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Biosynthesis of 12-, 14- and 16-membered macrolides

State Icon Reaction EC-Number Confidence maximal confidence score from EnzymeDetector
S-adenosyl-L-methionine + Demethylmacrocin <=> H+ + S-adenosyl-L-homocysteine + macrocin 2.1.1.102 demethylmacrocin O-methyltransferase
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Avermectin_B2b_aglycone + S-adenosyl-L-methionine <=> Avermectin_A2b_aglycone + S-adenosyl-L-homocysteine 2.1.1
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TDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + narbonolide <=> narbomycin + dTDP + H+ 2.4.1.277 10-deoxymethynolide desosaminyltransferase
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Megalomicin_A <=> Megalomicin_B not assigned
 –
Mycinamicin_VIII + O2 + NADPH + H+ <=> Mycinamicin_VII + H2O + NADP+ 1.14.13
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S-adenosyl-L-methionine + L-olivosyl-oleandolide <=> S-adenosyl-L-homocysteine + L-oleandrosyl-oleandolide + H+ 2.1.1.239 L-olivosyl-oleandolide 3-O-methyltransferase
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TDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + L-oleandrosyl-oleandolide <=> oleandomycin + dTDP + H+ 2.4.1
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malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> narbonolide + CoA + CO2 + H2O + NADP+ 2.3.1.240 narbonolide synthase
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6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''1b''''_aglycone + NADPH + O2 <=> 5-Oxoavermectin_''''1b''''_aglycone + NADP+ + H2O 1.14
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S-adenosyl-L-methionine + erythromycin_C <=> S-adenosyl-L-homocysteine + erythromycin + H+ 2.1.1.254 erythromycin 3''-O-methyltransferase
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S-adenosyl-L-methionine + erythromycin_D <=> S-adenosyl-L-homocysteine + erythromycin_B + H+ 2.1.1.254 erythromycin 3''-O-methyltransferase
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8,8a-deoxyoleandolide + 2 NADPH + 2 H+ + 2 O2 <=> Oleandolide + 2 NADP+ + 3 H2O not assigned
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6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''2a''''_aglycone + NADPH + O2 <=> 5-Oxoavermectin_''''2a''''_aglycone + NADP+ + H2O 1.14
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S-adenosyl-L-methionine + mycinamicin_VI <=> S-adenosyl-L-homocysteine + mycinamicin_III + H+ 2.1.1.238 mycinamicin VI 2''-O-methyltransferase
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20-oxo-5-O-beta-mycaminosyltylactone + O2 + reduced_ferredoxin_[iron-sulfur]_cluster + H+ <=> 5-O-beta-mycaminosyltylonolide + H2O + oxidized_ferredoxin 1.14.15.34 20-oxo-5-O-mycaminosyltylactone 23-monooxygenase
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Avermectin_B2b_monosaccharide + dTDP-L-oleandrose <=> Avermectin_B2b + dTDP 2.4.1
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TDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + Protomycinolide_IV <=> Mycinamicin_VIII + dTDP + H+ 2.4.1
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2-methylbutanoyl-CoA + 5 methylmalonyl-CoA + 7 malonyl-CoA + 9 NADPH + 9 H+ <=> 6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''2a''''_aglycone + 12 CO2 + 13 CoA + 5 H2O + 9 NADP+ not assigned
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Avermectin_A2b_monosaccharide + dTDP-L-oleandrose <=> Avermectin_A2b + dTDP 2.4.1
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dTDP-6-deoxy-alpha-D-allose + Mycinamicin_VII <=> mycinamicin_VI + dTDP + H+ 2.4.1
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Mycinamicin_V + O2 + NADPH + H+ <=> mycinamicin_II + H2O + NADP+ 1.14.13
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10-deoxymethymycin + O2 + reduced_ferredoxin_[iron-sulfur]_cluster + H+ <=> methymycin + oxidized_ferredoxin + H2O 1.14.15.33 pikromycin synthase
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Avermectin_A1a_monosaccharide + dTDP-L-oleandrose <=> Avermectin_A1a + dTDP 2.4.1
