2.0 2012-05-31 13:48:33 -0600 2015-06-03 15:53:53 -0600 ECMDB01261 M2MDB000314 Coproporphyrinogen III In the metabolism of porphyrin, the enzyme uroporphyrinogen III decarboxylase generates coproporphyrinogen III from uroporphyrinogen III, and coproporphyrinogen III oxidase converts it into protoporphyrinogen IX. (Wikipedia) 3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate 3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-Porphinetetrapropionate 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-Porphinetetrapropionic acid 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-Porphine-2,7,12,18-tetrapropanoate 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-Porphine-2,7,12,18-tetrapropanoic acid CoPorgen III Coproporphyrinogen Coproporphyrinogen I Coproporphyrinogen-III C36H44N4O8 660.7566 660.315914404 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid 2624-63-7 CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3 InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48) NIUVHXTXUXOFEB-UHFFFAOYSA-N Solid Inner membrane Membrane Outer membrane logp 1.96 ALOGPS logs -4.77 ALOGPS solubility 1.12e-02 g/l ALOGPS logp 4.89 ChemAxon pka_strongest_acidic 3.8 ChemAxon iupac 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid ChemAxon average_mass 660.7566 ChemAxon mono_mass 660.315914404 ChemAxon smiles CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3 ChemAxon formula C36H44N4O8 ChemAxon inchi InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48) ChemAxon inchikey NIUVHXTXUXOFEB-UHFFFAOYSA-N ChemAxon polar_surface_area 212.36 ChemAxon refractivity 181.86 ChemAxon polarizability 72.85 ChemAxon rotatable_bond_count 12 ChemAxon acceptor_count 8 ChemAxon donor_count 8 ChemAxon physiological_charge -4 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Porphyrin metabolism The metabolism of porphyrin begins with with glutamic acid being processed by an ATP-driven glutamyl-tRNA synthetase by interacting with hydrogen ion and tRNA(Glu), resulting in amo, pyrophosphate and L-glutamyl-tRNA(Glu) Glutamic acid. Glutamic acid can be obtained as a result of L-glutamate metabolism pathway, glutamate / aspartate : H+ symporter GltP, glutamate:sodium symporter or a glutamate / aspartate ABC transporter . L-glutamyl-tRNA(Glu) Glutamic acid interacts with a NADPH glutamyl-tRNA reductase resulting in a NADP, a tRNA(Glu) and a (S)-4-amino-5-oxopentanoate. This compound interacts with a glutamate-1-semialdehyde aminotransferase resulting a 5-aminolevulinic acid. This compound interacts with a porphobilinogen synthase resulting in a hydrogen ion, water and porphobilinogen. The latter compound interacts with water resulting in hydroxymethylbilane synthase resulting in ammonium, and hydroxymethylbilane. Hydroxymethylbilane can either be dehydrated to produce uroporphyrinogen I or interact with a uroporphyrinogen III synthase resulting in a water molecule and a uroporphyrinogen III. Uroporphyrinogen I interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a coproporphyrinogen I Uroporphyrinogen III can be metabolized into precorrin by interacting with a S-adenosylmethionine through a siroheme synthase resulting in hydrogen ion, an s-adenosylhomocysteine and a precorrin-1. On the other hand, Uroporphyrinogen III interacts with hydrogen ion through a uroporphyrinogen decarboxylase resulting in a carbon dioxide and a Coproporphyrinogen III. Precorrin-1 reacts with a S-adenosylmethionine through a siroheme synthase resulting in a S-adenosylhomocysteine and a Precorrin-2. The latter compound is processed by a NAD dependent uroporphyrin III C-methyltransferase [multifunctional] resulting in a NADH and a sirohydrochlorin. This compound then interacts with Fe 2+ uroporphyrin III C-methyltransferase [multifunctional] resulting in a hydrogen ion and a siroheme. The siroheme is then processed in sulfur metabolism pathway. Uroporphyrinogen III can be processed in anaerobic or aerobic condition. Anaerobic: Uroporphyrinogen III interacts with an oxygen molecule, a hydrogen ion through a coproporphyrinogen III oxidase resulting in water, carbon dioxide and