KEGG   PATHWAY: rn00624
Entry
rn00624                     Pathway                                

Name
Polycyclic aromatic hydrocarbon degradation
Class
Metabolism; Xenobiotics biodegradation and metabolism
Pathway map
rn00624  Polycyclic aromatic hydrocarbon degradation
rn00624

Module
M00623  Phthalate degradation, phthalate => protocatechuate [PATH:rn00624]
M00624  Terephthalate degradation, terephthalate => 3,4-dihydroxybenzoate [PATH:rn00624]
M00636  Phthalate degradation, phthalate => protocatechuate [PATH:rn00624]
Other DBs
UMBBD: flu ant pha pyr bap pth
Reaction
R00818  salicylate,NADH:oxygen oxidoreductase (1-hydroxylating, decarboxylating)
R01628  3-hydroxybenzoate,NADPH:oxygen oxidoreductase (4-hydroxylating)
R01631  Protocatechuate:oxygen 3,4-oxidoreductase (decyclizing)
R01632  protocatechuate:oxygen 4,5-oxidoreductase (decyclizing)
R01633  (3S,4R)-3,4-dihydroxycyclohexa-1,5-diene-1,4-dicarboxylate:NAD+ oxidoreductase
R01634  3,4-dihydroxyphthalate carboxy-lyase (3,4-dihydroxybenzoate-forming)
R01635  4,5-Dihydroxyphthalate carboxy-lyase (3,4-dihydroxybenzoate-forming)
R03630  phthalate,NADH:oxygen oxidoreductase (4,5-hydroxylating)
R03692  Dihydrocoumarin lactonohydrolase
R04151  (+)-cis-3,4-dihydrophenanthrene-3,4-diol:NAD+ 3,4-oxidoreductase
R05148  benzene-1,4-dicarboxylate, NADH:oxygen oxidoreductase (1,2-hydroxylating)
R05275  cis-4,5-dihydroxycyclohexa-1(6),2-diene-1,2-dicarboxylate:NAD+ oxidoreductase
R05349   
R05350   
R05375  4-Hydroxyphthalate carboxy-lyase
R05410   
R05412   
R05422  fluorene,NADH:oxygen oxidoreductase
R05423   
R05430   
R05431   
R05432   
R05433   
R05435   
R05436   
R05437   
R05438   
R05537   
R05538   
R05540   
R05541   
R05542   
R05543   
R05544   
R05545   
R05632  1-hydroxy-2-naphthoate,NADH:oxygen oxidoreductase (2-hydroxylating, decarboxylating)
R05642   
R05643  2-formylbenzoate:NAD+ oxidoreductase
R05648   
R05649   
R05650   
R05653  phenanthrene 9,10-monooxygenase
R05654  phenanthrene 1,2-monooxygenase
R05655   
R05656   
R05657   
R05658   
R05843   
R07657  1-hydroxy-2-naphthoate:oxygen 1,2-oxidoreductase (decyclizing)
R07687   
R07688   
R07689   
R07690   
R07691   
R07692   
R07693   
R07694   
R07695   
R07696   
R07701   
R07702   
R07703  1,2-dihydrophthalic acid:NAD+ oxidoreductase
R07704  anthracene,NADH:oxygen oxidoreductase (1,2-hydroxylating)
R07705  anthracene cis-1,2-dihydrodiol:NAD+ 1,2-oxidoreductase
R07707   
R07708   
R07713  (3Z)-4-(2-carboxyphenyl)-2-oxobut-3-enoate 2-formylbenzoate-lyase (pyruvate-forming)
R07799   
R07800   
R07801   
R07802   
R07803   
R07804   
R09159   
R09160   
R09161   
R09162  cis-4,5-Dihydroxy-4,5-dihydropyrene:NAD+ 4,5-oxidoreductase
R09163   
R09164   
R09165   
R09166   
R09167   
R09168   
R09169   
R09170   
R09171   
R09172   
R09173   
R09174   
R09175   
R09176   
R09177   
