|
|
dimethylallyl_diphosphate + naringenin <=> diphosphate + sophoraflavanone_B
|
2.5.1.70
naringenin 8-dimethylallyltransferase
|
–
|
M
|
|
BRENDA:
BR48848
KEGG:
R08951
MetaCyc:
2.5.1.70-RXN
|
|
|
|
S-adenosyl-L-methionine + naringenin <=> sakuranetin + S-adenosyl-L-homocysteine + H+
|
2.1.1.232
naringenin 7-O-methyltransferase
2.1.1.B75
2.1.1.B76
|
–
–
–
|
MK
|
|
BRENDA:
BR49706
KEGG:
R09791
MetaCyc:
RXN-7773
|
|
|
|
Apiforol + NADP+ <=> naringenin + NADPH + H+
|
1.1.1.234
flavanone 4-reductase
|
–
|
MK
|
|
BRENDA:
BS187859
KEGG:
R06610
MetaCyc:
RXN-14425
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> (+)-dihydrokaempferol + succinate + CO2
|
1.14.11.9
flavanone 3-dioxygenase
|
–
|
MK
|
|
BRENDA:
BS288657;
BS402787
KEGG:
R02444
MetaCyc:
NARINGENIN-3-DIOXYGENASE-RXN
|
|
|
|
UDP-glucose + naringenin <=> UDP + naringenin_7-O-glucoside + H+
|
2.4.1.170
isoflavone 7-O-glucosyltransferase
2.4.1.185
flavanone 7-O-beta-glucosyltransferase
2.4.1.237
flavonol 7-O-beta-glucosyltransferase
2.4.1.357
phlorizin synthase
2.4.1.81
flavone 7-O-beta-glucosyltransferase
|
–
–
–
–
–
|
MK
|
|
BRENDA:
BS322991
KEGG:
R02897
MetaCyc:
RXN-5381
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> apigenin + succinate + CO2 + H2O + H+
|
1.14.20.4
anthocyanidin synthase
1.14.20.5
flavone synthase I
|
–
–
|
MK
|
|
BRENDA:
BS371268
KEGG:
R02445
MetaCyc:
RXN-7686
|
|
|
|
naringenin_chalcone <=> naringenin
|
5.5.1.6
chalcone isomerase
|
–
|
MK
|
|
BRENDA:
BS380128
KEGG:
R02446
MetaCyc:
APIGNAR-RXN
SABIO-RK:
2380
|
|
|
|
S-adenosyl-L-methionine + naringenin <=> H+ + isosakuranetin + S-adenosyl-L-homocysteine
|
2.1.1.231
flavonoid 4'-O-methyltransferase
|
–
|
MK
|
|
BRENDA:
BS415301
KEGG:
R12213
MetaCyc:
RXN-7777
|
|
|
|
naringenin + O2 + reduced_flavodoxin <=> 2,4'',5,7-tetrahydroxyisoflavanone + H2O + flavin
|
1.14.14.87
2-hydroxyisoflavanone synthase
|
–
|
K
|
|
BRENDA:
BR50515
KEGG:
R07778
|
|
|
|
naringenin + reduced_flavodoxin + O2 <=> eriodictyol + flavin + H2O
|
1.14.14.81
flavanoid 3',5'-hydroxylase
1.14.14.82
flavonoid 3'-monooxygenase
|
–
–
|
K
|
|
BRENDA:
BS288543;
BS372123
KEGG:
R02442
|
|
|
|
naringenin + 2 reduced_flavodoxin + 2 O2 <=> (2S)-5,7,3'',4'',5''-pentahydroxyflavanone + 2 flavin + 2 H2O
|
1.14.14.81
flavanoid 3',5'-hydroxylase
|
–
|
|
|
BRENDA:
BS372122
KEGG:
R02443
|
|
|
|
naringenin + reduced_flavodoxin + O2 <=> apigenin + flavin + 2 H2O
|
1.14.19.76
flavone synthase II
|
–
|
K
|
|
BRENDA:
BS446316
KEGG:
R12278
|
|
|
|
naringenin_7-O-glucoside + H2O <=> naringenin + beta-D-glucose
|
3.2.1.21
beta-glucosidase
|
–
|
|
|
BRENDA:
BS371074
SABIO-RK:
12346
|
|
|
|
naringenin <=> genistein
|
not assigned
|
–
|
|
|
KEGG:
R06553
|
|
|
|
naringenin <=> hesperetin
|
not assigned
|
–
|
K
|
|
KEGG:
