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DraconiticBiochemistryBiomolecules · Catabolism · Biosynthesis · MetabolismMap
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Phase I functionalization

Oxidation, reduction and hydrolysis that expose or introduce functional groups. 104 reactions, from Reactome R-HSA-211945.

  1. FMO3:FAD N-oxidises TMA to TMAOTMA + O2 + NADPH + H+ → TMAO + H2O + NADP+
  2. Arachidonate is oxidised to PGG2 by PTGS12 O2 + AA → PGG2
  3. PGG2 is reduced to PGH2 by PTGS1PGG2 + hydrogen donor → H2O + PGH2 + hydrogen acceptor
  4. MAOA:FAD oxidatively deaminates of 5HTO2 + H2O + 5HT → 5HIALD + H2O2 + NH4+
  5. MAOB:FAD oxidatively deaminates of PEAPEA + H2O + O2 → Phenylacetaldehyde + NH3 + H2O2
  6. MAOB:FAD oxidatively deaminates TYRTYR + H2O + O2 → HPHAC + NH3 + H2O2
  7. SMOX-3 oxidises SPN to SPMSPN + H2O + O2 → SPM + 3APAL + H2O2
  8. PAO:FAD oxidises NASPM to PTCNNASPM + H2O + O2 → PTCN + H2O2 + 3AAPNAL
  9. PAOX:FAD oxidises NASPN to SPMNASPN + H2O + O2 → SPM + H2O2 + 3AAPNAL
  10. MEOS oxidizes ethanol to acetaldehydeEtOH + NADPH + H+ + O2 → CH3CHO + 2 H2O + NADP+
  11. CYP7A1 7-hydroxylates CHOLCHOL + NADPH + H+ + O2 → H2O + NADP+ + 7 alpha-hydroxycholesterol
  12. CYP46A1 24-hydroxylates CHOLCHOL + NADPH + H+ + O2 → 24OH-CHOL + NADP+ + H2O
  13. CYP7B1 7-hydroxylates 25OH-CHOL25OH-CHOL + NADPH + H+ + O2 → CHOL3b,7a,25TRIOL + H2O + NADP+
  14. CYP27A1 27-hydroxylates CHOLCHOL + NADPH + H+ + O2 → 27OH-CHOL + H2O + NADP+
  15. CYP8B1 12-hydroxylates 4CHOL7aOLONE4CHOL7aOLONE + NADPH + H+ + O2 → 4CHOL7a,12aDONE + NADP+ + H2O
  16. CYP39A1 7-hydroxylates 24OH-CHOL24OH-CHOL + O2 + hydrogen donor → CHOL7a,24(S)DIOL + H2O + hydrogen acceptor + H+
  17. CYP19A1 hydroxylates ANDST to E1ANDST + 3 NADPH + 3 H+ + 3 O2 → 4 H+ + E1 + 3 NADP+ + 4 H2O + HCOOH
  18. CYP11A1 cleaves 20a,22b-DHCHOL20a,22b-DHCHOL + O2 + 2 CYP11A1:FDXR:FDX1,FDX1L (red.) + 2 NADPH + 2 H+ → PREG + ISCAL + 2 H2O + 2 CYP11A1:FDXR:FDX1,FDX1L (ox.) + 2 NADP+
  19. CYP8B1 12-hydroxylates 4CHOL7a,27DONE4CHOL7a,27DONE + NADPH + H+ + O2 → 4CHOL7a,12a,27TONE + NADP+ + H2O
  20. CYP21A2 21-hydroxylates PROGP4 + NADPH + H+ + O2 → 11DCORST + NADP+ + H2O
  21. CYP11B2 oxidises 18HCORST to ALDO18HCORST + 2 NADPH + 2 H+ + O2 → ALDO + 2 NADP+ + 2 H2O
  22. CYP11B2 18-hydroxylates CORST to 18HCORSTCORST + 2 NADPH + 2 H+ + O2 → 18HCORST + 2 NADP+ + H2O
