2.0 2012-05-31 13:02:06 -0600 2015-06-03 15:53:37 -0600 ECMDB00916 M2MDB000201 Uroporphyrin III Uroporphyrin is the porphyrin produced by oxidation of the methylene bridges in uroporphyrinogen. Uroporphyrins have four acetic acid and four propionic acid side chains attached to the pyrrole rings. Uroporphyrinogen I and III are formed from polypyrryl methane in the presence of uroporphyrinogen III cosynthetase and uroporphyrin I synthetase, respectively. They can yield uroporphyrins by autooxidation or coproporphyrinogens by decarboxylation. 3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoate 3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoic acid 3,8,13,17-Tetramethyl-2,7,12,18-Porphinetetrapropionate 3,8,13,17-Tetramethyl-2,7,12,18-Porphinetetrapropionic acid Coproporphyrin III Uroporphyrin III C40H38N4O16 830.7469 830.228281188 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid 18273-06-8 OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CCC(O)=O)=C3CC(O)=O InChI=1S/C40H38N4O16/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/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- VZVFNUAIRVUCEW-UJJXFSCMSA-N Solid Inner membrane Membrane Outer membrane logp 0.79 ALOGPS logs -4.35 ALOGPS solubility 3.75e-02 g/l ALOGPS logp 3.51 ChemAxon pka_strongest_acidic 3.11 ChemAxon iupac 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid ChemAxon average_mass 830.7469 ChemAxon mono_mass 830.228281188 ChemAxon smiles OC(=O)CCC1=C(CC(O)=O)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(CC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CC(O)=O)=C4CCC(O)=O)/C(CCC(O)=O)=C3CC(O)=O ChemAxon formula C40H38N4O16 ChemAxon inchi InChI=1S/C40H38N4O16/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/h13-16,41,44H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16- ChemAxon inchikey VZVFNUAIRVUCEW-UJJXFSCMSA-N ChemAxon polar_surface_area 355.76 ChemAxon refractivity 201.32 ChemAxon polarizability 85.12 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 18 ChemAxon donor_count 10 ChemAxon physiological_charge -8 ChemAxon formal_charge 0 ChemAxon Porphyrin and chlorophyll metabolism ec00860 Specdb::EiMs 3118 Specdb::NmrOneD 330442 Specdb::NmrOneD 330443 Specdb::NmrOneD 330444 Specdb::NmrOneD 330445 Specdb::NmrOneD 330446 Specdb::NmrOneD 330447 Specdb::NmrOneD 330448 Specdb::NmrOneD 330449 Specdb::NmrOneD 330450 Specdb::NmrOneD 330451 Specdb::NmrOneD 330452 Specdb::NmrOneD 330453 Specdb::NmrOneD 330454 Specdb::NmrOneD 330455 Specdb::NmrOneD 330456 Specdb::NmrOneD 330457 Specdb::NmrOneD 330458 Specdb::NmrOneD 330459 Specdb::NmrOneD 330460 Specdb::NmrOneD 330461 Specdb::MsMs 320530 Specdb::MsMs 320531 Specdb::MsMs 320532 Specdb::MsMs 367912 Specdb::MsMs 367913 Specdb::MsMs 367914 Specdb::MsMs 2326587 Specdb::MsMs 2326588 Specdb::MsMs 2326589 Specdb::MsMs 2611600 Specdb::MsMs 2611601 Specdb::MsMs 2611602 HMDB00916 C02469 15436 UROPORPHYRIN_III Keseler, I. 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Arch Toxicol. 1999 Mar;73(2):90-5. 10350189 To-Figueras J, Ozalla D, Mateu CH: Long-standing changes in the urinary profile of porphyrin isomers after clinical remission of porphyria cutanea tarda. Ann Clin Lab Sci. 2003 Summer;33(3):251-6. 12956438 Kajiwara, Masahiro; Mizutani, Minoru; Kojima, Ichiro. Manufacture of uroporphyrin III with Arthrobacter. Jpn. Kokai Tokkyo Koho (1993), 7 pp. 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