Detailed information for compound 302102
Basic information
Technical information
- TDR Targets ID: 302102
- Name: 7-butan-2-yl-8-ethylpyrrolo[3,2-f]quinazoline -1,3-diamine
- MW: 283.371 | Formula: C16H21N5
-
H donors: 2
H acceptors: 2
LogP: 2.99
Rotable bonds: 3
Rule of 5 violations (Lipinski): 1 - SMILES: CCC(n1c(CC)cc2c1ccc1c2c(N)nc(n1)N)C
- InChi: 1S/C16H21N5/c1-4-9(3)21-10(5-2)8-11-13(21)7-6-12-14(11)15(17)20-16(18)19-12/h6-9H,4-5H2,1-3H3,(H4,17,18,19,20)
- InChiKey: YXDFKDLEMSYJPR-UHFFFAOYSA-N
Network
Hover on a compound node to display the structore
Synonyms
- 8-ethyl-7-sec-butyl-pyrrolo[3,2-f]quinazoline-1,3-diamine
- 8-ethyl-7-sec-butylpyrrolo[3,2-f]quinazoline-1,3-diamine
- 7-butan-2-yl-8-ethyl-pyrrolo[3,2-f]quinazoline-1,3-diamine
- (1-amino-8-ethyl-7-sec-butyl-pyrrolo[3,2-f]quinazolin-3-yl)amine
- (3-amino-8-ethyl-7-sec-butyl-pyrrolo[3,2-f]quinazolin-1-yl)amine
- 2-Ethyl-3-(methylpropyl)pyrrolo[3,2-f]quinazoline-7,9-diamine
- AIDS-057266
- AIDS057266
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Homo sapiens | solute carrier family 2 (facilitated glucose transporter), member 1 | Starlite/ChEMBL | No references |
| Homo sapiens | dihydrofolate reductase | Starlite/ChEMBL | References |
| Leishmania mexicana | glucose transporter, lmgt2 | Starlite/ChEMBL | No references |
| Candida albicans | dihydrofolate reductase | Starlite/ChEMBL | References |
| Plasmodium falciparum | hexose transporter | Starlite/ChEMBL | No references |
Predicted pathogen targets for this compound
By orthology
By sequence similarity to non orthologous known druggable targets
| Species | Potential target | Known druggable target | Length | Alignment span | Identity |
|---|---|---|---|---|---|
| Trypanosoma brucei | glucose transporter, putative | solute carrier family 2 (facilitated glucose transporter), member 1 | 492 aa | 395 aa | 23.5 % |
| Trypanosoma brucei | glucose transporter, putative | hexose transporter | 504 aa | 426 aa | 22.3 % |
| Plasmodium falciparum | bifunctional dihydrofolate reductase-thymidylate synthase | dihydrofolate reductase | 187 aa | 202 aa | 29.7 % |
Obtained from network model
Ranking Plot
Putative Targets List
| Species | Potential target | Raw | Global | Species |
|---|---|---|---|---|
| Plasmodium falciparum | bifunctional dihydrofolate reductase-thymidylate synthase | 0.0159 | 0.3181 | 1 |
| Echinococcus multilocularis | solute carrier family 2 facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
| Leishmania major | dihydrofolate reductase-thymidylate synthase | 0.0159 | 0.3181 | 1 |
| Mycobacterium ulcerans | dihydrofolate reductase DfrA | 0.0415 | 1 | 0.5 |
| Echinococcus granulosus | solute carrier family 2 facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
| Echinococcus multilocularis | solute carrier family 2 facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
| Schistosoma mansoni | dihydrofolate reductase | 0.0415 | 1 | 1 |
| Echinococcus multilocularis | dihydrofolate reductase | 0.0415 | 1 | 1 |
| Echinococcus multilocularis | solute carrier family 2 facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
| Echinococcus granulosus | dihydrofolate reductase | 0.0415 | 1 | 1 |
| Trichomonas vaginalis | conserved hypothetical protein | 0.0126 | 0.2316 | 1 |
| Loa Loa (eye worm) | dihydrofolate reductase | 0.0415 | 1 | 1 |
| Mycobacterium tuberculosis | Dihydrofolate reductase DfrA (DHFR) (tetrahydrofolate dehydrogenase) | 0.0415 | 1 | 0.5 |
| Echinococcus granulosus | solute carrier family 2 facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
| Trypanosoma cruzi | dihydrofolate reductase-thymidylate synthase | 0.0159 | 0.3181 | 1 |
| Toxoplasma gondii | bifunctional dihydrofolate reductase-thymidylate synthase | 0.0159 | 0.3181 | 1 |
| Echinococcus multilocularis | solute carrier family 2, facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
| Echinococcus granulosus | solute carrier family 2 facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
| Trypanosoma brucei | dihydrofolate reductase-thymidylate synthase | 0.0159 | 0.3181 | 1 |
| Chlamydia trachomatis | dihydrofolate reductase | 0.0415 | 1 | 0.5 |
| Brugia malayi | Dihydrofolate reductase | 0.0415 | 1 | 1 |
| Plasmodium vivax | bifunctional dihydrofolate reductase-thymidylate synthase, putative | 0.0159 | 0.3181 | 1 |
| Mycobacterium leprae | DIHYDROFOLATE REDUCTASE DFRA (DHFR) (TETRAHYDROFOLATE DEHYDROGENASE) | 0.0415 | 1 | 0.5 |
| Echinococcus granulosus | solute carrier family 2 facilitated glucose | 0.0126 | 0.2316 | 0.0579 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| IC50 (functional) | = 0.82 nM | Activity was evaluated against HCT-8 tumor cells | ChEMBL. | 8632413 |
| IC50 (functional) | = 0.82 nM | Activity was evaluated against HCT-8 tumor cells | ChEMBL. | 8632413 |
