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Literature summary extracted from

  • Vasquez-Martinez, Y.; Ohri, R.V.; Kenyon, V.; Holman, T.R.; Sepulveda-Boza, S.
    Structure-activity relationship studies of flavonoids as potent inhibitors of human platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2 (2007), Bioorg. Med. Chem., 15, 7408-7425.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.13.11.31 expression of His-tagged enzyme Homo sapiens
1.13.11.33 expression of His-tagged isozyme 15-hLO-1, expression of isozyme 15-hLO-2 in Spodoptera frugiperda Sf9 cells using the baculovirus transfection system Homo sapiens

Inhibitors

EC Number Inhibitors Comment Organism Structure
1.13.11.31 2-alkyl benzopyran-4-ones weak inhibition Homo sapiens
1.13.11.31 2-alkyl-6-hydroxy-4-H-benzopyran-4-one weak inhibition Homo sapiens
1.13.11.31 3'-chloro-7,8-dihydroxyisoflavone
-
 Homo sapiens
1.13.11.31 4',6,7-trihydroxyisoflavan
-
 Homo sapiens
1.13.11.31 4',6,7-trihydroxyisoflavanone
-
 Homo sapiens
1.13.11.31 4',6,7-trihydroxyisoflavone
-
 Homo sapiens
1.13.11.31 4'-chloro-7,8-dihydroxyisoflavone
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-3',4'-methylenedioxyisoflavan
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-3',4'-methylenedioxyisoflavone
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-3'-methylisoflavan
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-3'-methylisoflavanone
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-4'-methoxyisoflavan
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-4'-methoxyisoflavanone
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-4'-methoxyisoflavone
-
 Homo sapiens
1.13.11.31 6,7-dihydroxy-4'-nitroisoflavone
-
 Homo sapiens
1.13.11.31 7,8-dihydroxy-3',4'-dimethoxyisoflavan
-
 Homo sapiens
1.13.11.31 7,8-dihydroxy-3'-methylisoflavone
-
 Homo sapiens
1.13.11.31 7,8-dihydroxy-3'-trifluoromethylisoflavone
-
 Homo sapiens
1.13.11.31 7,8-dihydroxy-4'-methoxyisoflavan
-
 Homo sapiens
1.13.11.31 7,8-dihydroxy-4'-methylisoflavan
-
 Homo sapiens
1.13.11.31 7,8-dihydroxy-4'-methylisoflavone
-
 Homo sapiens
1.13.11.31 7,8-dihydroxyisoflavone
-
 Homo sapiens
1.13.11.31 7-hydroxy-H-benzopyran-4-one derivatives weak inhibition Homo sapiens
1.13.11.31 H-benzopyran-4-one derivatives weak inhibition Homo sapiens
1.13.11.31 additional information comparison of structural requirements for flavonoid inhibitory potency and selectivity against platelet 12-hLO, reticulocyte 15-hLO-1, and prostate epithelial 15-hLO-2, the two latter belong to EC 1.13.11.33, overview, catechols are essential for high potency, isoflavones and isoflavanones tend to select against 12-hLO, isoflavans tend to select against isozyme 15-hLO-1, but few flavonoids target isozyme 15-hLO-2, molecular modeling analysis, overview Homo sapiens
1.13.11.33 2-alkyl benzopyran-4-ones weak inhibition of isozymes 15-hLO-1 and 15-hLO-2 Homo sapiens
1.13.11.33 2-alkyl-6-hydroxy-4-H-benzopyran-4-one weak inhibition of isozymes 15-hLO-1 and 15-hLO-2 Homo sapiens
1.13.11.33 3'-chloro-7,8-dihydroxyisoflavone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 3-hydroxy-H-benzopyran-4-one derivatives weak inhibition of isozymes 15-hLO-1 and 15-hLO-2 Homo sapiens
1.13.11.33 4',6,7-trihydroxyisoflavan
-
 Homo sapiens
1.13.11.33 4',6,7-trihydroxyisoflavanone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 4',6,7-trihydroxyisoflavone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 4'-chloro-7,8-dihydroxyisoflavone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 6,7-dihydroxy-2-t-butylbenzopyran-4-one weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 6,7-dihydroxy-3',4'-methylenedioxyisoflavan
-
 Homo sapiens
1.13.11.33 6,7-dihydroxy-3'-methylisoflavan
-
 Homo sapiens
1.13.11.33 6,7-dihydroxy-3'-methylisoflavanone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 6,7-dihydroxy-4'-methoxyisoflavan
-
 Homo sapiens
1.13.11.33 6,7-dihydroxy-4'-methoxyisoflavanone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 6,7-dihydroxyisoflavones weak inhibition of isozymes 15-hLO-1 and 15-hLO-2 Homo sapiens
1.13.11.33 6-hydroxy-2-pentyl-4H-benzopyran-4-one weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 7,8-dihydroxy-3',4'-dimethoxyisoflavan
-
 Homo sapiens
1.13.11.33 7,8-dihydroxy-3'-methylisoflavone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 7,8-dihydroxy-3'-trifluoromethylisoflavone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 7,8-dihydroxy-4'-methoxyisoflavan
-
 Homo sapiens
1.13.11.33 7,8-dihydroxy-4'-methylisoflavan
-
 Homo sapiens
1.13.11.33 7,8-dihydroxy-4'-methylisoflavone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 7,8-dihydroxyisoflavone weak inhibition of isozyme 15-hLO-2 Homo sapiens
1.13.11.33 7-hydroxy-H-benzopyran-4-one derivatives weak inhibition of isozymes 15-hLO-1 and 15-hLO-2 Homo sapiens
1.13.11.33 additional information comparison of structural requirements for flavonoid inhibitory potency and selectivity against platelet 12-hLO, EC 1.13.11.31, and reticulocyte 15-hLO-1 and prostate epithelial 15-hLO-2, overview, catechols are essential for high potency, isoflavones and isoflavanones tend to select against 12-hLO, isoflavans tend to select against isozyme 15-hLO-1, but few flavonoids target isozyme 15-hLO-2, molecular modeling analysis, overview Homo sapiens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.13.11.31 arachidonate + O2 Homo sapiens
-
 (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
 ?
1.13.11.33 arachidonate + O2 Homo sapiens
-
 (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.13.11.31 Homo sapiens
-
 isozyme 12-hLO
-
1.13.11.33 Homo sapiens
-
 isozymes 15-hLO-1 and 15-hLO-2
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.13.11.31 recombinant His-tagged enzyme Homo sapiens
1.13.11.33 recombinant isozyme 15-hLO-2 from Spodoptera frugiperda Sf9 cells by anion exchange chromatography, recombinant His-tagged isozyme 15-hLO-1 Homo sapiens

