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DraconiticBiochemistryBiomolecules · Catabolism · Biosynthesis · MetabolismMap
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Specialized pro-resolving mediators

Enzymatic routes to lipoxins, resolvins, protectins and maresins from polyunsaturated fatty acids. 125 reactions, from Reactome R-HSA-9018678.

  1. ALOX12 oxidises LTA4 to LXA42 LTA4 + O2 + 2 H2O → 2 LXA4
  2. LXA4 is oxidised to 15k-LXA4 by HPGDLXA4 + NAD+ → 15k-LXA4 + NADH + H+
  3. 15k-LXA4 is reduced to dhk-LXA4 by PTGR115k-LXA4 + H+ + NADH → dhk-LXA4 + NAD+
  4. ALOX5 oxidises 15R-HETE to 15epi-LXA4/B415R-HETE + O2 → 15epi-LXA4/B4
  5. ALOX5 oxidises 15S-HpETE to LXA4/B4O2 + 2 15S-HpETE → 2 LXA4/B4
  6. 5S-HpETE is dehydrated to LTA4 by ALOX55S-HpETE → LTA4 + H2O
  7. ALOX5 oxidises 18(S)-HEPE to 5(S)-Hp-18(S)-HEPE18(S)-HEPE + O2 → 5(S)-Hp-18(S)-HEPE
  8. ALOX5 oxidises 5(S)-Hp-18(S)-HEPE to 5S,6S-epoxy-18(S)-HEPE5(S)-Hp-18(S)-HEPE + O2 → 5S,6S-epoxy-18(S)-HEPE
  9. LTA4H:Zn2+ hydrolyses 5S,6S-epoxy-18(S)-HEPE to 18(S)-RvE15S,6S-epoxy-18(S)-HEPE + H2O → 18(S)-RvE1
  10. ALOX5 oxidises 18(R)-HEPE to 5(S)-Hp-18(R)-HEPE18(R)-HEPE + O2 → 5(S)-Hp-18(R)-HEPE
  11. 5-HEDH dehydrogenates 5(S)-Hp-18(S)-HpEPE to 18(S)-RvE25(S)-Hp-18(S)-HEPE + hydrogen donor → 18(S)-RvE2 + hydrogen acceptor + H2O
  12. GPX4-2 reduces 18(S)-HpEPE to 18(S)-HEPE18(S)-HpEPE + 2 GSH → 18(S)-HEPE + GSSG + H2O
  13. CYP monooxygenates EPA to 18(S)-HpEPEEPA + NADPH + O2 + H+ → 18(S)-HpEPE + NADP+
  14. LTA4H:Zn2+ hydrolyses 5S,6S-epoxy-18(R)-HEPE to 18(R)-RvE15S,6S-epoxy-18(R)-HEPE + H2O → 18(R)-RvE1
  15. Ac-PTGS2 dimer oxidises EPA to 18(R)-HpEPE or 18(S)-HpEPEEPA + O2 → 18(S)-HpEPE, 18(R)-HpEPE
  16. ALOX5 oxidises 5(S)-Hp-18(R)-HEPE to 5S,6S-epoxy-18(R)-HEPE5(S)-Hp-18(R)-HEPE + O2 → 5S,6S-epoxy-18(R)-HEPE
  17. GPX4-2 reduces 18(R)-HpEPE to 18(R)-HEPE18(R)-HpEPE + 2 GSH → 18(R)-HEPE + GSSG + H2O
  18. 5-HEDH dehydrogenates 5(S)-Hp-18(R)-HEPE to 18(R)-RvE25(S)-Hp-18(R)-HEPE + hydrogen donor → 18(R)-RvE2 + hydrogen acceptor + H2O
  19. ALOX15 oxidises 18(R)-HEPE to 18(R)-RvE318(R)-HEPE + O2 → (18R)-resolvin E3
  20. Hydroperoxy reductase reduces 4(S)-Hp-17(S)-HDHA to RvD64(S)-Hp-17(S)-HDHA + reduced acceptor → resolvin D6 + oxidised acceptor
  21. ALOX5 oxidises 17(R)-HDHA to 7(S)-Hp-17(R)-HDHA17(R)-HDHA + O2 → 7(S)-Hp-17(R)-HDHA
  22. LTA4H:Zn2+ hydrolyses 7S(8)-epoxy-17(R)-HDHA to AT-RvD1 or AT-RvD27S(8)-epoxy-17(R)-HDHA + H2O → AT-RvD1, AT-RvD2
