PATHWAY: rn00860 Help
Entry
Name
Porphyrin metabolism
Description
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.
Class
Metabolism; Metabolism of cofactors and vitamins
Pathway map
Ortholog table
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
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)
R00310 protoheme ferro-lyase (protoporphyrin-forming)
R00311 protoheme,NADPH---hemoprotein reductase:oxygen oxidoreductase (alpha-methene-oxidizing, hydroxylating)
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)
R03194 S-adenosyl-L-methionine:uroporphyrinogen-III C-methyltransferase
R03197 Uroporphyrinogen-III carboxy-lyase
R03220 Coproporphyrinogen:oxygen oxidoreductase(decarboxylating)
R03222 protoporphyrinogen-IX:oxygen oxidoreductase
R03678 (3Z)-phytochromobilin:ferredoxin oxidoreductase
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
R04972 Uroporphyrinogen I carboxy-lyase
R04979 Bilirubin beta-diglucuronide glucuronosohydrolase
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
R05220 ATP:cob(I)yrinic acid-a,c-diamide Cobeta-adenosyltransferase
R05222 GTP:adenosylcobinamide-phosphate guanylyltransferase
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
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
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)
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
R06529 adenosylcobyric acid:(R)-1-aminopropan-2-yl phosphate ligase
R06530 L-threonine-O-3-phosphate carboxy-lyase
R06531 ATP:L-threonine O-phosphotransferase
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)
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)
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
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
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)
R11919 5-amino-1-(5-phospho-beta-D-ribosyl)imidazole formate-lyase (5-hydroxybenzimidazole-forming)
R12002 Fe-coproporphyrin III:S-adenosyl-L-methionine oxidoreductase (decarboxylating)
R12184 ATP:Cob(II)yrinate diamide Cobeta-adenosyltransferase
Compound
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
C05787 Bilirubin beta-diglucuronide
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
C06509 Adenosyl cobinamide phosphate
C06510 Adenosine-GDP-cobinamide
C11538 Cobalt-sirohydrochlorin
C11543 Cobalt-dihydro-precorrin 6
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
C11851 Zn-Bacteriochlorophyll a
C12147 L-Threonine O-3-phosphate
C16540 7(1)-Hydroxychlorophyllide a
C18022 Red chlorophyll catabolite
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
C21217 Geranylgeranyl bacteriochlorophyllide a
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
C21835 12,18-Didecarboxysiroheme
C22451 5-Methoxy-6-methylbenzimidazole
Reference
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
Reference
Authors
Johansson P, Hederstedt L
Title
Organization of genes for tetrapyrrole biosynthesis in gram--positive bacteria.
Journal
Reference
Authors
Maggio-Hall LA, Escalante-Semerena JC.
Title
In vitro synthesis of the nucleotide loop of cobalamin by Salmonella typhimurium enzymes.
Journal
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
Reference
Authors
Scott AI, Roessner CA.
Title
Biosynthesis of cobalamin (vitamin B(12)).
Journal
Reference
Authors
Warren MJ, Raux E, Schubert HL, Escalante-Semerena JC.
Title
The biosynthesis of adenosylcobalamin (vitamin B12).
Journal
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
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
Reference
Authors
Chew AG, Bryant DA
Title
Chlorophyll biosynthesis in bacteria: the origins of structural and functional diversity.
Journal
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
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
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
Related pathway
rn00250 Alanine, aspartate and glutamate metabolism
rn00260 Glycine, serine and threonine metabolism
KO pathway