ENTRY ko00860 Pathway 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 ko00860 Porphyrin metabolism 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) D08034 Halofuginone (INN) DBLINKS GO: 0006778 ORTHOLOGY K00643 5-aminolevulinate synthase [EC:2.3.1.37] K01885 glutamyl-tRNA synthetase [EC:6.1.1.17] K14163 bifunctional glutamyl/prolyl-tRNA synthetase [EC:6.1.1.17 6.1.1.15] K02492 glutamyl-tRNA reductase [EC:1.2.1.70] K01845 glutamate-1-semialdehyde 2,1-aminomutase [EC:5.4.3.8] K01698 porphobilinogen synthase [EC:4.2.1.24] K01749 hydroxymethylbilane synthase [EC:2.5.1.61] K01719 uroporphyrinogen-III synthase [EC:4.2.1.75] K01599 uroporphyrinogen decarboxylase [EC:4.1.1.37] K00228 coproporphyrinogen III oxidase [EC:1.3.3.3] K02495 oxygen-independent coproporphyrinogen III oxidase [EC:1.3.98.3] K00230 menaquinone-dependent protoporphyrinogen oxidase [EC:1.3.5.3] K00231 protoporphyrinogen/coproporphyrinogen III oxidase [EC:1.3.3.4 1.3.3.15] K08973 protoporphyrinogen IX oxidase [EC:1.3.99.-] K01772 protoporphyrin/coproporphyrin ferrochelatase [EC:4.98.1.1 4.99.1.9] K00435 hydrogen peroxide-dependent heme synthase [EC:1.3.98.5] K25033 hydrogen peroxide-dependent heme synthase [EC:1.3.98.5] K13542 uroporphyrinogen III methyltransferase / synthase [EC:2.1.1.107 4.2.1.75] K13543 uroporphyrinogen III methyltransferase / synthase [EC:2.1.1.107 4.2.1.75] K02496 uroporphyrin-III C-methyltransferase [EC:2.1.1.107] K02302 uroporphyrin-III C-methyltransferase / precorrin-2 dehydrogenase / sirohydrochlorin ferrochelatase [EC:2.1.1.107 1.3.1.76 4.99.1.4] K02303 uroporphyrin-III C-methyltransferase [EC:2.1.1.107] K00589 uroporphyrin-III C-methyltransferase [EC:2.1.1.107] K02304 precorrin-2 dehydrogenase / sirohydrochlorin ferrochelatase [EC:1.3.1.76 4.99.1.4] K24866 precorrin-2 dehydrogenase [EC:1.3.1.76] K03794 sirohydrochlorin ferrochelatase [EC:4.99.1.4] K22225 siroheme decarboxylase [EC:4.1.1.111] K22226 Fe-coproporphyrin III synthase K22227 AdoMet-dependent heme synthase [EC:1.3.98.6] K24867 dihydro-heme d1 dehydrogenase K02257 heme o synthase [EC:2.5.1.141] K02259 heme a synthase [EC:1.17.99.9] K02190 sirohydrochlorin cobaltochelatase [EC:4.99.1.3] K03795 sirohydrochlorin cobaltochelatase [EC:4.99.1.3] K22011 sirohydrochlorin cobalto/nickelchelatase [EC:4.99.1.3 4.99.1.11] K03394 precorrin-2/cobalt-factor-2 C20-methyltransferase [EC:2.1.1.130 2.1.1.151] K13540 precorrin-2 C20-methyltransferase / precorrin-3B C17-methyltransferase [EC:2.1.1.130 2.1.1.131] K02229 precorrin-3B synthase [EC:1.14.13.83] K05934 precorrin-3B C17-methyltransferase / cobalt-factor III methyltransferase [EC:2.1.1.131 2.1.1.272] K13541 cobalt-precorrin 5A hydrolase / cobalt-factor III methyltransferase / precorrin-3B C17-methyltransferase [EC:3.7.1.12 2.1.1.272 2.1.1.131] K21479 cobalt-factor III methyltransferase [EC:2.1.1.272] K05936 precorrin-4/cobalt-precorrin-4 C11-methyltransferase [EC:2.1.1.133 2.1.1.271] K02189 cobalt-precorrin 5A hydrolase [EC:3.7.1.12] K02228 precorrin-6A synthase [EC:2.1.1.152] K05895 precorrin-6A/cobalt-precorrin-6A reductase [EC:1.3.1.54 1.3.1.106] K02188 cobalt-precorrin-5B (C1)-methyltransferase [EC:2.1.1.195] K00595 precorrin-6B C5,15-methyltransferase / cobalt-precorrin-6B C5,C15-methyltransferase [EC:2.1.1.132 2.1.1.289 2.1.1.196] K02191 cobalt-precorrin-6B (C15)-methyltransferase [EC:2.1.1.196] K03399 cobalt-precorrin-7 (C5)-methyltransferase [EC:2.1.1.289] K06042 precorrin-8X/cobalt-precorrin-8 methylmutase [EC:5.4.99.61 5.4.99.60] K02224 cobyrinic acid a,c-diamide synthase [EC:6.3.5.9 6.3.5.11] K02230 cobaltochelatase CobN [EC:6.6.1.2] K09882 cobaltochelatase CobS [EC:6.6.1.2] K09883 cobaltochelatase CobT [EC:6.6.1.2] K13786 cob(II)yrinic acid a,c-diamide reductase [EC:1.16.8.