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1.14.12.12: naphthalene 1,2-dioxygenase

This is an abbreviated version!
For detailed information about naphthalene 1,2-dioxygenase, go to the full flat file.

Word Map on EC 1.14.12.12

Reaction

Naphthalene
+
NADH
+
H+
+
O2
=
(1R,2S)-1,2-dihydronaphthalene-1,2-diol
+
NAD+

Synonyms

NAG, NAHA, nahAc, naphthalene 1,2-dioxygenase, naphthalene dioxygenase, naphthalene oxygenase, NDO, oxygenase, naphthalene di-

ECTree

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.12 With NADH or NADPH as one donor, and incorporation of two atoms of oxygen into the other donor
                1.14.12.12 naphthalene 1,2-dioxygenase

Substrates Products

Substrates Products on EC 1.14.12.12 - naphthalene 1,2-dioxygenase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(1S)-indanol + NADH + O2
(1S)-indanol + trans-1,3-indandiol
show the reaction diagram
-
recombinant enzyme
85.5% indanol, 11.5% 1,3-indandiol, minor products: (1S)-indenol and 1-indanone
?
(2S)-flavanone + NADH + H+ + O2
8-hydroxy-(2S)-flavanone + NAD+ + ?
show the reaction diagram
(3S)-isoflavanone + NADH + H+ + O2
8-hydroxy-(3S)-isoflavanone + NAD+ + ?
show the reaction diagram
(R)-1-indanol + NADH + H+ + O2
cis-1,3-indandiol + (R)-3-hydroxy-1-indanone + cis-1,2,3-indantriol + NAD+
show the reaction diagram
-
activity in E. coli cells expressing recombinant naphthalene dioxygenase
71% cis-1,3-indandiol, 18.2% (R)-3-hydroxy-1-indanone and 10.8% cis-1,2,3-indantriol
?
(S)-1-indanol + NADH + H+ + O2
trans-(1S,3S)-indan-1,3-diol + (R)-3-hydroxy-1-indanone + NAD+
show the reaction diagram
-
activity in E. coli cells expressing recombinant naphthalene dioxygenase
95.5% trans-(1S,3S)-indan-1,3-diol
?
(S)-1-indenol + NADH + O2
syn-2,3-dihydroxy-1-indanol + anti-2,3-dihydroxy-1-indanol
show the reaction diagram
-
recombinant enzyme system
-
?
1,2,4-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
1,2,5-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
1,2-dihydronaphthalene + NADH + O2
cis-(1R,2S)-dihydroxy-1,2,3,4-tetrahydronaphthalene + cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene + NAD+
show the reaction diagram
-
naphthalene dioxygenase activity in cells induced by salicylate
-
?
1,3-benzodithiole + NADH + O2
(R)-1,3-benzodithiole-1-oxide + NAD+
show the reaction diagram
1,4-benzo[d]dithiine + NADH + O2
(S)-1,4-benzo[d]dithiin-1-oxide + NAD+
show the reaction diagram
1,4-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
1,5-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
1-chloronaphthalene + NADH + H+ + O2
(1R,2S)-5-chloro-1,2-dihydronaphthalene-1,2-diol + (1S,2R)-8-chloro-1,2-dihydronaphthalene-1,2-diol + NAD+
show the reaction diagram
1-methylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
-
-
generation of dioxygenated product, but mainly formation of side-chain monooxygenated product
-
?
2,3-dihydro-1,4-benzo[d]dithiine + NADH + O2
(S)-2,3-dihydrobenzo[d]dithiin-1-oxide + NAD+
show the reaction diagram
2,3-dimethylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
-
-
generation of mono- and mostly dioxygenated products
-
?
2,4,6-trimethylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
-
-
generation of mostly mono- and some dioxygenated products
-
?
2-chlorobiphenyl + NADH + O2
2-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
show the reaction diagram
2-chlorophenol + NADH + O2
chlorohydroquinone + NAD+
show the reaction diagram
2-methoxynaphthalene + NADH + O2
(1R,2S)-dihydroxy-7-methoxy-1,2-dihydronaphthalene + NAD+
show the reaction diagram
-
naphtalene dioxygenase activity in whole cells and activity in E. coli cells expressing naphtalene dioxygenase
minor product (1R,2S)-dihydroxy-6-methoxy-1,2-dihydronaphthalene
?
2-methyl-1,3-benzodithiole + NADH + O2
(1S,2R)-2-methyl-1,3-benzodithiole-1-oxide + (1S,2S)-2-methyl-1,3-benzodithiole-1-oxide + NAD+
show the reaction diagram