  23. CYP11B1 oxidises 11DCORT11DCORT + 2 NADPH + 2 H+ + O2 → CORT + 2 NADP+ + H2O
  24. CYP11B2 oxidises 11DCORST to CORST11DCORST + 2 NADPH + 2 H+ + O2 → CORST + H2O + 2 NADP+
  25. CYP51A1 demethylates LANLAN + 3 H+ + 3 NADPH + 3 O2 → 4,4DMCHtOL + HCOOH + 4 H2O + 3 NADP+
  26. CYP2R1 25-hydroxylates VD3 to 25(OH)DVD3 + O2 + H+ + NADPH → 25(OH)D + H2O + NADP+
  27. CYP27B1 hydroxylates 25(OH)D to 1,25(OH)2D25(OH)D + H+ + NADPH + O2 → 1,25(OH)2D + H2O + NADP+
  28. CYP4F2, 4F3 20-hydroxylate LTB4LTB4 + NADPH + H+ + O2 → 20OH-LTB4 + H2O + NADP+
  29. CYP2S1 4-hydroxylates atRAatRA + NADPH + H+ + O2 → 4OH-atRA + NADP+ + H2O
  30. Coumarin is 7-hydroxylated by CYP2A13COUM + O2 + NADPH + H+ → HCOU + H2O + NADP+
  31. CYP3A7 can 6beta-hydroxylate testosteroneTES + NADPH + H+ + O2 → 6BHT + H2O + NADP+
  32. CYP4F12 18-hydroxylates ARAAA + O2 + NADPH + H+ → 18OH-ARA + H2O + NADP+
  33. CYP2C8 inactivates paclitaxel by 6alpha-hydroxylationPTXL + O2 + NADPH + H+ → HPTXL + H2O + NADP+
  34. CYP4F8 19-hydroxylates PGH2PGH2 + NADPH + H+ + O2 → NADP+ + H2O + 19OH-PGH2
  35. CYP26C1 4-hydroxylates 9cRA9cRA + NADPH + H+ + O2 → 4OH-9cRA + NADP+ + H2O
  36. CYP4B1 12-hydroxylates ARAAA + H+ + NADPH + O2 → 12-HETE + NADP+ + H2O
  37. CYP2C19 5-hydroxylates omeprazoleLosec + NADPH + H+ + O2 → HOMZ + NADP+ + H2O
  38. CYP3A4 can N-demethylate loperamideLPAM + H+ + NADPH + O2 → N-demethylated loperamide + H2O + NADP+
  39. CYP24A1 24-hydroxylates CTLCTL + NADPH + H+ + O2 → CTLA + NADP+ + H2O
  40. CYP1B1 4-hydroxylates EST17bEST17b + H+ + NADPH + O2 → 4OH-EST17b + H2O + NADP+
  41. CYP3A43 6b-hydroxylates TESTTES + NADPH + H+ + O2 → H2O + NADP+ + 6BHT
  42. CYP2U1 19-hydroxylates ARAAA + NADPH + H+ + O2 → 19HETE + H2O + NADP+
  43. CYP4F11 16-hydroxylates 3OH-PALM3OH-PALM + NADPH + H+ + O2 → 3,16DOH-PALM + NADP+ + H2O
  44. CYP2D6 4-hydroxylates debrisoquineDSQ + O2 + NADPH + H+ → HDBQ + H2O + NADP+
  45. CYP2W1 oxidises INDOLINDOL + NADPH + H+ + O2 → Oxindole + NADP+ + H2O
  46. CYP2J2 oxidises ARAAA + NADPH + H+ + O2 → cis-EET + NADP+ + H2O
  47. CYP2C9 inactivates tolbutamide by 4methyl-hydroxylationO2 + NADPH + H+ + TBM → HTOLB + H2O + NADP+
  48. Cyclophosphamide is 4-hydroxylated by CYP2B6CPM + O2 + NADPH + H+ → HCPM + H2O + NADP+
  49. CYP2C18 initiates bioactivation of phenytoin by 4-hydroxylationPhenytoin + O2 + NADPH + H+ → HPHT + H2O + NADP+
