KEGG   PATHWAY: ko00860
ko00860                     Pathway                                
Porphyrin metabolism
Porphyrins are a group of chemical compounds with the backbone ring structure consisting of four linked pyrrole units. Metal complexes of porphyrins, as well as those of corrinoids with the one-carbon shorter ring structure, play important biological roles. They include iron-containing heme, magnesium-containing chlorophyll, nickel-containing coenzyme F430 and cobalt-containing cobamide (such as vitamin B12 coenzyme) as shown in this map.
Metabolism; Metabolism of cofactors and vitamins
Pathway map
ko00860  Porphyrin metabolism

M00121  Heme biosynthesis, plants and bacteria, glutamate => heme [PATH:ko00860]
M00122  Cobalamin biosynthesis, cobyrinate a,c-diamide => cobalamin [PATH:ko00860]
M00836  Coenzyme F430 biosynthesis, sirohydrochlorin => coenzyme F430 [PATH:ko00860]
M00846  Siroheme biosynthesis, glutamyl-tRNA => siroheme [PATH:ko00860]
M00847  Heme biosynthesis, archaea, siroheme => heme [PATH:ko00860]
M00868  Heme biosynthesis, animals and fungi, glycine => heme [PATH:ko00860]
M00924  Cobalamin biosynthesis, anaerobic, uroporphyrinogen III => sirohydrochlorin => cobyrinate a,c-diamide [PATH:ko00860]
M00925  Cobalamin biosynthesis, aerobic, uroporphyrinogen III => precorrin 2 => cobyrinate a,c-diamide [PATH:ko00860]
M00926  Heme biosynthesis, bacteria, glutamyl-tRNA => coproporphyrin III => heme [PATH:ko00860]
D04413  Halofuginone hydrobromide (USAN)
D08034  Halofuginone (INN)
Other DBs
GO: 0006778
K00643  5-aminolevulinate synthase [EC:]
K01885  glutamyl-tRNA synthetase [EC:]
K14163  bifunctional glutamyl/prolyl-tRNA synthetase [EC:]
K02492  glutamyl-tRNA reductase [EC:]
K01845  glutamate-1-semialdehyde 2,1-aminomutase [EC:]
K01698  porphobilinogen synthase [EC:]
K01749  hydroxymethylbilane synthase [EC:]
K01719  uroporphyrinogen-III synthase [EC:]
K01599  uroporphyrinogen decarboxylase [EC:]
K00228  coproporphyrinogen III oxidase [EC:]
K02495  oxygen-independent coproporphyrinogen III oxidase [EC:]
K00230  menaquinone-dependent protoporphyrinogen oxidase [EC:]
K00231  protoporphyrinogen/coproporphyrinogen III oxidase [EC:]
K08973  protoporphyrinogen IX oxidase [EC:1.3.99.-]
K01772  protoporphyrin/coproporphyrin ferrochelatase [EC:]
K00435  hydrogen peroxide-dependent heme synthase [EC:]
K25033  hydrogen peroxide-dependent heme synthase [EC:]
K13542  uroporphyrinogen III methyltransferase / synthase [EC:]
K13543  uroporphyrinogen III methyltransferase / synthase [EC:]
K02496  uroporphyrin-III C-methyltransferase [EC:]
K02302  uroporphyrin-III C-methyltransferase / precorrin-2 dehydrogenase / sirohydrochlorin ferrochelatase [EC:]
K02303  uroporphyrin-III C-methyltransferase [EC:]
K00589  uroporphyrin-III C-methyltransferase [EC:]
K02304  precorrin-2 dehydrogenase / sirohydrochlorin ferrochelatase [EC:]
K24866  precorrin-2 dehydrogenase [EC:]
K03794  sirohydrochlorin ferrochelatase [EC:]
K22225  siroheme decarboxylase [EC:]
K22226  Fe-coproporphyrin III synthase
K22227  AdoMet-dependent heme synthase [EC:]
K24867  dihydro-heme d1 dehydrogenase
K02257  heme o synthase [EC:]
K02259  heme a synthase [EC:]
K02190  sirohydrochlorin cobaltochelatase [EC:]
K03795  sirohydrochlorin cobaltochelatase [EC:]
K22011  sirohydrochlorin cobalto/nickelchelatase [EC:]
K03394  precorrin-2/cobalt-factor-2 C20-methyltransferase [EC:]