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10-deoxymethymycin + 4 reduced_ferredoxin_[iron-sulfur]_cluster + 4 H+ + 2 O2 <=> novamethymycin + 4 oxidized_ferredoxin + 2 H2O 1.14.15.33 pikromycin synthase
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10-deoxymethymycin + O2 + reduced_ferredoxin_[iron-sulfur]_cluster + H+ <=> neomethymycin + oxidized_ferredoxin + H2O 1.14.15.33 pikromycin synthase
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isobutyryl-CoA + 5 methylmalonyl-CoA + 7 malonyl-CoA + 9 NADPH + 9 H+ <=> 6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''1b''''_aglycone + 12 CO2 + 13 CoA + 6 H2O + 9 NADP+ not assigned
 –
6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''1a''''_aglycone + NADPH + O2 <=> 5-Oxoavermectin_''''1a''''_aglycone + NADP+ + H2O 1.14
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erythromycin_B + O2 + NADPH + H+ <=> erythromycin + H2O + NADP+ 1.14.13.154 erythromycin 12-hydroxylase
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Avermectin_B1a_aglycone + dTDP-L-oleandrose <=> Avermectin_B1a_monosaccharide + dTDP 2.4.1
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demethyllactenocin + dTDP-beta-L-mycarose <=> Demethylmacrocin + dTDP + H+ 2.4.1.318 demethyllactenocin mycarosyltransferase
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5-O-beta-D-mycaminosyltylactone + 2 NADPH + 2 O2 + 2 H+ <=> 20-oxo-5-O-beta-mycaminosyltylactone + 2 NADP+ + 3 H2O not assigned
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5-Oxoavermectin_''''1a''''_aglycone + NADPH + H+ <=> Avermectin_B1a_aglycone + NADP+ not assigned
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S-adenosyl-L-methionine + macrocin <=> tylosin + S-adenosyl-L-homocysteine + H+ 2.1.1.101 macrocin O-methyltransferase
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malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> 10-deoxymethynolide + CoA + CO2 + H2O + NADP+ 2.3.1.239 10-deoxymethynolide synthase
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Avermectin_B1a_aglycone + S-adenosyl-L-methionine <=> Avermectin_A1a_aglycone + S-adenosyl-L-homocysteine 2.1.1
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Avermectin_A2a_aglycone + dTDP-L-oleandrose <=> Avermectin_A2a_monosaccharide + dTDP 2.4.1
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Avermectin_B1a_monosaccharide + dTDP-L-oleandrose <=> avermectin_B1a + dTDP 2.4.1
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Avermectin_B2b_aglycone + dTDP-L-oleandrose <=> Avermectin_B2b_monosaccharide + dTDP 2.4.1
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Megalomicin_A <=> Megalomicin_C1 not assigned
 –
TDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + 10-deoxymethynolide <=> 10-deoxymethymycin + dTDP + H+ 2.4.1.277 10-deoxymethynolide desosaminyltransferase
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Avermectin_B2a_aglycone + S-adenosyl-L-methionine <=> Avermectin_A2a_aglycone + S-adenosyl-L-homocysteine 2.1.1
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isobutyryl-CoA + 5 methylmalonyl-CoA + 7 malonyl-CoA + 9 NADPH + 9 H+ <=> 6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''2b''''_aglycone + 12 CO2 + 13 CoA + 5 H2O + 9 NADP+ not assigned
 –
Avermectin_A1b_monosaccharide + dTDP-L-oleandrose <=> Avermectin_A1b + dTDP 2.4.1
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Oleandolide + dTDP-L-olivose <=> L-olivosyl-oleandolide + dTDP + H+ 2.4.1
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Avermectin_A1b_aglycone + dTDP-L-oleandrose <=> Avermectin_A1b_monosaccharide + dTDP 2.4.1
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propionyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> 6-Deoxyerythronolide_b + CoA + CO2 + H2O + NADP+ 2.3.1.94 6-deoxyerythronolide-B synthase
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Avermectin_A1a_aglycone + dTDP-L-oleandrose <=> Avermectin_A1a_monosaccharide + dTDP 2.4.1
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Avermectin_B1b_monosaccharide + dTDP-L-oleandrose <=> avermectin_B1b + dTDP 2.4.1
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erythromycin_C + dTDP-L-megosamine <=> Megalomicin_A + dTDP + H+ 2.4.1
