|
|
ATP + propionyl-CoA + HCO3- <=> H+ + (S)-methylmalonyl-CoA + phosphate + ADP
|
6.4.1.2
acetyl-CoA carboxylase
6.4.1.3
propionyl-CoA carboxylase
|
–
–
|
BMK
|
|
BRENDA:
BR155
KEGG:
R01859
MetaCyc:
PROPIONYL-COA-CARBOXY-RXN
SABIO-RK:
1929
|
|
|
|
(R)-2-methylmalonyl-CoA <=> (S)-methylmalonyl-CoA
|
5.1.99.1
methylmalonyl-CoA epimerase
|
–
|
BMK
|
|
BRENDA:
BR204;
BS970
KEGG:
R02765
MetaCyc:
METHYLMALONYL-COA-EPIM-RXN
SABIO-RK:
2642
|
|
|
|
(S)-methylmalonyl-CoA + H+ + Na+ <=> CO2 + propionyl-CoA + Na+
|
7.2.4.3
(S)-methylmalonyl-CoA decarboxylase (sodium-transporting)
|
–
|
M
|
|
BRENDA:
BR301
MetaCyc:
RXN-19738
|
|
|
|
pyruvate + (S)-methylmalonyl-CoA <=> oxaloacetate + propionyl-CoA
|
2.1.3.1
methylmalonyl-CoA carboxytransferase
|
–
|
BMK
|
|
BRENDA:
BR43948
KEGG:
R00930
MetaCyc:
2.1.3.1-RXN
|
|
|
|
propionyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> 6-Deoxyerythronolide_b + CoA + CO2 + H2O + NADP+
|
2.3.1.94
6-deoxyerythronolide-B synthase
|
–
|
MK
|
|
BRENDA:
BR44097
KEGG:
R00918
MetaCyc:
ERYTHRONOLIDE-SYNTHASE-RXN
|
|
|
|
H2O + (S)-methylmalonyl-CoA <=> H+ + CoA + methylmalonate
|
3.1.2.17
(S)-methylmalonyl-CoA hydrolase
3.1.2.20
acyl-CoA hydrolase
3.1.2.4
3-hydroxyisobutyryl-CoA hydrolase
|
–
–
–
|
K
|
|
BRENDA:
BR47932;
BS401387
KEGG:
R02764
MetaCyc:
S-METHYLMALONYL-COA-HYDROLASE-RXN
SABIO-RK:
11293;
2641
|
|
|
|
malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> 10-deoxymethynolide + CoA + CO2 + H2O + NADP+
|
2.3.1.239
10-deoxymethynolide synthase
|
–
|
MK
|
|
BRENDA:
BR51189
KEGG:
R06458
MetaCyc:
RXN-15103
|
|
|
|
malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> narbonolide + CoA + CO2 + H2O + NADP+
|
2.3.1.240
narbonolide synthase
|
–
|
MK
|
|
BRENDA:
BR51190
KEGG:
R06459
MetaCyc:
RXN-15105
|
|
|
|
a_palmitoyl-[(hydroxy)phthioceranic_acid_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> C40-phthioceranyl-[(hydroxy)phthioceranic_acid_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.287
phthioceranic/hydroxyphthioceranic acid synthase
|
–
|
|
|
BRENDA:
BR52737
KEGG:
R12380
MetaCyc:
RXN-17321
|
|
|
|
a_palmitoyl-[(hydroxy)phthioceranic_acid_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> C37-phthioceranyl-[(hydroxy)phthioceranic_acid_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.287
phthioceranic/hydroxyphthioceranic acid synthase
|
–
|
|
|
BRENDA:
BR52738
KEGG:
R12381
MetaCyc:
RXN-17202
|
|
|
|
4-nitrobenzoyl-CoA + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> demethylluteothin + CO2 + CoA + NADP+ + H2O
|
2.3.1.289
aureothin polyketide synthase system
|
–
|
|
|
BRENDA:
BR52829
KEGG:
R12467
MetaCyc:
RXN-20241
|
|
|
|
4-nitrobenzoyl-CoA + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> demethyldeoxyspectinabilin + CO2 + CoA + NADP+ + H2O
|
2.3.1.290
spectinabilin polyketide synthase system
|
–
|
|
|
BRENDA:
BR52830
KEGG:
R12468
MetaCyc:
RXN-20242
|
|
|
|
19-(4-hydroxyphenyl)nonadecanoyl-[(phenol)carboxyphthiodiolenone_synthase] + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> C37-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone_synthase] + CO2 + CoA + NADP+ + H2O
|
2.3.1.292
(phenol)carboxyphthiodiolenone synthase
|
–
|
M
|
|
BRENDA:
BR52913
MetaCyc:
RXN-17246
|
|
|
|
