TDR Targets

Basic information

Technical information

Name: Unnamed compound
MW: 333.424 | Formula: C17H20FN3OS
H donors: 1 H acceptors: 1 LogP: 3.39 Rotable bonds: 8
Rule of 5 violations (Lipinski): 1
SMILES: N#Cc1c(NCCSCc2ccc(o2)CN(C)C)cccc1F
InChi: 1S/C17H20FN3OS/c1-21(2)11-13-6-7-14(22-13)12-23-9-8-20-17-5-3-4-16(18)15(17)10-19/h3-7,20H,8-9,11-12H2,1-2H3
InChiKey: ADLLVJJAMGWNEL-UHFFFAOYSA-N

Network

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Target Layer

Model Organisms

Species	Viewmode
Arabidopsis thaliana
Caenorhabditis elegans
Dictyostelium discoideum
Drosophila melanogaster
Escherichia coli
Homo sapiens
Mus musculus
Oryza sativa
Saccharomyces cerevisiae
Schmidtea mediterranea
Other organisms

TDR Pathogens:

Species	Viewmode
Brugia malayi
Chlamydia trachomatis
Echinococcus granulosus
Entamoeba histolytica
Echinococcus multilocularis
Giardia lamblia
Leishmania major
Loa Loa (eye worm)
Mycobacterium leprae
Mycobacterium tuberculosis
Mycobacterium ulcerans
Onchocerca volvulus
Plasmodium falciparum
Plasmodium vivax
Schistosoma mansoni
Trypanosoma brucei
Trypanosoma cruzi
Toxoplasma gondii
Treponema pallidum
Trichomonas vaginalis
Wolbachia endosymbiont of Brugia malayi

Other Pathogens:

Species	Viewmode
Babesia bovis
Candida albicans
Cryptosporidium hominis
Cryptosporidium parvum
Leishmania braziliensis
Leishmania donovani
Leishmania infantum
Leishmania mexicana
Neospora caninum
Plasmodium berghei
Plasmodium knowlesi
Plasmodium yoelii
Schistosoma japonicum
Trypanosoma brucei gambiense
Trypanosoma congolense
Theileria parva

Compound Layer

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Clustering layers

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Synonyms

No synonyms found for this compound

Targets

Known targets for this compound

Species	Target name	Source	Bibliographic reference
Homo sapiens	acetylcholinesterase (Yt blood group)	Starlite/ChEMBL	References

Predicted pathogen targets for this compound

By orthology

Species	Potential target	Known druggable target/s	Ortholog Group
Schistosoma japonicum	Acetylcholinesterase 1 precursor, putative	Get druggable targets OG5_126875	All targets in OG5_126875
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	Get druggable targets OG5_126875	All targets in OG5_126875
Brugia malayi	Carboxylesterase family protein	Get druggable targets OG5_126875	All targets in OG5_126875
Loa Loa (eye worm)	acetylcholinesterase 1	Get druggable targets OG5_126875	All targets in OG5_126875
Loa Loa (eye worm)	hypothetical protein	Get druggable targets OG5_126875	All targets in OG5_126875
Schistosoma japonicum	ko:K01049 acetylcholinesterase [EC3.1.1.7], putative	Get druggable targets OG5_126875	All targets in OG5_126875
Echinococcus multilocularis	acetylcholinesterase	Get druggable targets OG5_126875	All targets in OG5_126875
Echinococcus granulosus	carboxylesterase 5A	Get druggable targets OG5_126875	All targets in OG5_126875
Echinococcus granulosus	acetylcholinesterase	Get druggable targets OG5_126875	All targets in OG5_126875
Brugia malayi	Carboxylesterase family protein	Get druggable targets OG5_126875	All targets in OG5_126875
Loa Loa (eye worm)	hypothetical protein	Get druggable targets OG5_126875	All targets in OG5_126875
Echinococcus multilocularis	acetylcholinesterase	Get druggable targets OG5_126875	All targets in OG5_126875
Echinococcus multilocularis	carboxylesterase 5A	Get druggable targets OG5_126875	All targets in OG5_126875
Loa Loa (eye worm)	carboxylesterase	Get druggable targets OG5_126875	All targets in OG5_126875
Echinococcus granulosus	acetylcholinesterase	Get druggable targets OG5_126875	All targets in OG5_126875