  50. CYP2F1 dehydrogenates 3-methylindoleMIND + H+ + NADPH + O2 → 3MEIN + H2O + NADP+
  51. CYP26A1,B1 4-hydroxylate atRAatRA + NADPH + H+ + O2 → 4OH-atRA + H2O + NADP+
  52. CYP3A4,5 oxidise AFB1 to AFXBOAFB1 + O2 + NADPH + H+ → AFXBO + H2O + NADP+
  53. CYP4F3 20-hydroxylates LTB4LTB4 + NADPH + H+ + O2 → 20OH-LTB4 + H2O + NADP+
  54. FMO1:FAD N-oxidises TAMO2 + NADPH + H+ + TAM → TAMO + H2O + NADP+
  55. FMO2:FAD:Mg2+ S-oxidises MTZMTZ + NADPH + H+ + O2 → MTZ-SOX + NADP+ + H2O
  56. acetaldehyde [cytosolic] => acetaldehyde [mitochondrial]CH3CHO → CH3CHO
  57. acetate + CoA + ATP => acetyl-CoA + AMP + pyrophosphate [mitochondrial]ATP + CH3COO- + CoA-SH → Ac-CoA + AMP + PPi
  58. CYP4F22 20-hydroxylates TrXA3H+ + NADPH + O2 + TrXA3 → H2O + NADP+ + 20OH-TrXA3
  59. AADAC deacetylates PHENPHEN + H2O → 4-ethoxyaniline + acetyl group
  60. ADH5 oxidises S-HMGSH to S-FGSHNAD+ + S-HMGSH → S-FGSH + H+ + NADH
  61. ALD3A1 oxidises 4HPCP to CXPA4HPCP + H2O + NADP+ → CXPA + H+ + NADPH
  62. CES1 trimer.CES2 hydrolyse COCN to BEGH2O + COCN → BEG + MeOH + H+
  63. EPHX1 hydrates BaP4,5O to BaP4,5-DHDBaP4,5O + H2O → BaP4,5-DHD
  64. ALDH1B1 tetramer oxidises CH3CHO to CH3COOHCH3CHO + H2O + NAD+ → CH3COO- + H+ + NADH
  65. AOC1 deaminates HistHist + H2O + O2 → I4AH + NH3 + H2O2 + H+
  66. AOC2 deaminates TYRTYR + H2O + O2 → 4HPAA + NH3 + H2O2 + H+
  67. AOC3 deaminates BZAMBZAM + H2O + O2 → NH3 + H2O2 + H+ + BZAL
  68. BPHL hydrolyses VACV to ACVVACV + H2O → ACV + L-Val
  69. CMBL hydrolyses OM to OLMSOM + H2O → diketone + OLMS
  70. CYP4V2 omega-hydroxylates DHA to HDoHEDHA + H+ + NADPH + O2 → HDoHE + H2O + NADP+
  71. acetaldehyde + NAD+ => acetate + NADH + H+ [cytosolic]CH3CHO + NAD+ + H2O → CH3COO- + NADH + H+
  72. ethanol + NAD+ => acetaldehyde + NADH + H+EtOH + NAD+ → CH3CHO + NADH + H+
  73. acetaldehyde + NAD+ => acetate + NADH + H+ [mitochondrial]CH3CHO + H2O + NAD+ → CH3COO- + H+ + NADH
  74. acetate + CoA + ATP => acetyl-CoA + AMP + pyrophosphate [cytosolic]ATP + CH3COO- + CoA-SH → AMP + PPi + Ac-CoA
  75. Vinyl chloride is oxidized to 2-Chloroethylene oxideVC + NADPH + H+ + O2 → H2O + NADP+ + 2CEO
  76. N-hydroxylation of 4-aminobiphenylABPH + O2 + NADPH + H+ → NHABP + H2O + NADP+
  77. Acetaminophen oxidised to N-acetylbenzoquinoneimine (NAPQI)Acetaminophen (TN TYLENOL) + NADP+ + H2 + O2 → NABQI + H2O + NADPH
  78. Benzene is hydroxylated to phenolC6H6 + O2 + NADPH + H+ → PhOH + H2O + NADP+
