2.0 2012-05-31 10:24:38 -0600 2015-09-13 12:56:07 -0600 ECMDB00241 M2MDB000101 Protoporphyrin IX Protoporphyrins are tetrapyrroles containing 4 methyl, 2 propionic and 2 vinyl side chains. Protopophyrin is produced by oxidation of the methylene bridge of protoporphyrinogen. Protoporphyrin IX is the only naturally occurring isomer; it is an intermediate in heme biosynthesis, combining with ferrous iron to form protoheme IX, the heme prosthetic group of hemoglobin. Protoporphyrin IX is created by the enzyme protoporphyrinogen oxidase. The enzyme ferrochelatase converts it into heme. Protoporphyrin IX naturally occurs in small amounts in feces. It is accumulated and excreted excessively in the feces in protoporphyria and variegate porphyria. Protoporphyrin IX is also responsible for the brown pigment (Ooporphyrin) of birds' eggs Protoporphyrin IX is used as a branch point in the biosynthetic pathway leading to Heme (by insertion of iron) and chlorophylls (by insertion of Mg and further side-chain transformation). 3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionate 3,3'-(3,7,12,17-Tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid 3,3'-(3,7,12,17-Tetramethyl-8,13-divinylporphine-2,18-diyl)di Kammerer'S prophyrin Ooporphyrin Por IX Porphyrinogen IX PpIX Protoporphyrin Protoporphyrin IX Protoporphyrin-"IX" Protoporphyrin-IX C34H34N4O4 562.6582 562.258005596 3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid 3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid 553-12-8 CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- KSFOVUSSGSKXFI-UJJXFSCMSA-N Solid Cytosol Membrane logp 4.40 ALOGPS logs -4.41 ALOGPS solubility 2.17e-02 g/l ALOGPS melting_point 300 oC logp 6.78 ChemAxon pka_strongest_acidic 3.68 ChemAxon pka_strongest_basic 4.96 ChemAxon iupac 3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid ChemAxon average_mass 562.6582 ChemAxon mono_mass 562.258005596 ChemAxon smiles CC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(C=C)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(C=C)=C4C)/C(C)=C3CCC(O)=O ChemAxon formula C34H34N4O4 ChemAxon inchi InChI=1S/C34H34N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,13-16,35,38H,1-2,9-12H2,3-6H3,(H,39,40)(H,41,42)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- ChemAxon inchikey KSFOVUSSGSKXFI-UJJXFSCMSA-N ChemAxon polar_surface_area 131.96 ChemAxon refractivity 163.81 ChemAxon polarizability 66.03 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Metabolic pathways eco01100 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 9947 Specdb::CMs 37381 Specdb::CMs 282028 Specdb::CMs 350319 Specdb::CMs 350320 Specdb::CMs 350321 Specdb::CMs 350322 Specdb::CMs 350323 Specdb::CMs 350324 Specdb::CMs 350325 Specdb::CMs 350326 Specdb::CMs 350327 Specdb::CMs 350328 Specdb::CMs 350329 Specdb::CMs 350330 Specdb::CMs 350331 Specdb::CMs 350332 Specdb::CMs 350333 Specdb::CMs 350334 Specdb::CMs 350335 Specdb::CMs 350336 Specdb::CMs 350337 Specdb::CMs 350338 Specdb::NmrOneD 318591 Specdb::NmrOneD 318592 Specdb::NmrOneD 318593 Specdb::NmrOneD 318594 Specdb::NmrOneD 318595 Specdb::NmrOneD 318596 Specdb::NmrOneD 318597 Specdb::NmrOneD 318598 Specdb::NmrOneD 318599 Specdb::NmrOneD 318600 Specdb::NmrOneD 318601 Specdb::NmrOneD 318602 Specdb::NmrOneD 318603 Specdb::NmrOneD 318604 Specdb::NmrOneD 318605 Specdb::NmrOneD 318606 Specdb::NmrOneD 318607 Specdb::NmrOneD 318608 Specdb::NmrOneD 318609 Specdb::NmrOneD 318610 Specdb::MsMs 288007 Specdb::MsMs 288008 Specdb::MsMs 288009 Specdb::MsMs 326989 Specdb::MsMs 326990 Specdb::MsMs 326991 Specdb::MsMs 2290971 Specdb::MsMs 2290972 Specdb::MsMs 2290973 Specdb::MsMs 2645022 Specdb::MsMs 2645023 Specdb::MsMs 2645024 HMDB00241 4971 C02191 15430 PROTOPORPHYRIN_IX Protoporphyrin IX Keseler, I. 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Journal of the Chemical Society, Chemical Communications (1976), (6), 187-8. http://hmdb.ca/system/metabolites/msds/000/000/176/original/HMDB00241.pdf?1358462064 Protoporphyrinogen oxidase P0ACB4 HEMG_ECOLI hemG http://ecmdb.ca/proteins/P0ACB4.xml Ferrochelatase P23871 HEMH_ECOLI hemH http://ecmdb.ca/proteins/P23871.xml Iron + Protoporphyrin IX >2 Hydrogen ion + Heme PROTOHEMEFERROCHELAT-RXN Oxygen + Protoporphyrinogen IX >3 Water + Protoporphyrin IX 3 Fumaric acid + Protoporphyrinogen IX > Protoporphyrin IX +3 Succinic acid Protoporphyrin IX + Fe2+ <> Heme +2 Hydrogen ion + Fe2+ R00310 Protoporphyrinogen IX + 3 Menaquinone + 3 Menaquinone <> Protoporphyrin IX +3 Menaquinol 6 R09489 Hydrogen ion + Heme Protoporphyrin IX + Iron RXN0-6258 Iron + Protoporphyrin IX > Heme + Hydrogen ion PROTOHEMEFERROCHELAT-RXN Protoporphyrinogen IX + Oxygen > Protoporphyrin IX + Hydrogen peroxide PROTOPORGENOXI-RXN Protoporphyrinogen IX + a menaquinone > Protoporphyrin IX + a menaquinol RXN0-6259 Protoporphyrinogen IX + 3 Menaquinone > Protoporphyrin IX +3 Menaquinol 6 R09489 Heme + 2 Hydrogen ion > Protoporphyrin IX + Iron Protoporphyrinogen IX + 3 Oxygen <> Protoporphyrin IX +3 Hydrogen peroxide R03222 Protoporphyrinogen IX + 3 Oxygen > Protoporphyrin IX +3 Hydrogen peroxide PW_R003484 Protoporphyrinogen IX + menaquinone-8 > Protoporphyrin IX + Menaquinol 6 PW_R003485 Protoporphyrin IX + Iron >2 Hydrogen ion + ferroheme b PW_R003486 Protoporphyrin IX + Fe2+ <> Heme +2 Hydrogen ion