protoporphyrinogen IX. The latter compound then interacts with an 3 oxygen molecule through a protoporphyrinogen oxidase resulting in 3 hydrogen peroxide and a Protoporphyrin IX Aerobic: Uroporphyrinogen III reacts with S-adenosylmethionine through a coproporphyrinogen III dehydrogenase resulting in carbon dioxide, 5-deoxyadenosine, L-methionine and protoporphyrinogen IX. The latter compound interacts with a meanquinone through a protoporphyrinogen oxidase resulting in protoporphyrin IX. The protoporphyrin IX interacts with Fe 2+ through a ferrochelatase resulting in a hydrogen ion and a ferroheme b. The ferroheme b can either be incorporated into the oxidative phosphorylation as a cofactor of the enzymes involved in that pathway or it can interact with hydrogen peroxide through a catalase HPII resulting in a heme D. Heme D can then be incorporated into the oxidative phosphyrlation pathway as a cofactor of the enzymes involved in that pathway. Ferroheme b can also interact with water and a farnesyl pyrophosphate through a heme O synthase resulting in a release of pyrophosphate and heme O. Heme O is then incorporated into the Oxidative phosphorylation pathway. PW000936 Metabolic heme biosynthesis from uroporphyrinogen-III I HEME-BIOSYNTHESIS-II superpathway of heme biosynthesis from uroporphyrinogen-III PWY0-1415 heme biosynthesis from uroporphyrinogen-III II HEMESYN2-PWY Specdb::CMs 16283 Specdb::CMs 674321 Specdb::CMs 674322 Specdb::CMs 674323 Specdb::CMs 674324 Specdb::CMs 674325 Specdb::CMs 674326 Specdb::CMs 674327 Specdb::CMs 674328 Specdb::CMs 674329 Specdb::CMs 674330 Specdb::CMs 674331 Specdb::CMs 674332 Specdb::CMs 674333 Specdb::CMs 674334 Specdb::CMs 674335 Specdb::CMs 674336 Specdb::CMs 674337 Specdb::CMs 674338 Specdb::CMs 674339 Specdb::CMs 674340 Specdb::CMs 674341 Specdb::CMs 674342 Specdb::CMs 674343 Specdb::CMs 674344 Specdb::NmrOneD 247688 Specdb::NmrOneD 247689 Specdb::NmrOneD 247690 Specdb::NmrOneD 247691 Specdb::NmrOneD 247692 Specdb::NmrOneD 247693 Specdb::NmrOneD 247694 Specdb::NmrOneD 247695 Specdb::NmrOneD 247696 Specdb::NmrOneD 247697 Specdb::NmrOneD 247698 Specdb::NmrOneD 247699 Specdb::NmrOneD 247700 Specdb::NmrOneD 247701 Specdb::NmrOneD 247702 Specdb::NmrOneD 247703 Specdb::NmrOneD 247704 Specdb::NmrOneD 247705 Specdb::NmrOneD 247706 Specdb::NmrOneD 247707 Specdb::MsMs 20705 Specdb::MsMs 20706 Specdb::MsMs 20707 Specdb::MsMs 20912 Specdb::MsMs 20913 Specdb::MsMs 20914 Specdb::MsMs 22256 Specdb::MsMs 22257 Specdb::MsMs 22258 Specdb::MsMs 22463 Specdb::MsMs 22464 Specdb::MsMs 22465 Specdb::MsMs 2373933 Specdb::MsMs 2373934 Specdb::MsMs 2373935 Specdb::MsMs 2564910 Specdb::MsMs 2564911 Specdb::MsMs 2564912 HMDB01261 321 315 C03263 15439 COPROPORPHYRINOGEN_III CP3 Coproporphyrinogen III Keseler, I. 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"Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Shoolingin-Jordan, Peter M. The biosynthesis of coproporphyrinogen III. Porphyrin Handbook (2003), 12 33-74. Uroporphyrinogen decarboxylase P29680 DCUP_ECOLI hemE http://ecmdb.ca/proteins/P29680.xml Oxygen-independent coproporphyrinogen-III oxidase P32131 HEMN_ECOLI hemN http://ecmdb.ca/proteins/P32131.xml Coproporphyrinogen-III oxidase, aerobic P36553 HEM6_ECOLI hemF http://ecmdb.ca/proteins/P36553.xml Coproporphyrinogen III + S-Adenosylmethionine > Protoporphyrinogen IX + Carbon dioxide + L-Methionine + 5'-Deoxyadenosine HEMN-RXN Coproporphyrinogen III + Oxygen + Hydrogen ion > Protoporphyrinogen IX + Carbon dioxide + Water RXN0-1461 Hydrogen ion + Uroporphyrinogen III > Carbon dioxide + Coproporphyrinogen III UROGENDECARBOX-RXN Uroporphyrinogen III > Coproporphyrinogen III +4 Carbon dioxide Coproporphyrinogen III + Oxygen + 2 Hydrogen ion > Protoporphyrinogen IX +2 Carbon dioxide +2 Water RXN0-1461 Coproporphyrinogen III + 2 S-adenosyl-L-methionine > Protoporphyrinogen IX +2 Carbon dioxide +2 L-Methionine +2 5'-Deoxyadenosine Uroporphyrinogen III + 4 Hydrogen ion >4 Carbon dioxide + Coproporphyrinogen III PW_R003480 S-adenosyl-L-methionine + Coproporphyrinogen III > 5'-Deoxyadenosine + L-Methionine + Carbon dioxide + Protoporphyrinogen IX PW_R003483