2.0 2012-05-31 13:44:54 -0600 2015-06-03 15:53:43 -0600 ECMDB01086 M2MDB000248 Uroporphyrinogen III Uroporphyrinogens are porphyrinogen variants in which each pyrrole ring has one acetate side chain and one propionate side chain; it is formed by condensation 4 four molecules of porphobilinogen. 4 isomers are possible but only 2 commoly are found, types I and III. Uroporphyrinogen III is a functional intermediate in heme biosynthesis while Uroporphyrinogen I is produced in an abortive side reaction. 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-Porphinetetrapropionate 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-2,7,12,18-Porphinetetrapropionic acid 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-Porphine-2,7,12,18-tetrapropanoate 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydro-21H,23H-Porphine-2,7,12,18-tetrapropanoic acid 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate 3,8,13,17-Tetrakis(carboxymethyl)-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid Urogen I Urogen III UroPorgen-III Uroporphyrinogen I Uroporphyrinogen III Uroporphyrinogen-III C40H44N4O16 836.7946 836.27523138 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid uroporphyrinogen-III 1976-85-8 OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3 InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60) HUHWZXWWOFSFKF-UHFFFAOYSA-N Solid Cytosol logp 0.67 ALOGPS logs -4.28 ALOGPS solubility 4.37e-02 g/l ALOGPS logp 1.39 ChemAxon pka_strongest_acidic 3.21 ChemAxon iupac 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1³,⁶.1⁸,¹¹.1¹³,¹⁶]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid ChemAxon average_mass 836.7946 ChemAxon mono_mass 836.27523138 ChemAxon smiles OC(=O)CCC1=C2CC3=C(CCC(O)=O)C(CC(O)=O)=C(CC4=C(CC(O)=O)C(CCC(O)=O)=C(CC5=C(CC(O)=O)C(CCC(O)=O)=C(CC(N2)=C1CC(O)=O)N5)N4)N3 ChemAxon formula C40H44N4O16 ChemAxon inchi InChI=1S/C40H44N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h41-44H,1-16H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60) ChemAxon inchikey HUHWZXWWOFSFKF-UHFFFAOYSA-N ChemAxon polar_surface_area 361.56 ChemAxon refractivity 206.93 ChemAxon polarizability 81.55 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 16 ChemAxon donor_count 12 ChemAxon physiological_charge -8 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 tetrapyrrole biosynthesis I PWY-5188 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 siroheme biosynthesis PWY-5194 Specdb::EiMs 5383 Specdb::NmrOneD 345048 Specdb::NmrOneD 345049 Specdb::NmrOneD 345050 Specdb::NmrOneD 345051 Specdb::NmrOneD 345052 Specdb::NmrOneD 345053 Specdb::NmrOneD 345054 Specdb::NmrOneD 345055 Specdb::NmrOneD 345056 Specdb::NmrOneD 345057 Specdb::NmrOneD 345058 Specdb::NmrOneD 345059 Specdb::NmrOneD 345060 Specdb::NmrOneD 345061 Specdb::NmrOneD 345062 Specdb::NmrOneD 345063 Specdb::NmrOneD 345064 Specdb::NmrOneD 345065 Specdb::NmrOneD 345066 Specdb::NmrOneD 345067 Specdb::MsMs 29585 Specdb::MsMs 29586 Specdb::MsMs 29587 Specdb::MsMs 36143 Specdb::MsMs 36144 Specdb::MsMs 36145 Specdb::MsMs 2375444 Specdb::MsMs 2375445 Specdb::MsMs 2375446 Specdb::MsMs 2559426 Specdb::MsMs 2559427 Specdb::MsMs 2559428 HMDB01086 1179 1146 C01051 15437 UROPORPHYRINOGEN-III UP2 Uroporphyrinogen III Keseler, I. 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Epub 2001 Aug 27. 11524417 Uroporphyrinogen-III synthase P09126 HEM4_ECOLI hemD http://ecmdb.ca/proteins/P09126.xml Putative uroporphyrinogen-III C-methyltransferase P09127 HEMX_ECOLI hemX http://ecmdb.ca/proteins/P09127.xml Siroheme synthase P0AEA8 CYSG_ECOLI cysG http://ecmdb.ca/proteins/P0AEA8.xml Uroporphyrinogen decarboxylase P29680 DCUP_ECOLI hemE http://ecmdb.ca/proteins/P29680.xml 2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion R03194 Hydroxymethylbilane <> Water + Uroporphyrinogen III R03165 UROGENIIISYN-RXN 4 Hydrogen ion + Uroporphyrinogen III <>4 Carbon dioxide + Coproporphyrin III R03197 2 S-Adenosylmethionine + Uroporphyrinogen III <>2 S-Adenosylhomocysteine + Precorrin 2 R03194 Uroporphyrinogen III <> Coproporphyrin III +4 Carbon dioxide R03197 S-Adenosylmethionine + Uroporphyrinogen III <> S-Adenosylhomocysteine + precorrin-1 + Hydrogen ion UROPORIIIMETHYLTRANSA-RXN Hydrogen ion + Uroporphyrinogen III > Carbon dioxide + Coproporphyrinogen III UROGENDECARBOX-RXN S-adenosyl-L-methionine + Uroporphyrinogen III > S-Adenosylhomocysteine + Precorrin-1 Uroporphyrinogen III > Coproporphyrinogen III +4 Carbon dioxide Hydroxymethylbilane > Uroporphyrinogen III + Water 2 S-Adenosylmethionine + Uroporphyrinogen III + Precorrin-1 <>2 S-Adenosylhomocysteine + Precorrin 2 R03194 Uroporphyrinogen III + 4 Hydrogen ion >4 Carbon dioxide + Coproporphyrinogen III PW_R003480 Uroporphyrinogen III + S-adenosyl-L-methionine > Hydrogen ion + S-Adenosylhomocysteine + Precorrin-1 PW_R003489 2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion 4 Hydrogen ion + Uroporphyrinogen III <>4 Carbon dioxide + Coproporphyrin III Hydroxymethylbilane <> Water + Uroporphyrinogen III 2 S-Adenosylmethionine + Uroporphyrinogen III >2 S-Adenosylhomocysteine + Precorrin 2 + Hydrogen ion