K13540  precorrin-2 C20-methyltransferase / precorrin-3B C17-methyltransferase [EC:]
K02229  precorrin-3B synthase [EC:]
K05934  precorrin-3B C17-methyltransferase / cobalt-factor III methyltransferase [EC:]
K13541  cobalt-precorrin 5A hydrolase / cobalt-factor III methyltransferase / precorrin-3B C17-methyltransferase [EC:]
K21479  cobalt-factor III methyltransferase [EC:]
K05936  precorrin-4/cobalt-precorrin-4 C11-methyltransferase [EC:]
K02189  cobalt-precorrin 5A hydrolase [EC:]
K02228  precorrin-6A synthase [EC:]
K05895  precorrin-6A/cobalt-precorrin-6A reductase [EC:]
K02188  cobalt-precorrin-5B (C1)-methyltransferase [EC:]
K00595  precorrin-6B C5,15-methyltransferase / cobalt-precorrin-6B C5,C15-methyltransferase [EC:]
K02191  cobalt-precorrin-6B (C15)-methyltransferase [EC:]
K03399  cobalt-precorrin-7 (C5)-methyltransferase [EC:]
K06042  precorrin-8X/cobalt-precorrin-8 methylmutase [EC:]
K02224  cobyrinic acid a,c-diamide synthase [EC:]
K02230  cobaltochelatase CobN [EC:]
K09882  cobaltochelatase CobS [EC:]
K09883  cobaltochelatase CobT [EC:]
K13786  cob(II)yrinic acid a,c-diamide reductase [EC:1.16.8.-]
K00798  cob(I)alamin adenosyltransferase [EC:]
K19221  cob(I)alamin adenosyltransferase [EC:]
K02232  adenosylcobyric acid synthase [EC:]
K02227  adenosylcobinamide-phosphate synthase [EC:]
K02225  cobalamin biosynthesis protein CobC
K08260  adenosylcobinamide hydrolase [EC:]
K02231  adenosylcobinamide kinase / adenosylcobinamide-phosphate guanylyltransferase [EC:]
K19712  adenosylcobinamide-phosphate guanylyltransferase [EC:]
K02233  adenosylcobinamide-GDP ribazoletransferase [EC:]
K25496  adenosylcobalamin phosphodiesterase
K22465  5-hydroxybenzimidazole synthase [EC:]
K22466  5-hydroxybenzimidazole synthase [EC:]
K25497  5-hydroxybenzimidazole methyltransferase [EC:2.1.1.-]
K25498  5-methoxybenzimidazole methyltransferase
K25499  5-methoxy-6-methylbenzimidazole methyltransferase
K00768  nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase [EC:]
K02226  alpha-ribazole phosphatase [EC:]
K22316  ribonuclease H / adenosylcobalamin/alpha-ribazole phosphatase [EC:]
K16651  L-threonine kinase [EC:]
K04720  threonine-phosphate decarboxylase [EC:]
K04032  ethanolamine utilization cobalamin adenosyltransferase [EC:]
K22012  Ni-sirohydrochlorin a,c-diamide synthase [EC:]
K21610  Ni-sirohydrochlorin a,c-diamide reductive cyclase subunit CfbC [EC:]
K21611  Ni-sirohydrochlorin a,c-diamide reductive cyclase subunit CfbD [EC:]
K21612  coenzyme F430 synthetase [EC:]
K03403  magnesium chelatase subunit H [EC:]
K03404  magnesium chelatase subunit D [EC:]
K03405  magnesium chelatase subunit I [EC:]
K03428  magnesium-protoporphyrin O-methyltransferase [EC:]
K04034  anaerobic magnesium-protoporphyrin IX monomethyl ester cyclase [EC:]
K04035  magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase [EC:]
K19073  divinyl chlorophyllide a 8-vinyl-reductase [EC:]
K21231  3,8-divinyl protochlorophyllide a 8-vinyl-reductase (ferredoxin) [EC:]
K04036  divinyl protochlorophyllide a 8-vinyl-reductase [EC:1.-.-.-]
K00218  protochlorophyllide reductase [EC:]
K04037  light-independent protochlorophyllide reductase subunit L [EC:]
K04038  light-independent protochlorophyllide reductase subunit N [EC:]
K04039  light-independent protochlorophyllide reductase subunit B [EC:]
K04040  chlorophyll/bacteriochlorophyll a synthase [EC:]
K08099  chlorophyllase [EC:]