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Avermectin_A2b_aglycone + dTDP-L-oleandrose <=> Avermectin_A2b_monosaccharide + dTDP 2.4.1
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Avermectin_B1b_aglycone + S-adenosyl-L-methionine <=> Avermectin_A1b_aglycone + S-adenosyl-L-homocysteine 2.1.1
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narbomycin + O2 + reduced_ferredoxin_[iron-sulfur]_cluster + H+ <=> pikromycin + oxidized_ferredoxin + H2O 1.14.15.33 pikromycin synthase
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erythromycin + O2 <=> Erythromycin_E + H2O not assigned
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5-Oxoavermectin_''''2a''''_aglycone + NADPH + H+ <=> Avermectin_B2a_aglycone + NADP+ not assigned
 –
Avermectin_B2a_aglycone + dTDP-L-oleandrose <=> Avermectin_B2a_monosaccharide + dTDP 2.4.1
–
Megalomicin_A <=> Megalomicin_C2 not assigned
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5-Oxoavermectin_''''1b''''_aglycone + NADPH + H+ <=> Avermectin_B1b_aglycone + NADP+ not assigned
 –
erythromycin_D + O2 + NADPH + H+ <=> erythromycin_C + H2O + NADP+ 1.14.13.154 erythromycin 12-hydroxylase
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2-methylbutanoyl-CoA + 5 methylmalonyl-CoA + 7 malonyl-CoA + 9 NADPH + 9 H+ <=> 6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''1a''''_aglycone + 12 CO2 + 13 CoA + 6 H2O + 9 NADP+ not assigned
 –
6,8a-Seco-6,8a-deoxy-5-oxoavermectin_''''2b''''_aglycone + NADPH + O2 <=> 5-Oxoavermectin_''''2b''''_aglycone + NADP+ + H2O 1.14
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narbomycin + O2 + reduced_ferredoxin_[iron-sulfur]_cluster + H+ <=> neopikromycin + oxidized_ferredoxin + H2O 1.14.15.33 pikromycin synthase
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tylactone + dTDP-3-dimethylamino-3,6-dideoxy-alpha-D-glucopyranose <=> 5-O-beta-D-mycaminosyltylactone + dTDP + H+ 2.4.1.316 tylactone mycaminosyltransferase
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Avermectin_B1b_aglycone + dTDP-L-oleandrose <=> Avermectin_B1b_monosaccharide + dTDP 2.4.1
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narbomycin + 4 reduced_ferredoxin_[iron-sulfur]_cluster + 4 H+ + 2 O2 <=> novapikromyin + 4 oxidized_ferredoxin + 2 H2O 1.14.15.33 pikromycin synthase
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Avermectin_A2a_monosaccharide + dTDP-L-oleandrose <=> Avermectin_A2a + dTDP 2.4.1
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mycinamicin_IV + O2 + NADPH + H+ <=> Mycinamicin_V + H2O + NADP+ 1.14.13
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6-Deoxyerythronolide_b + O2 + reduced_ferredoxin_[iron-sulfur]_cluster + H+ <=> erythronolide_B + H2O + oxidized_ferredoxin 1.14.15.35 6-deoxyerythronolide B hydroxylase
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S-adenosyl-L-methionine + mycinamicin_III <=> S-adenosyl-L-homocysteine + mycinamicin_IV + H+ 2.1.1.237 mycinamicin III 3''-O-methyltransferase
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dTDP-beta-L-mycarose + erythronolide_B <=> 3-alpha-mycarosylerythronolide_B + dTDP + H+ 2.4.1.328 erythronolide mycarosyltransferase
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malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ + (2S)-ethylmalonyl-CoA <=> tylactone + CoA + CO2 + H2O + NADP+ 2.3.1
–
5-Oxoavermectin_''''2b''''_aglycone + NADPH + H+ <=> Avermectin_B2b_aglycone + NADP+ not assigned
 –
TDP-3-dimethylamino-4,6-dideoxy-alpha-D-glucopyranose + 3-alpha-mycarosylerythronolide_B <=> erythromycin_D + dTDP + H+ 2.4.1.278 3-alpha-mycarosylerythronolide B desosaminyl transferase
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malonyl-CoA + 6 methylmalonyl-CoA + 6 NADPH + 6 H+ <=> 8,8a-deoxyoleandolide + 7 CoA + 7 CO2 + H2O + 6 NADP+ not assigned
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5-O-beta-mycaminosyltylonolide + dTDP-6-deoxy-alpha-D-allose <=> demethyllactenocin + dTDP + H+ 2.4.1.317 O-mycaminosyltylonolide 6-deoxyallosyltransferase
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Avermectin_B2a_monosaccharide + dTDP-L-oleandrose <=> Avermectin_B2a + dTDP 2.4.1
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Visualization of the pathway