By sequence similarity to non orthologous known druggable targets

Species	Potential target	Known druggable target	Length	Alignment span	Identity
Brugia malayi	Carboxylesterase family protein	acetylcholinesterase (Yt blood group)	614 aa	510 aa	26.5 %

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Schistosoma mansoni	phosphatidylinositol-45-bisphosphate 3-kinase catalytic subunit alpha PI3K	0.0282	0.0505	0.0468
Trichomonas vaginalis	phosphatidylinositol 3-kinase class, putative	0.0282	0.0505	0.0494
Trichomonas vaginalis	PIKK family atypical protein kinase	0.4374	1	1
Echinococcus granulosus	phosphatidylinositol 4 kinase beta	0.0282	0.0505	0.0483
Loa Loa (eye worm)	hypothetical protein	0.0082	0.004	0.004
Loa Loa (eye worm)	hypothetical protein	0.0282	0.0505	0.0505
Trypanosoma brucei	FAT domain/Rapamycin binding domain/Phosphatidylinositol 3- and 4-kinase, putative	0.1817	0.4066	0.375
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0282	0.0505	0.0483
Echinococcus granulosus	PIK kinase FAT and Armadillo domain containing protein	0.064	0.1334	0.1314
Leishmania major	phosphatidylinositol 3-kinase, putative	0.1467	0.3254	0.2895
Echinococcus multilocularis	serine protein kinase ATM	0.0827	0.177	0.1751
Echinococcus multilocularis	acetylcholinesterase	0.0082	0.004	0.0017
Trypanosoma cruzi	phosphatidylinositol kinase related protein, putative	0.0545	0.1115	0.0642
Entamoeba histolytica	phosphatidylinositol3-kinaseTor2, putative	0.4374	1	1
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.1467	0.3254	0.3238
Schistosoma mansoni	phosphatidylinositol 3-kinase class	0.0282	0.0505	0.0468
Echinococcus granulosus	phosphatidylinositol 3 kinase catalytic subunit	0.0282	0.0505	0.0483
Schistosoma mansoni	phosphatidylinositol-45-bisphosphate 3-kinase catalytic subunit alpha PI3K	0.0282	0.0505	0.0468
Entamoeba histolytica	protein kinase rad3, putative	0.0827	0.177	0.1332
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3253	0.7399	0.7396
Trichomonas vaginalis	phosphatidylinositol kinase, putative	0.0282	0.0505	0.0494
Plasmodium vivax	phosphatidylinositol 3-kinase, putative	0.0282	0.0505	0.5
Trichomonas vaginalis	PIKK family atypical protein kinase	0.0827	0.177	0.176
Trichomonas vaginalis	phosphatidylinositol kinase, putative	0.0282	0.0505	0.0494
Echinococcus multilocularis	Phosphatidylinositol 4 kinase type 2 beta	0.0282	0.0505	0.0483
Echinococcus multilocularis	DNA dependent protein kinase catalytic subunit	0.0282	0.0505	0.0483
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2358	0.5322	0.5317
Echinococcus multilocularis	acetylcholinesterase	0.0082	0.004	0.0017
Entamoeba histolytica	FKBP-rapamycin associated protein (FRAP), putative	0.4374	1	1
Trichomonas vaginalis	phosphatidylinositol 3-kinase class, putative	0.0282	0.0505	0.0494
Echinococcus multilocularis		0.0282	0.0505	0.0483
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3479	0.7923	0.7921
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2362	0.5331	0.5325
Leishmania major	phosphatidylinositol 3-related kinase, putative	0.1467	0.3254	0.2895
Entamoeba histolytica	Phosphatidylinositol 3- and 4-kinase family	0.0827	0.177	0.1332
Loa Loa (eye worm)	phosphatidylinositol 3	0.1467	0.3254	0.3254
Schistosoma mansoni	fkbp-rapamycin associated protein	0.0827	0.177	0.1738
Echinococcus granulosus	acetylcholinesterase	0.0082	0.004	0.0017
Echinococcus multilocularis	phosphatidylinositol 4 phosphate 3 kinase C2	0.0282	0.0505	0.0483
Echinococcus multilocularis	Zinc finger, PHD finger	0.0282	0.0505	0.0483
Trichomonas vaginalis	phosphatidylinositol 3-kinase class, putative	0.0282	0.0505	0.0494
Leishmania major	target of rapamycin (TOR) kinase 1, putative	0.4374	1	1
Loa Loa (eye worm)	phosphatidylinositol 3	0.4374	1	1