2-methylnaphthalene + NADH + H+ + O2
? + NAD+
show the reaction diagram
-
-
generation of two different dioxygenated products
-
?
2-methylquinoline + NADH + H+ + O2
(5R,6S)-2-methyl-5,6-dihydroquinoline-5,6-diol + 2-methylquinolin-8-ol + NAD+
show the reaction diagram
3 benz[a]anthracene + 3 NADH + 3 O2 + 3 H+
benz[a]anthracene-10,11-cis-dihydrodiol + benz[a]anthracene-8,9-cis-dihydrodiol + benz[a]anthracene-1,2-cis-dihydrodiol + 3 NAD+
show the reaction diagram
-
-
-
-
?
3,4-dihydro-2H-1lambda4,5-benzodithiepin + NADH + O2
(S)-1,2,3,4-tetrahydro-1lambda4,5-benzodithiepin-1-oxide + NAD+
show the reaction diagram
3-chlorobiphenyl + NADH + O2
3-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
show the reaction diagram
3-chlorophenol + NADH + O2
chlorohydroquinone + 4-chlorocatechol + NAD+
show the reaction diagram
3-methylisoquinoline + NADH + H+ + O2
cis-3-methyl-7,8-dihydroisoquinoline-7,8-diol + 3-methylisoquinolin-5-ol + NAD+
show the reaction diagram
3-nitrotoluene + NADH + O2
4-nitrobenzyl alcohol + NAD+
show the reaction diagram
4-chlorobiphenyl + NADH + O2
4-chloro-2',3'-dihydrobiphenyl-2',3'-diol + NAD+
show the reaction diagram
4-chlorophenol + NADH + O2
4-chlorocatechol + NAD+
show the reaction diagram
6,7-dihydro-5H-benzocycloheptene + NADH + O2
(1R,2S)-cis-dihydroxybenzocycloheptane + NAD+
show the reaction diagram
-
naphthalene dioxygenase activity in cells induced by salicylate
enantiomeric excess greater than 98%
?
8-methylquinoline + NADH + H+ + O2
5,6-dihydroquinolin-8-ylmethanol + (5R,6S)-8-methyl-5,6-dihydroquinoline-5,6-diol + NAD+
show the reaction diagram
9,10-dihydroanthracene + NADH + O2
cis-(1R,2S)-1,2-dihydroxy-1,2,9,10-tetrahydroanthracene + NAD+
show the reaction diagram
-
naphthalene dioxygenase activity in cells induced by salicylate
more than 95% yield, enantiomeric excess greater than 95%, minor product: 9-hydroxy-9,10-dihydroanthracene
?
9,10-dihydrophenanthrene + NADH + O2
cis-(3S,4R)-3,4-dihydroxy-3,4,9,10-tetrahydrophenanthrene + (S)-9-hydroxy-9,10-dihydrophenanthrene
show the reaction diagram
-
naphthalene dioxygenase activity in cells induced by salicylate
70% cis-(3S,4R)-3,4-dihydroxy-3,4,9,10-tetrahydrophenanthrene, enantiomeric excess greater than 95%, 30% (S)-9-hydroxy-9,10-dihydrophenanthrene
?
acenaphthene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
acenaphthylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
anthanthrene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
anthracene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
anthracene + NADH + O2
(1R,2S)-1,2-dihydroanthracene-1,2-diol + (1S,2R)-1,2-dihydroanthracene-1,2-diol + NAD+
show the reaction diagram
benzamide + NADH + H+ + O2
?
show the reaction diagram
benzene + NADH + O2
H2O2 + cis-benzene-1,2-dihydrodiol + NAD+
show the reaction diagram
-
40-50% of O2 is reduced to H2O2 by an uncoupling reaction, only trace amounts of cis-benzene-1,2-dihydrodiol are formed
-
?
benzocyclobutene + NADH + O2
benzocyclobutene-1-ol + benzocyclobutene-1-one
show the reaction diagram
-
naphtalene dioxygenase activity in intact cells
-
?
benzo[a]coronene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[a]naphthacene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[a]pyrene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[a]pyrene + NADH + H+ + O2
cis-9,10-dihydroxy-9,10-dihydrobenzo[a]pyrene + NAD+
show the reaction diagram
-
-
-
-
?
benzo[b]chrysene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[b]fluorene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[c]chrysene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[c]phenanthrene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[e]pyrene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[ghi]fluoranthene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[ghi]naphtho[cde]perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[ghi]perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[j]fluoranthene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[rst]dinaphtho[defg,ijkl]pentaphene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzo[rst]phenanthro[1,10,9-cde]pentaphene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benzpyrene + NADH + H+ + O2