R09178   
R09179   
R09180   
R09181   
R09182   
R09183   
R09184  9,10-dihydroxybenzo[a]pyrene:oxygen 10,10a-oxidoreductase (decyclizing)
R09185   
R09202   
R09203   
R09204   
R09205   
R09206   
R09207   
R09208   
R09209   
R09210   
R09211   
R09212   
R09216   
R09218   
R09219   
R09227   
R09228   
R09239   
R11540  poly(ethylene terephthalate) hydrolase
R11541  4-[(2-hydroxyethoxy)carbonyl]benzoate acylhydrolase
Compound
C00090  Catechol
C00230  3,4-Dihydroxybenzoate
C00587  3-Hydroxybenzoate
C00805  Salicylate
C01163  3-Carboxy-cis,cis-muconate
C01198  3-(2-Hydroxyphenyl)propanoate
C01504  Indanone
C01606  Phthalate
C02274  Dihydrocoumarin
C03012  Naphthalene-1,2-diol
C03057  2-Carboxybenzaldehyde
C03164  Phenanthrene-3,4-diol
C03203  1-Hydroxy-2-naphthoate
C03223  3,4-Dihydroxyphthalate
C03233  4,5-Dihydroxyphthalate
C04468  (+)-cis-3,4-Dihydrophenanthrene-3,4-diol
C04484  4-Carboxy-2-hydroxymuconate semialdehyde
C04783  cis-4,5-Dihydroxycyclohexa-1(6),2-diene-1,2-dicarboxylate
C06318  (3S,4R)-3,4-Dihydroxycyclohexa-1,5-diene-1,4-dicarboxylate
C06337  Terephthalate
C06680  4-Hydroxyphthalate
C06711  Fluoren-9-ol
C06712  Fluoren-9-one
C07535  Benzo[a]pyrene
C07715  Fluorene
C07717  3,4-Dihydroxyfluorene
C07718  2-Hydroxy-4-(1-oxo-1,3-dihydro-2H-inden-2-ylidene)-but-2-enoic acid
C07719  2-Formyl-1-indanone
C07720  3-Hydroxy-1-indanone
C07721  (+)-(3S,4R)-cis-3,4-Dihydroxy-3,4-dihydrofluorene
C07722  3,4-Dihydroxy-3,4-dihydro-9-fluorenone
C07723  4-Hydroxy-9-fluorenone
C07724  1,2-Dihydroxyfluorene
C07725  2-Hydroxy-4-(2-oxo-1,3-dihydro-2H-inden-1-ylidene)but-2-enoic acid
C07726  1-Formyl-2-indanone
C07727  2-Indanone
C07728  3-Isochromanone
C11422  Phenanthrene
C11425  2-Hydroxy-2H-benzo[h]chromene-2-carboxylate
C11426  cis-4-(1'-Hydroxynaphth-2'-yl)-2-oxobut-3-enoate
C11427  1-Hydroxy-2-naphthaldehyde
C11428  trans-9(S),10(S)-Dihydrodiolphenanthrene
C11429  Phenanthrene-9,10-oxide
C11430  9-Hydroxyphenanthrene
C11431  Phenanthrene-1,2-oxide
C11432  1-Phenanthrol
C11433  1-Methoxyphenanthrene
C14315  Anthracene
C14335  Pyrene
C14519  1-Hydroxypyrene
C16149  (3Z)-4-(2-Carboxyphenyl)-2-oxobut-3-enoate
C16203  Anthracene-cis-1,2-dihydrodiol
C16204  1,2-Anthracenediol
C16205  Anthracene-9,10-dihydrodiol
C16206  9,10-Dihydroxyanthracene
C16207  Anthraquinone
C16208  1-Methoxy-2-hydroxyanthracene
C16209  3-(2-Carboxyvinyl)naphthalene-2-carboxylic acid
C16210  4-(3-Hydroxy-2-naphthyl)-2-oxobut-3-enoic acid
C16211  6,7-Benzocoumarin
C16212  3-Hydroxy-2-naphthoate
C16213  2,3-Dihydroxynaphthalene
C16214  3-[6-(Carboxymethylene)cyclohexa-2,4-dien-1-ylidene]-2-oxopropanate
C16215  1,2-Dihydrophthalic acid
C16262  1-Hydro-1,1a-dihydroxy-9-fluorenone
C16263  2,3-Dihydroxy-2'-carboxybiphenyl
C16264  2-Hydroxy-6-oxo-6-(2-carboxyphenyl)-hexa-2,4-dienoate
C18249  cis-4,5-Dihydroxy-4,5-dihydropyrene