17-(4-hydroxyphenyl)heptadecanoyl-[(phenol)carboxyphthiodiolenone_synthase] + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> C35-(phenol)carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone_synthase] + CO2 + CoA + NADP+ + H2O
|
2.3.1.292
(phenol)carboxyphthiodiolenone synthase
|
–
|
M
|
|
BRENDA:
BR52914
MetaCyc:
RXN-17215
|
|
|
|
(S)-methylmalonyl-CoA + H+ <=> CO2 + propionyl-CoA
|
2.3.1.226
carboxymethylproline synthase
4.1.1
4.1.1.9
malonyl-CoA decarboxylase
4.1.1.94
ethylmalonyl-CoA decarboxylase
4.1.1.M5
6.4.1.3
propionyl-CoA carboxylase
|
–
–
–
–
–
–
|
BMK
|
|
BRENDA:
BS1620;
BS410118
KEGG:
R00923;
R05373
MetaCyc:
METHYLMALONYL-COA-DECARBOXYLASE-RXN;
RXN0-310
SABIO-RK:
4979
|
|
|
|
malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ + (2S)-ethylmalonyl-CoA <=> tylactone + CoA + CO2 + H2O + NADP+
|
2.3.1
|
–
|
MK
|
|
KEGG:
R06448
MetaCyc:
RXN-15064
|
|
|
|
long-chain_fatty_acyl-[mycocerosate_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> tetramethylated_mycocerosyl-[mycocerosate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.111
mycocerosate synthase
|
–
|
|
|
MetaCyc:
MYCOCEROSATE-SYNTHASE-RXN
|
|
|
|
acetyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> 8,8a-deoxyoleandolide + CO2 + CoA + H2O + NADP+
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-12914
|
|
|
|
malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> spinosyn_macrolactone + CO2 + CoA + H2O + NADP+
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-13625
|
|
|
|
malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> Protomycinolide_IV + CoA + CO2 + H2O + NADP+
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-15055
|
|
|
|
4-aminobenzoyl-CoA + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> candicinolide + CoA + CO2 + H2O + NADP+
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-15954
|
|
|
|
acetyl-CoA + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> decarboxy-dehydroxy-demycosaminyl-nystatin + CoA + CO2 + H2O + NADP+
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-16253
|
|
|
|
arachidoyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ + holo_mycolipanoate_synthase <=> C29-mycolipanoyl-[mycolipanoate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.252
mycolipanoate synthase
|
–
|
|
|
MetaCyc:
RXN-17180
|
|
|
|
stearoyl-[mycocerosate_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> C30-mycocerosyl-[mycocerosate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.111
mycocerosate synthase
|
–
|
|
|
MetaCyc:
RXN-17184
|
|
|
|
icosanoyl-[mycocerosate_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> C32-mycocerosyl-[mycocerosate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.111
mycocerosate synthase
|
–
|
|
|
MetaCyc:
RXN-17185
|
|
|
|
stearoyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ + holo_mycolipanoate_synthase <=> C27-mycolipanoyl-[mycolipanoate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.252
mycolipanoate synthase
|
–
|
|
|
MetaCyc:
RXN-17186
|
|
|
|
heptanoyl-CoA + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> C32-mycoketide-CoA + CoA + CO2 + NADP+ + H2O
|
2.3.1.295
mycoketide-CoA synthase
|
–
|
|
|
MetaCyc:
RXN-17206
|
|
|
|
behenoyl-[(phenol)carboxyphthiodiolenone_synthase] + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> C34-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone_synthase] + NADP+ + H2O + CO2 + CoA
|
2.3.1.292