R08026
|
|
|
|
naringenin <=> 8-C-Glucosylnaringenin
|
not assigned
|
–
|
K
|
|
KEGG:
R08129
|
|
|
|
naringenin + O2 + reduced_[NADPH-hemoprotein_reductase] <=> (2S)-dihydrotricetin + H2O + oxidized_[NADPH-hemoprotein_reductase] + H+
|
1.14.14.81
flavanoid 3',5'-hydroxylase
|
–
|
|
|
MetaCyc:
RXN-13717
|
|
|
|
naringenin + reduced_[NADPH-hemoprotein_reductase] + O2 <=> 2-hydroxynaringenin + oxidized_[NADPH-hemoprotein_reductase] + H2O + H+
|
1.14.14.162
flavanone 2-hydroxylase
|
–
|
M
|
|
MetaCyc:
RXN-14069
|
|
|
|
naringenin + O2 + reduced_[NADPH-hemoprotein_reductase] <=> 2,5,7,4'-tetrahydroxyisoflavanone + oxidized_[NADPH-hemoprotein_reductase] + H2O
|
1.14.14.87
2-hydroxyisoflavanone synthase
|
–
|
M
|
|
MetaCyc:
RXN-1541
|
|
|
|
naringenin + reduced_[NADPH-hemoprotein_reductase] + O2 <=> apigenin + oxidized_[NADPH-hemoprotein_reductase] + H2O + H+
|
1.14.19.76
flavone synthase II
|
–
|
M
|
|
MetaCyc:
RXN-7650
|
|
|
|
naringenin + O2 + reduced_[NADPH-hemoprotein_reductase] <=> eriodictyol + oxidized_[NADPH-hemoprotein_reductase] + H2O + H+
|
1.14.14.82
flavonoid 3'-monooxygenase
|
–
|
M
|
|
MetaCyc:
RXN-7652
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> dihydrokaempferol + succinate + O2
|
1.14.20.4
anthocyanidin synthase
|
–
|
|
|
BRENDA:
BS377345
|
|
|
|
dimethylallyl_diphosphate + naringenin <=> diphosphate + 3''-C-dimethylallyl_naringenin
|
2.5.1.111
4-hydroxyphenylpyruvate 3-dimethylallyltransferase
|
–
|
|
|
BRENDA:
BS423399
|
|
|
|
dimethylallyl_diphosphate + naringenin <=> diphosphate + 4''-O-dimethylallyl_naringenin
|
2.5.1.111
4-hydroxyphenylpyruvate 3-dimethylallyltransferase
|
–
|
|
|
BRENDA:
BS423400
|
|
|
|
dimethylallyl_diphosphate + naringenin <=> diphosphate + 6-(3-methylbut-2-enyl)naringenin
|
2.5.1.80
7-dimethylallyltryptophan synthase
|
–
|
|
|
BRENDA:
BS423401
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> 3-O-methylkaempferol + kaempferol + CO2 + H2O
|
1.14.20.6
flavonol synthase
|
–
|
|
|
BRENDA:
BS421117
|
|
|
|
naringenin + 2-oxoadipate + O2 <=> dihydrokaempferol + Glutarate + CO2
|
1.14.11.9
flavanone 3-dioxygenase
|
–
|
|
|
BRENDA:
BS288659
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> dihydroquercetin + succinate + CO2
|
1.14.11.9
flavanone 3-dioxygenase
|
–
|
|
|
BRENDA:
BS443791
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> dihydrokaempferol + kaempferol + succinate + CO2 + H2O
|
1.14.20.6
flavonol synthase
|
–
|
|
|
BRENDA:
BS395072
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> (2R,3S)-cis-dihydrokaempferol + (2S,3S)-dihydrokaempferol + kaempferol + succinate + CO2 + H2O
|
1.14.20.6
flavonol synthase
|
–
|
|
|
BRENDA:
BS371266
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> (2R,3S)-cis-dihydrokaempferol + (+)-dihydrokaempferol + apigenin + kaempferol + succinate + CO2 + H2O