K13600  chlorophyllide a oxygenase [EC:]
K13606  chlorophyll(ide) b reductase [EC:]
K18010  7-hydroxymethyl chlorophyll a reductase [EC:]
K22013  magnesium dechelatase [EC:]
K13544  pheophorbidase [EC:]
K13071  pheophorbide a oxygenase [EC:]
K13545  red chlorophyll catabolite reductase [EC:]
K11333  3,8-divinyl chlorophyllide a/chlorophyllide a reductase subunit X [EC:]
K11334  3,8-divinyl chlorophyllide a/chlorophyllide a reductase subunit Y [EC:]
K11335  3,8-divinyl chlorophyllide a/chlorophyllide a reductase subunit Z [EC:]
K11336  3-vinyl bacteriochlorophyllide hydratase [EC:]
K11337  bacteriochlorophyllide a dehydrogenase [EC:]
K10960  geranylgeranyl diphosphate/geranylgeranyl-bacteriochlorophyllide a reductase [EC:]
K21058  chlorophyllide a hydrolase [EC:]
K13602  bacteriochlorophyllide d C-12(1)-methyltransferase [EC:]
K13601  bacteriochlorophyllide d C-8(2)-methyltransferase [EC:]
K13603  3-vinyl bacteriochlorophyllide hydratase [EC:]
K13604  bacteriochlorophyllide d C-20 methyltransferase [EC:]
K13605  bacteriochlorophyll c synthase [EC:2.5.1.-]
K21312  bacteriochlorophyllide c C-7(1)-hydroxylase [EC:]
K07215  heme oxygenase (biliverdin-IX-beta and delta-forming) [EC:]
K07226  heme oxygenase (biliverdin-IX-beta and delta-forming) [EC:]
K07145  heme oxygenase (staphylobilin-producing) [EC:]
K00510  heme oxygenase 1 [EC:]
K21418  heme oxygenase 2 [EC:]
K21480  heme oxygenase (biliverdin-producing, ferredoxin) [EC:]
K00214  biliverdin reductase [EC:]
K05901  biliverdin reductase / flavin reductase [EC:]
K23825  F420H(2)-dependent biliverdin reductase [EC:1.3.98.-]
K08100  bilirubin oxidase [EC:]
K00699  glucuronosyltransferase [EC:]
K01195  beta-glucuronidase [EC:]
K05369  15,16-dihydrobiliverdin:ferredoxin oxidoreductase [EC:]
K05370  phycoerythrobilin:ferredoxin oxidoreductase [EC:]
K08101  phytochromobilin:ferredoxin oxidoreductase [EC:]
K05371  phycocyanobilin:ferredoxin oxidoreductase [EC:]
K21796  Prochlorococcus phage phycoerythrobilin synthase [EC:]
K01764  cytochrome c heme-lyase [EC:]
K13624  ceruloplasmin [EC:]
K14735  hephaestin [EC:]
K19054  frataxin [EC:]
K00522  ferritin heavy chain [EC:]
K13625  ferritin light chain
K18495  ferritin, mitochondrial [EC:]
K03594  bacterioferritin [EC:]
K22336  bacterioferritin B [EC:]
K22552  multicopper oxidase [EC:]
C00025  L-Glutamate
C00032  Heme
C00037  Glycine
C00188  L-Threonine
C00194  Cobamide coenzyme
C00430  5-Aminolevulinate
C00486  Bilirubin
C00500  Biliverdin
C00524  Cytochrome c
C00541  Cob(II)alamin
C00748  Siroheme
C00853  Cob(I)alamin
C00931  Porphobilinogen
C00992  Aquacob(III)alamin
C01024  Hydroxymethylbilane
C01051  Uroporphyrinogen III
C01079  Protoporphyrinogen IX
C01708  Hemoglobin
C02139  Chlorophyllide
C02191  Protoporphyrin
C02463  Precorrin 2
C02469  Uroporphyrin III
C02800  4,5-Dioxopentanoate
C02823  Cyanocobalamin
C02880  Protochlorophyllide
C02987  L-Glutamyl-tRNA(Glu)
C03029  Transferrin[Fe(II)]2
C03114  Dimethylbenzimidazole
C03179  Transferrin[Fe(III)]2
C03194  (R)-1-Aminopropan-2-ol
C03263  Coproporphyrinogen III
C03373  Aminoimidazole ribotide
C03516  Magnesium protoporphyrin
C03741  (S)-4-Amino-5-oxopentanoate
C04122  D-1-Aminopropan-2-ol O-phosphate
C04536  Magnesium protoporphyrin monomethyl ester
C04778  N1-(5-Phospho-alpha-D-ribosyl)-5,6-dimethylbenzimidazole
C05306  Chlorophyll a
C05307  Chlorophyll b
C05766  Uroporphyrinogen I