-] K00798 cob(I)alamin adenosyltransferase [EC:2.5.1.17] K19221 cob(I)alamin adenosyltransferase [EC:2.5.1.17] K02232 adenosylcobyric acid synthase [EC:6.3.5.10] K02227 adenosylcobinamide-phosphate synthase [EC:6.3.1.10] K02225 cobalamin biosynthesis protein CobC K08260 adenosylcobinamide hydrolase [EC:3.5.1.90] K02231 adenosylcobinamide kinase / adenosylcobinamide-phosphate guanylyltransferase [EC:2.7.1.156 2.7.7.62] K19712 adenosylcobinamide-phosphate guanylyltransferase [EC:2.7.7.62] K02233 adenosylcobinamide-GDP ribazoletransferase [EC:2.7.8.26] K25496 adenosylcobalamin phosphodiesterase K22465 5-hydroxybenzimidazole synthase [EC:4.1.99.23] K22466 5-hydroxybenzimidazole synthase [EC:4.1.99.23] K25497 5-hydroxybenzimidazole methyltransferase [EC:2.1.1.-] K25498 5-methoxybenzimidazole methyltransferase K25499 5-methoxy-6-methylbenzimidazole methyltransferase K00768 nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase [EC:2.4.2.21] K02226 alpha-ribazole phosphatase [EC:3.1.3.73] K22316 ribonuclease H / adenosylcobalamin/alpha-ribazole phosphatase [EC:3.1.26.4 3.1.3.73] K16651 L-threonine kinase [EC:2.7.1.177] K04720 threonine-phosphate decarboxylase [EC:4.1.1.81] K04032 ethanolamine utilization cobalamin adenosyltransferase [EC:2.5.1.154] K22012 Ni-sirohydrochlorin a,c-diamide synthase [EC:6.3.5.12] K21610 Ni-sirohydrochlorin a,c-diamide reductive cyclase subunit CfbC [EC:6.3.3.7] K21611 Ni-sirohydrochlorin a,c-diamide reductive cyclase subunit CfbD [EC:6.3.3.7] K21612 coenzyme F430 synthetase [EC:6.4.1.9] K03403 magnesium chelatase subunit H [EC:6.6.1.1] K03404 magnesium chelatase subunit D [EC:6.6.1.1] K03405 magnesium chelatase subunit I [EC:6.6.1.1] K03428 magnesium-protoporphyrin O-methyltransferase [EC:2.1.1.11] K04034 anaerobic magnesium-protoporphyrin IX monomethyl ester cyclase [EC:1.21.98.3] K04035 magnesium-protoporphyrin IX monomethyl ester (oxidative) cyclase [EC:1.14.13.81] K19073 divinyl chlorophyllide a 8-vinyl-reductase [EC:1.3.1.75] K21231 3,8-divinyl protochlorophyllide a 8-vinyl-reductase (ferredoxin) [EC:1.3.7.13] K04036 divinyl protochlorophyllide a 8-vinyl-reductase [EC:1.-.-.-] K00218 protochlorophyllide reductase [EC:1.3.1.33] K04037 light-independent protochlorophyllide reductase subunit L [EC:1.3.7.7] K04038 light-independent protochlorophyllide reductase subunit N [EC:1.3.7.7] K04039 light-independent protochlorophyllide reductase subunit B [EC:1.3.7.7] K04040 chlorophyll/bacteriochlorophyll a synthase [EC:2.5.1.62 2.5.1.133] K08099 chlorophyllase [EC:3.1.1.14] K13600 chlorophyllide a oxygenase [EC:1.14.13.122] K13606 chlorophyll(ide) b reductase [EC:1.1.1.294] K18010 7-hydroxymethyl chlorophyll a reductase [EC:1.17.7.2] K22013 magnesium dechelatase [EC:4.99.1.10] K13544 pheophorbidase [EC:3.1.1.82] K13071 pheophorbide a oxygenase [EC:1.14.15.17] K13545 red chlorophyll catabolite reductase [EC:1.3.7.12] K11333 3,8-divinyl chlorophyllide a/chlorophyllide a reductase