| IC50 (functional) | = 619 nM | ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes LmPfHT that are glucose transport deficient and complemented with the Plasmodium falciparum hexose transporter. Activity is measured by by DNA content using SYBR green in vitro | ChEMBL. | No reference |
| IC50 (functional) | = 693 nM | ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes LmGT2 that are glucose transport deficient and complemented with the L. Mexicana glucose transporter 2. Activity is measured by by DNA content using SYBR green in vitro | ChEMBL. | No reference |
| IC50 (functional) | = 1011 nM | ST_JUDE_LEISH: Cytotoxicity against transgenic Leishmania Mexicana promastigotes LmGLUT1 that are glucose transport deficient and complemented with the human glucose transporter GLUT1. Activity is measured by DNA content using SYBR green in vitro | ChEMBL. | No reference |
| Inhibition (functional) | = 0 % | GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 LDH activity, using an LDH reporter assay. Test compounds present at 2uM | ChEMBL. | 20485427 |
| Inhibition (functional) | = 73 % | GSK_TCMDC: Percent inhibition of human HepG2 cell line. Test compounds present at 10uM. | ChEMBL. | 20485427 |
| Inhibition (functional) | = 80.31 % | ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmGT2 that are glucose transport deficient and complemented with the L. Mexicana glucose transporter 2. Activity is measured by by DNA content using SYBR green in vitro | ChEMBL. | No reference |
| Inhibition (functional) | = 85.24 % | ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmGLUT1 that are glucose transport deficient and complemented with the human glucose transporter GLUT1. Activity is measured by DNA content using SYBR green in vitro | ChEMBL. | No reference |
| Inhibition (functional) | = 86.6 % | ST_JUDE_LEISH: Cytotoxicity at 2uM final concentration against transgenic Leishmania Mexicana promastigotes LmPfHT that are glucose transport deficient and complemented with the Plasmodium falciparum hexose transporter. Activity is measured by by DNA content using SYBR green in vitro | ChEMBL. | No reference |
| Inhibition (functional) | = 99 % | GSK_TCMDC: Inhibition of Plasmodium falciparum Dd2 in whole red blood cells, using parasite LDH activity as an index of growth. Test compounds present at 2uM | ChEMBL. | 20485427 |
| Inhibition (functional) | = 100 % | GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 in whole red blood cells, using parasite LDH activity as an index of growth. Test compounds present at 2uM | ChEMBL. | 20485427 |
| Inhibition frequency index (IFI) (functional) | = 8.57 | Inhibition Frequency Index (IFI) | GSK. | 20485427 |
| Ki (binding) | < 0.05 nM | Inhibition of Dihydrofolate reductase enzyme from Candida albicans | ChEMBL. | 8632413 |
| Ki (binding) | < 0.05 nM | Inhibition of Dihydrofolate reductase enzyme from Candida albicans | ChEMBL. | 8632413 |
| Ki (binding) | = 0.1 nM | Inhibition of human recombinant Dihydrofolate reductase enzyme | ChEMBL. | 8632413 |
| Ki (binding) | = 0.1 nM | Inhibition of human recombinant Dihydrofolate reductase enzyme | ChEMBL. | 8632413 |
| MIC (functional) | = 0.1 ug ml-1 | Minimum inhibitory concentration evaluated against Candida albicans | ChEMBL. | 8632413 |
| MIC (functional) | = 0.1 ug ml-1 | Minimum inhibitory concentration evaluated against Candida albicans | ChEMBL. | 8632413 |
| Percent growth inhibition (functional) | = 0 % | Percent inhibition of P. falciparum lactate dehydrogenase activity (at 2 uM) | GSK. | 20485427 |
| Percent growth inhibition (functional) | = 73 % | Percent inhibition of HepG2 growth (at 10 uM) | GSK. | 20485427 |
| Percent growth inhibition (functional) | = 99 % | Percent inhibition of P. falciparum Dd2 growth (at 2 uM) | GSK. | 20485427 |
| Percent growth inhibition (functional) | = 100 % | Percent inhibition of P. falciparum 3D7 growth (at 2 uM) | GSK. | 20485427 |
| XC50 (functional) | = 8.49 | XC50 determination of P. falciparum 3D7 growth | GSK. | 20485427 |
| XC50 (functional) | = 0.0032 uM | GSK_TCMDC: Inhibition of Plasmodium falciparum 3D7 in whole erythrocytes, using parasite LDH activity as an index of growth. | ChEMBL. | 20485427 |
Phenotypes
Whole-cell/tissue/organism interactions
| Species name | Source | Reference | Is orphan |
|---|---|---|---|
| Homo sapiens | ChEMBL23 | 8632413 |
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.
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
- ChEMBL: CHEMBL170760
- Search by GSK
- PubChem: 467900
Bibliographic References
2 literature references were collected for this gene.
If you have references for this compound, please enter them in a user comment (below) or Contact us.