransferase Hpt (HGPRT) (HGPRTase) (hypoxanthine phosphoribosyltransferase) (IMP pho 0.0137 0.26 1
Mycobacterium tuberculosis Probable bifunctional membrane-associated penicillin-binding protein 1A/1B PonA2 (murein polymerase) [includes: penicillin-insen 0.007 0.0913 0.2923
Leishmania major orotidine-5-phosphate decarboxylase/orotate phosphoribosyltransferase, putative,OMPDCase-OPRTase, putative 0.0042 0.0217 0.0536
Mycobacterium ulcerans penicillin-binding lipoprotein 0.007 0.0913 0.2029
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0042 0.0217 0.0536
Plasmodium vivax hypoxanthine-guanine phosphoribosyltransferase, putative 0.0178 0.3649 1
Entamoeba histolytica hypothetical protein 0.0035 0.0047 1
Wolbachia endosymbiont of Brugia malayi cell division protein FtsI 0.007 0.0913 1
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0178 0.3649 1
Leishmania major hypoxanthine-guanine phosphoribosyltransferase 0.0178 0.3649 1
Echinococcus multilocularis geminin 0.0167 0.3372 0.4185
Echinococcus granulosus transcription factor btf3 0.0034 0.0022 0.0028
Echinococcus granulosus hypoxanthine guanine phosphoribosyltransferase 0.0178 0.3649 0.453
Treponema pallidum penicillin-binding protein (pbp-1) 0.007 0.0913 1
Plasmodium falciparum basic transcription factor 3b, putative 0.0034 0.0022 0.0062
Trichomonas vaginalis hypoxanthine-guanine phosphoribosyltransferase, putative 0.0178 0.3649 1
Schistosoma mansoni uracil phosphoribosyltransferase 0.0042 0.0217 0.0269
Echinococcus granulosus uridine 5' monophosphate synthase 0.0042 0.0217 0.0269
Schistosoma mansoni hypothetical protein 0.0354 0.8056 1
Brugia malayi RNA, U transporter 1 0.0094 0.1535 0.1535
Trypanosoma brucei hypoxanthine-guanine phosphoribosyltransferase, putative 0.0178 0.3649 1
Mycobacterium leprae PROBABLE BIFUNCTIONAL MEMBRANE-ASSOCIATED PENICILLIN-BINDING PROTEIN 1A/1B PONA2 (MUREIN POLYMERASE) [INCLUDES: PENICILLIN-INSEN 0.007 0.0913 0.2923
Schistosoma mansoni hypothetical protein 0.0034 0.0013 0.0016
Leishmania major xanthine phosphoribosyltransferase 0.0178 0.3649 1
Schistosoma mansoni orotidine 5'-phosphate decarboxylase 0.0042 0.0217 0.0269
Loa Loa (eye worm) hypothetical protein 0.0431 1 1
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0042 0.0217 0.0536
Echinococcus multilocularis Protein lozenge 0.0054 0.0526 0.0653
Echinococcus multilocularis hypoxanthine guanine phosphoribosyltransferase 0.0178 0.3649 0.453
Entamoeba histolytica hypothetical protein 0.0035 0.0047 1
Schistosoma mansoni hypothetical protein 0.0035 0.0047 0.0059
Brugia malayi Calcitonin receptor-like protein seb-1 0.0049 0.0404 0.0404
Echinococcus multilocularis hypoxanthine guanine phosphoribosyltransferase 0.0178 0.3649 0.453
Entamoeba histolytica hypothetical protein 0.0035 0.0047 1
Mycobacterium ulcerans hypoxanthine-guanine phosphoribosyltransferase Hpt 0.0178 0.3649 1
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0178 0.3649 1
Echinococcus multilocularis uridine 5' monophosphate synthase 0.0042 0.0217 0.0269
Plasmodium falciparum orotate phosphoribosyltransferase 0.0042 0.0217 0.0594
Loa Loa (eye worm) nucleolar RNA-associated protein alpha 0.0354 0.8056 0.8056
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0178 0.3649 0.453
Mycobacterium tuberculosis Probable penicillin-binding protein PbpA 0.007 0.0913 0.2923
Echinococcus multilocularis adenine phosphoribosyltransferase 0.0042 0.0217 0.0269
Trypanosoma brucei transcription factor BTF3, putative 0.0034 0.0022 0.0062
Trypanosoma brucei orotidine-5-phosphate decarboxylase/orotate phosphoribosyltransferase, putative 0.0042 0.0217 0.0594
Trypanosoma brucei hypoxanthine-guanine phosphoribosyltransferase 0.0178 0.3649 1
Schistosoma mansoni hypothetical protein 0.0167 0.3372 0.4185