subunit X [EC:1.3.7.14 1.3.7.15] K11334 3,8-divinyl chlorophyllide a/chlorophyllide a reductase subunit Y [EC:1.3.7.14 1.3.7.15] K11335 3,8-divinyl chlorophyllide a/chlorophyllide a reductase subunit Z [EC:1.3.7.14 1.3.7.15] K11336 3-vinyl bacteriochlorophyllide hydratase [EC:4.2.1.165] K11337 bacteriochlorophyllide a dehydrogenase [EC:1.1.1.396] K10960 geranylgeranyl diphosphate/geranylgeranyl-bacteriochlorophyllide a reductase [EC:1.3.1.83 1.3.1.111] K21058 chlorophyllide a hydrolase [EC:3.1.1.100] K13602 bacteriochlorophyllide d C-12(1)-methyltransferase [EC:2.1.1.331] K13601 bacteriochlorophyllide d C-8(2)-methyltransferase [EC:2.1.1.332] K13603 3-vinyl bacteriochlorophyllide hydratase [EC:4.2.1.169] K13604 bacteriochlorophyllide d C-20 methyltransferase [EC:2.1.1.333] K13605 bacteriochlorophyll c synthase [EC:2.5.1.-] K21312 bacteriochlorophyllide c C-7(1)-hydroxylase [EC:1.17.98.2] K07215 heme oxygenase (biliverdin-IX-beta and delta-forming) [EC:1.14.99.58] K07226 heme oxygenase (biliverdin-IX-beta and delta-forming) [EC:1.14.99.58] K07145 heme oxygenase (staphylobilin-producing) [EC:1.14.99.48] K00510 heme oxygenase 1 [EC:1.14.14.18] K21418 heme oxygenase 2 [EC:1.14.14.18] K21480 heme oxygenase (biliverdin-producing, ferredoxin) [EC:1.14.15.20] K00214 biliverdin reductase [EC:1.3.1.24] K05901 biliverdin reductase / flavin reductase [EC:1.3.1.24 1.5.1.30] K23825 F420H(2)-dependent biliverdin reductase [EC:1.3.98.-] K08100 bilirubin oxidase [EC:1.3.3.5] K00699 glucuronosyltransferase [EC:2.4.1.17] K01195 beta-glucuronidase [EC:3.2.1.31] K05369 15,16-dihydrobiliverdin:ferredoxin oxidoreductase [EC:1.3.7.2] K05370 phycoerythrobilin:ferredoxin oxidoreductase [EC:1.3.7.3] K08101 phytochromobilin:ferredoxin oxidoreductase [EC:1.3.7.4] K05371 phycocyanobilin:ferredoxin oxidoreductase [EC:1.3.7.5] K21796 Prochlorococcus phage phycoerythrobilin synthase [EC:1.3.7.6] K01764 cytochrome c heme-lyase [EC:4.4.1.17] K13624 ceruloplasmin [EC:1.16.3.1] K14735 hephaestin [EC:1.16.3.1] K19054 frataxin [EC:1.16.3.1] K00522 ferritin heavy chain [EC:1.16.3.1] K13625 ferritin light chain K18495 ferritin, mitochondrial [EC:1.16.3.1] K03594 bacterioferritin [EC:1.16.3.1] K22336 bacterioferritin B [EC:1.16.3.1] K22552 multicopper oxidase [EC:1.16.3.1] 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 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 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 PMID:10217486 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 PMID:10518530 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 PMID:11007789 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 PMID:12196148 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 PMID:12195810 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 PMID:12055304 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 PMID:11283349 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 PMID:17506685 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 PMID:16245042 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 PMID:23042036 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 PMID:23922391 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 REL_PATHWAY ko00230 Purine metabolism ko00250 Alanine, aspartate and glutamate metabolism ko00260 Glycine, serine and threonine metabolism ko00740 Riboflavin metabolism ///