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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 vitaminsBRITE hierarchy
Pathway map Module 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 ]
Drug D04413 Halofuginone hydrobromide (USAN)
Other DBs Orthology K00230 hemG; menaquinone-dependent protoporphyrinogen oxidase [EC:1.3.5.3 ]
K00768 E2.4.2.21, cobU, cobT; nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase [EC:2.4.2.21 ]
K01845 hemL; glutamate-1-semialdehyde 2,1-aminomutase [EC:5.4.3.8 ]
K02225 cobC1, cobC; cobalamin biosynthesis protein CobC
K02227 cbiB, cobD; adenosylcobinamide-phosphate synthase [EC:6.3.1.10 ]
K02231 cobP, cobU; adenosylcobinamide kinase / adenosylcobinamide-phosphate guanylyltransferase [EC:2.7.1.156 2.7.7.62 ]
K02233 E2.7.8.26, cobS, cobV; adenosylcobinamide-GDP ribazoletransferase [EC:2.7.8.26 ]
K02495 hemN, hemZ; oxygen-independent coproporphyrinogen III oxidase [EC:1.3.98.3 ]
K03428 bchM, chlM; magnesium-protoporphyrin O-methyltransferase [EC:2.1.1.11 ]
K04032 eutT; ethanolamine utilization cobalamin adenosyltransferase [EC:2.5.1.154 ]
K04034 bchE; anaerobic magnesium-protoporphyrin IX monomethyl ester cyclase [EC:1.21.98.3 ]
K04035 E1.14.13.81, acsF, chlE; magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase [EC:1.14.13.81 ]
K04036 bchJ; divinyl protochlorophyllide a 8-vinyl-reductase [EC:1.-.-.-]
K04037 chlL; light-independent protochlorophyllide reductase subunit L [EC:1.3.7.7 ]
K04038 chlN; light-independent protochlorophyllide reductase subunit N [EC:1.3.7.7 ]
K04039 chlB; light-independent protochlorophyllide reductase subunit B [EC:1.3.7.7 ]
K05369 pebA; 15,16-dihydrobiliverdin:ferredoxin oxidoreductase [EC:1.3.7.2 ]
K05370 pebB; phycoerythrobilin:ferredoxin oxidoreductase [EC:1.3.7.3 ]
K05371 pcyA; phycocyanobilin:ferredoxin oxidoreductase [EC:1.3.7.5 ]
K07215 pigA, hemO; heme oxygenase (biliverdin-IX-beta and delta-forming) [EC:1.14.99.58 ]
K07226 hutZ, hugZ; heme oxygenase (biliverdin-IX-beta and delta-forming) [EC:1.14.99.58 ]
K08101 HY2; phytochromobilin:ferredoxin oxidoreductase [EC:1.3.7.4 ]
K08973 hemJ; protoporphyrinogen IX oxidase [EC:1.3.99.-]
K10960 chlP, bchP; geranylgeranyl diphosphate/geranylgeranyl-bacteriochlorophyllide a reductase [EC:1.3.1.83 1.3.1.111 ]
K13601 bchQ; bacteriochlorophyllide d C-8(2)-methyltransferase [EC:2.1.1.332 ]
K13602 bchR; bacteriochlorophyllide d C-12(1)-methyltransferase [EC:2.1.1.331 ]
K13604 bchU; bacteriochlorophyllide d C-20 methyltransferase [EC:2.1.1.333 ]
K13605 bchK; bacteriochlorophyll c synthase [EC:2.5.1.-]
K13625 FTL; ferritin light chain
K13786 cobR; cob(II)yrinic acid a,c-diamide reductase [EC:1.16.8.-]
K19712 cobY; adenosylcobinamide-phosphate guanylyltransferase [EC:2.7.7.62 ]
K21231 bciB; 3,8-divinyl protochlorophyllide a 8-vinyl-reductase (ferredoxin) [EC:1.3.7.13 ]
K21480 HO, pbsA1, hmuO; heme oxygenase (biliverdin-producing, ferredoxin) [EC:1.14.15.20 ]
K21610 cfbC; Ni-sirohydrochlorin a,c-diamide reductive cyclase subunit CfbC [EC:6.3.3.7 ]
K21611 cfbD; Ni-sirohydrochlorin a,c-diamide reductive cyclase subunit CfbD [EC:6.3.3.7 ]
K21796 pebS; Prochlorococcus phage phycoerythrobilin synthase [EC:1.3.7.6 ]
K22226 ahbC; Fe-coproporphyrin III synthase
K24866 sirC; precorrin-2 dehydrogenase
K24867 nirN; dihydro-heme d1 dehydrogenase
K25033 chdC, hemQ; hydrogen peroxide-dependent heme synthase
K25496 cbiR; adenosylcobalamin phosphodiesterase
K25497 bzaC; 5-hydroxybenzimidazole methyltransferase
K25498 bzaD; 5-methoxybenzimidazole methyltransferase
K25499 bzaE; 5-methoxy-6-methylbenzimidazole methyltransferase
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 ko00250 Alanine, aspartate and glutamate metabolism
ko00260 Glycine, serine and threonine metabolism
