KEGG   PATHWAY: rn00860
Entry
rn00860                     Pathway                                

Name
Porphyrin and chlorophyll metabolism
Class
Metabolism; Metabolism of cofactors and vitamins
Pathway map
rn00860  Porphyrin and chlorophyll metabolism
rn00860

Module
M00121  Heme biosynthesis, plants and bacteria, glutamate => heme [PATH:rn00860]
M00122  Cobalamin biosynthesis, cobyrinate a,c-diamide => cobalamin [PATH:rn00860]
M00836  Coenzyme F430 biosynthesis, sirohydrochlorin => coenzyme F430 [PATH:rn00860]
M00846  Siroheme biosynthesis, glutamyl-tRNA => siroheme [PATH:rn00860]
M00847  Heme biosynthesis, archaea, siroheme => heme [PATH:rn00860]
M00868  Heme biosynthesis, animals and fungi, glycine => heme [PATH:rn00860]
M00924  Cobalamin biosynthesis, anaerobic, uroporphyrinogen III => sirohydrochlorin => cobyrinate a,c-diamide [PATH:rn00860]
M00925  Cobalamin biosynthesis, aerobic, uroporphyrinogen III => precorrin 2 => cobyrinate a,c-diamide [PATH:rn00860]
M00926  Heme biosynthesis, bacteria, glutamyl-tRNA => coproporphyrin III => heme [PATH:rn00860]
Other DBs
GO: 0006778
Reaction
R00036  5-aminolevulinate hydro-lyase (adding 5-aminolevulinate and cyclizing; porphobilinogen-forming)
R00070  D-urobilinogen:oxygen oxidoreductase
R00078  Fe(II):oxygen oxidoreductase
R00084  porphobilinogen:(4-[2-carboxyethyl]-3-[carboxymethyl]pyrrol-2-yl)methyltransferase (hydrolysing)
R00097   
R00099  cob(I)alamin:NAD+ oxidoreductase
R00310  protoheme ferro-lyase (protoporphyrin-forming)
R00311  protoheme,NADPH---hemoprotein reductase:oxygen oxidoreductase (alpha-methene-oxidizing, hydroxylating)
R00312   
R00313   
R00314   
R00830  succinyl-CoA:glycine C-succinyltransferase (decarboxylating)
R01492  ATP:cob(I)alamin Co-beta-adenosyltransferase
R02271  5-Aminolevulinate:pyruvate aminotransferase
R02272  (S)-4-Amino-5-oxopentanoate 4,5-aminomutase
R02389  UDPglucuronate beta-D-glucuronosyltransferase(acceptor-unspecific)
R02391  Bilirubin:NAD+ oxidoreductase
R02393  Bilirubin:NADP+ oxidoreductase
R02394  Bilirubin:oxygen oxidoreductase
R02480  Cytochrome c apocytochrome-c-lyase
R02864  S-Adenosyl-L-methionine:uroporphyrin-III C-methyltransferase
R02999  NADPH:cyanocob(III)alamin oxidoreductase (cyanide-eliminating)
R03165  Hydroxymethylbilane hydro-lyase(cyclizing)
R03166   
R03194  S-adenosyl-L-methionine:uroporphyrinogen-III C-methyltransferase
R03195   
R03197  Uroporphyrinogen-III carboxy-lyase
R03220  Coproporphyrinogen:oxygen oxidoreductase(decarboxylating)
R03222  protoporphyrinogen-IX:oxygen oxidoreductase
R03678  (3Z)-phytochromobilin:ferredoxin oxidoreductase
R03682   
R03684   
R03845  Chlorophyllide-a:NADP+ 7,8-oxidoreductase
R03877  Magnesium-protoporphyrin IX chelatase
R03947  S-Adenosyl-L-methionine:uroporphyrin-III C-methyltransferase
R03948  S-adenosyl-L-methionine:precorrin-4 C20-methyltransferase
R04109  L-glutamate-semialdehyde: NADP+ oxidoreductase(L-glutamyl-tRNA(Glu)-forming)
R04123  Transferrin[Fe(II)]2:NAD+ oxidoreductase
R04148  Nicotinate-nucleotide:dimethylbenzimidazole phospho-D-ribosyltransferase
R04178  coproporphyrinogen-III:oxygen oxidoreductase (coproporphyrin-forming)
R04237  S-adenosyl-L-methionine:magnesium-protoporphyrin-IX O-methyltransferase
R04594   
R04795   
R04971   
R04972  Uroporphyrinogen I carboxy-lyase
R04973   
R04977   
R04978   
R04979  Bilirubin beta-diglucuronide glucuronosohydrolase
R05040   
R05149  S-Adenosyl-L-methionine:1-precorrin-6Y C5,15-methyltransferase (C-12-decarboxylating)
R05150  precorrin-6Y:NADP+ oxidoreductase