Leishmania major	target of rapamycin (TOR) kinase 2, putative	0.4374	1	1
Loa Loa (eye worm)	hypothetical protein	0.0922	0.1989	0.1989
Echinococcus multilocularis	PIK kinase, FAT and Armadillo domain containing protein	0.064	0.1334	0.1314
Brugia malayi	Carboxylesterase family protein	0.0082	0.004	0.0017
Loa Loa (eye worm)	phosphatidylinositol 4-kinase type 3 alpha isoform 1	0.0282	0.0505	0.0505
Trypanosoma cruzi	phosphatidylinositol 3-kinase, putative	0.0827	0.177	0.1332
Brugia malayi	FAT domain containing protein	0.064	0.1334	0.1314
Trypanosoma brucei	target of rapamycin kinase 3, putative	0.3483	0.7932	0.7822
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2934	0.6658	0.6655
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3253	0.7399	0.7396
Entamoeba histolytica	hypothetical protein	0.0827	0.177	0.1332
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3253	0.7399	0.7396
Echinococcus granulosus	phosphatidylinositol 45 bisphosphate 3 kinase	0.0282	0.0505	0.0483
Brugia malayi	phosphatidylinositol 4-kinase, catalytic, alpha polypeptide	0.0282	0.0505	0.0483
Schistosoma mansoni	phosphatidylinositol-45-bisphosphate 3-kinase catalytic subunit alpha PI3K	0.0282	0.0505	0.0468
Trypanosoma brucei	phosphatidylinositol 4-kinase, putative	0.4374	1	1
Loa Loa (eye worm)	acetylcholinesterase 1	0.0082	0.004	0.004
Schistosoma mansoni	phosphatidylinositol 4-kinase	0.0282	0.0505	0.0468
Trichomonas vaginalis	PIKK family atypical protein kinase	0.1467	0.3254	0.3246
Echinococcus granulosus	phosphatidylinositol 4 kinase alpha	0.0282	0.0505	0.0483
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3253	0.7399	0.7396
Trichomonas vaginalis	PIKK family atypical protein kinase	0.0827	0.177	0.176
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3253	0.7399	0.7396
Trichomonas vaginalis	phosphatidylinositol 3-kinase catalytic subunit gamma, putative	0.0282	0.0505	0.0494
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2614	0.5915	0.591
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2358	0.5322	0.5317
Toxoplasma gondii	target of rapamycin (TOR), putative	0.3253	0.7399	1
Trypanosoma cruzi	target of rapamycin kinase 3	0.3483	0.7932	0.7822
Trypanosoma brucei	Phosphatidylinositol 3-kinase tor1	0.4374	1	1
Toxoplasma gondii	non-specific serine/threonine protein kinase	0.0922	0.1989	0.2153
Trypanosoma brucei	phosphatidylinositol kinase related protein, putative	0.0827	0.177	0.1332
Echinococcus multilocularis	phosphatidylinositol 4 kinase alpha	0.0282	0.0505	0.0483
Loa Loa (eye worm)	hypothetical protein	0.0545	0.1115	0.1115
Loa Loa (eye worm)	carboxylesterase	0.0082	0.004	0.004
Loa Loa (eye worm)	phosphatidylinositol 3	0.0282	0.0505	0.0505
Trypanosoma cruzi	phosphatidylinositol 3-related kinase, putative	0.1467	0.3254	0.2895
Trichomonas vaginalis	PIKK family atypical protein kinase	0.1467	0.3254	0.3246
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2614	0.5915	0.591
Trypanosoma cruzi	phosphatidylinositol 3-related kinase, putative	0.1467	0.3254	0.2895
Echinococcus multilocularis	serine:threonine protein kinase SMG1	0.0827	0.177	0.1751
Plasmodium falciparum	phosphatidylinositol 3-kinase	0.0282	0.0505	0.5
Plasmodium vivax	hypothetical protein	0.0282	0.0505	0.5
Trichomonas vaginalis	PIKK family atypical protein kinase	0.4374	1	1
Echinococcus multilocularis	Phosphatidylinositol 4 kinase type 2 beta	0.0282	0.0505	0.0483
Schistosoma mansoni	phosphatidylinositol 4-kinase type-II	0.0282	0.0505	0.0468
Trichomonas vaginalis	phopsphatidylinositol 3-kinase, drosophila, putative	0.0282	0.0505	0.0494
Echinococcus multilocularis	FKBP12 rapamycin complex associated protein	0.4374	1	1
Trichomonas vaginalis	conserved hypothetical protein	0.0922	0.1989	0.198