  23. LTA4H:Zn2+ hydrolyses 4S(5)-epoxy-17(S)-HDHA to RvD3 or RvD44S(5)-epoxy-17(S)-HDHA + H2O → RvD3, RvD4
  24. ALOX5 dehydrogenates 7(S)-Hp-17(S)-HDHA to 7S(8)-epoxy-17S-HDHA7(S)-Hp-17(S)-HDHA + NADP+ → 7S(8)-epoxy-17(S)-HDHA + NADPH
  25. ALOX5 dehydrogenates 7(S)-Hp-17R-HDHA to 7S(8)-epoxy-17R-HDHA7(S)-Hp-17(R)-HDHA + NADP+ → 7S(8)-epoxy-17(R)-HDHA + NADPH
  26. LTA4H:Zn2+ hydrolyses 17R(16)-epoxy-DHA to AT-(N)PD117R(16)-epoxy-DHA + H2O → AT-(N)PD1
  27. LTA4H:Zn2+ hydrolyses 7S(8)-epoxy-17(S)-HDHA to RvD1 or RvD27S(8)-epoxy-17(S)-HDHA + H2O → RvD1, RvD2
  28. ALOX5 oxidises 17(R)-HDHA to 4(S)-Hp-17(R)-HDHA17(R)-HDHA + O2 → 4(S)-Hp-17(R)-HDHA
  29. Hydroperoxy reductase reduces 7(S)-Hp-17(S)-HDHA to RvD57(S)-Hp-17(S)-HDHA + reduced acceptor → resolvin D5 + oxidised acceptor
  30. Ac-PTGS2 dimer oxidises DHA to 17(R)-Hp-DHADHA + O2 → 17(R)-Hp-DHA
  31. ALOX15 dehydrogenates 17(R)-Hp-DHA to 17R(16)-epoxy-DHA17(R)-Hp-DHA + NADP+ → 17R(16)-epoxy-DHA + NADPH
  32. ALOX5 oxidises 17(S)-HDHA to 4(S)-Hp-17(S)-HDHA17(S)-HDHA + O2 → 4(S)-Hp-17(S)-HDHA
  33. LTA4H:Zn2+ hydrolyses 4S(5)-epoxy-17(R)-HDHA to AT-RvD3 or AT-RvD44S(5)-epoxy-17(R)-HDHA + H2O → AT-RvD3, AT-RvD4
  34. GPX4-2 reduces 17(R)-Hp-DHA to 17(R)-HDHA17(R)-Hp-DHA + 2 GSH → 17(R)-HDHA + GSSG + H2O
  35. GPX4-2 reduces 17(S)-Hp-DHA to 17(S)-HDHA17(S)-Hp-DHA + 2 GSH → 17(S)-HDHA + GSSG + H2O
  36. ALOX12:Fe2+ oxidises DHA to 14(S)-Hp-DHADHA + O2 → 14(S)-Hp-DHA
  37. ALOX15 oxidises DHA to 17(S)-Hp-DHADHA + O2 → 17(S)-Hp-DHA
  38. ALOX5 dehydrogenates 4(S)-Hp-17(S)-HDHA to 4S(5)-epoxy-17(S)-HDHA4(S)-Hp-17(S)-HDHA + NADP+ → 4S(5)-epoxy-17(S)-HDHA + NADPH
  39. ALOX5 dehydrogenates 4(S)-Hp-17(R)-HDHA to 4S(5)-epoxy-17(R)-HDHA4(S)-Hp-17(R)-HDHA + NADP+ → 4S(5)-epoxy-17(R)-HDHA + NADPH
  40. ALOX5 oxidises 17(S)-HDHA to 7(S)-Hp-17(S)-HDHA17(S)-HDHA + O2 → 7(S)-Hp-17(S)-HDHA
  41. ALOX15 oxidises 18(S)-HEPE to 18(S)-RvE318(S)-HEPE + O2 → 18(S)-RvE3
  42. HPGD dimer oxidises 18(S)-RvE1 to 18-oxo-RvE118(S)-RvE1 + NAD+ → 18-oxo-RvE1 + NADH
  43. 18(S)-RvE1, E2 and E3 translocate from cytosol to extracellular region18(S)-RvE1,E2,E3 → 18(S)-RvE1,E2,E3
  44. 18(R)-RvE1, E2 and E3 translocate from cytosol to extracellular region18(R)-RvE1,E2,E3 → 18(R)-RvE1,E2,E3
  45. AT-RvD1-6 translocate from cytosol to extracellular regionAT-RvD1-6 → AT-RvD1-6
  46. Hydroperoxy reductase reduces 4(S)-Hp-17(R)-HDHA to AT-RvD64(S)-Hp-17(R)-HDHA + reduced acceptor → AT-RvD6 + oxidised acceptor
  47. Hydroperoxy reductase reduces 7(S)-Hp-17(R)-HDHA to AT-RvD57(S)-Hp-17(R)-HDHA + reduced acceptor → AT-RvD5 + oxidised acceptor