|
1.14.20.6
flavonol synthase
|
–
|
|
|
BRENDA:
BS371265
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> kaempferol + succinate + CO2 + H2O
|
1.14.20.6
flavonol synthase
|
–
|
|
|
BRENDA:
BS371270
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> apigenin + (+)-dihydrokaempferol + succinate + CO2 + 2 H2O
|
1.14.20.4
anthocyanidin synthase
|
–
|
|
|
BRENDA:
BS443790
|
|
|
|
naringenin + 2-oxoglutarate + O2 <=> apigenin + 2-hydroxynaringenin + succinate + CO2 + H2O
|
1.14.20.5
flavone synthase I
|
–
|
|
|
BRENDA:
BS441756
|
|
|
|
naringenin + reduced_flavodoxin + O2 <=> eriodictyol + 6-hydroxyeriodictyol + 8-hydroxyeriodictyol + flavin + H2O
|
1.14.14.1
unspecific monooxygenase
|
–
|
|
|
BRENDA:
BS443792
|
|
|
|
naringenin + reduced_flavodoxin + O2 <=> 2-hydroxynaringenin + flavin + H2O
|
1.14.14.162
flavanone 2-hydroxylase
|
–
|
|
|
BRENDA:
BS371271
|
|
|
|
naringenin + O2 + reduced_flavodoxin <=> genistein + 2 H2O + flavin
|
1.14.14.87
2-hydroxyisoflavanone synthase
|
–
|
|
|
BRENDA:
BS442645
|
|
|
|
naringenin + reduced_flavodoxin + O2 <=> eriodyctiol + flavin + H2O
|
1.14.14.82
flavonoid 3'-monooxygenase
|
–
|
|
|
BRENDA:
BS394928
|
|
|
|
UDP-glucuronate + naringenin <=> UDP + naringenin_beta-D-glucuronide
|
2.4.1.17
glucuronosyltransferase
|
–
|
|
|
BRENDA:
BS378153
|
|
|
|
S-adenosyl-L-methionine + naringenin <=> S-adenosyl-L-homocysteine + sakuranetin + 5-hydroxy-7,4''-dimethoxyflavanone + 4''-hydroxy-5,7-dimethoxyflavanone
|
2.1.1.B75
|
–
|
|
|
BRENDA:
BS456578
|
|
|
|
S-adenosyl-L-methionine + naringenin <=> S-adenosyl-L-homocysteine + 4''-O-methylnaringenin
|
2.1.1.B127
|
–
|
|
|
BRENDA:
BS456577
|
|
|
|
narirutin + H2O <=> naringenin + neohesperidose
|
3.2.1.B28
|
–
|
|
|
BRENDA:
BS426834
|
|
|
|
narirutin + H2O <=> naringenin + rutinose
|
3.2.1.168
hesperidin 6-O-alpha-L-rhamnosyl-beta-D-glucosidase
|
–
|
|
|
BRENDA:
BS409960
|
|
|
|
naringin + H2O <=> naringenin + rutinose
|
3.2.1.B28
|
–
|
|
|
BRENDA:
BS426833
|
|
|
|
6''-hydroxychalcone <=> naringenin
|
5.5.1.6
chalcone isomerase
|
–
|
|
|
BRENDA:
BS444832
|
|
|
|
chalcone <=> naringenin
|
5.5.1.6
chalcone isomerase
|
–
|
|
|
BRENDA:
BS400650
|
|
|
|
sucrose + naringenin <=> D-fructose + naringenin_glucoside
|
2.4.1.373
alpha-(1->2) branching sucrase
|
–
|
|
|
BRENDA:
BS450705
|
|
|
|
naringenin + NADPH + H+ <=> apiferol + NADP+
|
1.1.1.219
dihydroflavonol 4-reductase
|
–
|
|
|
BRENDA:
BS409959
|
|
|
|
UDP-glucose + naringenin <=> UDP + naringenin_3-O-glucoside
|
2.4.1.91
flavonol 3-O-glucosyltransferase
|
–
|
|
|
BRENDA:
BS323099
|
|
|
|
naringenin + H2O <=> beta-D-glucose + naringenin
|
3.2.1.21
beta-glucosidase
|
–
|
|
|
BRENDA:
BS374019
|
|