R05177  precorrin 8X 11,12-methylmutase
R05180  S-adenosyl-L-methionine:precorrin-3B C17-methyltransferase
R05181  S-adenosyl-L-methionine:precorrin-4 C11 methyltransferase
R05217  precorrin-3A,NADH:oxygen oxidoreductase (20-hydroxylating)
R05218  cob(II)yrinic acid-a,c-diamide:FMN oxidoreductase
R05219   
R05220  ATP:cob(I)yrinic acid-a,c-diamide Cobeta-adenosyltransferase
R05221   
R05222  GTP:adenosylcobinamide-phosphate guanylyltransferase
R05223   
R05224   
R05225   
R05226  adenosylcobinamide amidohydrolase
R05227  hydrogenobyrinic-acid-a,c-diamide:cobalt cobalt-ligase (ADP-forming)
R05578  L-glutamate:tRNA(Glu) ligase (AMP-forming)
R05618  chlorophyll chlorophyllidohydrolase
R05807  sirohydrochlorin cobalt-lyase
R05808  S-adenosyl-L-methionine:cobalt-factor-II C20-methyltransferase
R05809   
R05810  cobalt-precorrin-4 methyltransferase
R05812  cobalt-precorrin-6B:NAD+ oxidoreductase
R05814  precorrin-8 11,12-methylmutase
R05815  cobyrinate:L-glutamine amido-ligase (ADP-forming)
R05817  (3Z)-phycocyanobilin:ferredoxin oxidoreductase
R05818  15,16-dihydrobiliverdin:ferredoxin oxidoreductase
R05819  (3Z)-phycoerythrobilin:ferredoxin oxidoreductase
R06254   
R06255   
R06256   
R06257   
R06265  magnesium-protoporphyrin-IX 13-monomethyl ester,NADPH:oxygen oxidoreductase (hydroxylating)
R06266  magnesium-protoporphyrin-IX 13-monomethyl ester,NADPH:oxygen oxidoreductase (hydroxylating)
R06267  magnesium-protoporphyrin-IX 13-monomethyl ester,NADPH:oxygen oxidoreductase (hydroxylating)
R06268  magnesium-protoporphyrin-IX 13-monomethyl ester,S-adenosyl-L-methionine:H2O oxidoreductase (hydroxylating)
R06269  magnesium-protoporphyrin-IX 13-monomethyl ester,S-adenosyl-L-methionine:H2O oxidoreductase (hydroxylating)
R06270  magnesium-protoporphyrin-IX 13-monomethyl ester,S-adenosyl-L-methionine:H2O oxidoreductase (hydroxylating)
R06271   
R06272  chlorophyllide-a:NADP+ oxidoreductase
R06282  ATP-dependent ferredoxin:protochlorophyllide-a 7,8-oxidoreductase
R06284  chlorophyllide-a:phytyl-diphosphate phytyltransferase
R06286  chlorophyllide-a:NADP+ 7,8-oxidoreductase
R06287   
R06288   
R06529  adenosylcobyric acid:(R)-1-aminopropan-2-yl phosphate ligase
R06530  L-threonine-O-3-phosphate carboxy-lyase
R06531  ATP:L-threonine O-phosphotransferase
R06558   
R06895  coproporphyrinogen-III:S-adenosyl-L-methionine oxidoreductase(decarboxylating)
R06896  chlorophyllide-a:NADP+ oxidoreductase
R07268  ATP:cobinamide Cobeta-adenosyltransferase
R07302  adenosylcobyric acid:(R)-1-aminopropan-2-ol ligase (ADP-forming)
R07411  (2E,6E)-farnesyl-diphosphate:protoheme IX farnesyltranstransferase
R07412  ferroheme o:acceptor C-81-oxidoreductase (heme a-forming)
R07772  cobalt-precorrin 5A acylhydrolase
R07773  S-adenosyl-L-methionine:cobalt-precorrin-5B (C1)-methyltransferase
R07774  S-adenosyl-L-methionine:cobalt-precorrin-6B C15-methyltransferase (C12-decarboxylating)
R07775  S-adenosyl-L-methionine:cobalt-precorrin-7 C5-methyltransferase
R08203  chlorophyllide-a,NADPH:oxygen 7(1)-oxidoreductase (hydroxylating)
R08204  7(1)-hydroxychlorophyllide-a,NADPH:oxygen 7(1)-oxidoreductase
R08584  chlorophyll-a magnesium-lyase (pheophytin-a-forming)
R08716  cobalt-precorrin 3 dehydrogenase
R08914  7(1)-hydroxychlorophyllide-a:NAD+ oxidoreductase
R08915  7(1)-hydroxychlorophyllide-a:NADP+ oxidoreductase
R08921  pheophorbide-a,ferredoxin:oxygen oxidoreductase (biladiene-forming)
R08974  pheophorbide-a hydrolase (decarboxylating)
R09032  primary fluorescent chlorophyll catabolite:ferredoxin oxidoreductase