?
show the reaction diagram
benz[a]anthracene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benz[a]anthracene + NADH + H+ + O2
cis,cis-1,2,10,11-tetrahydroxy-1,2,10,11-tetrahydrobenz[a]anthracene + NAD+
show the reaction diagram
-
-
-
-
?
benz[a]anthracene-1,2-cis-dihydrodiol + NADH + O2
benz[a]anthracene-1,2,10,11-bis-cis-dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
benz[a]anthracene-10,11-cis-dihydrodiol + NADH + O2
benz[a]anthracene-1,2,10,11-bis-cis-dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
benz[e]acephenanthrylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
benz[rst]anthra[cde]pentaphene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
biphenyl + NADH + O2
? + NAD+
show the reaction diagram
chrysene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
chrysene + NADH + H+ + O2
cis-3,4-dihydroxy-3,4-dihydrochrysene + NAD+
show the reaction diagram
-
-
-
-
?
chrysene + NADH + O2
chrysene-3,4-cis-dihydrodiol + chrysene-3,4,9,10-bis-cis-dihydrodiol + NAD+
show the reaction diagram
-
-
-
-
?
coronene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dibenzofuran + NADH + H+ + O2
1,2-dihydroxydibenzofuran + NAD+
show the reaction diagram
-
-
-
-
?
dibenzofuran + NADH + O2
(1R,2S)-cis-1,2-dihydroxy-1,2-dihydrodibenzofuran + (3S,4R)-cis-3,4-dihydroxy-3,4-dihydrodibenzofuran + NAD+
show the reaction diagram
-
naphthalene dioxygenase activity in cells induced by salicylate
-
-
?
dibenzothiophene + NADH + H+ + O2
1,2-dihydroxydibenzothiophene + NAD+
show the reaction diagram
-
-
-
-
?
dibenzothiophene + NADH + O2
(1R,2S)-cis-1,2-dihydroxy-dihydrodibenzothiophene + dibenzothiophene sulfoxide
show the reaction diagram
-
naphthalene dioxygenase activity in cells induced by salicylate
84-87% (1R,2S)-cis-1,2-dihydroxy-dihydrodibenzothiophene, enantiomeric excess greater than 95%, 15% dibenzothiophene sulfoxide
?
dibenzo[b,def]chrysene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dibenzo[bc,ef]coronene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dibenzo[g,p]chrysene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dibenzo[j,lm]naphtho[ab]perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dibenz[a,c]anthracene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dibenz[a,h]anthracene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dibenz[a,j]anthracene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
dinaphtho[defg,opqr]pentacene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
ethylbenzene + NADH + H+ + O2
(S)-1-phenylethanol + (R)-1-phenylethanol + NAD+
show the reaction diagram
ethylphenyl sulfide + NADH + H+ + O2
(R)-ethylphenyl sulfoxide + NAD+
show the reaction diagram
fluoranthene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
fluoranthene + NADH + H+ + O2
cis-7,8-dihydroxy-7,8-dihydrofluoranthene + cis-2,3-dihydroxy-2,3-dihydrofluoranthene + NAD+
show the reaction diagram
-
-
-
-
?
fluorene + NADH + O2
(3S,4R)-cis-3,4dihydroxy-3,4-dihydrofluorene + 9-fluorenol + NAD+
show the reaction diagram
-
naphthalene dioxygenase activity in cells induced by salicylate
-
-
?
fluorine + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
fulvic acid + NADH + H+ + O2
?
show the reaction diagram
hexabenzo[a,cd,f,j,lm,o]perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
humic acid + NADH + H+ + O2
?
show the reaction diagram
indan + NADH + H+ + O2
(1S)-indenol + (1S)-indanol + NAD+
show the reaction diagram
-
recombinant enzyme, enantiospecific monooxygenation
20% indenol, 67.1% indanol, minor products: indene, 1-indanone and (1R,2S)-indandiol
?
indan + NADH + H+ + O2
(S)-1-indanol + (R)-1-indanol + NAD+
