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Literature summary extracted from

  • Sivendran, S.; Jones, V.; Sun, D.; Wang, Y.; Grzegorzewicz, A.E.; Scherman, M.S.; Napper, A.D.; McCammon, J.A.; Lee, R.E.; Diamond, S.L.; McNeil, M.
    Identification of triazinoindol-benzimidazolones as nanomolar inhibitors of the Mycobacterium tuberculosis enzyme TDP-6-deoxy-D-xylo-4-hexopyranosid-4-ulose 3,5-epimerase (RmlC) (2010), Bioorg. Med. Chem., 18, 896-908.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
5.1.3.13 1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfonyl)-propyl)-1H-benzo[d]imidazol-2(3H)-one
-
Mycobacterium tuberculosis
5.1.3.13 1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one i.e. 77074, a SID 7975595 analogue Mycobacterium tuberculosis
5.1.3.13 1-(3-(5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
-
Mycobacterium tuberculosis
5.1.3.13 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfonyl)-propyl)-1H-benzo[d]imidazol-2(3H)-one
-
Mycobacterium tuberculosis
5.1.3.13 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one i.e. SID 7975595, a competitive, fast-on rate, fully reversible inhibitor of RmlC. Increases the Km for TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose. Cytotoxic SID 7975595 has an IC50 of approximately 0.075 mM in HAE cells Mycobacterium tuberculosis
5.1.3.13 1-(3-(5-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one i.e. 77072, a SID 7975595 analogue Mycobacterium tuberculosis
5.1.3.13 1-(3-(5-methylphenyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one i.e. 77070, a SID 7975595 analogue Mycobacterium tuberculosis
5.1.3.13 1-(3-(5-propyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one i.e. 77071, a SID 7975595 analogue Mycobacterium tuberculosis
5.1.3.13 1-(3-(5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one i.e. 77073, a SID 7975595 analogue Mycobacterium tuberculosis
5.1.3.13 additional information modeling of triazinoindol-benzimidazolones into the active site of RmlC, overview Mycobacterium tuberculosis

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
5.1.3.13 additional information
-
additional information Michaelis-Menten kinetics Mycobacterium tuberculosis

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
5.1.3.13 cell wall
-
Mycobacterium tuberculosis 5618
-

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
5.1.3.13 Mg2+
-
Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.1.3.13 TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose Mycobacterium tuberculosis conversion of TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose to TDP-L-rhamnose, catalyzed by the two enzymes TDP-6-deoxy-D-xylo-4-hexulose 3,5-epimerase, RmlC, and TDP-deoxy-L-lyxo-4-hexulose reductase, RmlD, overview TDP-L-rhamnose
-
?

Organism

EC Number Organism UniProt Comment Textmining
5.1.3.13 Mycobacterium tuberculosis P9WH11
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.1.3.13 TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose conversion of TDP-6-deoxy-D-xylo-hexopyranosid-4-ulose to TDP-L-rhamnose, catalyzed by the two enzymes TDP-6-deoxy-D-xylo-4-hexulose 3,5-epimerase, RmlC, and TDP-deoxy-L-lyxo-4-hexulose reductase, RmlD, overview Mycobacterium tuberculosis TDP-L-rhamnose
-
?

Synonyms

EC Number Synonyms Comment Organism
5.1.3.13 RmlC
-
Mycobacterium tuberculosis
5.1.3.13 TDP-6-deoxy-D-xylo-4-hexopyranosid-4-ulose 3,5-epimerase
-
Mycobacterium tuberculosis

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
5.1.3.13 25
-
assay at Mycobacterium tuberculosis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
5.1.3.13 7.4
-
assay at Mycobacterium tuberculosis

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
5.1.3.13 0.00012
-
-
Mycobacterium tuberculosis 1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.0002
-
pH 7.4, 25°C Mycobacterium tuberculosis 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.0004
-
pH 7.4, 25°C Mycobacterium tuberculosis 1-(3-(5-allyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfonyl)-propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.0005
-
pH 7.4, 25°C Mycobacterium tuberculosis 1-(3-(5-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.0008
-
pH 7.4, 25°C Mycobacterium tuberculosis 1-(3-(5-ethyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylsulfonyl)-propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.00125
-
pH 7.4, 25°C Mycobacterium tuberculosis 1-(3-(5-propyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.0029
-
pH 7.4, 25°C Mycobacterium tuberculosis 1-(3-(5-methylphenyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.0033
-
pH 7.4, 25°C Mycobacterium tuberculosis 1-(3-(5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one
5.1.3.13 0.02
-
-
Mycobacterium tuberculosis 1-(3-(5-allyl-8-methyl-5H-[1,2,4]triazino[5,6-b]indol-3-ylthio)propyl)-1H-benzo[d]imidazol-2(3H)-one