Source Tissue

EC Number Source Tissue Comment Organism Textmining
1.13.11.31 blood platelet isozyme 12-hLO Homo sapiens
-
1.13.11.33 epithelial cell isozyme 15-hLO-2 Homo sapiens
-
1.13.11.33 prostate epithelium, isozyme 15-hLO-2 Homo sapiens
-
1.13.11.33 reticulocyte isozyme 15-hLO-1 Homo sapiens
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.13.11.31 arachidonate + O2
-
 Homo sapiens (5Z,8Z,10E,14Z)-(12S)-12-hydroperoxyeicosa-5,8,10,14-tetraenoate
-
 ?
1.13.11.33 arachidonate + O2
-
 Homo sapiens (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
 ?
1.13.11.33 arachidonate + O2 preferred substrate of isozyme 15-hLO-2, reaction of EC 1.13.11.33 Homo sapiens (5Z,8Z,11Z,13E)-(15S)-15-hydroperoxyeicosa-5,8,11,13-tetraenoate
-
 ?
1.13.11.33 linoleic acid + O2 preferred substrate of isozyme 15-hLO-1, reaction of EC 1.13.11.12 Homo sapiens (9Z,11E)-(13S)-13-hydroperoxy-octadeca-9,11-dienoate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.13.11.31 12-hLO
-
 Homo sapiens
1.13.11.33 15-hLO
-
 Homo sapiens
1.13.11.33 More cf. EC 1.13.11.12 Homo sapiens

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
1.13.11.33 22
-
 assay at room temperature Homo sapiens

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
1.13.11.33 7.5
-
 assay at Homo sapiens