C05767  Uroporphyrin I
C05768  Coproporphyrinogen I
C05769  Coproporphyrin I
C05770  Coproporphyrin III
C05772  Precorrin 3A
C05773  Cobyrinate
C05774  Cobinamide
C05775  alpha-Ribazole
C05777  Coenzyme F430
C05778  Sirohydrochlorin
C05779  Apoferritin
C05780  Apotransferrin
C05781  Oxyhemoglobin
C05782  Myoglobin
C05783  Cytochrome a
C05784  Catalase
C05785  Peroxidase
C05786  (3Z)-Phycocyanobilin
C05787  Bilirubin beta-diglucuronide
C05789  L-Urobilinogen
C05790  I-Urobilinogen
C05791  D-Urobilinogen
C05793  L-Urobilin
C05794  Urobilin
C05795  D-Urobilin
C05797  Pheophytin a
C05798  Bacteriopheophytin
C05912  (3Z)-Phycoerythrobilin
C05913  (3Z)-Phytochromobilin
C06319  Precorrin 6Y
C06320  Precorrin 6X
C06399  Hydrogenobyrinate
C06406  Precorrin 3B
C06407  Precorrin 4
C06408  Precorrin 8X
C06416  Precorrin 5
C06503  Hydrogenobyrinate a,c diamide
C06504  Cob(II)yrinate a,c diamide
C06505  Cob(I)yrinate a,c diamide
C06506  Adenosyl cobyrinate a,c diamide
C06507  Adenosyl cobyrinate hexaamide
C06508  Adenosyl cobinamide
C06509  Adenosyl cobinamide phosphate
C06510  Adenosine-GDP-cobinamide
C11242  Bacteriochlorophyll a
C11243  Bacteriochlorophyll b
C11538  Cobalt-sirohydrochlorin
C11540  Cobalt-precorrin 4
C11542  Cobalt-precorrin 6
C11543  Cobalt-dihydro-precorrin 6
C11545  Cobalt-precorrin 8
C11630  15,16-Dihydrobiliverdin
C11829  13(1)-Hydroxy-magnesium-protoporphyrin IX 13-monomethyl ester
C11830  13(1)-Oxo-magnesium-protoporphyrin IX 13-monomethyl ester
C11831  Divinylprotochlorophyllide
C11832  Divinyl chlorophyllide a
C11850  Divinylchlorophyll a
C11851  Zn-Bacteriochlorophyll a
C12147  L-Threonine O-3-phosphate
C14818  Fe2+
C14819  Fe3+
C15670  Heme A
C15672  Heme O
C16242  Cobalt-precorrin 5A
C16243  Cobalt-precorrin 5B
C16244  Cobalt-precorrin 7
C16540  7(1)-Hydroxychlorophyllide a
C16541  Chlorophyllide b
C17401  Cobalt-factor III
C18021  Pheophorbide a
C18022  Red chlorophyll catabolite
C18064  Pyropheophorbide a
C18098  Primary fluorescent chlorophyll catabolite
C18151  7(1)-Hydroxychlorophyll a
C18152  3-Vinylbacteriochlorophyllide a
C18153  3-Hydroxyethylbacteriochlorophyllide a
C18154  3-Hydroxyethylchlorophyllide a
C18155  Bacteriochlorophyllide a
C18156  Bacteriochlorophyllide b
C18157  8-Ethyl-12-methyl-3-vinylbacteriochlorophyllide d
C18160  Bacteriochlorophyllide d
C18161  Bacteriochlorophyllide c
C18162  Bacteriochlorophyll d
C18163  Bacteriochlorophyll c
C19608  Ferritin
C20666  5-Oxo-delta-bilirubin
C21217  Geranylgeranyl bacteriochlorophyllide a
C21284  Fe-coproporphyrin III
C21427  8,12-Diethyl-3-vinylbacteriochlorophyllide d
C21428  12-Ethyl-8-propyl-3-vinylbacteriochlorophyllide d
C21429  12-Ethyl-8-isobutyl-3-vinylbacteriochlorophyllide d
C21431  8-Ethyl-12-methylbacteriochlorophyllide d
C21432  8,12-Diethylbacteriochlorophyllide d
C21433  12-Ethyl-8-propylbacteriochlorophyllide d
C21434  12-Ethyl-8-isobutylbacteriochlorophyllide d
C21435  Geranylgeranyl bacteriochlorophyllide b
C21510  Nickel-sirohydrochlorin
C21511  Nickel-sirohydrochlorin a,c-diamide
C21512  15,17(3)-Seco-F430-17(3)-acid
C21582  Bacteriochlorophyllide e
C21723  Biliverdin-IX-delta
C21724  Biliverdin-IX-beta
C21764  5-Hydroxybenzimidazole
C21835  12,18-Didecarboxysiroheme
C22338  Dihydro-heme d1
C22339  Heme d1
C22450  5-Methoxybenzimidazole
C22451  5-Methoxy-6-methylbenzimidazole
Woodcock SC, Raux E, Levillayer F, Thermes C, Rambach A, Warren MJ.