C18250  4,5-Dihydroxypyrene
C18251  Pyrene-4,5-dione
C18252  Phenanthrene-4,5-dicarboxylate
C18253  Phenanthrene-4-carboxylate
C18254  Pyrene-4,5-oxide
C18255  trans-4,5-Dihydroxy-4,5-dihydropyrene
C18256  cis-3,4-Phenanthrenedihydrodiol-4-carboxylate
C18257  Pyrene-1,6-dione
C18258  Pyrene-1,8-dione
C18259  1-Methoxypyrene
C18260  1,6-Dimethoxypyrene
C18261  1-Hydroxy-6-methoxypyrene
C18262  1-Methoxypyrene-6,7-oxide
C18263  1,6-Dihydroxypyrene
C18264  1,8-Dihydroxypyrene
C18265  1-Hydroxypyrene-6,7-oxide
C18266  1-Hydroxypyrene-7,8-oxide
C18267  Pyrene-1,2-oxide
C18269  1-Pyrenylsulfate
C18270  Benzo[a]pyrene-cis-4,5-dihydrodiol
C18271  cis-4-(7-Hydroxtpyren-8-yl)-2-oxobut-3-enoate
C18272  cis-4-(8-Hydroxypyren-7-yl)-2-oxobut-3-enoate
C18273  7,8-Dihydropyrene-8-carboxylate
C18274  7,8-Dihydropyrene-7-carboxylate
C18275  Benzo[a]pyrene-cis-7,8-dihydrodiol
C18276  Benzo[a]pyrene-cis-9,10-dihydrodiol
C18277  4,5-Chrysenedicarboxylate
C18278  9,10-Dihydroxybenzo[a]pyrene
C18279  4,5-Dihydroxybenzo[a]pyrene
C18280  11,12-Dihydroxybenzo[a]pyrene
C18281  10-Oxabenzo[def]chrysen-9-one
C18282  5-Chrysenecarboxylate
C18283  4-Chrysenecarboxylate
C18284  Benzo[a]pyrene-cis-11,12-dihydrodiol
C18285  Benzo[a]pyrene-trans-11,12-dihydrodiol
C18286  Benzo[a]pyrene-11,12-epoxide
C18314  Phthalate 3,4-cis-dihydrodiol
C21450  4-(2-Hydroxyethoxycarbonyl)benzoate
C21451  Poly(ethylene terephthalate)
Reference
  Authors
Wattiau P, Bastiaens L, van Herwijnen R, Daal L, Parsons JR, Renard ME, Springael D, Cornelis GR.
  Title
Fluorene degradation by Sphingomonas sp. LB126 proceeds through protocatechuic acid: a genetic analysis.
  Journal
Res Microbiol 152:861-72 (2001)
DOI:10.1016/S0923-2508(01)01269-4
Reference
  Authors
Story SP, Kline EL, Hughes TA, Riley MB, Hayasaka SS.
  Title
Degradation of aromatic hydrocarbons by Sphingomonas paucimobilis strain EPA505.
  Journal
Arch Environ Contam Toxicol 47:168-76 (2004)
DOI:10.1007/s00244-004-3069-2
Reference
  Authors
Habe H, Chung JS, Kato H, Ayabe Y, Kasuga K, Yoshida T, Nojiri H, Yamane H, Omori T.
  Title
Characterization of the upper pathway genes for fluorene metabolism in Terrabacter sp. strain DBF63.
  Journal
J Bacteriol 186:5938-44 (2004)
DOI:10.1128/JB.186.17.5938-5944.2004
Reference
  Authors
Nojiri H, Habe H, Omori T.
  Title
Bacterial degradation of aromatic compounds via angular dioxygenation.
  Journal
J Gen Appl Microbiol 47:279-305 (2001)
DOI:10.2323/jgam.47.279
Reference
  Authors
Pagnout C, Frache G, Poupin P, Maunit B, Muller JF, Ferard JF.
  Title
Isolation and characterization of a gene cluster involved in PAH degradation in Mycobacterium sp. strain SNP11: expression in Mycobacterium smegmatis mc(2)155.
  Journal
Res Microbiol 158:175-86 (2007)
DOI:10.1016/j.resmic.2006.11.002
Reference
  Authors
Dean-Ross D, Moody JD, Freeman JP, Doerge DR, Cerniglia CE.