  48. HPGD dimer oxidises RvD1 to 17(S)-oxo-RvD1 and 8-oxo-17(S)-RvD1RvD1 + NAD+ → 17(S)-oxo-RvD1, 8-oxo-17(S)-RvD1 + NADH + H+
  49. RvD1-6 translocate from cytosol to extracellular regionRvD1-6 → RvD1-6
  50. ALOX15 oxidises 17(S)-Hp-DHA to PDX17(S)-Hp-DHA + O2 → PDX
  51. ALOX15 dehydrogenates 17(S)-Hp-DHA to 16S,17S-epoxy-DHA17(S)-Hp-DHA + NADP+ → 16S,17S-epoxy-DHA + NADPH
  52. LTA4H:Zn2+ hydrolyses 16S,17S-epoxy-DHA to (N)PD116S,17S-epoxy-DHA + H2O → (N)PD1
  53. Epoxide hydrolase hydrolyses 13(S),14(S)-epoxy-DHA to MaR113(S),14(S)-epoxy-DHA + H2O → MaR1
  54. ALOX12:Fe2+ dehydrogenates 14(S)-Hp-DHA to 13(S),14(S)-epoxy-DHA14(S)-Hp-DHA + NADP+ → 13(S),14(S)-epoxy-DHA + NADPH
  55. EPHX2 dimer hydrolyses 13(S),14(S)-epoxy-DHA to MaR213(S),14(S)-epoxy-DHA + H2O → MaR2
  56. ALOX5 oxidises 14(S)-Hp-DHA to 7(S),14(S)-diHp-DHA14(S)-Hp-DHA + O2 → 7(S),14(S)-diHp-DHA
  57. Hydroperoxy reductase reduces 7(S),14(S)-diHp-DHA to 7-epi-MaR17(S),14(S)-diHp-DHA + reduced acceptor → 7-epi-MaR1 + oxidised acceptor
  58. ALOX15 oxidises DPAn-6 to 17(S)-HDPAn-6 and 10(S),17(S)-diHDPAn-6O2 + DPAn-6 → 17(S)-HDPAn-6, 10(S),17(S)-diHDPAn-6
  59. ALOX12:Fe2+ oxidises DPAn-6 to 14(S)-HDPAn-6O2 + DPAn-6 → 14(S)-HDPAn-6
  60. ALOX5 dehydrogenates 7,17-diHp-DPAn-3 to 7,8-epoxy,17-HDPAn-37,17-diHp-DPAn-3 + NADP+ → 7,8-epoxy,17-HDPAn-3 + NADPH
  61. ALOX5 oxidises 17(S)-Hp-DPAn-3 to 7,17-diHp-DPAn-317(S)-Hp-DPAn-3 + O2 → 7,17-diHp-DPAn-3
  62. Epoxide hydrolase hydrolyses 13,14-epoxy-DPAn-3 to MaR1n-3 DPA or MaR2n-3 DPA13,14(S)-epoxy-DPAn-3 + H2O → MaR1n-3 DPA, MaR2n-3 DPA
  63. ALOX5 dehydrogenates 17(S)-Hp-DPAn-3 to 16(S),17(S)-epoxy-DPAn-317(S)-Hp-DPAn-3 + NADP+ → 16(S),17(S)-epoxy-DPAn-3 + NADPH
  64. Epoxide hydrolase hydrolyses 16(S),17(S)-epoxy-DPAn-3 to PD1n-3DPA or PD2n-3DPA16(S),17(S)-epoxy-DPAn-3 + H2O → PD1n-3DPA,PD2n-3DPA
  65. Hydroperoxy reductase reduces 7,17-diHp-DPAn-3 to RvD5n-3DPA7,17-diHp-DPAn-3 + reduced acceptor → RvD5n-3DPA + oxidised acceptor
  66. ALOX15 oxidises DPAn-3 to 17(S)-Hp-DPAn-3DPAn-3 + O2 → 17(S)-Hp-DPAn-3
  67. ALOX5 oxidises 14(S)-Hp-DPAn-3 to MaR3n-3 DPA14(S)-Hp-DPAn-3 + O2 → MaR3n-3 DPA
  68. ALOX12:Fe2+ oxidises DPAn-3 to 14(S)-Hp-DPAn-3DPAn-3 + O2 → 14(S)-Hp-DPAn-3
  69. ALOX12:Fe2+ dehydrogenates 14(S)-Hp-DPAn-3 to 13,14-epoxy-DPAn-314(S)-Hp-DHA + NADP+ → 13,14(S)-epoxy-DPAn-3 + NADPH
  70. Epoxide hydrolase hydrolyses 7,8-epoxy-HDPAn-3 to RvD1n-3DPA or RvD2n-3DPA7,8-epoxy,17-HDPAn-3 + H2O → RvD1n-3DPA, RvD2n-3DPA