R09033  chlorophyllide magnesium-lyase (pheophorbide-forming)
R09053  3-vinylbacteriochlorophyllide a:ferredoxin 7,8-oxidoreductase
R09054  3-hydroxyethylbacteriochlorophyllide-a hydro-lyase (3-vinylbacteriochlorophyllide-a-forming)
R09055  3-deacetyl-3-(1-hydroxyethyl)bacteriochlorophyllide-a:NAD+ oxidoreductase (bacteriochlorophyllide a-forming)
R09056   
R09059  3-hydroxyethylchlorophyllide-a hydro-lyase (chlorophyllide-a-forming)
R09060  3-hydroxyethylbacteriochlorophyllide-a:ferredoxin oxidoreductase
R09061  chlorophyllide-a hydrolase
R09063  S-adenosyl-L-methionine:bacteriochlorophyllide-d C20-methyltransferase
R09064  trans,trans-farnesyl-diphosphate:bacteriochlorophyllide-c farnesyltransferase
R09065  trans,trans-farnesyl-diphosphate:bacteriochlorophyllide-d farnesyltransferase
R09066   
R09067  chlorophyllide-b:phytyl-diphosphate phytyltransferase
R09068  chlorophyll chlorophyllidohydrolase
R09069  7(1)-hydroxychlorophyll-a:NAD+ oxidoreductase
R09070  7(1)-hydroxychlorophyll-a:NADP+ oxidoreductase
R09071  7(1)-hydroxychlorophyll a:ferredoxin oxidoreductase
R09489  protoporphyrinogen IX:quinone oxidoreductase
R09491  (3Z)-phycoerythrobilin:ferredoxin oxidoreductase (from biliverdin IXalpha)
R10468  protoheme,hydrogen-donor:oxygen oxidoreductase (delta-methene-oxidizing, hydroxylating)
R11226  bacteriochlorophyll a:NADP+ oxidoreductase (geranylgeranyl-reducing)
R11329  Fe-coproporphyrin-III ferro-lyase (coproporphyrin-III-forming)
R11507  S-adenosyl-L-methionine:8-ethyl-12-methyl-3-vinylbacteriochlorophyllide-d C-12(1)-methyltransferase
R11508  S-adenosyl-L-methionine:8,12-diethyl-3-vinylbacteriochlorophyllide-d C-8(2)-methyltransferase
R11509  S-adenosyl-L-methionine:12-ethyl-8-propyl-3-vinylbacteriochlorophyllide d C-8(2)-methyltransferase
R11510   
R11511   
R11512   
R11513   
R11514  geranylgeranyl-diphosphate:bacteriochlorophyllide-a geranylgeranytransferase
R11517  geranylgeranyl-diphosphate:bacteriochlorophyllide-b geranylgeranytransferase
R11518  bacteriochlorophyll-b:NADP+ oxidoreductase (geranylgeranyl-reducing)
R11519  protochlorophyllide-a:ferredoxin C-8(1)-oxidoreductase
R11522  Fe-coproporphyrin III:hydrogen peroxide oxidoreductase (decarboxylating)
R11579  protoheme,reduced ferredoxin:oxygen oxidoreductase (alpha-methene-oxidizing, hydroxylating)
R11580  S-adenosyl-L-methionine:cobalt-factor III 17-methyltransferase (ring contracting)
R11626  Ni-sirohydrochlorin nickel-lyase (sirohydrochlorin-forming)
R11627  Ni-sirohydrochlorin:L-glutamine amido-ligase (ADP-forming)
R11628  Ni-sirohydrochlorin a,c-diamide reductive cyclo-ligase (ADP-forming)
R11629  15,17(3)-seco-F430-17(3)-acid cyclo-ligase (ADP-forming)
R11710  bacteriochlorophyllide-c:S-adenosyl-L-methionine oxidoreductase (C-7(1)-hydroxylating)
R11816  protoheme,donor:oxygen oxidoreductase (biliverdin-IX-delta-forming)
R11817  protoheme,donor:oxygen oxidoreductase (biliverdin-IX-beta-forming)
R12000  siroheme carboxy-lyase
R12001   
R12002  Fe-coproporphyrin III:S-adenosyl-L-methionine oxidoreductase (decarboxylating)
R12184  ATP:Cob(II)yrinate diamide Cobeta-adenosyltransferase
R12481   
R12605   
Compound
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
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
C11539  Cobalt-precorrin 3
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
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
C21835  12,18-Didecarboxysiroheme
Reference
PMID:9461500
  Authors
Woodcock SC, Raux E, Levillayer F, Thermes C, Rambach A, Warren MJ.
