1.0 2011-09-21 00:08:52 UTC 2015-10-09 22:32:57 UTC FDB022126 Deuteroporphyrin IX Deuteroporphyrin IX is a non-natural dicarboxylic porphyrin. Deuteroporphyrins are porphyrins with four methyl and two propionic acid side chains attached to the pyrrole rings. Deuteroporphyrin IX is described as a fecal porphyrin in patients with endemic chronic arsenic poisoning. (Environmental Sciences (Tokyo, Japan) (2001), 8(6), 561-570.) Excess accumulation of the biosynthetic intermediate protoporphyrin can lead to extensive tissue damage upon exposure to light since protoporpyhyrin is a potent photosensitizing agent, giving rise to membrane-destroying oxygen radicals or singlet oxygen. For instance, in the human porphyria disease porphyria variegata, a genetic deficiency in a heme biosynthetic enzyme, protoporphyrinogen oxidase, leads to protoporphyrin accumulation and lightdependent skin photosensitivity. Horseradish peroxidase (HRP) in the presence of glutathione (GSH) could oxidize the non-natural porphyrin deuteroporphyrin IX, which is closely related to protoporphyrin IX. The product is a unique green chlorin. One of the pyrrole rings had been modified by addition of an hydroxy and an oxo group, thus giving the characteristic reduced pyrrole ring of the chlorine. Of most importance for human medicine, peroxidative enzymes present in mammalian cells can also carry out these GSH-dependent oxidative conversions of protoporphyrin and deuteroporphyrin. (PMID: 10334939) [HMDB] Deuteroporphyrin Deuteroporphyrin-IX C30H30N4O4 510.5836 510.226705468 3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-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-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-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 448-65-7 CC1=C/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(C=C4C)\C=C\1/N\2)/C(CCC(O)=O)=C3C InChI=1S/C30H30N4O4/c1-15-9-20-12-25-17(3)21(5-7-29(35)36)27(33-25)14-28-22(6-8-30(37)38)18(4)26(34-28)13-24-16(2)10-19(32-24)11-23(15)31-20/h9-14,31,34H,5-8H2,1-4H3,(H,35,36)(H,37,38)/b19-11-,20-12-,23-11-,24-13-,25-12-,26-13-,27-14-,28-14- KWKUIRGQJJFUCG-LMKUSPAJSA-N belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Porphyrins Organic compounds Organoheterocyclic compounds Tetrapyrroles and derivatives Porphyrins Solid logp 3.55 ALOGPS logs -4.29 ALOGPS solubility 2.60e-02 g/l ALOGPS logp 5.04 ChemAxon pka_strongest_acidic 3.78 ChemAxon pka_strongest_basic 5.13 ChemAxon iupac 3-[20-(2-carboxyethyl)-5,9,14,19-tetramethyl-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 510.5836 ChemAxon mono_mass 510.226705468 ChemAxon smiles CC1=C/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C(N4)/C=C4\N=C(C=C4C)\C=C\1/N\2)/C(CCC(O)=O)=C3C ChemAxon formula C30H30N4O4 ChemAxon inchi InChI=1S/C30H30N4O4/c1-15-9-20-12-25-17(3)21(5-7-29(35)36)27(33-25)14-28-22(6-8-30(37)38)18(4)26(34-28)13-24-16(2)10-19(32-24)11-23(15)31-20/h9-14,31,34H,5-8H2,1-4H3,(H,35,36)(H,37,38)/b19-11-,20-12-,23-11-,24-13-,25-12-,26-13-,27-14-,28-14- ChemAxon inchikey KWKUIRGQJJFUCG-LMKUSPAJSA-N ChemAxon polar_surface_area 131.96 ChemAxon refractivity 144.44 ChemAxon polarizability 58.99 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 6 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 301027 Specdb::MsMs 301028 Specdb::MsMs 301029 Specdb::MsMs 343450 Specdb::MsMs 343451 Specdb::MsMs 343452 Specdb::MsMs 2416036 Specdb::MsMs 2416037 Specdb::MsMs 2416038 Specdb::MsMs 2546217 Specdb::MsMs 2546218 Specdb::MsMs 2546219 Specdb::CMs 15808 Specdb::CMs 37636 Specdb::CMs 1066921 Specdb::CMs 1066923 Specdb::CMs 1066925 Specdb::CMs 1066927 Specdb::CMs 1066928 Specdb::CMs 1066930 Specdb::CMs 1066932 Specdb::CMs 1066933 Specdb::CMs 1066935 Specdb::CMs 1066937 Specdb::CMs 1066939 Specdb::CMs 1066941 Specdb::CMs 1066942 Specdb::CMs 1066944 Specdb::CMs 1066946 Specdb::CMs 1066948 Specdb::CMs 1066950 Specdb::CMs 1066951 Specdb::CMs 1066953 Specdb::CMs 1066955 HMDB00579 #<Reference:0x000055ce317662b8> #<Reference:0x000055ce31766038> #<Reference:0x000055ce31765e30> #<Reference:0x000055ce31765c50> #<Reference:0x000055ce31765a70> #<Reference:0x000055ce31765868> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823