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
1.13.11.31 0.00048
-
 pH 7.5, 22°C Homo sapiens 4'-chloro-7,8-dihydroxyisoflavone
1.13.11.31 0.00062
-
 pH 7.5, 22°C Homo sapiens 7,8-dihydroxy-3'-trifluoromethylisoflavone
1.13.11.31 0.00078
-
 pH 7.5, 22°C Homo sapiens 3'-chloro-7,8-dihydroxyisoflavone
1.13.11.31 0.0016
-
 pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-4'-methoxyisoflavanone
1.13.11.31 0.0016
-
 pH 7.5, 22°C Homo sapiens 7,8-dihydroxy-4'-methylisoflavone
1.13.11.31 0.0036
-
 pH 7.5, 22°C Homo sapiens 7,8-dihydroxy-3'-methylisoflavone
1.13.11.31 0.0038
-
 pH 7.5, 22°C Homo sapiens 4',6,7-trihydroxyisoflavanone
1.13.11.31 0.0058
-
 pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-4'-nitroisoflavone
1.13.11.31 0.0064
-
 pH 7.5, 22°C Homo sapiens 7,8-dihydroxyisoflavone
1.13.11.31 0.0076
-
 pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-4'-methoxyisoflavan
1.13.11.31 0.0087
-
 pH 7.5, 22°C Homo sapiens 4',6,7-trihydroxyisoflavone
1.13.11.31 0.011
-
 pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-3',4'-methylenedioxyisoflavan
1.13.11.31 0.014
-
 pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-3'-methylisoflavanone
1.13.11.31 0.015
-
 pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-3'-methylisoflavan
1.13.11.31 0.017
-
 pH 7.5, 22°C Homo sapiens 4',6,7-trihydroxyisoflavan
1.13.11.31 0.026
-
 pH 7.5, 22°C Homo sapiens 7,8-dihydroxy-4'-methoxyisoflavan
1.13.11.31 0.07
-
 pH 7.5, 22°C Homo sapiens 7,8-dihydroxy-4'-methylisoflavan
1.13.11.31 0.1
-
 above, pH 7.5, 22°C Homo sapiens 7,8-dihydroxy-3',4'-dimethoxyisoflavan
1.13.11.31 0.1
-
 above, pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-4'-methoxyisoflavone
1.13.11.31 0.1
-
 above, pH 7.5, 22°C Homo sapiens 6,7-dihydroxy-3',4'-methylenedioxyisoflavone
1.13.11.33 0.00015
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 6,7-dihydroxy-4'-methoxyisoflavan
1.13.11.33 0.00021
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 6,7-dihydroxy-3'-methylisoflavan
1.13.11.33 0.00021
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 6,7-dihydroxy-3'-methylisoflavanone
1.13.11.33 0.00035
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 6,7-dihydroxy-3',4'-methylenedioxyisoflavan
1.13.11.33 0.00051
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 4',6,7-trihydroxyisoflavan
1.13.11.33 0.0016
-
 pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 6,7-dihydroxy-4'-methoxyisoflavanone
1.13.11.33 0.0037
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 7,8-dihydroxy-4'-methoxyisoflavan
1.13.11.33 0.0038
-
 pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 4',6,7-trihydroxyisoflavanone
1.13.11.33 0.0057
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 7,8-dihydroxy-4'-methylisoflavan
1.13.11.33 0.0062
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 3'-chloro-7,8-dihydroxyisoflavone
1.13.11.33 0.0078
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 7,8-dihydroxy-4'-methylisoflavone
1.13.11.33 0.0083
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 7,8-dihydroxy-3'-trifluoromethylisoflavone
1.13.11.33 0.0083
-
 pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 6,7-dihydroxy-3'-methylisoflavan
1.13.11.33 0.009
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 4'-chloro-7,8-dihydroxyisoflavone
1.13.11.33 0.011
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 7,8-dihydroxy-3'-methylisoflavone
1.13.11.33 0.013
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 7,8-dihydroxyisoflavone
1.13.11.33 0.014
-
 pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 6,7-dihydroxy-3'-methylisoflavanone
1.13.11.33 0.016
-
 pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 6,7-dihydroxy-3',4'-methylenedioxyisoflavan
1.13.11.33 0.018
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 6,7-dihydroxy-2-t-butylbenzopyran-4-one
1.13.11.33 0.019
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 6,7-dihydroxy-4'-methoxyisoflavanone
1.13.11.33 0.038
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 6-hydroxy-2-pentyl-4H-benzopyran-4-one
1.13.11.33 0.049
-
 pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 4',6,7-trihydroxyisoflavone
1.13.11.33 0.071
-
 pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 4',6,7-trihydroxyisoflavan
1.13.11.33 0.1
-
 above, pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 7,8-dihydroxy-3',4'-dimethoxyisoflavan
1.13.11.33 0.1
-
 above, pH 7.5, 22°C, isozyme 15-hLO-1 Homo sapiens 4',6,7-trihydroxyisoflavanone
1.13.11.33 0.1
-
 above, pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 7,8-dihydroxy-4'-methylisoflavan
1.13.11.33 0.1
-
 above, pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 7,8-dihydroxy-3',4'-dimethoxyisoflavan
1.13.11.33 0.1
-
 above, pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 7,8-dihydroxy-4'-methoxyisoflavan
1.13.11.33 0.1
-
 above, pH 7.5, 22°C, isozyme 15-hLO-2 Homo sapiens 6,7-dihydroxy-4'-methoxyisoflavan