TDR Targets

Basic information

Technical information

TDR Targets ID: 178708
Name: N-[4-[(12aS)-6-cyclohexyl-1,4-diketo-2,3,6,7, 12,12a-hexahydropyrazino[1,2-b]$b-carbolin-3- yl]butyl]carbamic acid tert-butyl ester
MW: 508.652 | Formula: C29H40N4O4
H donors: 3 H acceptors: 3 LogP: 4.81 Rotable bonds: 9
Rule of 5 violations (Lipinski): 2
SMILES: O=C(OC(C)(C)C)NCCCCC1NC(=O)[C@H]2N(C1=O)C(C1CCCCC1)c1c(C2)c2c([nH]1)cccc2
InChi: 1S/C29H40N4O4/c1-29(2,3)37-28(36)30-16-10-9-15-22-27(35)33-23(26(34)32-22)17-20-19-13-7-8-14-21(19)31-24(20)25(33)18-11-5-4-6-12-18/h7-8,13-14,18,22-23,25,31H,4-6,9-12,15-17H2,1-3H3,(H,30,36)(H,32,34)/t22?,23-,25?/m0/s1
InChiKey: GRVNDNOOQYQOGD-KJXWVISYSA-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

N-[4-[(12aS)-6-cyclohexyl-1,4-diketo-2,3,6,7,12,12a-hexahydropyrazino[4,5-b]$b-carbolin-3-yl]butyl]carbamic acid tert-butyl ester
NCI60_037329
NSC704578

Targets

Known targets for this compound

No curated genes were found associated with this compound

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

Ranking Plot

Putative Targets List

Species	Potential target	Raw	Global	Species
Trypanosoma cruzi	cysteine peptidase, clan CA, family C1, cathepsin L-like, putative	0.0064	0.7196	0.8859
Loa Loa (eye worm)	hypothetical protein	0.0047	0.4581	0.4799
Trichomonas vaginalis	Clan CA, family C1, cathepsin L or K-like cysteine peptidase	0.0018	0.0242	0.5
Echinococcus granulosus	bromodomain adjacent to zinc finger domain	0.0065	0.7437	1
Trypanosoma cruzi	cysteine peptidase, putative	0.007	0.8123	1
Toxoplasma gondii	cathepsin CPL	0.0018	0.0242	0.5
Loa Loa (eye worm)	hypothetical protein	0.0042	0.3864	0.4006
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Entamoeba histolytica	cysteine protease, putative	0.0018	0.0242	0.5
Leishmania major	cathepsin L-like protease	0.007	0.8123	1
Plasmodium vivax	vivapain-2	0.0018	0.0242	0.5
Schistosoma mansoni	methyl-cpg binding protein mbd	0.0019	0.0294	0.0366
Trichomonas vaginalis	Clan CA, family C1, cathepsin L or K-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Echinococcus multilocularis	methyl CpG binding domain protein 2	0.0019	0.0294	0.0072
Onchocerca volvulus		0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Echinococcus granulosus	fetal alzheimer antigen falz	0.0025	0.1214	0.135
Leishmania major	cathepsin L-like protease	0.0018	0.0242	0.0298
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Leishmania major	cathepsin L-like protease	0.007	0.8123	1
Loa Loa (eye worm)	PHD-finger family protein	0.0022	0.0894	0.0721
Echinococcus multilocularis	fetal alzheimer antigen, falz	0.0025	0.1214	0.135
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Echinococcus multilocularis	histone lysine methyltransferase setb histone lysine methyltransferase eggless	0.0019	0.0294	0.0072
Loa Loa (eye worm)	hypothetical protein	0.0044	0.4261	0.4445
Leishmania major	cathepsin L-like protease	0.0018	0.0242	0.0298
Trypanosoma cruzi	major cysteine proteinase, putative	0.0055	0.5836	0.7185
Onchocerca volvulus	Cathepsin F homolog	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Onchocerca volvulus		0.0018	0.0242	0.5
Leishmania major	cysteine peptidase A (CPA)	0.0018	0.0242	0.0298
Leishmania major	cathepsin L-like protease	0.0018	0.0242	0.0298
Echinococcus multilocularis	bromodomain adjacent to zinc finger domain	0.0039	0.3456	0.4467
Schistosoma mansoni	methyl-cpg binding protein mbd	0.0019	0.0294	0.0366
Echinococcus multilocularis	bromodomain adjacent to zinc finger domain	0.0065	0.7437	1
Leishmania major	cathepsin L-like protease	0.0018	0.0242	0.0298
Schistosoma mansoni	histone-lysine n-methyltransferase setb1	0.0019	0.0294	0.0366
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Echinococcus multilocularis	zinc finger protein	0.0021	0.0717	0.0659
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Onchocerca volvulus		0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Plasmodium vivax	vivapain-2	0.0018	0.0242	0.5
Trypanosoma cruzi	cruzipain precursor, putative	0.007	0.8123	1
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Trypanosoma cruzi	cysteine peptidase, putative	0.0018	0.0242	0.0298
Plasmodium falciparum	cysteine proteinase falcipain 2a	0.0018	0.0242	0.5
Schistosoma mansoni	cathepsin F (C01 family)	0.0018	0.0242	0.0301
Echinococcus granulosus	histone lysine methyltransferase setb	0.0019	0.0294	0.0072
Onchocerca volvulus	Cathepsin L homolog	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Echinococcus granulosus	methyl CpG binding domain protein 2	0.0019	0.0294	0.0072
Onchocerca volvulus	Cathepsin L homolog	0.0018	0.0242	0.5
Brugia malayi	Bromodomain containing protein	0.0042	0.3853	0.37
Trypanosoma cruzi	cysteine peptidase, putative	0.007	0.8123	1
Loa Loa (eye worm)	bromodomain containing protein	0.0019	0.0397	0.0171
Leishmania major	cathepsin L-like protease	0.007	0.8123	1
Schistosoma mansoni	acetyl-CoA C-acetyltransferase	0.0025	0.1214	0.151
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trypanosoma cruzi	cysteine peptidase, putative	0.007	0.8123	1
Echinococcus granulosus	bromodomain adjacent to zinc finger domain	0.0039	0.3456	0.4467
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Onchocerca volvulus		0.0018	0.0242	0.5
Onchocerca volvulus		0.0018	0.0242	0.5
Schistosoma mansoni	cathepsin F (C01 family)	0.0018	0.0242	0.0301
Brugia malayi	PHD-finger family protein	0.0027	0.161	0.1402
Echinococcus granulosus	zinc finger protein	0.0021	0.0717	0.0659
Plasmodium falciparum	cysteine proteinase falcipain 2b	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Schistosoma mansoni	bromodomain containing protein	0.0069	0.8037	1
Onchocerca volvulus		0.0018	0.0242	0.5
Entamoeba histolytica	cysteine proteinase, putative	0.0018	0.0242	0.5
Schistosoma mansoni	histone-lysine n-methyltransferase setb1	0.0019	0.0294	0.0366
Loa Loa (eye worm)	hypothetical protein	0.0019	0.0294	0.0057
Leishmania major	cathepsin L-like protease	0.0018	0.0242	0.0298
Trichomonas vaginalis	Clan CA, family C1, papain-like cysteine peptidase	0.0018	0.0242	0.5
Schistosoma mansoni	hypothetical protein	0.0022	0.0894	0.1112
Loa Loa (eye worm)	hypothetical protein	0.0077	0.9283	1
Plasmodium falciparum	cysteine proteinase falcipain 3	0.0018	0.0242	0.5
Entamoeba histolytica	cysteine proteinase, putative	0.0018	0.0242	0.5
Trichomonas vaginalis	Clan CA, family C1, cathepsin L-like cysteine peptidase	0.0018	0.0242	0.5
Trypanosoma brucei	cysteine peptidase, Clan CA, family C1, Cathepsin L-like	0.007	0.8123	1
Schistosoma mansoni	zinc finger protein	0.0021	0.0717	0.0891
Onchocerca volvulus		0.0018	0.0242	0.5