Trichomonas vaginalis	PIKK family atypical protein kinase	0.1467	0.3254	0.3246
Echinococcus multilocularis	phosphatidylinositol 4,5 bisphosphate 3 kinase	0.0282	0.0505	0.0483
Echinococcus granulosus	carboxylesterase 5A	0.0082	0.004	0.0017
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0282	0.0505	0.0483
Trichomonas vaginalis	conserved hypothetical protein	0.064	0.1334	0.1324
Trichomonas vaginalis	PIKK family atypical protein kinase	0.1467	0.3254	0.3246
Schistosoma mansoni	phosphatidylinositol 3-and 4-kinase	0.1467	0.3254	0.3228
Trichomonas vaginalis	PIKK family atypical protein kinase	0.4374	1	1
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3479	0.7923	0.7921
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0827	0.177	0.1751
Trichomonas vaginalis	phosphatidylinositol kinase, putative	0.0282	0.0505	0.0494
Trichomonas vaginalis	PIKK family atypical protein kinase	0.1467	0.3254	0.3246
Schistosoma mansoni	ataxia telangiectasia mutated (atm)	0.0827	0.177	0.1738
Echinococcus granulosus	serine protein kinase ATM	0.0827	0.177	0.1751
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2362	0.5331	0.5325
Mycobacterium tuberculosis	Conserved hypothetical protein	0.0282	0.0505	0.5
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0282	0.0505	0.0483
Echinococcus granulosus	FKBP12 rapamycin complex associated protein	0.4374	1	1
Trichomonas vaginalis	PIKK family atypical protein kinase	0.0282	0.0505	0.0494
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3253	0.7399	0.7396
Echinococcus multilocularis	carboxylesterase 5A	0.0082	0.004	0.0017
Toxoplasma gondii	FATC domain-containing protein	0.0827	0.177	0.1835
Echinococcus granulosus	acetylcholinesterase	0.0082	0.004	0.0017
Loa Loa (eye worm)	hypothetical protein	0.0282	0.0505	0.0505
Trichomonas vaginalis	PIKK family atypical protein kinase	0.0282	0.0505	0.0494
Loa Loa (eye worm)	hypothetical protein	0.0827	0.177	0.177
Loa Loa (eye worm)	voltage and ligand gated potassium channel	0.0074	0.0023	0.0023
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3479	0.7923	0.7921
Loa Loa (eye worm)	hypothetical protein	0.064	0.1334	0.1334
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2614	0.5915	0.591
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0282	0.0505	0.0483
Echinococcus granulosus	DNA dependent protein kinase catalytic subunit	0.0282	0.0505	0.0483
Trichomonas vaginalis	PIKK family atypical protein kinase	0.0545	0.1115	0.1105
Leishmania major	target of rapamycin kinase (TOR) kinase 3	0.3483	0.7932	0.7822
Loa Loa (eye worm)	phosphatidylinositol 3	0.0282	0.0505	0.0505
Schistosoma mansoni	hypothetical protein	0.0282	0.0505	0.0468
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2588	0.5855	0.585
Loa Loa (eye worm)	hypothetical protein	0.0082	0.004	0.004
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2358	0.5322	0.5317
Onchocerca volvulus		0.0282	0.0505	0.5
Loa Loa (eye worm)	phosphatidylinositol 3	0.0282	0.0505	0.0505
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0282	0.0505	0.0483
Trypanosoma brucei	phosphatidylinositol 3-kinase tor, putative	0.2069	0.465	0.4366
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3479	0.7923	0.7921
Echinococcus granulosus	Phosphatidylinositol 4 kinase type 2 beta	0.0282	0.0505	0.0483
Loa Loa (eye worm)	phosphatidylinositol 3	0.0282	0.0505	0.0505
Trichomonas vaginalis	phosphatidylinositol 4-kinase, putative	0.0282	0.0505	0.0494
Brugia malayi	Carboxylesterase family protein	0.0082	0.004	0.0017
Plasmodium vivax	hypothetical protein, conserved	0.0282	0.0505	0.5
Trypanosoma cruzi	Phosphatidylinositol 3-kinase tor2	0.4374	1	1
Plasmodium vivax	phosphatidylinositol 4-kinase, putative	0.0282	0.0505	0.5
Echinococcus multilocularis	phosphatidylinositol 3 and 4 kinase	0.1467	0.3254	0.3238