(phenol)carboxyphthiodiolenone synthase
|
–
|
M
|
|
MetaCyc:
RXN-17222
|
|
|
|
arachidoyl-[(phenol)carboxyphthiodiolenone_synthase] + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> C32-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone_synthase] + CoA + CO2 + H2O + NADP+
|
2.3.1.292
(phenol)carboxyphthiodiolenone synthase
|
–
|
|
|
MetaCyc:
RXN-17224
|
|
|
|
stearoyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ + holo_mycolipanoate_synthase <=> mycolipanoyl-[mycolipanoate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.252
mycolipanoate synthase
|
–
|
M
|
|
MetaCyc:
RXN-17254
|
|
|
|
palmitoleoyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> 2-methyl-octadec-2,9-dienoate + CoA + CO2 + NADP+
|
2.3.1.M8
|
–
|
|
|
MetaCyc:
RXN-17257
|
|
|
|
a_long-chain_acyl-[(phenol)carboxyphthiodiolenone_synthase] + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone_synthase] + NADP+ + H2O + CO2 + CoA
|
2.3.1.292
(phenol)carboxyphthiodiolenone synthase
|
–
|
|
|
MetaCyc:
RXN-17272
|
|
|
|
medium-chain_fatty_acyl-CoA + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> a_mycoketide-CoA + CoA + CO2 + NADP+ + H2O
|
2.3.1.295
mycoketide-CoA synthase
|
–
|
M
|
|
MetaCyc:
RXN-17308
|
|
|
|
a_palmitoyl-[(hydroxy)phthioceranic_acid_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> C37-hydroxyphthioceranyl-[(hydroxy)phthioceranate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.287
phthioceranic/hydroxyphthioceranic acid synthase
|
–
|
M
|
|
MetaCyc:
RXN-17323
|
|
|
|
a_palmitoyl-[(hydroxy)phthioceranic_acid_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> C40-hydroxyphthioceranyl-[(hydroxy)phthioceranate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.287
phthioceranic/hydroxyphthioceranic acid synthase
|
–
|
|
|
MetaCyc:
RXN-17324
|
|
|
|
long-chain_fatty_acyl-[mycocerosate_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> trimethylated_mycocerosyl-[mycocerosate_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.111
mycocerosate synthase
|
–
|
|
|
MetaCyc:
RXN-18051
|
|
|
|
long-chain_fatty_acyl-[mycocerosate_synthase] + (S)-methylmalonyl-CoA + NADPH + H+ <=> a_mycocerosyl-[mycocerosic_acid_synthase] + CoA + CO2 + NADP+ + H2O
|
2.3.1.111
mycocerosate synthase
|
–
|
M
|
|
MetaCyc:
RXN-18052
|
|
|
|
holo-[aureothin_polyketide_synthase] + 4-nitrobenzoyl-CoA + malonyl-CoA + (S)-methylmalonyl-CoA + NADPH + H+ <=> (8E,10E)-2,4,8,10-tetramethyl-11-(4-nitrophenyl)-3,5-dioxoundeca-8,10-dienoyl-[aureothin_polyketide_synthase] + CO2 + CoA + NADP+ + H2O
|
not assigned
|
–
|
M
|
|
MetaCyc:
RXN-20206
|
|
|
|
holo-[spectinabilin_polyketide_synthase] + 4-nitrobenzoyl-CoA + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> (2Z,4Z,8E,10E,12E,14E)-3,5-dihydroxy-2,4,8,10,12,14-hexamethyl-15-(4-nitrophenyl)pentadeca-2,4,8,10,12,14-hexaenoyl-[spectinabilin_polyketide_synthase] + CO2 + CoA + NADP+ + H2O
|
not assigned
|
–
|
M
|
|
MetaCyc:
RXN-20234
|
|
|
|
3-amino-5-hydroxybenzoyl-[streptovaricin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> tetraketide-[streptovaricin_PKS] + CoA + NADP+ + CO2
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-20269
|
|
|
|
7-(5-amino-3,6-dioxocyclohexa-1,4-dien-1-yl)-7-hydroxy-2,6-dimethyl-3,5-dioxoheptanoyl-[streptovaricin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> undecaketide-[streptovaricin-PKS] + CoA + NADP+ + CO2 + H2O