  71. ALOX5 oxidises 13(R)-HDPAn-3 to RvT1-413(R)-HDPAn-3 + O2 → RvT1-4
  72. PTGS2 dimer oxidises DPAn-3 to 13(R)-HDPAn-3DPAn-3 + O2 + hydrogen donor → 13(R)-HDPAn-3 + hydrogen acceptor + H2O
  73. 13(R)-HDPAn-3 translocates from endothelial cell to neutrophil13(R)-HDPAn-3 → 13(R)-HDPAn-3
  74. Non-enzymatic hydrolysis hydrolyses 13(S),14(S)-epoxy-DHA to 7-epi-MaR113(S),14(S)-epoxy-DHA + H2O → 7-epi-MaR1
  75. GGT hydrolyses MCTR1 to MCTR2MCTR1 + H2O → MCTR2 + L-Glu
  76. DPEP hydrolyses MCTR2 to MCTR3MCTR2 + H2O → MCTR3 + Gly
  77. GSTM4 dimer transfers GSH to 13(S),14(S)-epoxy-DHA to form MCTR113(S),14(S)-epoxy-DHA + GSH → MCTR1
  78. LTC4S trimer transfers GSH to 13(S),14(S)-epoxy-DHA to form MCTR113(S),14(S)-epoxy-DHA + GSH → MCTR1
  79. GGT transfers GSH to 16S,17S-epoxy-DHA to form PCTR116S,17S-epoxy-DHA + GSH → PCTR1
  80. GGT hydrolyses PCTR2 to PCTR3PCTR2 + H2O → PCTR3 + Gly
  81. LTC4S trimer transfers GSH to 7S(8)-epoxy-17(S)-HDHA to form RCTR17S(8)-epoxy-17(S)-HDHA + GSH → RCTR1
  82. GGT hydrolyses PCTR1 to PCTR2PCTR1 + H2O → PCTR2 + L-Glu
  83. GGT hydrolyses RCTR2 to RCTR3RCTR2 + H2O → RCTR3 + Gly
  84. Lipoxygenase dehydrogenates 7(S),17(S)-diHp-DHA to 7S(8)-epoxy-17(S)-HDHA7(S),17(S)-diHp-DHA + NADP+ → 7S(8)-epoxy-17(S)-HDHA + NADPH
  85. Lipoxygenase oxidises 17(S)-Hp-DHA to 7(S),17(S)-diHp-DHA17(S)-Hp-DHA + O2 → 7(S),17(S)-diHp-DHA
  86. GGT hydrolyses RCTR1 to RCTR2RCTR1 + H2O → RCTR2 + L-Glu
  87. Hydroperoxy reducatase reduces 14(S)-Hp-DHA to 14(S)-HDHA14(S)-Hp-DHA + reduced acceptor → 14(S)-HDHA + oxidised acceptor
  88. CPY4 ω-oxidises 14(S)-HDHA to MaR-L114(S)-HDHA + NADPH + O2 + H+ → MaR-L1 + H2O + NADP+
  89. CYPs hydroxylate DHA to 14(R)-HDHADHA + H+ + NADPH + O2 → 14(R)-HDHA + H2O + NADP+
  90. CYP4 ω-oxidises 14(R)-HDHA to MaR-L214(R)-HDHA + NADPH + O2 + H+ → MaR-L2 + H2O + NADP+
  91. CYP2E1 oxidises 14(S)-HDHA to 14(S),21(R)-diHDHA and 14(S),21(S)-diHDHA14(S)-HDHA + NADPH + O2 + H+ → 14(S),21(S/R)-diHDHA + NADP+ + H2O
  92. CYP2E1 oxidises 14(R)-HDHA to 14(R),21(R)-diHDHA and 14(R),21(S)-diHDHA14(R)-HDHA + NADPH + O2 + H+ → 14(R),21(S/R)-diHDHA + NADP+ + H2O
  93. Dehydrogenase dehydrogenates 13-HDHA to 13-oxo-DHA13-HDHA + NADP+ → 13-oxo-DHA + NADPH
  94. PTGS2 dimer oxidises DHA to 13-HDHADHA + O2 + hydrogen donor → 13-HDHA + hydrogen acceptor
  95. Dehydrogenase dehydrogenates 17-HDHA to 17-oxo-DHA17-HDHA + NADP+ → 17-oxo-DHA + NADPH
  96. Dehydrogenase dehydrogenates 13(R)-HDPAn-3 to 13-oxo-DPAn-313(R)-HDPAn-3 + NADP+ → 13-oxo-DPAn-3 + NADPH