  Title
Metabolism of anthracene by a Rhodococcus species.
  Journal
FEMS Microbiol Lett 204:205-11 (2001)
DOI:10.1111/j.1574-6968.2001.tb10886.x
Reference
  Authors
Moody JD, Freeman JP, Doerge DR, Cerniglia CE.
  Title
Degradation of phenanthrene and anthracene by cell suspensions of Mycobacterium sp. strain PYR-1.
  Journal
Appl Environ Microbiol 67:1476-83 (2001)
DOI:10.1128/AEM.67.4.1476-1483.2001
Reference
  Authors
van Herwijnen R, Springael D, Slot P, Govers HA, Parsons JR.
  Title
Degradation of anthracene by Mycobacterium sp. strain LB501T proceeds via a novel pathway, through o-phthalic acid.
  Journal
Appl Environ Microbiol 69:186-90 (2003)
DOI:10.1128/AEM.69.1.186-190.2003
Reference
  Authors
Haritash AK, Kaushik CP
  Title
Biodegradation aspects of polycyclic aromatic hydrocarbons (PAHs): a review.
  Journal
J Hazard Mater 169:1-15 (2009)
DOI:10.1016/j.jhazmat.2009.03.137
Reference
  Authors
Liang Y, Gardner DR, Miller CD, Chen D, Anderson AJ, Weimer BC, Sims RC
  Title
Study of biochemical pathways and enzymes involved in pyrene degradation by Mycobacterium sp. strain KMS.
  Journal
Appl Environ Microbiol 72:7821-8 (2006)
DOI:10.1128/AEM.01274-06
Reference
  Authors
da Silva M, Esposito E, Moody JD, Canhos VP, Cerniglia CE
  Title
Metabolism of aromatic hydrocarbons by the filamentous fungus Cyclothyrium sp.
  Journal
Chemosphere 57:943-52 (2004)
DOI:10.1016/j.chemosphere.2004.07.051
Reference
  Authors
Kim SJ, Kweon O, Jones RC, Freeman JP, Edmondson RD, Cerniglia CE
  Title
Complete and integrated pyrene degradation pathway in Mycobacterium vanbaalenii PYR-1 based on systems biology.
  Journal
J Bacteriol 189:464-72 (2007)
DOI:10.1128/JB.01310-06
Reference
PMID:9094229
  Authors
Wunder T, Marr J, Kremer S, Sterner O, Anke H
  Title
1-Methoxypyrene and 1,6-dimethoxypyrene: two novel metabolites in fungal metabolism of polycyclic aromatic hydrocarbons.
  Journal
Arch Microbiol 167:310-6 (1997)
DOI:10.1007/s002030050449
Reference
PMID:8572690
  Authors
Schneider J, Grosser R, Jayasimhulu K, Xue W, Warshawsky D
  Title
Degradation of pyrene, benz[a]anthracene, and benzo[a]pyrene by Mycobacterium sp. strain RJGII-135, isolated from a former coal gasification site.
  Journal
Appl Environ Microbiol 62:13-9 (1996)
DOI:10.1128/AEM.62.1.13-19.1996
Reference
  Authors
Moody JD, Freeman JP, Fu PP, Cerniglia CE
  Title
Degradation of benzo[a]pyrene by Mycobacterium vanbaalenii PYR-1.
  Journal
Appl Environ Microbiol 70:340-5 (2004)
DOI:10.1128/AEM.70.1.340-345.2004
Reference
  Authors
Eaton RW
  Title
Plasmid-encoded phthalate catabolic pathway in Arthrobacter keyseri 12B.
  Journal
J Bacteriol 183:3689-703 (2001)
DOI:10.1128/JB.183.12.3689-3703.2001
Reference
  Authors
Yoshida S, Hiraga K, Takehana T, Taniguchi I, Yamaji H, Maeda Y, Toyohara K, Miyamoto K, Kimura Y, Oda K
  Title
A bacterium that degrades and assimilates poly(ethylene terephthalate).
  Journal
Science 351:1196-9 (2016)
DOI:10.1126/science.aad6359
Related
pathway
rn00362  Benzoate degradation
rn00626  Naphthalene degradation
KO pathway
ko00624   

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