Loa Loa (eye worm) orotate phosphoribosyltransferase 0.0042 0.0217 0.0217
Brugia malayi beta-NAC-like protein 0.0034 0.0022 0.0022
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0042 0.0217 0.0536
Brugia malayi hypothetical protein 0.0149 0.2917 0.2917
Trypanosoma brucei Adenine phosphoribosyltransferase, putative 0.0042 0.0217 0.0594
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.0049 0.0404 0.0404
Mycobacterium tuberculosis Possible penicillin-binding lipoprotein 0.007 0.0913 0.2923
Chlamydia trachomatis transglycolase/transpeptidase 0.007 0.0913 0.5
Trypanosoma cruzi orotidine-5-phosphate decarboxylase/orotate phosphoribosyltransferase, putative 0.0042 0.0217 0.0536
Trypanosoma cruzi Adenine phosphoribosyltransferase, putative 0.0042 0.0217 0.0536
Onchocerca volvulus 0.0178 0.3649 0.3509
Loa Loa (eye worm) ICD-1 protein 0.0034 0.0022 0.0022
Trichomonas vaginalis ribose-phosphate pyrophosphokinase, putative 0.0042 0.0217 0.0536
Onchocerca volvulus 0.0149 0.2917 0.276
Echinococcus granulosus geminin 0.0167 0.3372 0.4185
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0035 0.0047 0.0059
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0178 0.3649 0.453
Mycobacterium ulcerans bifunctional membrane-associated penicillin-binding protein 1A/1B PonA2 0.007 0.0913 0.2029
Trypanosoma cruzi orotidine-5-phosphate decarboxylase/orotate phosphoribosyltransferase, putative 0.0042 0.0217 0.0536
Brugia malayi Adenine phosphoribosyltransferase 0.0042 0.0217 0.0217
Mycobacterium ulcerans bifunctional penicillin-binding protein 1A/1B PonA1 0.007 0.0913 0.2029
Trypanosoma cruzi hypoxanthine-guanine phosphoribosyltransferase, putative 0.0178 0.3649 1
Loa Loa (eye worm) hypothetical protein 0.0049 0.0404 0.0404
Leishmania major adenine phosphoribosyltransferase 0.0042 0.0217 0.0536
Entamoeba histolytica hypothetical protein 0.0035 0.0047 1
Plasmodium falciparum hypoxanthine-guanine phosphoribosyltransferase 0.0178 0.3649 1
Echinococcus multilocularis transcription factor btf3 0.0034 0.0022 0.0028
Schistosoma mansoni Adenine phosphoribosyltransferase 0.0042 0.0217 0.0269
Echinococcus multilocularis snurportin 1 0.0354 0.8056 1
Mycobacterium ulcerans penicillin-binding membrane protein PbpB 0.007 0.0913 0.2029
Treponema pallidum penicillin-binding protein (pbp-3) 0.007 0.0913 1
Trichomonas vaginalis Ribose-phosphate pyrophosphokinase, putative 0.0042 0.0217 0.0536
Loa Loa (eye worm) pigment dispersing factor receptor c 0.0049 0.0404 0.0404
Loa Loa (eye worm) hypothetical protein 0.0034 0.0013 0.0013
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0035 0.0047 0.0059
Chlamydia trachomatis transglycolase/transpeptidase 0.007 0.0913 0.5
Mycobacterium leprae POSSIBLE PENICILLIN-BINDING LIPOPROTEIN 0.007 0.0913 0.2923
Mycobacterium leprae Probable penicillin-binding protein PbpA 0.007 0.0913 0.2923
Plasmodium vivax orotate phosphoribosyltransferase, putative 0.0042 0.0217 0.0594
Giardia lamblia Guanine phosphoribosyltransferase 0.0178 0.3649 1
Trypanosoma brucei hypoxanthine-guanine phosphoribosyltransferase 0.0178 0.3649 1
Schistosoma mansoni transcription factor LCR-F1 0.0035 0.0047 0.0059
Trypanosoma brucei Adenine phosphoribosyltransferase, putative 0.0042 0.0217 0.0594
Schistosoma mansoni lozenge 0.0054 0.0526 0.0653
Loa Loa (eye worm) hypothetical protein 0.0149 0.2917 0.2917
Mycobacterium ulcerans penicillin-binding protein PbpA 0.007 0.0913 0.2029
Schistosoma mansoni transcription factor btf3 0.0034 0.0022 0.0028
Brugia malayi Phosphoribosyl transferase domain containing protein 0.0178 0.3649 0.3649
Schistosoma mansoni hypoxanthine-guanine phosphoribosyltransferase 0.0042 0.0217 0.0269
Schistosoma mansoni hypothetical protein 0.0167 0.3372 0.4185