|
not assigned
|
–
|
M
|
|
MetaCyc:
RXN-20272
|
|
|
|
7-(5-amino-3,6-dioxocyclohexa-1,4-dien-1-yl)-7-hydroxy-2,6-dimethyl-3,5-dioxoheptanoyl-[chaxamycin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> undecaketide-[chaxamycin-PKS] + CoA + NADP+ + CO2 + H2O
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-20287
|
|
|
|
3-amino-5-hydroxybenzoyl-[chaxamycin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> tetraketide-[chaxamycin_PKS] + CoA + NADP+ + CO2
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-20290
|
|
|
|
7-(5-amino-3,6-dioxocyclohexa-1,4-dien-1-yl)-7-hydroxy-2,6-dimethyl-3,5-dioxoheptanoyl-[naphthomycin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> tetradecaketide-[naphthomycin-PKS] + CoA + NADP+ + CO2 + H2O
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-20305
|
|
|
|
3-amino-5-hydroxybenzoyl-[naphthomycin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> tetraketide-[naphthomycin_PKS] + CoA + NADP+ + CO2
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-20308
|
|
|
|
3-amino-5-hydroxybenzoyl-[ansatrienin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> nonaketide-[ansatrienin_PKS] + CoA + NADP+ + CO2 + H2O
|
2.3.1.M77
|
–
|
M
|
|
MetaCyc:
RXN-20327
|
|
|
|
3-amino-5-hydroxybenzoyl-[rifamycin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> tetraketide-[rifamycin_PKS] + CoA + NADP+ + CO2
|
2.3.1
|
–
|
M
|
|
MetaCyc:
RXN-9594
|
|
|
|
7-(5-amino-3,6-dioxocyclohexa-1,4-dien-1-yl)-7-hydroxy-2,6-dimethyl-3,5-dioxoheptanoyl-[rifamycin_PKS] + (S)-methylmalonyl-CoA + malonyl-CoA + NADPH + H+ <=> undecaketide-[rifamycin-PKS] + CoA + NADP+ + CO2 + H2O
|
not assigned
|
–
|
M
|
|
MetaCyc:
RXN-9602
|
|
|
|
GTP + propionyl-CoA + HCO3- <=> GDP + phosphate + (S)-methylmalonyl-CoA
|
6.4.1.3
propionyl-CoA carboxylase
|
–
|
|
|
BRENDA:
BS369193
|
|
|
|
propionyl-CoA + 5 (S)-methylmalonyl-CoA + (2S)-ethylmalonyl-CoA + 6 NADPH + 6 H+ <=> 8-ethyl-8-desmethyl-6-deoxyerythronolide_B + 7 CoA + 6 CO2 + H2O + 6 NADP+
|
2.3.1.94
6-deoxyerythronolide-B synthase
|
–
|
|
|
BRENDA:
BS435754
|
|
|
|
palmitoyl-CoA + 3 (S)-methylmalonyl-CoA + 6 NADPH + 6 H+ + holo-[mycolipanoate_synthase] <=> mycolipanoyl-[mycolipanoate_synthase] + 4 CoA + 3 CO2 + 6 NADP+ + 3 H2O
|
2.3.1.252
mycolipanoate synthase
|
–
|
|
|
BRENDA:
BR51705
|
|
|
|
hexanoyl-CoA + 5 malonyl-CoA + 5 (S)-methylmalonyl-CoA + 22 NADPH + 22 H+ <=> a_mycoketide-CoA + 10 CO2 + 10 CoA + 22 NADP+ + 11 H2O
|
2.3.1.295
mycoketide-CoA synthase
|
–
|
|
|
BRENDA:
BR52917
|
|
|
|
3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + icosanoyl-[(phenol)carboxyphthiodiolenone_synthase] + 5 NADPH <=> C32-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone_synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O
|
2.3.1.292
(phenol)carboxyphthiodiolenone synthase
|
–
|
|
|
BRENDA:
BR52911
|
|
|
|
3 malonyl-CoA + 2 (S)-methylmalonyl-CoA + docosanoyl-[(phenol)carboxyphthiodiolenone_synthase] + 5 NADPH <=> C34-carboxyphthiodiolenone-[(phenol)carboxyphthiodiolenone_synthase] + 5 CoA + 5 NADP+ + 5 CO2 + 2 H2O
|
2.3.1.292
(phenol)carboxyphthiodiolenone synthase
|
–
|
|
|
BRENDA:
BR52912
|
|
|
|
UTP + propionyl-CoA + HCO3- <=> UDP + phosphate + (S)-methylmalonyl-CoA
|
6.4.1.3
propionyl-CoA carboxylase
|
–
|
|
|
BRENDA:
BS369192
|
|