Effect of mutations in the transmethylase and dehydrogenase/chelatase domains of sirohaem synthase (CysG) on sirohaem and cobalamin biosynthesis.
Biochem J 330:121-9 (1998)
Johansson P, Hederstedt L
Organization of genes for tetrapyrrole biosynthesis in gram--positive bacteria.
Microbiology 145 ( Pt 3):529-38 (1999)
Maggio-Hall LA, Escalante-Semerena JC.
In vitro synthesis of the nucleotide loop of cobalamin by Salmonella typhimurium enzymes.
Proc Natl Acad Sci USA 96:11798-803 (1999)
Roper JM, Raux E, Brindley AA, Schubert HL, Gharbia SE, Shah HN, Warren MJ.
The enigma of cobalamin (Vitamin B12) biosynthesis in Porphyromonas gingivalis. Identification and characterization of a functional corrin pathway.
J Biol Chem 275:40316-23 (2000)
Scott AI, Roessner CA.
Biosynthesis of cobalamin (vitamin B(12)).
Biochem Soc Trans 30:613-20 (2002)
Warren MJ, Raux E, Schubert HL, Escalante-Semerena JC.
The biosynthesis of adenosylcobalamin (vitamin B12).
Nat Prod Rep 19:390-412 (2002)
Roessner CA, Huang KX, Warren MJ, Raux E, Scott AI.
Isolation and characterization of 14 additional genes specifying the anaerobic biosynthesis of cobalamin (vitamin B12) in Propionibacterium freudenreichii (P. shermanii).
Microbiology 148:1845-53 (2002)
Frankenberg N, Mukougawa K, Kohchi T, Lagarias JC.
Functional genomic analysis of the HY2 family of ferredoxin-dependent bilin reductases from oxygenic photosynthetic organisms.
Plant Cell 13:965-78 (2001)
Chew AG, Bryant DA
Chlorophyll biosynthesis in bacteria: the origins of structural and functional diversity.
Annu Rev Microbiol 61:113-29 (2007)
Frigaard NU, Chew AG, Li H, Maresca JA, Bryant DA
Chlorobium tepidum: insights into the structure, physiology, and metabolism of a green sulfur bacterium derived from the complete genome sequence.
Photosynth Res 78:93-117 (2003)
Deery E, Schroeder S, Lawrence AD, Taylor SL, Seyedarabi A, Waterman J, Wilson KS, Brown D, Geeves MA, Howard MJ, Pickersgill RW, Warren MJ
An enzyme-trap approach allows isolation of intermediates in cobalamin biosynthesis.
Nat Chem Biol 8:933-40 (2012)
Moore SJ, Lawrence AD, Biedendieck R, Deery E, Frank S, Howard MJ, Rigby SE, Warren MJ
Elucidation of the anaerobic pathway for the corrin component of cobalamin (vitamin B12).
Proc Natl Acad Sci U S A 110:14906-11 (2013)
ko00230  Purine metabolism
ko00250  Alanine, aspartate and glutamate metabolism
ko00260  Glycine, serine and threonine metabolism
ko00740  Riboflavin metabolism

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