  79. N-atom dealkylation of caffeineCAF + O2 + NADPH + H+ → Paraxanthine + H2O + NADP+ + CH2O
  80. Dehalogenation of carbon tetrachloride to form a free radicalCCl4 → Trichloromethyl radical + Cl-
  81. Coumarin is 7-hydroxylated by CYP2A6COUM + O2 + NADPH + H+ → HCOU + H2O + NADP+
  82. O-atom dealkylation of dextromethorphanDEXM + NADPH + O2 + H+ → DEXT + H2O + NADP+ + CH2O
  83. CYP4A11 omega-hydroxylates DDCXDDCX + O2 + NADPH + H+ → 12OH-DDCX + H2O + NADP+
  84. Ethylene is oxidized to Ethylene oxide by CYP1A1C2H4 + O2 + NADPH + H+ → EtO + H2O + NADP+
  85. Dehalogenation of the poly-halogenated hydrocarbon Halothane to form the acylhalide Trifluoroacetlychloride and hydrogen bromideHALO + NADPH + H+ + O2 → TFAC + HBr + NADP+ + H2O
  86. POR reduces CYP450:Fe3+ to CYP450:Fe2+NADPH + 2 CYP450:Fe3+ → NADP+ + 2 CYP450:Fe2+ + H+
  87. PTGIS, CYP8A1 isomerise PGH2 to PGI2PGH2 → PGI2
  88. TBXAS1 isomerises PGH2 to TXA2PGH2 → TXA2
  89. MARC1,MARC2 reduce N-hydroxylated compoundsNOHA + H+ + NADH → L-Arg + NAD+ + H2O
  90. NQO2:FAD dimer reduces quinones to hydroquinonesquinone + RFDHN → hydroquinone + RFNA
  91. AHR:2xHSP90:AIP:PTGES3 binds TCDDAHR:2xHSP90AB1:AIP:PTGES3 + TCDD → AHR:TCDD:2xHSP90AB1:AIP:PTGES3
  92. AHRR binds ARNTAHRR + ARNT, ARNT2 → AHRR:ARNT
  93. AHR:TCDD:2xHSP90AB1:AIP:PTGES3 translocates from cytosol to nucleoplasmAHR:TCDD:2xHSP90AB1:AIP:PTGES3 → AHR:TCDD:2xHSP90AB1:AIP:PTGES3
  94. AHR:TCDD binds ARNTAHR:TCDD + ARNT, ARNT2 → AHR:TCDD:ARNT
  95. AHR:TCDD:2xHSP90AB1:AIP:PTGES3 dissociatesAHR:TCDD:2xHSP90AB1:AIP:PTGES3 → AHR:TCDD + 2xHSP90AB1:AIP:PTGES3
  96. CBR3 reduces DOX to DOXOLNADPH + doxorubicin → DOXOL + NADP+
  97. CES3 hydrolyses CHEST to CHOL and LCFA(-)H2O + CHEST → CHOL + LCFA(-)
  98. MAOA inhibitors bind MAOA:FADMAOA:FAD + MAOA Inhibitors → MAOA:FAD:MAOA Inhibitors
  99. MAOB inhibitors bind MAOB:FADMAOB:FAD + MAOB Inhibitors → MAOB:FAD:MAOB Inhibitors
  100. CYP3A4 binds CYP3A4 inhibitorsCYP3A4 + CYP3A4 inhibitors → CYP3A4:CYP3A4 inhibitors
  101. CYP3A4, CYP2B6 bind ritonavirCYP3A4, CYP2B6 + ritonavir → CYP3A4,CYP2B6:ritinovir
  102. Unknown CYP 450 omega-hydroxylates C10 fatty acidO2 + NADPH + DECA → H2O + NADP+ + 10-OH-DECA + H+
  103. ADH7 dehydrogenates 10-OH-DECANAD+ + 10-OH-DECA → 10-oxo-DECA + NADH + H+
  104. Unknown ALDH oxidizes 10-oxo-DECAH2O + 10-oxo-DECA + NAD+ → 2 H+ + sebacate + NADH