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) = 0 Inhibition of FeCl3-induced vessel occlusion in rat arterial thrombosis model; 0 out of 6 occlusions ChEMBL. 15801822
Activity (functional) = 0 Inhibition of FeCl3-induced vessel occlusion in rat arterial thrombosis model; 0 out of 5 occlusions ChEMBL. 15801822
Activity (functional) = 12 % Percent of free compound observed in human plasma (unbound to plasma protein) ChEMBL. 15801822
Activity (functional) = 12 % Percent of free compound observed in human plasma (unbound to plasma protein) ChEMBL. 15801822
Activity (functional) = 13 % Percent of free compound observed in rat plasma (unbound to plasma protein) ChEMBL. 15801822
Activity (functional) = 36 % Percent of free compound observed in rat plasma (unbound to plasma protein) ChEMBL. 15801822
AUC (ADMET) = 14 uM.h Area under concentration time curve in plasma was determined upon per oral dose at 1.0 mg/kg in male beagle dogs (n=2) ChEMBL. 15801822
CL (ADMET) 1.9 ml min-1 kg-1 Total clearance in plasma upon i.v. (1 mg/kg) and p.o. (2 mg/kg) dose in male rhesus macaques (n=2) ChEMBL. 15801822
CL (ADMET) 2.5 ml min-1 kg-1 Total clearance in dog upon i.v. and p.o. dose at 1 mg/kg in male beagle dogs (n=2) ChEMBL. 15801822
CL (ADMET) 53 ml min-1 kg-1 Total clearance in plasma upon i.v. (2 mg/kg) and p.o. (10 mg/kg) dose in male rats (n=3) ChEMBL. 15801822
Concentration (functional) 0.17 uM Inhibition of human plasma coagulation triggered by intrinsic pathway by doubling the activated partial thromboplastin time (2x APTT) ChEMBL. 15801822
Concentration (functional) 0.17 uM Inhibition of human plasma coagulation triggered by intrinsic pathway by doubling the activated partial thromboplastin time (2x APTT) ChEMBL. 15801822
Concentration (functional) 0.23 uM Inhibition of human plasma coagulation triggered by intrinsic pathway by doubling the activated partial thromboplastin time (2x APTT) ChEMBL. 15801822
Concentration (functional) 0.23 uM Inhibition of human plasma coagulation triggered by intrinsic pathway by doubling the activated partial thromboplastin time (2x APTT) ChEMBL. 15801822
F (ADMET) = 15 % Bioavailability in rat (male) (dose 2 mg/kg i.v. and 10 mg/kg p.o.) ChEMBL. 15801822
F (ADMET) = 35 % Bioavailability in Rhesus macaques (male) (dose 1 mg/kg i.v. and 2 mg/kg p.o.) ChEMBL. 15801822
F (ADMET) = 88 % Bioavailability in dog (male beagle) (dose 1 mg/kg i.v. and p.o.) ChEMBL. 15801822
Ki (binding) = 0.78 nM Inhibition of coagulation factor II (thrombin) of human ChEMBL. 15801822
Ki (binding) = 0.78 nM Inhibition of coagulation factor II (thrombin) of human ChEMBL. 15801822
Ki (binding) = 1.4 nM Inhibition of coagulation factor II (thrombin) of human ChEMBL. 15801822
Ki (binding) = 1.4 nM Inhibition of coagulation factor II (thrombin) of human ChEMBL. 15801822
T1/2 (ADMET) = 1.8 hr Plasma half-life of compound upon i.v. (2 mg/kg) and p.o. (10 mg/kg) dose in male rats (n=3) ChEMBL. 15801822
T1/2 (ADMET) = 3.6 hr Plasma half-life of compound upon per oral dose at 1.0 mg/kg in male beagle dogs (n=2) ChEMBL. 15801822
T1/2 (ADMET) = 5.5 hr Plasma half-life of compound upon i.v. and p.o. dose at 1 mg/kg in male beagle dogs (n=2) ChEMBL. 15801822
T1/2 (ADMET) = 6.1 hr Plasma half-life of compound upon per oral dose at 1.0 mg/kg in male beagle dogs (n=2) ChEMBL. 15801822
T1/2 (ADMET) = 7.7 hr Plasma half-life of compound upon i.v. (1 mg/kg) and p.o. (2 mg/kg) dose in male rhesus macaques (n=2) ChEMBL. 15801822
Vd (ADMET) = 1.2 l kg-1 Volume of distribution upon i.v. and p.o. dose at 1 mg/kg in male beagle dogs (n=2) ChEMBL. 15801822
Vd (ADMET) = 1.2 l kg-1 Volume of distribution upon i.v. (1 mg/kg) and p.o. (2 mg/kg) dose in male rhesus macaques (n=2) ChEMBL. 15801822
Vd (ADMET) = 4.5 l kg-1 Volume of distribution upon i.v. (2 mg/kg) and p.o. (10 mg/kg) dose in male rats (n=3) ChEMBL. 15801822

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.
 
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External resources for this compound

Bibliographic References

1 literature reference was collected for this gene.

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