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3734	0.8516	0.8514
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0282	0.0505	0.0483
Echinococcus granulosus	Phosphatidylinositol 4 kinase type 2 beta	0.0282	0.0505	0.0483
Trypanosoma brucei	phosphatidylinositol 3-kinase, putative	0.1467	0.3254	0.2895
Echinococcus granulosus	serine:threonine protein kinase SMG1	0.0827	0.177	0.1751
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2362	0.5331	0.5325
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3479	0.7923	0.7921
Schistosoma mansoni	hypothetical protein	0.064	0.1334	0.1301
Trichomonas vaginalis	phosphatidylinositol kinase, putative	0.0282	0.0505	0.0494
Plasmodium vivax	phosphatidylinositol 3- and 4-kinase, putative	0.0282	0.0505	0.5
Schistosoma mansoni	family S9 non-peptidase homologue (S09 family)	0.0082	0.004	0.0001
Brugia malayi	Phosphatidylinositol 3- and 4-kinase family protein	0.0827	0.177	0.1751
Trypanosoma cruzi	phosphatidylinositol kinase related protein, putative	0.0827	0.177	0.1332
Trichomonas vaginalis	phosphatidylinositol 3-kinase catalytic subunit alpha, beta, delta, putative	0.0282	0.0505	0.0494
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2362	0.5331	0.5325
Trichomonas vaginalis	PIKK family atypical protein kinase	0.3253	0.7399	0.7396
Onchocerca volvulus		0.0282	0.0505	0.5
Trichomonas vaginalis	phopsphatidylinositol 3-kinase, drosophila, putative	0.0282	0.0505	0.0494
Plasmodium vivax	phosphatidylinositol 4-kinase, putative	0.0282	0.0505	0.5
Schistosoma mansoni	ataxia telangiectasia mutated (atm)-related	0.4374	1	1
Plasmodium falciparum	phosphatidylinositol 3- and 4-kinase, putative	0.0282	0.0505	0.5
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2839	0.6439	0.6435
Loa Loa (eye worm)	hypothetical protein	0.0891	0.1918	0.1918
Mycobacterium leprae	conserved hypothetical protein	0.0282	0.0505	0.5
Echinococcus granulosus	phosphatidylinositol 4 phosphate 3 kinase C2	0.0282	0.0505	0.0483
Trichomonas vaginalis	phosphatidylinositol 3-kinase catalytic subunit alpha, beta, delta, putative	0.0282	0.0505	0.0494
Trichomonas vaginalis	conserved hypothetical protein	0.0545	0.1115	0.1105
Trypanosoma brucei	phosphatidylinositol 3-related kinase, putative	0.1467	0.3254	0.2895
Loa Loa (eye worm)	phosphatidylinositol kinase	0.0282	0.0505	0.0505
Plasmodium falciparum	phosphatidylinositol 4-kinase	0.0282	0.0505	0.5
Trichomonas vaginalis	PIKK family atypical protein kinase	0.1174	0.2573	0.2565
Trichomonas vaginalis	PIKK family atypical protein kinase	0.2588	0.5855	0.585
Trypanosoma cruzi	Phosphatidylinositol 3-kinase tor1	0.4374	1	1
Schistosoma mansoni	phosphatidylinositol 4-kinase	0.0282	0.0505	0.0468
Echinococcus granulosus	phosphatidylinositol 3 and 4 kinase	0.1467	0.3254	0.3238
Loa Loa (eye worm)	phosphatidylinositol 3	0.0282	0.0505	0.0505
Trichomonas vaginalis	PIKK family atypical protein kinase	0.0827	0.177	0.176
Giardia lamblia	GTOR	0.4374	1	1

Activities

Activity type	Activity value	Assay description	Source	Reference
IC50 (binding)	= 2.1 uM	In vitro acetyl cholinesterase(AChE-I) inhibitory activity of the compound to determine its ability to reverse the cholinergic deficit characteristic of AD	ChEMBL.	1507203
IC50 (binding)	= 2.1 uM	In vitro acetyl cholinesterase(AChE-I) inhibitory activity of the compound to determine its ability to reverse the cholinergic deficit characteristic of AD	ChEMBL.	1507203

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

No external resources registered for this compound

Bibliographic References

1 literature reference was collected for this gene.

If you have references for this compound, please enter them in a user comment (below) or Contact us.

Detailed information for compound 176388