  Title
Effect of mutations in the transmethylase and dehydrogenase/chelatase domains of sirohaem synthase (CysG) on sirohaem and cobalamin biosynthesis.
  Journal
Biochem J 330:121-9 (1998)
DOI:10.1042/bj3300121
Reference
  Authors
Johansson P, Hederstedt L
  Title
Organization of genes for tetrapyrrole biosynthesis in gram--positive bacteria.
  Journal
Microbiology 145 ( Pt 3):529-38 (1999)
DOI:10.1099/13500872-145-3-529
Reference
  Authors
Maggio-Hall LA, Escalante-Semerena JC.
  Title
In vitro synthesis of the nucleotide loop of cobalamin by Salmonella typhimurium enzymes.
  Journal
Proc Natl Acad Sci USA 96:11798-803 (1999)
DOI:10.1073/pnas.96.21.11798
Reference
  Authors
Roper JM, Raux E, Brindley AA, Schubert HL, Gharbia SE, Shah HN, Warren MJ.
  Title
The enigma of cobalamin (Vitamin B12) biosynthesis in Porphyromonas gingivalis. Identification and characterization of a functional corrin pathway.
  Journal
J Biol Chem 275:40316-23 (2000)
DOI:10.1074/jbc.M007146200
Reference
  Authors
Scott AI, Roessner CA.
  Title
Biosynthesis of cobalamin (vitamin B(12)).
  Journal
Biochem Soc Trans 30:613-20 (2002)
DOI:10.1042/bst0300613
Reference
  Authors
Warren MJ, Raux E, Schubert HL, Escalante-Semerena JC.
  Title
The biosynthesis of adenosylcobalamin (vitamin B12).
  Journal
Nat Prod Rep 19:390-412 (2002)
DOI:10.1039/b108967f
Reference
  Authors
Roessner CA, Huang KX, Warren MJ, Raux E, Scott AI.
  Title
Isolation and characterization of 14 additional genes specifying the anaerobic biosynthesis of cobalamin (vitamin B12) in Propionibacterium freudenreichii (P. shermanii).
  Journal
Microbiology 148:1845-53 (2002)
DOI:10.1099/00221287-148-6-1845
Reference
  Authors
Frankenberg N, Mukougawa K, Kohchi T, Lagarias JC.
  Title
Functional genomic analysis of the HY2 family of ferredoxin-dependent bilin reductases from oxygenic photosynthetic organisms.
  Journal
Plant Cell 13:965-78 (2001)
DOI:10.1105/tpc.13.4.965
Reference
  Authors
Chew AG, Bryant DA
  Title
Chlorophyll biosynthesis in bacteria: the origins of structural and functional diversity.
  Journal
Annu Rev Microbiol 61:113-29 (2007)
DOI:10.1146/annurev.micro.61.080706.093242
Reference
  Authors
Frigaard NU, Chew AG, Li H, Maresca JA, Bryant DA
  Title
Chlorobium tepidum: insights into the structure, physiology, and metabolism of a green sulfur bacterium derived from the complete genome sequence.
  Journal
Photosynth Res 78:93-117 (2003)
DOI:10.1023/B:PRES.0000004310.96189.b4
Reference
  Authors
Deery E, Schroeder S, Lawrence AD, Taylor SL, Seyedarabi A, Waterman J, Wilson KS, Brown D, Geeves MA, Howard MJ, Pickersgill RW, Warren MJ
  Title
An enzyme-trap approach allows isolation of intermediates in cobalamin biosynthesis.
  Journal
Nat Chem Biol 8:933-40 (2012)
DOI:10.1038/nchembio.1086
Reference
  Authors
Moore SJ, Lawrence AD, Biedendieck R, Deery E, Frank S, Howard MJ, Rigby SE, Warren MJ
  Title
Elucidation of the anaerobic pathway for the corrin component of cobalamin (vitamin B12).
  Journal
Proc Natl Acad Sci U S A 110:14906-11 (2013)
DOI:10.1073/pnas.1308098110
Related
pathway
rn00250  Alanine, aspartate and glutamate metabolism
rn00260  Glycine, serine and threonine metabolism
rn00740  Riboflavin metabolism
KO pathway
ko00860   

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