show the reaction diagram
-
-
-
?
indan + NADH + H+ + O2
1-indanol + NAD+
show the reaction diagram
-
-
-
?
indene + NADH + H+ + O2
(S)-1-indenol + (R)-1-indenol + NAD+
show the reaction diagram
-
-
-
?
indene + NADH + O2
(1S)-indenol + (1R,2S)-indandiol + NAD+
show the reaction diagram
-
recombinant enzyme
57.9% indenol, 29.6% indandiol
?
indole + ?
2,3-dihydroxy-2,3-dihydroindole + ?
show the reaction diagram
indole + ? + O2
cis-indole-2,3-dihydrodiol
show the reaction diagram
indole + NADH + H+ + O2
?
show the reaction diagram
indole + NADH + H+ + O2
cis-indole-2,3-dihydrodiol + NAD+
show the reaction diagram
-
-
-
?
indole + NADH + O2
(2S,3S)-2,3-dihydro-1H-indole-2,3-diol + NAD+
show the reaction diagram
indole-3-acetate + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
m-cresol + NADH + O2
methylhydroquinone + 3-methylcatechol + 4-methylcatechol + NAD+
show the reaction diagram
naphthacene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
naphthalene + NAD(P)H + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD(P)+
show the reaction diagram
naphthalene + NADH + H+ + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
show the reaction diagram
naphthalene + NADH + H+ + O2
1,2-dihydronaphthalene-1,2-diol + NAD+
show the reaction diagram
naphthalene + NADH + O2
(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
show the reaction diagram
naphthalene + NADH + O2
cis-(1R,2S)-1,2-dihydronaphthalene-1,2-diol + NAD+
show the reaction diagram
naphtho[a]anthracene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
naphtho[bcd]perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
naphtho[d]coronene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
o-cresol + NADH + O2
methylhydroquinone + 3-methylcatechol + NAD+
show the reaction diagram
-
-
-
-
?
p-cresol + NADH + O2
4-methylcatechol + NAD+
show the reaction diagram
-
-
-
-
?
pentabenzo[a,cd,f,j,lm]perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
pentacene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
pentaphene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
phenanthrene + NADH + H+ + O2
?
show the reaction diagram
phenanthrene + NADH + O2
(1R,2S)-1,2-dihydrophenanthrene-1,2-diol + (1S,2R)-1,2-dihydrophenanthrene-1,2-diol + (3R,4S)-3,4-dihydrophenanthrene-3,4-diol + (3S,4R)-3,4-dihydrophenanthrene-3,4-diol + NAD+
show the reaction diagram
phenanthrene + NADH + O2
? + NAD+
show the reaction diagram
-
-
-
-
?
phenanthro[3,4-c]phenanthrene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
phenetole + NADH + H+ + O2
phenol + vinyloxybenzene + (S)-ethylphenyl sulfoxide + NAD+
show the reaction diagram
-
-
-
?
phenol + NADH + O2
catechol + hydroquinone + NAD+
show the reaction diagram
-
-
-
-
?
picene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
pyranthrene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
pyrene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
pyrene + NADH + H+ + O2
pyrene cis-4,5-dihydrodiol + NAD+
show the reaction diagram
quinazoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinazoline-5,6-diol + quinazolin-8-ol
show the reaction diagram
quinoline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinoline-5,6-diol + quinolin-3-ol + NAD+
show the reaction diagram
quinoxaline + NADH + H+ + O2
(5R,6S)-5,6-dihydroquinoxaline-5,6-diol + NAD+
show the reaction diagram
-
-
exclusive product
-
?
styrene + NADH + H+ + O2
(R)-1-phenylethane-1,2-diol + (S)-1-phenylethane-1,2-diol + NAD+
show the reaction diagram
-
-
-
?
styrene + NADH + O2
(R)-1-phenyl-1,2-ethanediol + NAD+
show the reaction diagram
-
recombinant enzyme system
78.6% enantiomeric excess
?
tetrabenzo[a,cd,f,lm]perylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
thioanisole + NADH + H+ + O2
methyl phenyl sulfoxide + NAD+
show the reaction diagram
-
-
-
?
triphenylene + NADH + H+ + O2
?
show the reaction diagram
-
-
-
?
additional information
?
-