Activities

Activity type	Activity value	Assay description	Source	Reference
Fluorescence (functional)	= 278 nM	Relative cellular accumulation of mitoxantrone determined with the compound at 2.5 microM and mitoxantrone at 10 microM on T6400 mouse cell line	ChEMBL.	11140726
Fluorescence (functional)	= 278 nM	Relative cellular accumulation of mitoxantrone determined with the compound at 2.5 microM and mitoxantrone at 10 microM on T6400 mouse cell line	ChEMBL.	11140726
Fluorescence (ADMET)	= 629 nM	Ability to inhibit P-gp activity at 2.5 microM and 200 ng/ml PSC833 in a mitoxantrone accumulation assay on T8 human cell line	ChEMBL.	11140726
Fluorescence (ADMET)	= 629 nM	Ability to inhibit P-gp activity at 2.5 microM and 200 ng/ml PSC833 in a mitoxantrone accumulation assay on T8 human cell line	ChEMBL.	11140726
GI50 (functional)	-4.595	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MDA-N Breast cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.585	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HOP-92 Non-Small Cell Lung cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.507	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HL-60(TB) Leukemia cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.474	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SK-MEL-5 Melanoma cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.455	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the UO-31 Renal cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.408	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SN12C Renal cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.341	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the ACHN Renal cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.303	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the NCI-H23 Non-Small Cell Lung cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4.261	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the DU-145 Prostate cell line. (Class of assay: confirmatory)	ChEMBL.	No reference
GI50 (functional)	-4	PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MALME-3M Melanoma cell line. (Class of assay: confirmatory)	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

PubChem: 397173

Bibliographic References

1 literature reference was collected for this gene.

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Detailed information for compound 178708