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Literature summary extracted from
- Discovery of a new class of inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B by biology-oriented synthesis (2008), Angew. Chem., 47, 5973-5977.
Application
| EC Number | Application | Comment | Organism |
|---|---|---|---|
| 3.1.3.48 | drug development | inhibition of MptpA and MptpB represents a promising strategy for the development of selective antibiotics against this severe pathogen | Mycobacterium tuberculosis |
Inhibitors
| EC Number | Inhibitors | Comment | Organism | Structure |
|---|---|---|---|---|
| 3.1.3.48 | methyl (6S,10S)-12-(2-chloro-3-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | - |
Mycobacterium tuberculosis |  |
| 3.1.3.48 | methyl (6S,10S)-12-(2-fluoro-5-iodobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | - |
Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-(2-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-(3,4-dichlorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-(3,4-difluorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | - |
Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-(3-bromo-4-fluorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-(3-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-benzyl-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | - |
Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-[(4,6-dichloro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-[(4-chloro-6-fluoro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA, inhibition kinetics, overview | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-[(5-chloro-1H-indol-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-12-[(5-methylfuran-2-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | absolutely specific for MptpB, no inhibition of MptpA | Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-9-hydroxy-12-(3-hydroxybenzyl)-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | - |
Mycobacterium tuberculosis | |
| 3.1.3.48 | methyl (6S,10S)-9-oxo-12-(pyridin-3-ylmethyl)-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | - |
Mycobacterium tuberculosis | |
Localization
| EC Number | Localization | Comment | Organism | GeneOntology No. | Textmining |
|---|---|---|---|---|---|
| 3.1.3.48 | extracellular | MptpA and MptpB are secreted in host lung | Mycobacterium tuberculosis | - |
- |
Organism
| EC Number | Organism | UniProt | Comment | Textmining |
|---|---|---|---|---|
| 3.1.3.48 | Mycobacterium tuberculosis | - |
- |
- |
Substrates and Products (Substrate)
| EC Number | Substrates | Comment Substrates | Organism | Products | Comment (Products) | Rev. | Reac. |
|---|---|---|---|---|---|---|---|
| 3.1.3.48 | 4-nitrophenyl phosphate + H2O | - |
Mycobacterium tuberculosis | 4-nitrophenol + phosphate | - |
? | |
Synonyms
| EC Number | Synonyms | Comment | Organism |
|---|---|---|---|
| 3.1.3.48 | MPtpA | - |
Mycobacterium tuberculosis |
| 3.1.3.48 | MPtpB | - |
Mycobacterium tuberculosis |
| 3.1.3.48 | protein tyrosine phosphatase B | - |
Mycobacterium tuberculosis |
Ki Value [mM]
| EC Number | Ki Value [mM] | Ki Value maximum [mM] | Inhibitor | Comment | Organism | Structure |
|---|---|---|---|---|---|---|
| 3.1.3.48 | 0.00134 | - |
methyl (6S,10S)-12-[(4-chloro-6-fluoro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | inhibition of MptpB | Mycobacterium tuberculosis | |
IC50 Value
| EC Number | IC50 Value | IC50 Value Maximum | Comment | Organism | Inhibitor | Structure |
|---|---|---|---|---|---|---|
| 3.1.3.48 | 0.00471 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-[(4,6-dichloro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
| 3.1.3.48 | 0.00595 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-[(5-methylfuran-2-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
| 3.1.3.48 | 0.0061 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-(3-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
| 3.1.3.48 | 0.00704 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-[(4-chloro-6-fluoro-2H-chromen-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
| 3.1.3.48 | 0.00826 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-(3,4-dichlorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
| 3.1.3.48 | 0.00964 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-(2-hydroxybenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
| 3.1.3.48 | 0.0107 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-(3-bromo-4-fluorobenzyl)-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
| 3.1.3.48 | 0.0116 | - |
inhibition of MptpB | Mycobacterium tuberculosis | methyl (6S,10S)-12-[(5-chloro-1H-indol-3-yl)methyl]-9-oxo-6,7,8,9,10,11-hexahydro-5H-6,10-epiminocycloocta[b]indole-8-carboxylate | |
General Information
| EC Number | General Information | Comment | Organism |
|---|---|---|---|
| 3.1.3.48 | physiological function | MptpA and MptpB selectively dephosphorylate human host proteins involved in interferon-gamma signaling pathways, thereby preventing the initiation of host defense mechanisms, overview | Mycobacterium tuberculosis |
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