  97. Dehydrogenase dehydrogenates 17-HDPAn-3 to 17-oxo-DPAn-317-HDPAn-3 + NADP+ → 17-oxo-DPAn-3 + NADPH
  98. Ac-PTGS2 dimer oxidises DPAn-3 to 17-HDPAn-3O2 + DPAn-3 → 17-HDPAn-3
  99. ALOX5 oxidises DHA to 7-HDHADHA + O2 → 7-HDHA
  100. 5-HEDH dehydrogenates 7-HDPAn-3 to 7-oxo-DPAn-37-HDPAn-3 + NADP+ → 7-oxo-DPAn-3 + NADPH + H+
  101. Ac-PTGS2 dimer oxidises DHA to 17-HDHA (macrophages)DHA + O2 → 17-HDHA
  102. ALOX5 oxidises EPA to 5-HEPEEPA + O2 → 5-HEPE
  103. 5-HEDH dehydrogenates 7-HDHA to 7-oxo-DHA7-HDHA + NADP+ → 7-oxo-DHA + NADPH + H+
  104. 5-HEDH dehydrogenates 5-HEPE to 5-oxo-EPA5-HEPE + NADP+ → 5-oxo-EPA + NADPH + H+
  105. ALOX5 oxidises DPAn-3 to 7-HDPAn-3O2 + DPAn-3 → 7-HDPAn-3
  106. PTGS2 dimer oxidises EPA to PGH3EPA + O2 → PGH3
  107. δ12-PGJ3 spontaneously dehydrates to 15d-PGJ3δ12-PGJ3 → 15d-PGJ3 + H2O
  108. PGJ3 isomerises to δ12-PGJ3PGJ3 → δ12-PGJ3
  109. PGH3 spontaneously dehydrates to PGJ3PGH3 → PGJ3 + H2O
  110. Maresins translocate from cytosol to extracellular regionMaresins → Maresins
  111. Maresin-like SPMs translocate from cytosol to extracellular regionMaresin-like SPMs → Maresin-like SPMs
  112. Protectins translocate from cytosol to extracellular regionProtectins → Protectins
  113. Sulfido conjugates translocate from cytosol to extracellular regionsulfido conjugates → sulfido conjugates
  114. DPAn-3 resolvins translocate from cytosol to extracellular regionDPAn-3 resolvins → DPAn-3 resolvins
  115. DPAn-6 SPMs translocate from cytosol to extracellular regionDPAn-6 SPMs → DPAn-6 SPMs
  116. DPAn-3 maresins translocate from cytosol to extracellular regionDPAn-3 maresins → DPAn-3 maresins
  117. PD1n-3, PD2n-3 translocate from cytosol to extracellular regionPD1n-3DPA,PD2n-3DPA → PD1n-3DPA,PD2n-3DPA
  118. RvT1-4 translocate from cytosol to extracellular regionRvT1-4 → RvT1-4
  119. LTA4 translocates from neutrophil cytosol to platelet cytosolLTA4 → LTA4
  120. LXA4/B4 translocate from cytosol to extracellular regionLXA4/B4 → LXA4/B4
  121. oxo-DHAs translocate from cytosol to extracellular regionoxo-DHAs → oxo-DHAs
  122. oxo-DPAn-3s translocate from cytosol to extracellular regionoxo-DPAn-3s → oxo-DPAn-3s
  123. 5-oxo-EPA, 15d-PGJ3 translocate from cytosol to extracellular region5-oxo-EPA + 15d-PGJ3 → 5-oxo-EPA + 15d-PGJ3
  124. CYP1, CYP2 hydroxylate (N)PD1 to 22-OH-(N)PD1(N)PD1 + H+ + NADPH + O2 → 22-OH-(N)PD1 + H2O + NADP+
  125. ALOX12 oxidises LTA4 to LXB42 LTA4 + O2 + 2 H2O → 2 LXB4